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Journal articles on the topic 'Carboline'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 January 2023

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1

Ferretti, Valeria, Paola Gilli, and Pier Andrea Borea. "Structural features controlling the binding of β-carbolines to the benzodiazepine receptor." Acta Crystallographica Section B Structural Science 60, no. 4 (July 19, 2004): 481–89. http://dx.doi.org/10.1107/s0108768104013564.

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β-Carbolines are a class of drug which can interact with a high affinity with the benzodiazepine (BDZ) binding site of the GABAA receptor. The present paper, aimed at obtaining a deeper insight into the structure–properties relationships of this class of molecules, reports the crystal structures of four β-carbolines: ZK93423 (3-carboethoxy-4-methoxymethyl-6-benzyloxy-β-carboline), ZK91296 (3-carboethoxy-4-methoxymethyl-5-benzyloxy-β-carboline), FG7142 (N-methyl-3-carbamoyl-β-carboline) and the low-affinity ligand harmine hydrochloride (1-methyl-7-methoxy-β-carboline). This set of structural data is completed by the X-ray structures of other carbolines of known biological activity retrieved from the Cambridge Crystallographic Database and by the structures of β-CCE (3-carboethoxy-β-carboline), 6-PBC (3-carboethoxy-4-methoxymethyl-6-isopropoxy-β-carboline), PRCC (3-isopropoxy-β-carboline) and ZK93426 (3-carboethoxy-4-methyl-5-isopropoxy-β-carboline), which have been obtained by molecular-mechanics simulations. The structural features of all these molecules have been compared according to the stereochemical model we proposed in 1987. The structural comparison is integrated by the Free–Wilson analysis on 32 β-carbolines of known binding affinity data.

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2

Singh, Dharmender, Vipin Kumar, and Virender Singh. "Et3N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties." Beilstein Journal of Organic Chemistry 16 (July 20, 2020): 1740–53. http://dx.doi.org/10.3762/bjoc.16.146.

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A robust transition-metal-free strategy is presented to access novel β-carboline-tethered benzothiophenone derivatives from 1(3)-formyl-β-carbolines using elemental sulfur activated by Et3N/DMSO. This expeditious catalyst-free reaction proceeds through the formation of β-carboline-based 2-nitrochalcones followed by an incorporation of sulfur to generate multifunctional β-carboline-linked benzothiophenones in good to excellent yields. The synthetic strategy could also be extended towards the synthesis of β-carboline-linked benzothiophenes. Moreover, the afforded products emerged as promising fluorophores and displayed excellent light-emitting properties with quantum yields (ΦF) up to 47%.

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3

Ribeiro, João L. P., Joana B. Loureiro, Susana M. M. Lopes, Lucília Saraiva, and Teresa M. V. D. Pinho e Melo. "3-(1,2,3-Triazol-4-yl)-β-Carbolines and 3-(1H-Tetrazol-5-yl)-β-Carbolines: Synthesis and Evaluation as Anticancer Agents." Pharmaceuticals 15, no. 12 (December 3, 2022): 1510. http://dx.doi.org/10.3390/ph15121510.

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Herein, the synthesis and anticancer activity evaluation of a series of novel β-carbolines is reported. The reactivity of nitrosoalkenes towards indole was explored for the synthesis of novel tryptophan analogs where the carboxylic acid was replaced by a triazole moiety. This tryptamine was used in the synthesis of 3-(1,2,3-triazol-4-yl)-β-carbolines via Pictet–Spengler condensation followed by an oxidative step. A library of compounds, including the novel 3-(1,2,3-triazol-4-yl)-β-carbolines as well as methyl β-carboline-3-carboxylate and 3-tetrazolyl-β-carboline derivatives, was evaluated for their antiproliferative activity against colorectal cancer cell lines. The 3-(1H-tetrazol-5-yl)-β-carbolines stood out as the most active compounds, with values of half-maximal inhibitory concentration (IC50) ranging from 3.3 µM to 9.6 µM against colorectal adenocarcinoma HCT116 and HT29 cell lines. The results also revealed a mechanism of action independent of the p53 pathway. Further studies with the 3-tetrazolyl-β-carboline derivative, which showed high selectivity for cancer cells, revealed IC50 values below 8 μM against pancreatic adenocarcinoma PANC-1, melanoma A375, hepatocarcinoma HEPG2, and breast adenocarcinoma MCF-7 cell lines. Collectively, this work discloses the 3-tetrazolyl-β-carboline derivative as a promising anticancer agent worthy of being further explored in future works.

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4

Meruva, Suresh Babu, Akula Raghunadh, Raghavendra Rao Kamaraju, U. K. Syam Kumar, and P. K. Dubey. "An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y." Beilstein Journal of Organic Chemistry 10 (February 25, 2014): 471–80. http://dx.doi.org/10.3762/bjoc.10.45.

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A novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation–Bischler–Napieralski reaction conditions using tryptamine and 2,2-dibromo-1-phenylethanone as key starting materials. A number of dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids.

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5

Cai, Rui, Li Zhu, Pengfei Wang, and Yu Zhao. "Bimetallic Catalyzed N-arylation Used in Synthesis of Novel β-carbolines Derivatives." Letters in Drug Design & Discovery 17, no. 5 (May 18, 2020): 520–25. http://dx.doi.org/10.2174/1570180815666181025124615.

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Background: Natural occurring β-Carbolines alkaloids are abundant in the plant kingdom or other organisms, and they were found to possess good antitumor activity through multiple mechanisms. Based on previous summarized SARs of β-carboline derivatives, the modification on pyridine ring would have a great impact on their antitumor activities. Therefore, we plan to synthesized arylated β-carboline-3-amides to find more valuable β-Carbolines derivatives. Methods: A novel bimetallic Pd(OAc)2/AgOAc catalyst system was developed for the amidation of aryl iodides under acid condition. A series of N-arylated β-carbolines derivatives were synthesized using this method. The structures of these compounds were confirmed by 1H NMR, 13C NMR and HRMS, and their in vitro antiproliferative activity was investigated against HepG2 and Hela tumor cell lines by MTT assay. Results: Eleven N-arylated β-carboline-3-amides were synthesized using this bimetallic catalyzed method in 58-98% yields. These synthesized N-arylated compounds showed no antiproliferative activity at 20 μM. Conclusion: We have discovered an efficient and bimetallic catalytic system allowing the Narylation of secondary acyclic amides. This is the first report that N-arylation of aliphatic secondary acyclic amides under acid condition.

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6

Berlin, J., I. N. Kuzovkina, C. Rügenhagen, L. Fecker, U. Commandeur, and V. Wray. "Hairy Root Cultures of Peganum harmala II. Characterization of Cell Lines and Effect of Culture Conditions on the Accumulation of ß-Carboline Alkaloids and Serotonin." Zeitschrift für Naturforschung C 47, no. 3-4 (April 1, 1992): 222–30. http://dx.doi.org/10.1515/znc-1992-3-410.

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Abstract Hairy root cultures of Peganum harmala established by genetic transformation with Agrobacterium rhizogenes wild type strains A4, 15834 or carrying the binary vector pLTCgus 1, respectively, were analyzed with respect to their tryptophan-derived metabolites. Beside the previously detected β-carboline alkaloids harmine, harmol, harmaline and harmalol all hairy root cultures were found to contain the β-carboline glucoside ruine and serotonin. The appearance of the root cultures and the levels of β-carboline alkaloids were greatly affected by the nitrogen source of the medium. In the presence of higher levels of ammonium ions (as in MS medium) the roots were short and thick, while in B50 medium (low ammonium) they were thin and long. Ammonium ions had a negative effect on the levels of β-carbolines. The best root cultures accumulated on B50 1.5-2% β-carbolines on a dry mass basis and in the presence of 6% sucrose ca. 10 mg β-carbolines/L x d were formed. In the presence of phytohorm ones root cultures were converted into low producing suspension cultures, from which the highly productive roots were reinduced on phytohormone-free medium.

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7

Kamal, Ahmed, Manda Sathish, A. V. G. Prasanthi, Jadala Chetna, Yellaiah Tangella, Vunnam Srinivasulu, Nagula Shankaraiah, and Abdullah Alarifi. "An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins." RSC Advances 5, no. 109 (2015): 90121–26. http://dx.doi.org/10.1039/c5ra16221a.

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8

Devi, Nisha, and Virender Singh. "Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products." Beilstein Journal of Organic Chemistry 18 (July 26, 2022): 926–34. http://dx.doi.org/10.3762/bjoc.18.92.

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β-Carboline is a privileged class of the alkaloid family and is associated with a broad spectrum of biological properties. 3-Formyl-9H-pyrido[3,4-b]indole is a such potent precursor belonging to this family which can be tailored for installing diversity at various positions of β-carboline to generate unique molecular hybrids of biological importance. The present work is a step towards this and assimilates the results related to the exploration of 3-formyl-9H-β-carbolines for the synthesis of β-carboline C-3 substituted MBH adducts followed by evaluation of their fluorescent characteristic. The effect of contact time, solvent system, concentration and substituents was also studied during investigation of fluorescence properties of these derivatives.

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9

Kolle, Shivalinga, and Sanjay Batra. "β-Carboline-directed decarboxylative acylation of ortho-C(sp2)–H of the aryl ring of aryl(β-carbolin-1-yl)methanones with α-ketoacids under palladium catalysis." RSC Advances 6, no. 56 (2016): 50658–65. http://dx.doi.org/10.1039/c6ra11811a.

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A Pd-catalysed β-carboline assisted decarboxylative acylation of ortho-C(sp²)–H of aryl ring of aryl(β-carbolin-1-yl)methanones using α-oxocarboxylic acid as the acyl ion source to form (2-aroylaryl)(β-carbolin-2-yl)methanones is demonstrated.

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10

Paula, Jéssica C., Nilma S. Fernandes, Thaysa K. Karam, Paula Baréa, Maria H. Sarragiotto, Tania Ueda-Nakamura, Sueli O. Silva, and Celso V. Nakamura. "β-carbolines RCC and C5 induce the death of Leishmania amazonensis intracellular amastigotes." Future Microbiology 17, no. 2 (January 2022): 99–110. http://dx.doi.org/10.2217/fmb-2020-0263.

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Background: Cutaneous leishmaniasis is caused by Leishmania spp., and its treatment is limited. The β-carbolines have shown activity against kinetoplastids. Aim: To evaluate the activity and effects of the β-carbolines, N-{2-[(4,6-bis(isopropylamino)-1,3,5-triazin-2-yl)amino]ethyl}-1-(4-methoxyphenyl)-β-carboline-3-carboxamide (RCC) and N-benzyl-1-(4-methoxy)phenyl-9H-beta-carboline-3-carboxamide (C5), against L. amazonensis intracellular amastigotes and to suggest their mechanism of action. Methods: We analyzed the activity and cytotoxicity of β-carbolines and the morphological alterations by electron microscopy. Mitochondrial membrane potential, production nitric oxide, reactive oxygen species, lipidic bodies, autophagic vacuoles and ATP were also evaluated. Results & conclusion: The results showed that RCC and C5 are active against intracellular amastigotes and were able to induce oxidative stress and ultrastructural alterations such as accumulation of lipid bodies and autophagic vacuoles, leading to parasite death.

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11

Glinsky-Olivier, Nicolas, and Xavier Guinchard. "Enantioselective Catalytic Methods for the Elaboration of Chiral Tetrahydro-β-carbolines and Related Scaffolds." Synthesis 49, no. 12 (May 2, 2017): 2605–20. http://dx.doi.org/10.1055/s-0036-1589003.

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Tetrahydro-β-carbolines are important synthetic intermediates in the total synthesis of natural products and of compounds exhibiting strong bioactivities. Over the last decades, catalytic methods using chiral catalysts have been described for their synthesis. This review covers catalytic and enantioselective methods to access chiral tetrahydro-β-carbolines and their applications in the elaboration of complex chiral molecules.1 Introduction2 Asymmetric Reduction of Dihydro-β-carbolines2.1 Asymmetric Transfer Hydrogenation Reactions2.2 Asymmetric Hydrogenation Reactions2.3 Biocatalyzed Reduction of Dihydro-β-carbolines3 Organocatalyzed Pictet–Spengler Reactions3.1 Chiral Thiourea-Catalyzed Reactions3.2 Chiral Phosphoric Acid Catalyzed Reactions4 Pictet–Spengler Reactions of In Situ Generated Cyclic Iminiums5 Organocatalyzed Functionalization of Dihydro-β-carboliniums6 Organocatalyzed Alkylation of Tetrahydro-β-carbolines7 Biocatalyzed Dynamic Kinetic Resolution of Tetrahydro-β-carbolines8 Conclusion and Perspectives

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12

Singh, Manpreet, Avijit Kumar Paul, and Virender Singh. "A transition metal-free approach towards the regioselective synthesis of β-carboline tethered pyrroles and 2,3-dihydro-1H-pyrroles." New Journal of Chemistry 44, no. 28 (2020): 12370–83. http://dx.doi.org/10.1039/d0nj02315a.

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A transition metal-free one-pot sequential approach has been unfolded for the synthesis of β-carboline tethered pyrroles and 2,3-dihydro-1H-pyrroles by using highly diverse 1-formyl-9H-β-carbolines as a template.

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13

Codding, Penelope W., Aleksander W. Roszak, Maria B. Szkaradzinska, James M. Cook, Timothy J. Hagen, and Michael S. Allen. "Structure – activity relationships in antagonist and inverse agonist ligands for the benzodiazepine receptor." Canadian Journal of Chemistry 73, no. 4 (April 1, 1995): 499–512. http://dx.doi.org/10.1139/v95-065.

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The X-ray crystal and molecular structures of the three benzodiazepine (BZD) receptor ligands are presented and the electronic character of inverse agonist ligands is probed through molecular orbital calculations. Two of the ligands have a 6-benzylamino substituent: 6-benzylamino-β-carboline-3-carboxylic acid methyl ester, 1, which is a high affinity antagonist with IC50 = 10 nM, and 6-benzylamino-β-carboline, 2, which is a moderate affinity inverse agonist with IC50 = 106 nM. The third compound, 3-ethoxy-β-carboline hydrochloride, 3, displays partial inverse agonist activity with an IC50 of 24 nM. Intermolecular interactions, including extensive hydrogen bonding involving both the pyridyl nitrogen atom and the indole N—H as well as π stacking of aromatic rings, are characteristic of β-carbolines and are found in these three structures. In addition, two of these compounds are protonated in the crystalline state, thereby providing a model for interactions in the absence of the 3-carboxylic acid ester function. Electronic calculations show that (1) the partial inverse agonist ligand has the highest charge on the N(2) atom and (2) high affinity β-carbolines possess two neighboring sites that have high electrostatic attraction for a hydrogen atom in an intermolecular interaction. These findings suggest that modifications to the 3-position side chain to enhance the charge on the pyridyl N atom and provide a hydrogen bond acceptor site will facilitate the development of partial inverse agonist ligands. Keywords: β-carbolines, benzodiazepine receptor, crystallography, structure–activity relationships.

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14

Baiget, Jessica, Sabin Llona-Minguez, Stuart Lang, Simon P. MacKay, Colin J. Suckling, and Oliver B. Sutcliffe. "Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine." Beilstein Journal of Organic Chemistry 7 (October 12, 2011): 1407–11. http://dx.doi.org/10.3762/bjoc.7.164.

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The carboline ring system is an important pharmacophore found in a number of biologically important targets. Development of synthetic routes for the preparation of these compounds is important in order to prepare a range of analogues containing the carboline heterocyclic moiety. A manganese dioxide mediated one-pot method starting with an activated alcohol and consisting of alcohol oxidation, Pictet–Spengler cyclisation, and oxidative aromatisation, offers a convenient process that allows access to β-carbolines. This one-pot process for the preparation of methyl 9H-pyrido[3,4-b]indole-1-carboxylate has subsequently been used as the key step in the synthesis of alangiobussinine and a closely related analogue.

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15

Bringmann, Gerhard, Doris Feineis, Miriam Münchbach, Ralf God, Karl Peters, Eva-Maria Peters, Rainald Mössner, and Klaus-Peter Lesch. "Toxicity and Metabolism of the Chloral-Derived Mammalian Alkaloid 1-Trichloromethyl-1,2,3,4-tetrahydro-β-carboline (TaClo) in PC12 Cells." Zeitschrift für Naturforschung C 61, no. 7-8 (August 1, 2006): 601–10. http://dx.doi.org/10.1515/znc-2006-7-822.

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Chloral-derived β-carbolines, which are structurally similar to the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP, 5), are discussed to contribute to neuronal cell death in idiopathic Parkinson’s disease. The cytotoxicity of 1-trichloromethyl- 1,2,3,4-tetrahydro-β-carboline (TaClo, 4) to neuronal-like clonal pheochromocytoma PC12 cells was examined by the determination of lactate dehydrogenase (LDH) release. After incubation for 48 h, 4 showed a strong dose-dependent cytotoxic activity towards PC12 cells with an ED50 value of 230 μᴍ. In PC12 cells reductive dehalogenation of 4 was observed giving rise to the formation of 1-dichloromethyl-1,2,3,4-tetrahydro-β-carboline (6) as a main TaClo metabolite exhibiting a cytotoxic potential comparable to that of TaClo. An X-ray structure analysis, performed for the trifluoroacetyl derivative of 6, revealed the N-substituent of such a highly chlorinated agent to be dramatically pushed out of the β-carboline ring ‘plane’ due to the high steric demand of the huge dichloromethyl group at C(1).

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16

Kolle, Shivalinga, and Sanjay Batra. "Pd(OAc)2-catalysed regioselective alkoxylation of aryl (β-carbolin-1-yl)methanones via β-carboline directed ortho-C(sp2)–H activation of an aryl ring." Organic & Biomolecular Chemistry 13, no. 41 (2015): 10376–85. http://dx.doi.org/10.1039/c5ob01500f.

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Synthesis of (2-alkoxyphenyl)(9H-pyrido[3,4-b]indol-1-yl)methanone via Pd(OAc)₂-catalyzed regioselective alkoxylation of aryl (β-carbolin-1-yl)methanones employing β-carboline directed ortho-C(sp²)–H activation of an aryl ring under oxidative conditions is described.

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17

Rentería-Gómez, Manuel A., Luis E. Cárdenas Galindo, and Rocío Gámez-Montaño. "Synthesis of the 2-tetrazolylmethyl-2,3,4,9-tetrahydro-1H-β-carbolines via Ultrasound-Assisted One-Pot Ugi-azide/Pictet–Spengler Process." Proceedings 41, no. 1 (November 14, 2019): 67. http://dx.doi.org/10.3390/ecsoc-23-06515.

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A serie of 2-tetrazolylmethyl-2,3,4,9-tetrahydro-1H-β-carbolines were synthesized via a one pot Ugi-azide/Pictet–Spengler process under mild ultrasound-assisted conditions. The products containing two privileged heterocyclic frameworks: 1,5-disubstituted-1H-tetrazole and tetrahydro-β-carboline, which are present in a variety of bioactive compounds and commercial drugs.

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18

Gu, Hongling, Na Li, Jiangkun Dai, Yaxi Xi, Shijun Wang, and Junru Wang. "Synthesis and In Vitro Antitumor Activity of Novel Bivalent β-Carboline-3-carboxylic Acid Derivatives with DNA as a Potential Target." International Journal of Molecular Sciences 19, no. 10 (October 15, 2018): 3179. http://dx.doi.org/10.3390/ijms19103179.

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A series of novel bivalent β-carboline derivatives were designed and synthesized, and in vitro cytotoxicity, cell apoptosis, and DNA-binding affinity were evaluated. The cytotoxic results demonstrated that most bivalent β-carboline derivatives exhibited stronger cytotoxicity than the corresponding monomer against the five selected tumor cell lines (A549, SGC-7901, Hela, SMMC-7721, and MCF-7), indicating that the dimerization at the C3 position could enhance the antitumor activity of β-carbolines. Among the derivatives tested, 4B, 6i, 4D, and 6u displayed considerable cytotoxicity against A549 cell line. Furthermore, 4B, 6i, 4D, and 6u induced cell apoptosis in a dose-dependent manner, and caused cell cycle arrest at the S and G2/M phases. Moreover, the levels of cytochrome C in mitochondria, and the expressions of bcl-2 protein, decreased after treatment with β-carbolines, which indicated that 6i and 6u could induce mitochondria-mediated apoptosis. In addition, the results of UV-visible spectral, thermal denaturation, and molecular docking studies revealed that 4B, 6i, 4D, and 6u could bind to DNA mainly by intercalation.

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19

Guzmàn, M. C. Carmona, M. Balôn Almeida, J. Hidalgo Toledo, M. A. Munoz Perez, and M. Lopez Poveda. "Sulfonation reactions of (β-carbolines." Canadian Journal of Chemistry 67, no. 4 (April 1, 1989): 720–26. http://dx.doi.org/10.1139/v89-110.

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The homogeneous sulfonations of (β-carboline derivatives norharmane 2, harmane 3, harmine 4, harmol 5, -N,N′-dimethyl-harmane 6, and harmaline 7 have been studied in 80–90% w/w sulfuric acid solutions at 25 °C. Ultraviolet–visible and 13C nuclear magnetic resonance spectra and chemical analysis of the reaction mixtures show that for all the substrates studied only C-6 sulfonated products are obtained. The sulfonation reactions of the benzene unsubstituted substrates 2, 3, and 6 and the partially aromatic substrate 7 proceed by direct electrophilic attack of the H3SO4+ cation on the benzene ring of the (β-carboline skeleton. Sulfonation of 4 and 5 at the lower sulfuric acid concentrations is effected by the H3SO4+ entity. With increasing sulfuric acid concentration there is a gradual changeover of the sulfonating entity from H3SO4+ to H2S2O7. The different mechanisms of sulfonation are discussed. Keywords: β-carbolines, sulfonation, kinetics.

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20

Cigáň, Marek, Peter Danko, Henrich Brath, Matúš Čakurda, Roman Fišera, Jana Donovalová, Juraj Filo, et al. "4-Azafluorenone and α-Carboline Fluorophores with Green and Violet/Blue Emission." Molecules 24, no. 13 (June 27, 2019): 2378. http://dx.doi.org/10.3390/molecules24132378.

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The emission properties of three 4-azafluorenone and five new α-carboline fluorophores in both solution and thin solid films were investigated. Fluorescence of the azafluorenone is clearly enhanced in thin solid films due to the presence of phenyl/biphenyl rotors, and these derivatives can be classified as green Aggregation-Induced Emission luminogens (AIEgens) with a non-emissive heteroaromatic core structure. Compared to azafluorenones, emission of α-carbolines is hypsochromically shifted to the blue region of the electromagnetic spectrum, and most of these derivatives exhibit strong violet-blue fluorescence in both solution and thin solid film layers. Further, the effective mobility and electroluminescence of new α-carbolines were investigated in prepared organic field-effect transistors and organic light-emitting diodes, respectively.

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21

Gonzales, Gustavo F., and Cynthia Gonzales-Castañeda. "The Methyltetrahydro-β-Carbolines in Maca (Lepidium meyenii)." Evidence-Based Complementary and Alternative Medicine 6, no. 3 (2009): 315–16. http://dx.doi.org/10.1093/ecam/nen041.

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Maca, a plant native to the Peruvian highlands, contains (1R,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (MTCA). The family of the tetrahydro-β-carbolines has been associated with both biologically helpful and harmful compounds. We present evidence that MTCA is a natural constituent of Maca, and on consumption no toxicity is found. This suggests that, when consumed as multi-component, MTCA may loose its adversity as drug action.

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22

Sokolova, Nadezhda V., Valentine G. Nenajdenko, Vladimir B. Sokolov, Daria V. Vinogradova, Elena F. Shevtsova, Ludmila G. Dubova, and Sergey O. Bachurin. "Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues." Beilstein Journal of Organic Chemistry 10 (January 15, 2014): 155–62. http://dx.doi.org/10.3762/bjoc.10.13.

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The synthesis of novel peptide conjugates of N-substituted-tetrahydro-γ-carbolines has been performed using the sequence of the Ugi multicomponent reaction and Cu(I)-catalyzed click chemistry. The effect of obtained γ-carboline–peptide conjugates on the rat liver mitochondria was evaluated. It was found that all compounds in the concentration of 30 µM did onot induce depolarization of mitochondria but possessed some inhibitory effect on the mitochondria permeability transition. The original N-substituted-tetrahydro-γ-carbolines containing an terminal alkyne group demonstrated a high prooxidant activity, whereas their conjugates with peptide fragments slightly inhibited both autooxidation and the t-BHP-induced lipid peroxidation.

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23

Prah, Alja, Tanja Gavranić, Andrej Perdih, Marija Sollner Dolenc, and Janez Mavri. "Computational Insights into β-Carboline Inhibition of Monoamine Oxidase A." Molecules 27, no. 19 (October 9, 2022): 6711. http://dx.doi.org/10.3390/molecules27196711.

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Monoamine oxidases (MAOs) are an important group of enzymes involved in the degradation of neurotransmitters and their imbalanced mode of action may lead to the development of various neuropsychiatric or neurodegenerative disorders. In this work, we report the results of an in-depth computational study in which we performed a static and a dynamic analysis of a series of substituted β-carboline natural products, found mainly in roasted coffee and tobacco smoke, that bind to the active site of the MAO-A isoform. By applying molecular docking in conjunction with structure-based pharmacophores and molecular dynamics simulations coupled with dynamic pharmacophores, we extensively investigated the geometric aspects of MAO-A binding. To gain insight into the energetics of binding, we used the linear interaction energy (LIE) method and determined the key anchors that allow productive β-carboline binding to MAO-A. The results presented herein could be applied in the rational structure-based design and optimization of β-carbolines towards preclinical candidates that would target the MAO-A enzyme and would be applicable especially in the treatment of mental disorders such as depression.

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24

S.S, Devi Nidana, Hima C.S, and Shaiju S Dharan. "Characterization, Chemistry, Structural Activity Relationship and Antimicrobial Activities of Tetrahydro-β-carboline." International Journal of Research and Review 9, no. 12 (December 8, 2022): 1–15. http://dx.doi.org/10.52403/ijrr.20221201.

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Tetrahydro-β-carboline, a derivative of β-carboline alkaloid, is found in a variety of plants, animals, insects, mammals, and human tissues and body fluids. It is found abundantly in nature and includes both natural and synthetic forms. Tetrahydro-β-carboline and their derivatives have been proven to exhibit important biological features, which makes it easier to build novel synthetic techniques for the alteration of Tetrahydro-β-carboline core to create high potential medications. Tetrahydro-β-carboline was proven to exhibit various pharmacological activities such as antiviral, antileishmanial, anticancer, antifungal, HDAC inhibitor, antithrombotic, antimalarial, analgesic, and anti-AD inhibitor action. The characterization, chemistry, structure activity relationship, and Antimicrobial activities of tetrahydro-β-carboline derivatives are highlighted in this review along with recent research and developments in these areas. Keywords: Tetrahydro-β-carboline, Tetrahydro-pyrido[3,4-b]-indole, Heterocycle, Alkaloid, Structure, Activity, Derivative, Antimicrobial activity, Occurrence.

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Wang, Zixing, Jun Zhu, Zhiwei Liu, Peng Wu, Hedan Wang, Zhen Zhang, and Bin Wei. "Thermally activated delayed fluorescence of co-deposited copper(i) complexes: cost-effective emitters for highly efficient organic light-emitting diodes." Journal of Materials Chemistry C 5, no. 28 (2017): 6982–88. http://dx.doi.org/10.1039/c7tc01531c.

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TADF copper(i) complexes were made by co-depositing carboline derivatives and copper iodide. δ-Carboline derivative-based OLEDs showed 6 times higher efficiency than α-carboline derivative-based ones.

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Zawirska-Wojtasiak, Renata, Agnieszka Fedoruk-Wyszomirska, Paulina Piechowska, Sylwia Mildner-Szkudlarz, Joanna Bajerska, Elżbieta Wojtowicz, Krzysztof Przygoński, Dorota Gurda, Wiktoria Kubicka, and Eliza Wyszko. "β-Carbolines in Experiments on Laboratory Animals." International Journal of Molecular Sciences 21, no. 15 (July 24, 2020): 5245. http://dx.doi.org/10.3390/ijms21155245.

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Some studies have ascribed a protective effect against neurodegenerative diseases to the β-carbolines harman (H) and norharman (NH), which occur mostly in coffee and coffee substitutes. We determined the concentrations of β-carbolines and undesirable compounds (such as acrylamide) in roasted coffee substitute ingredients and found that chicory coffee was optimal. Two in vivo experiments were conducted with seventeen-month-old male Sprague Dawley rats fed a diet with the addition of pure carboline standards in the first stage, and chicory in the second. We observed an increase in the level of H and NH in blood plasma, as well as higher activity of animals in the battery behavioral test, particularly in the second stage. The results of in vitro studies—particularly the level of the expression in brain tissue of genes associated with aging processes and neurodegenerative diseases—clearly show the benefits of a diet rich in β-carbolines.

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Chang, Wong-Jin, Kaushik Chanda, and Chung-Ming Sun. "Microwave-Assisted Synthesis of Tetracyclic 2,5-Diketopiperazines on a Soluble Polymer Support: A Structural Analogue of Tadalafil." Australian Journal of Chemistry 62, no. 1 (2009): 42. http://dx.doi.org/10.1071/ch08334.

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Structural analogues of tadalafil that contain two diversity points have been synthesized from a soluble polymer support employing a Pictet–Spengler reaction using focussed microwave irradiation. Polymer-bound deprotected tryptophan reacts with various aldehydes to generate the tetrahydro-β-carbolines on the support. Subsequently immobilized tetrahydro-β-carboline underwent a highly efficient intramolecular N-heterocyclization in a traceless fashion from various in-situ generated α-alkyl and heteroalkyl amides in two steps to generate tetracyclic 2,5-diketopiperazines in high purity. All the compounds were isolated as cis and trans isomers with good yields.

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Voznesenskaia, Natalia G., Olga I. Shmatova, and Valentine G. Nenajdenko. "Pictet–Spengler Synthesis of Perfluoroalkylated Tetrahydro-γ-carbolines and Tetrahydropyrrolopyrazines." Synthesis 52, no. 02 (October 28, 2019): 263–72. http://dx.doi.org/10.1055/s-0039-1690729.

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A new method for the synthesis of perfluoroalkylated derivatives of γ-carboline and pyrrolopyrazine was elaborated. Pictet–Spengler reaction of isotryptamine and 2-(pyrrol-1-yl)ethanamine with trifluoromethylated carbonyls and 2-perfluoroalkyl-substituted five-, six-, and seven-membered cyclic imines was studied. It was found that this approach opens efficient access to a family of alkaloid-like compounds bearing a CF3 or C2F5 group in the structure. In the case of the iso-Pictet–Spengler reaction with 2-perfluoroalkyl-substituted cyclic imines, a series of γ-carbolines bearing an aminoalkyl group were prepared.

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Bracher, F., and J. Daab. "β-Carboline Alkaloids, Part 8.1Regioselective Homolytic Acetylation of β-Carbolines." Synthetic Communications 25, no. 10 (May 1995): 1557–62. http://dx.doi.org/10.1080/00397919508011768.

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Chourasiya, Ravindra Kumar, Ram Kishore Agrawal, and Ankur Vaidya. "Promising Anticancer Activity of β-Carboline Derivatives: Design, Synthesis, and Pharmacological Evaluation." Chemistry 4, no. 4 (October 28, 2022): 1395–406. http://dx.doi.org/10.3390/chemistry4040091.

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β-carboline consists of a pyridine ring fused to an indole skeleton; it possesses numerous pharmacological activities, including anticancer. Previously, we reported a satisfactory 2D and 3D QSAR study on β-carboline derivatives. Based on QSAR studies, we designed, synthesized, characterized, and screened fourteen β-carboline derivatives for anticancer activity. Eleven of them demonstrated potent anticancer activity against both liver (HepG2) and adenocarcinoma (A549) cell lines. Compound 1-(N, N-dimethylbenzenamine)-3-(4-(p-tolylmethanimine)-5-thio-1, 2, 4-triazol-3-yl) β-carboline (9) was found to be most potent against both cancer cell lines and equipotent towards standard drug Adriamycin. Compounds 1-(p-tolyl)-3-(4-(p-(iminomethyl)-N, N-dimethylbenzenamine) -5-thio-1, 2, 4-triazol-3-yl) β-carboline (4) and 1-(N, N-dimethylbenzenamine)-3-(4-(m-tolylmethanimine)-5-thio-1, 2, 4-triazol-3-yl) β-carboline (10) were found to be 7 to 10 times less potent as compared to Adriamycin against the HepG2 cell line. Molecular docking was also performed with the Glide docking program to explore the binding mode between the synthesized β-carboline derivatives and the receptor CDK2 [1AQ1] protein.

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Zhang, Jiwen, Longbo Li, Wenjia Dan, Jian Li, Qianliang Zhang, Hongjin Bai, and Junru Wang. "Synthesis and Antimicrobial Activities of 3-Methyl-β-Carboline Derivatives." Natural Product Communications 10, no. 6 (June 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000627.

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The β-carboline alkaloids possess a diverse range of important biochemical effects and pharmacological properties. Sixteen 3-methyl-β-carboline derivatives were synthesized from indole formaldehyde and nitroethane via the Henry reaction, LAH/THF reduction, the Pictet-Spengler reaction and Pd/C/xylene oxidation, including four 1-substituted and twelve 9-substituted 3-methyl- β-carboline derivatives. The structures of all the derivatives were confirmed by 1H NMR, 13C NMR and ESI-MS. Most of these 3-methyl-β-carboline derivatives showed some antibacterial activity.

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Herraiz, Tomás, Hugo Guillén, and Juan Galisteo. "Metabolite Profile Resulting from the Activation/Inactivation of 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine and 2-Methyltetrahydro-β-carboline by Oxidative Enzymes." BioMed Research International 2013 (2013): 1–10. http://dx.doi.org/10.1155/2013/248608.

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Metabolic enzymes are involved in the activation/deactivation of the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyiridine (MPTP) neurotoxin and its naturally occurring analogs 2-methyltetrahydro-β-carbolines. The metabolic profile and biotransformation of these protoxins by three enzymes, monoamine oxidase (MAO), cytochrome P450, and heme peroxidases (myeloperoxidase and lactoperoxidase), were investigated and compared. The metabolite profile differed among the enzymes investigated. MAO and heme peroxidases activated these substances to toxic pyridinium andβ-carbolinium species. MAO catalyzed the oxidation of MPTP to 1-methyl-4-phenyl-2,3-dihydropyridinium cation (MPDP+), whereas heme peroxidases catalyzed the oxidation of MPDP+to 1-methyl-4-phenylpyridinium (MPP+) and of 2-methyltetrahydro-β-carboline to 2-methyl-3,4-dihydro-β-carbolinium cation (2-Me-3,4-DHβC+). These substances were inactivated by cytochrome P450 2D6 throughN-demethylation and aromatic hydroxylation (MPTP) and aromatic hydroxylation (2-methyltetrahydro-β-carboline). In conclusion, the toxicological effects of these protoxins might result from a balance between the rate of their activation to toxic products (i.e.,N-methylpyridinium-MPP+and MPDP+- andN-methyl-β-carbolinium—βC+—) by MAO and heme peroxidases and the rate of inactivation (i.e.,N-demethylation, aromatic hydroxylation) by cytochrome P450 2D6.

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Chen, Hao, Pengchao Gao, Meng Zhang, Wei Liao, and Jianwei Zhang. "Synthesis and biological evaluation of a novel class of β-carboline derivatives." New J. Chem. 38, no. 9 (2014): 4155–66. http://dx.doi.org/10.1039/c4nj00262h.

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Wahyuningsih, Tutik Dwi. "SYNTHESIS OF NOVEL INDOLO[3,2-c]QUINOLINES; ETHYL 3-CHLORO-9,11-DIMETHOXY INDOLO[3,2-c]QUINOLINE-6-CARBOXYLATE." Indonesian Journal of Chemistry 5, no. 3 (June 15, 2010): 189–92. http://dx.doi.org/10.22146/ijc.21786.

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-Carboline and its derivatives are significant due to their pharmacological importance. The synthesis of indolo[3,2-c]quinolines as a benzo analog of -carboline has been carried out via an oxime ether intermediate. Reaction of 2'-glyoxylic ester with hydroxylamine hydrochloride in the presence of sodium acetate afforded the oxime acetate in 82%. It was then treated with natrium and fluoro-2,4-dinitrobenzene in ethanol to give an orange solid of oxime ether acetate which is in subsequent treatment with a base yielded a pale yellow solid of indolo[3,2-c]carboline in 43%. Keywords: -carboline, oxime, indolo[3,2-c]quinoline.

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35

Tsuchiya, Hironori. "Comparative Effects ofα-,β-, andγ-Carbolines on Platelet Aggregation and Lipid Membranes." Journal of Toxicology 2011 (2011): 1–9. http://dx.doi.org/10.1155/2011/151596.

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Cigarette smoking and alcohol consumption possibly affect platelet functions. To verify the hypothesis that someα-,β-, andγ-carboline components in cigarette smoke and alcoholic beverages may change platelet aggregability, their effects on human platelets were determined by aggregometry together with investigating their membrane effects by turbidimetry. Carbolines inhibited platelet aggregation induced by five agents with the potency being 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole > 3-amino-1-methyl-5H-pyrido[4,3-b]indole > 1-methyl-9H-pyrido[3,4-b]indole. The most potent 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole showed 50% aggregation-inhibitory concentrations of 6–172 μM. Bothγ-carbolines interacted with phosphatidylcholine membranes to lower the lipid phase transition temperature with the potency correlating to the antiplatelet activity, suggesting that the interaction with platelet membranes to increase their fluidity underlies antiplatelet effects. Given their possible concentration and accumulation in platelets,γ- andβ-carbolines would provide cigarette smokers and alcohol drinkers with reduced platelet aggregability, and they may be responsible for the occurrence of hemorrhagic diseases associated with heavy smoking and alcoholics.

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36

Kumar, Vipin, Dharmender Singh, Avijit Kumar Paul, Rahul Shrivastava, and Virender Singh. "ZnO-NP assisted synthesis of fluorescent β-carboline C-1 tethered benzimidazole/benzothiazole/benzoxazole derivatives and assessment of their photophysical properties." New Journal of Chemistry 43, no. 46 (2019): 18304–15. http://dx.doi.org/10.1039/c9nj04256c.

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37

Sarragiotto, Maria, George Brand, Carla Gomes, Willian Costa, Mary Foglio, and Ana Ruiz. "Synthesis and Antitumor Activity of Novel 1-Substituted 3-(4,5-Substituted 1,2,4-Triazol-3-yl)-β-carboline Derivatives." Synthesis 51, no. 02 (September 26, 2018): 573–77. http://dx.doi.org/10.1055/s-0037-1610291.

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Schiff bases, 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazoles, and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles carrying the β-carboline nucleus were synthesized from 3-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-β-carbolines. The compounds were evaluated for their in vitro antitumor activity against eight human cancer cell lines. The 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazole derivatives showed a broad spectrum of antitumor activity, with GI50 values lower than 13 μM for all cell lines tested. In general, all tested compounds showed potent activity against the breast (MCF-7) cancer cell line, with GI50 values in the range of 2.07 to 4.58 μM.

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Liu, Wei, Zhaoyu Yang, Lili Shi, and Yun Li. "Bioactive β-Carbolines Harman and Norharman in Sesame Seed Oils in China." Molecules 27, no. 2 (January 9, 2022): 402. http://dx.doi.org/10.3390/molecules27020402.

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The β-carbolines in our diet, mainly including harman and norharman, are a group of biologically active, naturally occurring plant-derived alkaloids. Fragrant sesame seed oil is one of the most popular flavor edible oils in China. Considering that sesame seeds are roasted at 200–240 °C during the processing of flavor sesame seed oils, it is meaningful to investigate the levels of β-carboline compounds in various sesame seed oils. In this work, the levels of β-carbolines (harman and norharman) in different types of sesame seed oils in China (e.g., pressed fragrant sesame oil, ground fragrant sesame oil) have been determined systematically. The results showed that the levels of total β-carbolines in pressed fragrant sesame oils (700.5~2423.2 μg/kg) were higher than that in ground fragrant sesame oils (660.4~1171.7 μg/kg). Roasting sesame seeds at high temperatures (200–240 °C) led to higher levels of β-carbolines (660~2400 μg/kg) in fragrant sesame seed oils. In addition, the loss of tryptophan might be attributed to the formation of β-carbolines in sesame seeds during the roasting process. In general, fragrant sesame seed oils (pressed fragrant sesame oils, ground fragrant sesame oils) contain higher levels of β-carbolines due to the formation of harman and norharman during the roasting sesame seed process.

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39

Zhao, Wen-Yu, Jing-Jie Chen, Chun-Xin Zou, Wei-Yu Zhou, Guo-Dong Yao, Xiao-Bo Wang, Bin Lin, Xiao-Xiao Huang, and Shao-Jiang Song. "Effects of Enantiomerically Pure β-Carboline Alkaloids from Picrasma quassioides on Human Hepatoma Cells." Planta Medica 85, no. 08 (April 11, 2019): 648–56. http://dx.doi.org/10.1055/a-0879-4721.

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AbstractFour pairs of β-carboline enantiomers (1a/1b–4a/4b), 2 β-carboline derivatives (5 – 6) with a single enantiomeric configuration, together with 2 known achiral congeners (7 – 8) were isolated from the stems of Picrasma quassioides. Their structures were elucidated on the basis of extensive spectroscopic analyses and quantum mechanical calculations. Compound 5 possesses a 4,5-seco β-carboline framework and represents the first example of this type of β-carboline alkaloids from nature. A possible biosynthetic pathway is proposed to generate the racemate 4 and the enantiomerically pure compounds 5 and 6. All isolates were screened for their cytotoxicity against hepatocellular carcinoma Hep3B and HepG2 cells, which revealed that enantiomeric compounds 4a and 4b had distinctive effects in HepG2 cells. Further investigation showed that 4b could induce apoptosis in HepG2 cells.

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40

Liu, Haicheng, Feng Han, Huan Li, Jianping Liu, and Qing Xu. "Selective construction of alkaloid scaffolds by alcohol-based direct and mild aerobic oxidative Pictet–Spengler reactions." Organic & Biomolecular Chemistry 18, no. 36 (2020): 7079–85. http://dx.doi.org/10.1039/d0ob01549k.

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Tetrahydro-β-carboline and β-carboline alkaloid scaffolds can be selectively obtained by direct aerobic oxidative Pictet–Spengler reactions of tryptamines with alcohols using TBN/TEMPO as the catalysts and oxygen as the oxidant under mild conditions.

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Thatcher, Robert J., and Richard E. Douthwaite. "β-Carboline (norharman)." Acta Crystallographica Section C Crystal Structure Communications 67, no. 7 (June 23, 2011): o241—o243. http://dx.doi.org/10.1107/s0108270111021706.

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Dardonville, Christophe, Henri Virelizier, Jean Boivin, and Christopher K. Jankowski. "Reactions of carboline." Spectroscopy 13, no. 4 (1997): 257–64. http://dx.doi.org/10.1155/1997/821241.

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The reactions of carboline under various oxidative conditions are reported. The soft aerobic radiolysis, hydroxylation and rearrangement transformations are studied using isotopic labelling and GC–MS techniques.

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43

Castro, José Luis, Daniel Ricci, Carlos Alberto Taira, and Agustín Ramirez. "Central benzodiazepine involvement in clonidine cardiovascular actions." Canadian Journal of Physiology and Pharmacology 77, no. 11 (October 25, 1999): 844–51. http://dx.doi.org/10.1139/y99-086.

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It is well known that the GABAergic and noradrenergic systems play an important role in blood pressure and heart rate regulation. Benzodiazepines and beta-carbolines, respectively, increase or decrease the probability of chloride-channel opening induced by GABA. The aim of this study was to determine, in conscious rats, the interaction existing between the central alpha2-adrenoceptor stimulation induced by clonidine and the facilitation or impairment of benzodiazepine receptor activity through the administration of either diazepam, a benzodiazepine receptor agonist, or methyl 6,7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate (DMCM), an inverse benzodiazepine agonist. Clonidine (5-10 µg, intracerebroventricularly) reduced heart rate and increased mean blood pressure by activation of central alpha2-adrenoceptors. Diazepam (2 mg/kg, intravenously (i.v.)) induced an increase in heart rate, while DMCM (0.3 mg/kg, i.v.) elicited a bradycardic effect. The bradycardic effects induced by both clonidine and DMCM were antagonized by the prior administration of methylatropine (1.5 mg/kg, i.v.). DMCM (0.3 mg/kg, i.v.) prevented the clonidine effects on heart rate and mean blood pressure, while diazepam (2 mg/kg, i.v.) failed to modify these effects. Our results suggest that the bradycardic effects of clonidine are mediated by a vagal stimulation and are related to the activation of a GABAergic pathway.Key words: blood pressure, clonidine, diazepam, methyl 6,7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate (DMCM), heart rate.

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44

Zayed, Rawia, and Michael Wink. "β-Carboline and Quinoline Alkaloids in Root Cultures and Intact Plants of Peganum harmala." Zeitschrift für Naturforschung C 60, no. 5-6 (June 1, 2005): 451–58. http://dx.doi.org/10.1515/znc-2005-5-614.

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Alkaloid profiles of root and shoot cultures, seedlings and mature plants were analysed by capillary GLC and GLC-MS. β-Carboline alkaloids, such as harmine, harmaline dominate in normal and root cultures transformed by Agrobacterium rhizogenes, as well as in roots and fruits of the plant. In shoots, flowers and shoot cultures quinoline alkaloids such as peganine, deoxypeganine, vasicinone and deoxyvasicinone widely replace the β-carboline alkaloids. In root cultures, the formation of β-carboline alkaloids can be induced by methyljasmonate and several other elicitors indicating that these alkaloids are part of the reactive chemical defence system of Peganum harmala.

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45

Kuzovkina, I. N., A. Gohar, and I. E. Alterman. "Production of β-Carboline Alkaloids in Transformed Root Cultures of Peganum harmala L." Zeitschrift für Naturforschung C 45, no. 6 (June 1, 1990): 727–28. http://dx.doi.org/10.1515/znc-1990-0626.

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Abstract Peganum harmala, Hairy Root Cultures, β-Carboline Alkaloids Hairy root cultures of Peganum harmala were established by genetic transformation with Agrobacterium rhizogenes strain A4. In contrast to suspension cultures the root cultures contained high levels of β-carboline alka loids (1 -1.5% of dry mass).

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46

El-Shazly, Assem, and Michael Wink. "Tetrahydroisoquinoline and β-Carboline Alkaloids from Haloxylon articulatum (Cav.) Bunge (Chenopodiaceae)." Zeitschrift für Naturforschung C 58, no. 7-8 (August 1, 2003): 477–80. http://dx.doi.org/10.1515/znc-2003-7-805.

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Abstract Salsolidine and 2-methyl,1,2,3,4-tetrahydro-β-carboline were isolated from Haloxylon articulatum (growing in Egypt) besides the known carnegine and N-methylisosalsoline. 2- methyl,1,2,3,4-tetrahydro-β-carboline was recorded for the first time in the genus Haloxylon. The alkaloids were identified by spectroscopic methods (MS, 1D and 2D NMR).

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47

Layne, Tanya H., Joy S. Roach, and Winston F. Tinto. "Review of β-carboline Alkaloids from the Genus Aspidosperma." Natural Product Communications 10, no. 1 (January 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000139.

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Plants belonging to the genus Aspidosperma, a member of the family Apocynaceae, provide a rich source of β-carboline alkaloids, which makes them potentially poisonous. However, some of these alkaloids possess antitumor and antimicrobial activity. The present review is a survey of the β-carboline alkaloids and shows that they comprise of a diverse array of structural modifications.

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48

Xia, Cheng-Cai, Ya-Fei Ji, Xiao-Pan Fu, Lu Chen, Gao-Rong Wu, and Hong-Wei Liu. "Cascade Access to Carboline Carboxylates from Indolyl Ketoximes and Acrylates via Palladium-Catalyzed C–H Bond Alkenylation/Annulation." Synlett 32, no. 01 (July 15, 2020): 69–74. http://dx.doi.org/10.1055/s-0040-1707192.

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An efficient palladium-catalyzed C–H bond alkenylation/annulation strategy to access carboline carboxylates from indolyl ketoximes and acrylates through C–C/C–N bond formation is reported. Indolyl ketoximes not only direct ortho-olefination with acrylates, but also undergo an intramolecular N–O bond cleavage/traceless annulation to construct carboline carboxylates straightforwardly in this concise method.

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BRACHER, F., and J. DAAB. "ChemInform Abstract: β-Carboline Alkaloids. Part 8. Regioselective Homolytic Acetylation of β-Carbolines." ChemInform 26, no. 36 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199536182.

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50

Venault, Patrice, and Georges Chapouthier. "From the Behavioral Pharmacology of Beta-Carbolines to Seizures, Anxiety, and Memory." Scientific World JOURNAL 7 (2007): 204–23. http://dx.doi.org/10.1100/tsw.2007.48.

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A number of beta-carbolines are inverse agonists of the GABA-A receptor complex, acting on the benzodiazepine site. They show convulsive properties when administered at high doses, anxiogenic properties at moderate doses, and learning-enhancing effects at low doses. These data suggest a possible physiological relationship, through the GABA-A receptor channel, between memory processes, anxiety, and ultimately, in pathological states, epileptic seizures. This relationship seems to be confirmed partially by experiments on mouse strains selected for their resistance (BR) and sensitivity (BS) to a single convulsive dose of a beta-carboline. These two strains also show differences in anxiety and learning abilities. However, some opposite results found while observing the behavior of the two strains suggest that in addition to pharmacologically induced anxiety, there is spontaneous anxiety, no doubt involving other brain mechanisms.

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