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Journal articles on the topic 'Indole compound'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

CHAUBAN, Vishal, Sbivkanya FULORIA, Neeraj K. FULORIA, Syed R. HASHIM, and Sokindra KUMAR. "SYNTHESIS, CHARACTERIZATION AND COMPARATIVE SCREENING OF SOME NEWER 2-PHENYL INDOLE AND 5-CHLORO-2-PHENYL INDOLE DERIVATIVES." SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 20, no. 20 (2012): 69–76. http://dx.doi.org/10.48141/sbjchem.v20.n20.2012.71_revista_2012a.pdf.

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Biologically active phenyl indole and chloro phenyl indole derivatives were efficiently synthesized. The reaction of 2-phenyl-1H-indole A and 5-chloro-2-phenyl-1H-indole B, with chloroacetylchloride yielded 2-chloro-1-(2-phenyl-1H-indol-1-yl)ethanone 1 and 2-chloro-1-(5-chloro-2-phenyl-1H-indol-1-yl)ethanone 4 respectively. Compound 1 and 4 on Friedal Crafts cyclization in presence of aluminium chloride and nitrobenzene yielded indolo[2,1 -alfa]isoquinolin-6(5H)-one 2 and 10-chloroindolo [2,1-alfa]isoquinolin-6(5H)-one 5 respectively, which upon hydrolysis afforded 2-(2-(1H-indol-2-yl)phenyl)a

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2

Boraei, Ahmed T. A., Ahmed A. M. Sarhan, Sammer Yousuf, and Assem Barakat. "Synthesis of a New Series of Nitrogen/Sulfur Heterocycles by Linking Four Rings: Indole; 1,2,4-Triazole; Pyridazine; and Quinoxaline." Molecules 25, no. 3 (2020): 450. http://dx.doi.org/10.3390/molecules25030450.

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A new series of nitrogen and sulfur heterocyclic systems were efficiently synthesized by linking the following four rings: indole; 1,2,4-triazole; pyridazine; and quinoxaline hybrids. The strength of the acid that catalyzes the condensation of 4-amino-5-(1H-indol-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 1 with aromatic aldehydes controlled the final product. Reflux in glacial acetic acid yielded Schiff bases 2–6, whereas concentrated HCl in ethanol resulted in a cyclization product at C-3 of the indole ring to create indolo-triazolo-pyridazinethiones 7–16. This fascinating cyclization appr

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3

Zendah, Imene, Khaled A. Shaaban, Elisabeth Helmke, Armin Maier, Heinz H. Fiebig, and Hartmut Laatsch. "Barakacin: A Thiazolyl-indole Alkaloid Isolated from a Ruminal Pseudomonas sp." Zeitschrift für Naturforschung B 67, no. 5 (2012): 417–20. http://dx.doi.org/10.5560/znb.2011-0277.

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A new thiazolyl-indole alkaloid, barakacin (1), has been isolated from the ruminal bacterium Pseudomonas aeruginosa strain ZIO. On the basis of detailed spectroscopic analyses and comparison with the data of related compounds, its structure has been determined as 2-{4-[bis-(1H-indol-3- yl)-methyl]-thiazol-2-yl}-phenol. In addition, the known compounds phenazine-1-carboxylic acid, 3-(hydroxyacetyl)-indole, indole-3-carbaldehyde, and glycolipid A were isolated. The discovery of compounds with a new skeleton emphasizes the importance for exploring new ecological niches like the rumen of bovines f

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4

Verma, Vaijinath A., Anand R. Saundane, and Rajkumar S. Meti. "Synthesis of Schiff Base Indolyl-1,3,4-Oxadiazole, Thiazolidinone and Azetidinone as Efficient Antimicrobial, Antioxidant, Antituberculosis and Anticancer Agents." Asian Journal of Organic & Medicinal Chemistry 4, no. 2 (2019): 77–88. http://dx.doi.org/10.14233/ajomc.2019.ajomc-p175.

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The present investigation was under-taken to synthesize the Schiff base indole derivatives bearing of 1,3,4-oxadiazole thiazolidinone and azetidinone moieties. New series of 5-(5-substituted-3-phenyl-1H-indol-2-yl)-N-[(5-substituted-2-phenyl-1H-indol-3-yl)methylene]-1,3,4-oxadiazol-2-amines and screened their biological activities. Compound 4a showed excellent antibacterial and radical scavenging activities. Compound 5a revealed efficient to antifungal activity. In addition, compound 4a was found to be most active against H37Rv strain Mycobacterium tuberculosis. In case of anticancer activity

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5

Ramkissoon, Antonio, Mohindra Seepersaud, Anderson Maxwell, Jayaraj Jayaraman, and Adesh Ramsubhag. "Isolation and Antibacterial Activity of Indole Alkaloids from Pseudomonas aeruginosa UWI-1." Molecules 25, no. 16 (2020): 3744. http://dx.doi.org/10.3390/molecules25163744.

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In this study, we report the first isolation of three antibiotic indole alkaloid compounds from a Pseudomonad bacterium, Pseudomonas aeruginosa UWI-1. The bacterium was batch fermented in a modified Luria Broth medium and compounds were solvent extracted and isolated by bioassay-guided fractionation. The three compounds were identified as (1) tris(1H-indol-3-yl) methylium, (2) bis(indol-3-yl) phenylmethane, and (3) indolo (2, 1b) quinazoline-6, 12 dione. A combination of 1D and 2D NMR, high-resolution mass spectrometry data and comparison from related data from the literature was used to deter

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6

Mandadi, Manoj Kumar, Ramana Reddy Bobbala, Balakrishna Kolli, and Rambabu Gundla. "Synthesis and Anticancer Activity of Novel Amide Tagged Trifluoromethyl Indole and Pyrimido Indole Derivatives." Asian Journal of Chemistry 33, no. 10 (2021): 2327–32. http://dx.doi.org/10.14233/ajchem.2021.23313.

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A series of novel amide tagged trifluoromethyl indole and pyrimido indole derivatives 4a-e & 5a-e and 6a-d & 7a-d were synthesized from 4-methyl-2-(methylamino)-6-(trifluoromethyl)isophthalonitrile (1) on reaction with bromoethyl acetate to obtain 2a and 2b isomers. Compound 2a treated with hydrazine hydrate followed by Schiff base reaction to get compounds 4a-e. In another way, compound 2a on reaction with aliphatic primary amine to get compounds 6a-d. For cyclization, compounds 4a-e & 6a-d treated with trifluoroacetic acid to obtain compounds 5a-e and 7a-d, respectively. All the

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7

Sweidan, Kamal, Dima A. Sabbah, Sanaa Bardaweel, et al. "Facile synthesis, characterization, and cytotoxicity study of new 3-(indol-2-yl)bicyclotetrazatridecahexaens." Canadian Journal of Chemistry 95, no. 8 (2017): 858–62. http://dx.doi.org/10.1139/cjc-2017-0120.

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A new series of thiosemicarbazone-based indole derivatives 12–15 has been prepared by condensation reaction of indole-2-carboxamide derivatives 8–11 with thiosemicarbazide. The former compounds underwent intracyclization in the presence of chloroacetic acid and sodium acetate to afford a set of new 3-(indol-2-yl)bicyclotetrazatridecahexaens 16–19. These newly synthesized compounds have been characterized by means of FTIR, 1H NMR, 13C NMR, and HRMS and by elemental analyses. Cytotoxic activities of the prepared compounds along with LY294002 were evaluated in vitro against normal human skin fibr

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8

Golubeva, I. S., N. P. Yavorskaya, L. V. Ektova, et al. "ANTITUMOR ACTIVITY OF SOME DERIVATIVES OF INDOLO[2,3-A]CARBAZOLES N-GLYCOSIDES WITH XYLOSE CARBOHYDRATE RESIDUE." Russian Journal of Biotherapy 19, no. 4 (2020): 86–93. http://dx.doi.org/10.17650/1726-9784-2020-19-4-86-93.

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Introduction. The search for new antineoplastic agents in a series of indolo[2,3-a]-carbazole derivatives is an urgent and promising direction, since compounds with antitumor activity have been found in this class. In the chemical fusion laboratory, N.N. Blokhin National Medical Research Center оf the Ministry of Health of Russia has developed an original and effective method for the synthesis of glycosides of indolo[2,3-a]-pyrrolo[3,4-c]carbazoles, which makes it possible to synthesize derivatives of N-glycosides of indolo[2,3-a]carbazoles with different substituents in the heterocyclic parts

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9

MahamadAlli Shaikh, Tanveer, and Habtamu Debebe. "Synthesis and Evaluation of Antimicrobial Activities of Novel N-Substituted Indole Derivatives." Journal of Chemistry 2020 (April 14, 2020): 1–9. http://dx.doi.org/10.1155/2020/4358453.

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Indole motifs are one of the most significant scaffolds in the discovery of new drugs. We have described a synthesis of new N-substituted indole derivatives (1-3), and their in vitro antimicrobial activities were investigated. The synthesis of titled compounds has been demonstrated by utilizing commercially available starting materials. The antibacterial and antifungal activities were performed using new strains of bacteria Staphylococcus aureus, Escherichia coli, and Candida albicans using the disc diffusion method. Notably, the compound 4-(1-(2-(1H-indol-1-yl) ethoxy) pentyl)-N,N-dimethyl an

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10

Almutairi, Maha S., Adnan A. Kadi, Reem I. Al-Wabli, Mohamed W. Attwa, and Mohamed I. Attia. "Fragmentation pattern of certain isatin–indole antiproliferative conjugates with application to identify their in vitro metabolic profiles in rat liver microsomes by liquid chromatography tandem mass spectrometry." Open Chemistry 18, no. 1 (2020): 503–15. http://dx.doi.org/10.1515/chem-2020-0095.

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AbstractThe fragmentation pattern of certain isatin-based compounds was carried out using collision-induced dissociation inside the triple quadrupole mass analyzer. These data were used as a clue for the identification of metabolites of the recently reported isatin-based antiproliferative agent, namely, N′-[5-bromo-1-methyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-5-methoxy-1H-indole-2-carbohydrazide (1) in rat liver microsomes (RLMs) using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Prediction of the vulnerable sites for metabolic pathways in compound 1 was performed by WhichP450

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11

Carvalho, Paulo, Edward B. Furr III, and Christopher McCurdy. "(E)-Methyl 2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyacrylate ethanol solvate." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (2009): o1441—o1442. http://dx.doi.org/10.1107/s1600536809017309.

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In the title compound, C23H30N2O4·C2H6O, the indole derivative has four fused rings, forming an indolo[2-3a]quinolizine system, in which one six-membered ring is directly connected to the indole unit and has a distorted chair conformation. The fourth ring is also a six-membered ring, depicting a regular chair conformation. In the crystal, the molecules are linked by N—H...O and O—H...N interactions, forming aC(7) chain.

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12

Panwar, Hemant, Shishupal Singh, and Nidhi Chaudhary. "SYDNONE DERIVATIVES A SYNTHONS FOR NOVEL MESOIONIC COMPOUNDS. SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL EVALUATION OF SOME 2-(4`-SUBSTITUTED ANILINOSYNDON-3`-YL)-1, 3, 4-THIADIAZINO (6, 5-B) INDOLES." Indonesian Journal of Chemistry 11, no. 3 (2011): 201–6. http://dx.doi.org/10.22146/ijc.21380.

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In the present study, a series of 2-(4´-Substitutedanilinosydnon-3´-yl)-1, 3, 4-thiadiazino (6, 5-b) indoles 7a-j have been synthesized. All the synthesized compounds have been characterized by elemental and spectral (I R, 1H- NMR and Mass) spectrometric analysis. Furthermore, above mentioned compounds were evaluated for their antibacterial and antifungal activities against selected panel of pathogenic strains. Ampicillin trihydrate, ofloxacin and fluconazole, griseofulvin were used as standard drugs for antibacterial and anifungal activity respectively. Compound 7j was found the most potent o

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13

Ramadan, El, Hanaa Rasheed, and Ashry El. "Synthesis and antimicrobial screening of novel 1,3-dioxolanes linked to N-5 of 5H-[1,2,4]triazino[5,6-b]indole-3-thiol." Journal of the Serbian Chemical Society 84, no. 1 (2019): 1–10. http://dx.doi.org/10.2298/jsc171127067r.

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Synthesis of 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1H-indole- -2,3-dione (10) was achieved by coupling 1H-indole-2,3-dione (16) with (R)- -(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (15) in the presence of sodium hydride in dry N,N-dimethylformamide at room temperature in a closed Erlenmeyer flask. Condensation of 10 with hydrazinecarbothioamide in water afforded the thiosemicarbazone derivative 17; its subsequent cyclization with potassium carbonate in water gave the corresponding thione 18 in good yield. The 3-allylthio and 3-benzylthio derivatives 20 and 21 were al

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14

Gumus, Ilkay, Ummuhan Solmaz, Serpil Gonca, and Hakan Arslan. "Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity." European Journal of Chemistry 8, no. 4 (2017): 349–57. http://dx.doi.org/10.5155/eurjchem.8.4.349-357.1637.

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Two new compounds, 1H-indole-7-amine (1) and N-(1H-indol-7-yl)-2-methylbenzamide (2) were synthesized and structurally characterized by NMR and FT-IR spectroscopic techniques. The molecular structure of compound 2 was further elucidated by single-crystal X-ray diffraction technique. Moreover, the crystal packing of compound 2 is analyzed in terms of non-covalent N-H···O, C-H···π, and parallel displaced π···π interactions. Hirshfeld surface analysis and decomposed fingerprint plots of the compound 2 were performed to visualize the presence of strong hydrogen bond N-H···O and C-H···π stacking in

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15

Seethaler, Marius, Tobias Hertlein, Björn Wecklein, et al. "Novel Small-molecule Antibacterials against Gram-positive Pathogens of Staphylococcus and Enterococcus Species." Antibiotics 8, no. 4 (2019): 210. http://dx.doi.org/10.3390/antibiotics8040210.

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Defeat of the antibiotic resistance of pathogenic bacteria is one great challenge today and for the future. In the last century many classes of effective antibacterials have been developed, so that upcoming resistances could be met with novel drugs of various compound classes. Meanwhile, there is a certain lack of research of the pharmaceutical companies, and thus there are missing developments of novel antibiotics. Gram-positive bacteria are the most important cause of clinical infections. The number of novel antibacterials in clinical trials is strongly restricted. There is an urgent need to

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16

Zhao, Yun-Hui, Zhihua Zhou, Yong-Cheng Ma, et al. "Synthesis of Potential Anticancer 1-(1H-Indol-3-yl)isoquinolines by Silver Nitrate Mediated Tandem Reactions of 2-Alkynylbenzaldehyde Azines and Indoles." Synlett 29, no. 06 (2018): 773–78. http://dx.doi.org/10.1055/s-0036-1591743.

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Novel antitumor compounds featuring isoquinoline and indole moieties were synthesized by a silver nitrate promoted domino reaction involving intramolecular cyclization, nucleophilic addition of indole, and subsequent N–N bond cleavage. The transformation from readily available starting materials into an interesting class of indole-substituted isoquinolines was completed under mild conditions and by simple operations in moderate to good yields. The antitumor activity of these compounds in vitro was significantly greater than that of a reference compound, 5-fluorouracil. The products might serve

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17

Lynch, Daniel E., Graham Smith, Karl A. Byriel, and Colin H. L. Kennard. "Designing Linear Hydrogen-Bonded Arrays by Using Substituted Charge-Transfer Complexes. The Crystal Structure of the 1 : 1 Adduct of Indole-2-carboxylic Acid with 3,5-Dinitrobenzoic Acid." Australian Journal of Chemistry 51, no. 11 (1998): 1019. http://dx.doi.org/10.1071/c98119.

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Five adducts consisting of carboxylic acid-substituted indoles with nitro-substituted benzoic acids have been synthesized and tested for second-order non-linear optical properties. These were indole-2-carboxylic acid with 2,4-dinitrobenzoic acid (1), 3,5-dinitrobenzoic acid (2), and 2,4,6-trinitrobenzoic acid (3), and indole-3-acetic acid with 3,5-dinitrobenzoic acid (4), and 2,4,6-trinitrobenzoic acid (5). Compound (2) produced clear, yellow crystals (space group P -1 with a 6·8400(7), b 15·150(2), c 16·097(2) Å, α 84·911(9), β 87·088(10), γ 77·865(9)°, Z 4) which allowed the structure to be

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18

Thilagam, C. Rama, S. Vijaya Sri, Waheeta Hopper, V. Mani Vannan, and P. r. Uma Rani. "SYNTHESIS, CRYSTAL STUDIES AND PHARMACOLOGICAL ROLE PREDICTION OF 3-IODO-2- METHYL-1 PHENYL SULFONYL-1H INDOLE." Asian Journal of Pharmaceutical and Clinical Research 10, no. 3 (2017): 341. http://dx.doi.org/10.22159/ajpcr.2017.v10i3.16231.

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ABSTRACTObjective: Indole-based compounds have established many pharmacological applications. Indole acts as a starting compound for various medicinalpreparations. Our objective is to determine the possible pharmacological roles of our crystallized indole-based ligand using computational approach.The activities studied are antibacterial, antitubercular, and antimelanoma.Methods: The structure of the indole compound, CR2 was studied using single crystal X-ray diffraction technique. To predict the pharmacologicalactivities, the structure-based docking method was followed. The protein targets wer

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19

Guan, Zong, Jan C. Namyslo, Martin H. H. Drafz, Martin Nieger, and Andreas Schmidt. "Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles." Beilstein Journal of Organic Chemistry 10 (April 10, 2014): 832–40. http://dx.doi.org/10.3762/bjoc.10.79.

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Deprotonation of indazolium salts at low temperatures gives N-heterocyclic carbenes of indazoles (indazol-3-ylidenes) which can be trapped as rhodium complexes (X-ray analysis). In the absence of Rh, the indazol-3-ylidenes spontaneously dimerize under ring cleavage of one of the N,N-bonds and ring closure to an indazole–indole spiro compound which possesses an exocyclic imine group. The E/Z isomers of the imines can be separated by column chromatography when methanol is used as eluent. We present results of a single crystal X-ray analysis of one of the E-isomers, which equilibrate in solution

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20

Shaikh, Iqbal N., Abdul Rahim, Shaikh Faazil, Syed Farooq Adil, Mohamed E. Assal, and Mohammad Rafe Hatshan. "BF3-OEt2 Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies." Molecules 26, no. 8 (2021): 2202. http://dx.doi.org/10.3390/molecules26082202.

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A simple and efficient BF3-OEt2 promoted C3-alkylation of indole has been developed to obtain3-indolylsuccinimidesfrom commercially available indoles and maleimides, with excellent yields under mild reaction conditions. Furthermore, anti-proliferative activity of these conjugates was evaluated against HT-29 (Colorectal), Hepg2 (Liver) and A549 (Lung) human cancer cell lines. One of the compounds, 3w, having N,N-Dimethylatedindolylsuccinimide is a potent congener amongst the series with IC50 value 0.02 µM and 0.8 µM against HT-29 and Hepg2 cell lines, respectively, and compound 3i was most acti

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Mphahlele, Malose, Mmakwena Mmonwa, Abimbola Aro, Lyndy McGaw, and Yee Choong. "Synthesis, Biological Evaluation and Molecular Docking of Novel Indole-Aminoquinazoline Hybrids for Anticancer Properties." International Journal of Molecular Sciences 19, no. 8 (2018): 2232. http://dx.doi.org/10.3390/ijms19082232.

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A series of indole-aminoquinazolines was prepared via amination of the 2-aryl-4-chloroquinazolines with the 7-amino-2-aryl-5-bromoindoles. It was then evaluated for cytotoxicity in vitro against human lung cancer (A549), epithelial colorectal adenocarcinoma (Caco-2), hepatocellular carcinoma (C3A), breast adenocarcinoma (MCF-7), and cervical cancer (HeLa) cells. A combination on the quinazoline and indole moieties of a 2-phenyl and 2-(4-fluorophenyl) rings in compound 4b; 2-(4-fluorophenyl) and 3-chlorophenyl rings in compound 4f; or the two 2-(4-fluorophenyl) rings in compound 4g, resulted in

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22

Gim, Hyo, Yong-Sung Choi, Hua Li, Yoon-Jung Kim, Jae-Ha Ryu та Raok Jeon. "Identification of a Novel PPAR-γ Agonist through a Scaffold Tuning Approach". International Journal of Molecular Sciences 19, № 10 (2018): 3032. http://dx.doi.org/10.3390/ijms19103032.

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Peroxisome proliferator-activated receptors (PPARs) are important targets in metabolic diseases including obesity, metabolic syndrome, diabetes, and non-alcoholic fatty liver disease. Recently, they have been highlighted as attractive targets for the treatment of cardiovascular diseases and chronic myeloid leukemia. The PPAR agonist structure is consists of a polar head, a hydrophobic tail, and a linker. Each part interacts with PPARs through hydrogen bonds or hydrophobic interactions to stabilize target protein conformation, thus increasing its activity. Acidic head is essential for PPAR agon

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23

Hamulakova, Slavka, Zuzana Kudlickova, Ladislav Janovec, et al. "Design and synthesis of novel tacrine–indole hybrids as potential multitarget-directed ligands for the treatment of Alzheimer's disease." Future Medicinal Chemistry 13, no. 9 (2021): 785–804. http://dx.doi.org/10.4155/fmc-2020-0184.

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The authors report on the synthesis and biological evaluation of new compounds whose structure combines tacrine and indole moieties. Tacrine–indole heterodimers were designed to inhibit cholinesterases and β-amyloid formation, and to cross the blood–brain barrier. The most potent new acetylcholinesterase inhibitors were compounds 3c and 4d (IC50 = 25 and 39 nM, respectively). Compound 3c displayed considerably higher selectivity for acetylcholinesterase relative to human plasma butyrylcholinesterase in comparison to compound 4d (selectivity index: IC50 [butyrylcholinesterase]/IC50 [acetylcholi

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Zhang, Dongdong, Yanhong Shi, Jingyi Li, et al. "Alkaloids with Nitric Oxide Inhibitory Activities from the Roots of Isatis tinctoria." Molecules 24, no. 22 (2019): 4033. http://dx.doi.org/10.3390/molecules24224033.

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As our ongoing research project on Ban Lan Gen (Isatis tinctoria roots), a total of 23 alkaloids were obtained. Compounds 1 and 2 contain an unusual C–C bond between the 2(1H)-quinolinone moiety and the phenol moiety and between the 2(1H)-quinolinone moiety and the 1H-indole moiety, respectively. Compound 3 possesses an unusual carbon skeleton and its putative biosynthetic pathway was discussed, and Compound 23 was deduced as a new indole alkaloid glycoside. Compounds 4–7 were identified as four new natural products by extensive spectroscopic experiments. Additionally, the anti-inflammatory ac

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Elkamhawy, Ahmed, Usama M. Ammar, Sora Paik, et al. "Scaffold Repurposing of In-House Small Molecule Candidates Leads to Discovery of First-in-Class CDK-1/HER-2 Dual Inhibitors: In Vitro and In Silico Screening." Molecules 26, no. 17 (2021): 5324. http://dx.doi.org/10.3390/molecules26175324.

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Recently, multitargeted drugs are considered a potential approach in treating cancer. In this study, twelve in-house indole-based derivatives were preliminary evaluated for their inhibitory activities over VEGFR-2, CDK-1/cyclin B and HER-2. Compound 15l showed the most inhibitory activities among the tested derivatives over CDK-1/cyclin B and HER-2. Compound 15l was tested for its selectivity in a small kinase panel. It showed dual selectivity for CDK-1/cyclin B and HER-2. Moreover, in vitro cytotoxicity assay was assessed for the selected series against nine NCI cell lines. Compound 15l showe

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Syahri, Jufrizal, Nurul Hidayah, Rahmiwati Hilma, Beta Achromi Nurohmah, and Emmy Yuanita. "Design of New 2,4-Substituted Furo [3,2-B] Indole Derivatives as Anticancer Compounds Using Quantitative Structure-Activity Relationship (QSAR) and Molecular Docking." Molekul 15, no. 1 (2020): 9. http://dx.doi.org/10.20884/1.jm.2020.15.1.582.

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This study aimed to propose new indole derivatives as anticancer through Quantitative Structure-Activity Relationship (QSAR) and molecular docking method. The best predicted anticancer activity of indole derivatives was recommended based on the QSAR equation. A data set consist of 18 indole derivatives from literature with anticancer activity against the A498 cell line was used to generate a QSAR model equation. The data set was divided randomly into training (14) and test (4) set compounds. The structure of indole compound was optimized first using AM1 semi-empirical methods, and the descript

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Suchentrunk, Christof, and Nikolaus Korber. "Reduktion von Isochinolin und Indol mit Cäsium in flüssigem Ammoniak / Reduction of Isoquinoline and Indole with Cesium in Liquid Ammonia." Zeitschrift für Naturforschung B 58, no. 10 (2003): 990–96. http://dx.doi.org/10.1515/znb-2003-1009.

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Isoquinoline and indole were reduced with solutions of cesium in liquid ammonia and the resulting crystalline compounds isolated as ammonia-rich solvate crystals. The reduction of isoquinoline yields the anion bisisoquinoline-2,2’-diide in the compound Cs2C18H14N2 · (7/2) NH3 as the result of a coupling reaction. Indole is reduced to the 5,8-dihydroindolide anion in the ammoniate CsC8H8N · 3NH3. Both anions display interactions between their aromatic π-systems and the cesium cations.

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28

Attia, Mohamed I., Nasser R. El-Brollosy, Hazem A. Ghabbour, Suhana Arshad, and Hoong-Kun Fun. "5-Methoxy-1-[(5-methoxy-1H-indol-2-yl)methyl]-1H-indole." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (2012): o971. http://dx.doi.org/10.1107/s1600536812009257.

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In the title compound, C19H18N2O2, the two indole ring systems are essentially planar [maximum deviation = 0.015 (2) Å in both indole ring systems] and make a dihedral angle of 72.17 (7)° with each other. In the crystal, the molecules are linked into a zigzag chain along theaaxisviaN—H...O hydrogen bonds.

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Trang, Do Thi, Bui Huu Tai, Dan Thuy Hang, et al. "Chemical Constituents of the Marine Sponge Aaptos aaptos (Schmidt, 1864) and Their Cytotoxic Activity." Natural Product Communications 16, no. 2 (2021): 1934578X2199334. http://dx.doi.org/10.1177/1934578x21993345.

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Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configur

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Black, DS, N. Chaichit, BM Gatehouse, and GI Moss. "Unusual Formation of New Indole-Containing Heterocyclic Ring Systems." Australian Journal of Chemistry 40, no. 12 (1987): 1965. http://dx.doi.org/10.1071/ch9871965.

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The oxazinoindoletrione (3) underwent reaction with aqueous ammonia in methanol or ethanol to yield the polycyclic methyl or ethyl esters (4) and (5) respectively. Reaction of trione (3) with gaseous ammonia in dry ethanol gave the aminobenzodiazepinone (7). This compound lost ammonia on heating in toluene to give compound (11) and in the presence of methanol or ethanol gave the methyl or ethyl esters (9) and (10) respectively. The structures of compounds (4), (7) and (10) were all established by X-ray crystallography.

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Ölgen, Süreyya, Nurten Altanlar, Ersin Karataylı, and Mithat Bozdayı. "Antimicrobial and Antiviral Screening of Novel Indole Carboxamide and Propanamide Derivatives." Zeitschrift für Naturforschung C 63, no. 3-4 (2008): 189–95. http://dx.doi.org/10.1515/znc-2008-3-405.

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A few series of indole derivatives were screened for antimicrobial, antifungal and anti- HBV activities. The compounds were tested for their in vitro antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and for their antifungal activity against Candida albicans using a disc diffusion method, which measures the diameter of the inhibition zone around a paper disc soaked in a solution of the test compounds. The antimicrobial activity results showed that all compounds are as a active as the standard compound ampicillin against Staphylococcus aureus. It was also

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Liu, Chengwei, Atsushi Minami, Motoyoshi Noike, Hiroaki Toshima, Hideaki Oikawa, and Tohru Dairi. "Regiospecificities and Prenylation Mode Specificities of the Fungal Indole Diterpene Prenyltransferases AtmD and PaxD." Applied and Environmental Microbiology 79, no. 23 (2013): 7298–304. http://dx.doi.org/10.1128/aem.02496-13.

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ABSTRACTWe recently reported the function ofpaxD, which is involved in the paxilline (compound 1) biosynthetic gene cluster inPenicillium paxilli. Recombinant PaxD catalyzed a stepwise regular-type diprenylation at the 21 and 22 positions of compound 1 with dimethylallyl diphosphate (DMAPP) as the prenyl donor. In this study,atmD, which is located in the aflatrem (compound 2) biosynthetic gene cluster inAspergillus flavusand encodes an enzyme with 32% amino acid identity to PaxD, was characterized using recombinant enzyme. When compound 1 and DMAPP were used as substrates, two major products a

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dela Peña, Ike, and Jae Hoon Cheong. "On Benzofuroindole Analogues as Smooth Muscle Relaxants." Journal of Biomedicine and Biotechnology 2011 (2011): 1–7. http://dx.doi.org/10.1155/2011/389056.

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At least two laboratories have independently reported the synthesis of benzofuroindole compounds having potential therapeutic implications in many disease states including those that involve smooth muscle hyperactivity. Through a series ofin vitroscreenings, they demonstrated the efficacy (and selectivity) of these compounds to potentiate large conductance calcium- (Ca2+-) activated K+(BKCa) channels, by far, the most characterized of all Ca2+-dependent K+channels. Interestingly, promising benzofuroindole derivatives such as compound 7 (10H-benzo[4,5]furo[3,2-b]indole) and compound 22 (4-chlor

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Forberg, Kallmeier, and Kempe. "Iridium Catalyzed Synthesis of Tetrahydro-1H-Indoles by Dehydrogenative Condensation." Inorganics 7, no. 8 (2019): 97. http://dx.doi.org/10.3390/inorganics7080097.

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Novel synthetic routes to the commonly encountered indole motif are highly sought after. Tetrahydro-1H-indoles were synthesized for the first time from secondary alcohols and 2aminocyclohexanol in the presence of a well-established iridium catalyst using a modified synthetic procedure recently developed for the synthesis of hydrocarbazoles. The catalyst is stabilized by an inexpensive and easy-to-synthesize triazine based PN5P pincer ligand. The reaction proceeds through acceptorless dehydrogenative condensation (ADC) and yields the title compound, dihydrogen, and water and can thus be classif

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Gopinath, S., K. Sethusankar, Bose Muthu Ramalingam, and Arasambattu K. Mohanakrishnan. "Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate." Acta Crystallographica Section E Crystallographic Communications 71, no. 9 (2015): 1036–41. http://dx.doi.org/10.1107/s2056989015014917.

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The title compounds, C17H13NO2S, (I), C17H13NO3S, (II), and C24H17ClN2O5S·CHCl3, (III), are indole derivatives. Compounds (I) and (II) crystalize with two independent molecules in the asymmetric unit. The indole ring systems in all three structures deviate only slightly from planarity, with dihedral angles between the planes of the pyrrole and benzene rings spanning the tight range 0.20 (9)–1.65 (9)°. These indole ring systems, in turn, are almost orthogonal to the phenylsulfonyl rings [range of dihedral angles between mean planes = 77.21 (8)–89.26 (8)°]. In the three compounds, the molecular

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Shehzad, Muhammad Tariq, Ajmal Khan, Sobia Ahsan Halim, et al. "Synthesis of indole-substituted thiosemicarbazones as an aldose reductase inhibitor: an in vitro, selectivity and in silico study." Future Medicinal Chemistry 13, no. 14 (2021): 1185–201. http://dx.doi.org/10.4155/fmc-2020-0060.

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Aim: Indole is an important component of many drug molecules, and its conjugation with thiosemicarbazone moiety would be advantageous in finding lead compounds for the development of diabetic complications. Methodology: We have designed, synthesized and evaluated a series of 17 indole-thiosemicarbazones (3a–q) as aldose reductase (ALR2) and aldehyde reductase (ALR1) inhibitors. Results: After in vitro evaluation, all indole-thiosemicarbazones showed significant inhibition against both enzyme ALR1 and ALR2 with IC50 in range of 0.42–20.7 and 1.02–19.1 μM, respectively. The docking study was als

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Bettanin, Luana, Filipe Penteado, Luiz H. Dapper, and Eder J. Lenardão. "Selenocyanation of Indoles Promoted by Visible Light." Chemistry Proceedings 2, no. 1 (2020): 29. http://dx.doi.org/10.3390/eccs2020-07562.

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We developed a promising synthetic methodology for the regioselective photocatalyzed 3-selenocyanation of indoles, employing potassium selenocyanate (KSeCN) and a blue LED light. The 3-selanylindoles have been emerging as a potentially bioactive class of compounds and already have demonstrated anti-inflammatory, antinociceptive and anticancer properties. There are in the literature several methodologies for their preparation; for example, applying intermolecular cyclization with Se-based electrophilic species. Therefore, it is of interest to seek innovative and effective methodologies to selec

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Abo-Salem, Heba M., Hayam A. Abd El Salam, Anhar M. Abdel-Aziem, Mohamed S. Abdel-Aziz, and Eslam Reda El-Sawy. "Synthesis, Molecular Docking, and Biofilm Formation Inhibitory Activity of Bis(Indolyl)Pyridines Analogues of the Marine Alkaloid Nortopsentin." Molecules 26, no. 14 (2021): 4112. http://dx.doi.org/10.3390/molecules26144112.

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An efficient and simple protocol for the synthesis of a new class of diverse bis(indolyl)pyridines analogues of the marine alkaloid nortopsentin has been reported. A one-pot four-component condensation of 3-cyanocarbomethylindole, various aldehyde, 3-acetylindole, and ammonium acetate in glacial acetic acid led to the formation of 2,6-bis(1H-indol-3-yl)-4-(substituted-phenyl)pyridine-5-carbonitriles. Additionally, 2,6-bis(1H-indol-3-yl)-4-(benzofuran) pyridine-5-carbonitriles were prepared via a one-pot four-component condensation of 3-cyanocarbomethylindole, various N-substituted-indole-3-ald

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Chelamalla, Radhika, and Ajitha Makula. "Design and Synthesis of Indole Pyrimidine Scaffolds as Potential KSP Inhibitors and Anticancer Agents." Current Enzyme Inhibition 15, no. 1 (2019): 28–35. http://dx.doi.org/10.2174/1573408014666181105144847.

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Background: Several biological activities like anticancer, anti-inflammatory, analgesic, antitubercular activities are reported for pyrimidine scaffolds. Extensive work on pyrimidine indole scaffolds is required for antimitotic activity. Objective: To synthesize a novel Indole Pyrimidine scaffold via an efficient synthetic method and to evaluate cytotoxic activity using various human cancer cell lines. Methods: 4,4-(3-substituted phenyl)-6-methyl-N-[(Z)-(5-methyl-2-oxo-indolin-3-ylidene)amino]-2- oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide derivatives were designed, synthesized and evaluated f

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Kimyashov, Aleksandr A., and Aleksandr V. Syromolotov. "SYNTHESIS OF DIBENZO[cd, g]INDOLE." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 64, no. 1 (2020): 22–26. http://dx.doi.org/10.6060/ivkkt.20216401.6291.

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In this paper, a synthesis method is proposed and discussed for a compound not previously described – dibenzo [cd, g] indole. For the successful synthesis of the target compound we used the classical method based on well-known procedure of indoles obtaining according to Fisher method with some changes. Commercially available derivatives of anthracene were used as the starting compound since they already contain a ready-made system of three condensed aromatic rings and they reaction activity is rather high. The corresponding diazonium salt was obtained from 9-amino anthracene by reaction with e

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Kimyashov, Aleksandr A., and Aleksandr V. Syromolotov. "SYNTHESIS OF DIBENZO[cd, g]INDOLE." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 64, no. 1 (2020): 22–26. http://dx.doi.org/10.6060/ivkkt.20216401.6291.

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In this paper, a synthesis method is proposed and discussed for a compound not previously described – dibenzo [cd, g] indole. For the successful synthesis of the target compound we used the classical method based on well-known procedure of indoles obtaining according to Fisher method with some changes. Commercially available derivatives of anthracene were used as the starting compound since they already contain a ready-made system of three condensed aromatic rings and they reaction activity is rather high. The corresponding diazonium salt was obtained from 9-amino anthracene by reaction with e

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Zefirov, N. A., E. A. Lavrushkina, S. A. Kuznetsov, and O. N. Zefirova. "Podophyllotoxin analogue with bicyclo[3.2.1]octane moiety annelated with indole: synthesis, molecular modeling, and biological testing." Biomeditsinskaya Khimiya 65, no. 2 (2019): 86–90. http://dx.doi.org/10.18097/pbmc20196502086.

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C4-Ester derivatives of the anticancer agent podophyllotoxin with bridged moieties can either inhibit polymerization of alpha,beta-tubulin with the formation of microtubules (analogously to the parent molecule) or cause an unusual effect of “curling and shortening” of the microtubules (MT). In order to predict the effect of bridged podophyllotoxin derivatives on the MT network using computer molecular modeling it is desirable to enhance the structural diversity of their bridged substituents. In the present work we synthesized novel podophyllotoxin ester with bicyclo[3.2.1]octane moiety annelat

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Kutschy, Peter, Marian Sabol, Renata Marušková та ін. "A Linear Synthesis of 1-(β-D-Glucopyranosyl)brassinin, -brassenin A, -brassenin B and 9-(β-D-Glucopyranosyl)cyclobrassinin". Collection of Czechoslovak Chemical Communications 69, № 4 (2004): 850–66. http://dx.doi.org/10.1135/cccc20040850.

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The first synthesis of 1-(β-D-glucopyranosyl)brassinin, 1-(β-D-glucopyranosyl)brassenin A, 1-(β-D-glucopyranosyl)brassenin B and 9-(β-D-glucopyranosyl)cyclobrassinin, nucleoside analogs derived from indole phytoalexins, was achieved by linear approach, using the 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carbaldehyde as a starting compound. Antiproliferative and antimicrobial activity of synthesized compounds against murine leukaemia tumor cell line L1210 and selected bacteria and fungi was examined and compared with the corresponding phytoalexin aglycons.

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Anand Raghunath, Saundane, and Kirankumar Nandibeoor Mathada. "Synthesis and Biological Evaluation of Aminonaphthols Incorporated Indole Derivatives." International Journal of Medicinal Chemistry 2014 (September 10, 2014): 1–12. http://dx.doi.org/10.1155/2014/673206.

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An efficient one pot condensation of naphthols (1), 2,5-disubstituted indole-3-carboxaldehydes (2), and secondary amines (3) has been achieved using dichloromethane as a solvent, stirring at room temperature. Some of the new [(disubstituted amino)(5-substituted 2-phenyl-1H-indol-3-yl)methyl]naphthalene-ols (4) derivatives were prepared in good yields. The significant features of this method are simple work-up procedure, inexpensive nontoxic solvent, shorter reaction times, and excellent product yields. The structures of newly synthesized compounds (4a–r) are confirmed by their elemental analys

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Jayasekera, Maithri M. K., Keysha Onheiber, John Keith, et al. "Identification of Novel Inhibitors of Bacterial Translation Elongation Factors." Antimicrobial Agents and Chemotherapy 49, no. 1 (2005): 131–36. http://dx.doi.org/10.1128/aac.49.1.131-136.2005.

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ABSTRACT Bacterial elongation factor Tu (EF-Tu) and EF-Ts are interacting proteins involved in polypeptide chain elongation in protein biosynthesis. A novel scintillation proximity assay for the detection of inhibitors of EF-Tu and EF-Ts, as well as the interaction between them, was developed and used in a high-throughput screen of a chemical library. Several compounds from a variety of chemical series with inhibitory properties were identified, including certain indole dipeptides, benzimidazole amidines, 2-arylbenzimidazoles, N-substituted imidazoles, and N-substituted guanidines. The in vitr

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Dhanalakshmi, G., Velu Saravanan, Arasambattu K. Mohanakrishnan, and S. Aravindhan. "Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole." Acta Crystallographica Section E Crystallographic Communications 73, no. 10 (2017): 1555–59. http://dx.doi.org/10.1107/s2056989017012804.

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In the title indole derivatives, C22H16N2O5S, (I) and C20H15NO3S2, (II), the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring system, subtending dihedral angles of 88.33 (10) and 87.58 (16)°, respectively. In both compounds, the sulfonyl S atom has a distorted tetrahedral geometry [O—S—O = 119.98 (9) and N—S—C = 104.01 (8)° for compound (I) and O—S—O = 120.08 (18) and N—S—C = 104.91 (14)° for compound (II)] and the sum of the bond angles at N indicatessp2hybridization. The molecules of both (I) and (II) feature intramolecular C—H...O hydrogen bonds that generateS(6) ring mo

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Hulinská, Hana, Petr Taufmann, Hana Frycová, and Miroslav Protiva. "1-Methyl-, 1-phenyl-, and 1-(2-(2-dimethylaminoethoxy)-phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and their 2-substituted derivatives: Synthesis and pharmacological screening." Collection of Czechoslovak Chemical Communications 53, no. 2 (1988): 373–80. http://dx.doi.org/10.1135/cccc19880373.

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1-Methyl- and 1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (I and IV) were transformed via the chloroacetyl derivatives II and V to the 4-methylpiperazinoacetyl compounds III and VI; compound VI inhibits effectively the formation of the indomethacin-induced gastric ulcers in rats but is devoid of anticholinergic activity and does not inhibit the gastric secretion in rats. Reaction of tryptamine with 2-(2-dimethylaminoethoxy)benzaldehyde afforded compound IX which proved inactive in tests for antidepressant activity. Compounds IV and IX were treated with ethyl chloroformate and gave carba

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Hasaninejad, Alireza, Abdolkarim Zare, Hashem Sharghi, et al. "A solvent-free protocol for facile condensation of indoles with carbonyl compounds using silica chloride as a new, highly efficient, and mild catalyst." Canadian Journal of Chemistry 85, no. 6 (2007): 416–20. http://dx.doi.org/10.1139/v07-051.

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A simple and efficient solvent-free procedure for the preparation of bis(indolyl)methanes via electrophilic substitution reactions of indoles with aldehydes and ketones is described. The reactions took place in the presence of a catalytic amount of silica chloride at room temperature. The advantages of this method are high yields, short reaction times, low cost, and compliance with green-chemistry protocols.Key words: silica chloride, indole, carbonyl compound, solvent-free, bis(indolyl)methane.

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Shephard, Logan E., and Nicholas B. Kingsley. "Synthesis, characterization and crystal structure of a 2-(diethylaminomethyl)indole ligated dimethylaluminium complex." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (2015): 1222–25. http://dx.doi.org/10.1107/s2056989015017053.

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The title compound, [Al(CH3)2(C13H17N2)] (systematic name; {2-[(diethylamino)methyl]indol-1-yl-κ2N,N′}dimethylaluminium), was prepared by methane elimination from the reaction of 2-(diethylaminomethyl)indole and trimethylaluminium. The complex crystallizes readily from a concentrated toluene solution in high yield. The asymmetric unit contains two crystallographically independent molecules. Each molecule has a four-coordinate aluminium atom that has pseudo-tetrahedral geometry. C—H...π interactions link the independent molecules into chains extending along theb-axis direction.

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Bingül, Murat. "Synthesis and characterisation of novel 4,6-dimethoxyindole-7- and -2-thiosemicarbazone derivatives: Biological evaluation as antioxidant and anticholinesterase candidates." Journal of Chemical Research 43, no. 9-10 (2019): 399–406. http://dx.doi.org/10.1177/1747519819868386.

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Two sets of novel indole-based thiosemicarbazone systems 8a–d and 9a–d are prepared by the Schiff base condensation reaction of indole carbaldehydes 4 and 6 with a range of thiosemicarbazides 7a–d in high yields and purity. The antioxidant properties of the synthesised compounds 8a–d and 9a–d are determined by employing three different assays, namely 2,2-diphenyl-1-picrylhydrazyl hydrate–free radical scavenging, ABTS [2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)] cationic radical decolarization and cupric ion reducing antioxidant capacity. The anticholinesterase properties of the pro

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