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Journal articles on the topic 'Pyrrole derive'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

Cordero, Franca, Bhushan Khairnar, Anna Ranzenigo, and Alberto Brandi. "Cycloaddition of Benzyne with Alkoxy-Substituted Pyrroline-N-oxides: Unexpected Rearrangement to an N-Phenylpyrrole." SynOpen 02, no. 01 (January 2018): 0025–29. http://dx.doi.org/10.1055/s-0037-1609082.

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Reaction of enantiopure 3,4-dialkoxy-pyrroline N-oxides with benzyne affords the expected tetrahydrobenzo[d]pyrrolo[1,2-b]isoxazoles along with an unexpected 2,3-disubstitued-N-phenyl-pyrrole derived from an unprecedented rearrangement of the adduct of nitrone with two molecules of benzyne. A mechanism for the unusual rearrangement is proposed. The benzo[d]isoxazolidine derivatives are conveniently converted into 2-(2-hydroxyphenyl)-3,4-dialkoxypyrrolidines by reductive opening of the N–O bond.

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2

Hu, Nan, Li Jun He, and Li Hui Wang. "Study on Surface Chemical Composition and Structure of PVP/Al Composite Powder Using XPS Analysis." Advanced Materials Research 476-478 (February 2012): 1101–4. http://dx.doi.org/10.4028/www.scientific.net/amr.476-478.1101.

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XPS analysis is used in studying surface chemical composition and structure of ultrafine raw Al powder and PVP/Al composite powder, respectively. It shows that: in PVP/Al composite powder’s surface, comparing with raw Al powder, relative content of Al decrease and relative contents of C and N increase. New chemical bonds are formed in PVP/Al composite powder’s surface, and it is certain that, these new chemical bonds derive from N atom and O atom of PVP’s pyrrole with Al atom in Al powder surface.

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3

Bi, Wenzhao, Geeng-Fu Jang, Lei Zhang, John W. Crabb, James Laird, Mikhail Linetsky, and Robert G. Salomon. "The Adductomics of Isolevuglandins: Oxidation of IsoLG Pyrrole Intermediates Generates Pyrrole–Pyrrole Crosslinks and Lactams." High-Throughput 8, no. 2 (May 10, 2019): 12. http://dx.doi.org/10.3390/ht8020012.

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Isoprostane endoperoxides generated by free radical-induced oxidation of arachidonates, and prostaglandin endoperoxides generated through enzymatic cyclooxygenation of arachidonate, rearrange nonenzymatically to isoprostanes and a family of stereo and structurally isomeric γ-ketoaldehyde seco-isoprostanes, collectively known as isolevuglandins (isoLGs). IsoLGs are stealthy toxins, and free isoLGs are not detected in vivo. Rather, covalent adducts are found to incorporate lysyl ε-amino residues of proteins or ethanolamino residues of phospholipids. In vitro studies have revealed that adduction occurs within seconds and is uniquely prone to cause protein–protein crosslinks. IsoLGs accelerate the formation of the type of amyloid beta oligomers that have been associated with neurotoxicity. Under air, isoLG-derived pyrroles generated initially are readily oxidized to lactams and undergo rapid oxidative coupling to pyrrole–pyrrole crosslinked dimers, and to more highly oxygenated derivatives of those dimers. We have now found that pure isoLG-derived pyrroles, which can be generated under anoxic conditions, do not readily undergo oxidative coupling. Rather, dimer formation only occurs after an induction period by an autocatalytic oxidative coupling. The stable free-radical TEMPO abolishes the induction period, catalyzing rapid oxidative coupling. The amine N-oxide TMAO is similarly effective in catalyzing the oxidative coupling of isoLG pyrroles. N-acetylcysteine abolishes the generation of pyrrole–pyrrole crosslinks. Instead pyrrole-cysteine adducts are produced. Two unified single-electron transfer mechanisms are proposed for crosslink and pyrrole-cysteine adduct formation from isoLG-pyrroles, as well as for their oxidation to lactams and hydroxylactams.

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4

Pravardhan Reddy, E., A. Sumankumar, B. Sridhar, Y. Hemasri, Y. Jayaprakash Rao, and B. V. Subba Reddy. "1,5-Electrocyclization of conjugated azomethine ylides derived from 3-formyl chromene and N-alkyl amino acids/esters." Organic & Biomolecular Chemistry 15, no. 36 (2017): 7580–83. http://dx.doi.org/10.1039/c7ob00705a.

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A novel strategy has been developed for the synthesis of chromeno[3,4-b]pyrrol-4(3H)-one and substituted pyrrole derivatives. This is the first example of the preparation of highly substituted pyrrole derivatives from chromene-3-carboxaldehydes.

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5

Allen, Annette D., Jean-Marc Kwong-Chip, Wing Cheung Lin, Paul Nguyen, and Thomas T. Tidwell. "Formation and reactivity of 1-pyrrolyl-2,2,2-trifluoroethyl cations." Canadian Journal of Chemistry 68, no. 10 (October 1, 1990): 1709–13. http://dx.doi.org/10.1139/v90-265.

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1-(1-Methyl-2-pyrrolyl)-2,2,2-trifluoroethyl p-nitrobenzoate (3) reacts by carbocation formation with an m value for the dependence of rate on the solvent polarity parameter YOTs of 0.56, and a rate 41 times slower than (1-methyl-2-pyrrolyl)methyl p-nitrobenzoate. The products from 3 include significant amounts of material derived from solvent attack at the 5-position of the pyrrole ring. The results indicate a high degree of charge delocalization by the strongly donating pyrrolyl group, resulting in a low k(H)/k(CF3) rate ratio and nucleophilic attack on the ring. 1,1, l-Trifluoro-2-(1-methyl-2-pyrrolyl)propan-2-ol (10) reacted with CF3CO2H via a tertiary carbocation, which led to dimeric products resulting from electrophilic substitution on the pyrrole ring. Keywords: pyrrole, trifluoromethyl substituents, carbocations.

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6

Bagherzadeh, Mojtaba, Mohammad Adineh Jonaghani, Mojtaba Amini, and Anahita Mortazavi-Manesh. "Synthesis of dipyroromethanes in water and investigation of electronic and steric effects in efficiency of olefin epoxidation by sodium periodate catalyzed by manganese tetraaryl andtransdisubstituted porphyrin complexes." Journal of Porphyrins and Phthalocyanines 23, no. 06 (May 28, 2019): 671–78. http://dx.doi.org/10.1142/s108842461950038x.

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Condensation of pyrrole with various aldehydes in the presence of BF3•etherate as an acid catalyst in water provides good yield of some dipyrromethanes. Prolongation of the reaction time with aldehydes substituted by electron-donating (mesityl) or electron-withdrawing (2,6-dichlorophenyl) groups on the ortho positions of the phenyl did not lead to decomposition or scrambling. Manganese trans disubstituted porphyrin complexes which derive from various dipyrromethanes and manganese tetraaryl porphyrin complexes including various substituents with different steric and electronic properties show good catalytic activity in epoxidation of alkenes by NaIO4in the presence of imidazole (ImH). The study of steric and electronic effects of the catalysts on the epoxidation of olefins shows that Mn-porphyrin complexes with more bulky and electron-releasing groups on meso phenyls could increase the epoxidation yield of most alkenes.

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7

Huang, Wenbo, Kaimei Wang, Ping Liu, Minghao Li, Shaoyong Ke, and Yanlong Gu. "Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access N-(hetero)aryl-4,5-unsubstituted pyrroles." Beilstein Journal of Organic Chemistry 16 (November 30, 2020): 2920–28. http://dx.doi.org/10.3762/bjoc.16.241.

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N-(Hetero)aryl-4,5-unsubstituted pyrroles were synthesized from (hetero)arylamines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal by using aluminum(III) chloride as a Lewis acid catalyst through [1 + 2 + 2] annulation. This new versatile methodology provides a wide scope for the synthesis of different functional N-(hetero)aryl-4,5-unsubstituted pyrrole scaffolds, which can be further derived to access multisubstituted pyrrole-3-carboxamides. In the presence of 1.2 equiv of KI, a polysubstituted pyrazolo[3,4-b]pyridine derivative was also successfully synthesized.

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8

Cozzi, Pier Giorgio, Sandro Gambarotta, Magda Monari, and Luca Zoli. "Convenient Preparation of Chiral Dipyrrolylmethanes Containing a Chiral Moiety." Collection of Czechoslovak Chemical Communications 72, no. 8 (2007): 1046–56. http://dx.doi.org/10.1135/cccc20071046.

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A variety of chiral bis-pyrroles have been made readily accessible via acid-catalyzed condensation of chiral ketones with pyrrole. Three representative chiral ketones 2-4 taken from the chiral pool were transformed into the corresponding bis-pyrrole derivatives in a straightforward acid-catalyzed condensation. Chiral β-hydroxy ketone derivatives, prepared through proline-catalyzed aldol condensation of acetone and an aldehyde, are readily transformed into the corresponding dipyrrolylmethane by the acid-catalyzed condensation carried out in the same conditions. The crystal structure of the chiral dipyrrolylmethane 2 derived from the (-)-menthone was determined.

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9

El Gamal, Abrahim, Vinayak Agarwal, Stefan Diethelm, Imran Rahman, Michelle A. Schorn, Jennifer M. Sneed, Gordon V. Louie, et al. "Biosynthesis of coral settlement cue tetrabromopyrrole in marine bacteria by a uniquely adapted brominase–thioesterase enzyme pair." Proceedings of the National Academy of Sciences 113, no. 14 (March 21, 2016): 3797–802. http://dx.doi.org/10.1073/pnas.1519695113.

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Halogenated pyrroles (halopyrroles) are common chemical moieties found in bioactive bacterial natural products. The halopyrrole moieties of mono- and dihalopyrrole-containing compounds arise from a conserved mechanism in which a proline-derived pyrrolyl group bound to a carrier protein is first halogenated and then elaborated by peptidic or polyketide extensions. This paradigm is broken during the marine pseudoalteromonad bacterial biosynthesis of the coral larval settlement cue tetrabromopyrrole (1), which arises from the substitution of the proline-derived carboxylate by a bromine atom. To understand the molecular basis for decarboxylative bromination in the biosynthesis of 1, we sequenced two Pseudoalteromonas genomes and identified a conserved four-gene locus encoding the enzymes involved in its complete biosynthesis. Through total in vitro reconstitution of the biosynthesis of 1 using purified enzymes and biochemical interrogation of individual biochemical steps, we show that all four bromine atoms in 1 are installed by the action of a single flavin-dependent halogenase: Bmp2. Tetrabromination of the pyrrole induces a thioesterase-mediated offloading reaction from the carrier protein and activates the biosynthetic intermediate for decarboxylation. Insights into the tetrabrominating activity of Bmp2 were obtained from the high-resolution crystal structure of the halogenase contrasted against structurally homologous halogenase Mpy16 that forms only a dihalogenated pyrrole in marinopyrrole biosynthesis. Structure-guided mutagenesis of the proposed substrate-binding pocket of Bmp2 led to a reduction in the degree of halogenation catalyzed. Our study provides a biogenetic basis for the biosynthesis of 1 and sets a firm foundation for querying the biosynthetic potential for the production of 1 in marine (meta)genomes.

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10

Ning, Jia, Ivonne M. C. M. Rietjens, and Marije Strikwold. "Integrating physiologically based kinetic (PBK) and Monte Carlo modelling to predict inter-individual and inter-ethnic variation in bioactivation and liver toxicity of lasiocarpine." Archives of Toxicology 93, no. 10 (September 11, 2019): 2943–60. http://dx.doi.org/10.1007/s00204-019-02563-x.

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Abstract The aim of the present study was to predict the effect of inter-individual and inter-ethnic human kinetic variation on the sensitivity towards acute liver toxicity of lasiocarpine in the Chinese and the Caucasian population, and to derive chemical specific adjustment factors (CSAFs) by integrating variation in the in vitro kinetic constants Vmax and Km, physiologically based kinetic (PBK) modelling and Monte Carlo simulation. CSAFs were derived covering the 90th and 99th percentile of the population distribution of pyrrole glutathione adduct (7-GS-DHP) formation, reflecting bioactivation. The results revealed that in the Chinese population, as compared to the Caucasian population, the predicted 7-GS-DHP formation at the geometric mean, the 90th and the 99th percentile were 2.1-, 3.3- and 4.3-fold lower respectively. The CSAFs obtained using the 99th percentile values were 8.3, 17.0 and 19.5 in the Chinese, the Caucasian population and the two populations combined, respectively, while the CSAFs were generally 3.0-fold lower at the 90th percentile. These results indicate that when considering the formation of 7-GS-DHP the Caucasian population may be more sensitive towards acute liver toxicity of lasiocarpine, and further point out that the default safety factor of 3.16 for inter-individual human kinetic differences may not be sufficiently protective. Altogether, the results obtained demonstrate that integrating PBK modelling with Monte Carlo simulations using human in vitro data is a powerful strategy to quantify inter-individual variations in kinetics, and can be used to refine the human risk assessment of pyrrolizidine alkaloids.

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11

Bubnov, Yu N., N. Yu Kuznetsov, M. E. Gurskii, A. L. Semenova, G. D. Kolomnikova, and T. V. Potapova. "Construction of nitrogen bicyclic and cage compounds with the use of allylic organoboranes." Pure and Applied Chemistry 78, no. 7 (January 1, 2006): 1357–68. http://dx.doi.org/10.1351/pac200678071357.

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It is shown that reactions of triallylborane with pyrrole, pyridines, isoquinolines, lactams, 1-pyrroline, and acetylenes offer versatile methodology for the construction of various bicyclic and polycyclic nitrogen compounds, some of which are skeletally related to important classes of alkaloids. Optically active 3-borabicyclo[3.3.1]non-6-enes are useful precursors for synthesis of chiral 3-aza- and 3-thiabicyclo[3.3.1]non-6-enes, as well as derived chiral cyclohexenoid systems. The convenient methodology for the transformation of 1-boraadamantanes into 1-azaadamantanes is also discussed.

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12

Lodowska, Jolanta, Daniel Wolny, Sławomir Kurkiewicz, and Ludmiła Węglarz. "The Pyrolytic Profile of Lyophilized and Deep-Frozen Compact Part of the Human Bone." Scientific World Journal 2012 (2012): 1–7. http://dx.doi.org/10.1100/2012/162406.

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Background. Bone grafts are used in the treatment of nonunion of fractures, bone tumors and in arthroplasty. Tissues preserved by lyophilization or deep freezing are used as implants nowadays. Lyophilized grafts are utilized in the therapy of birth defects and bone benign tumors, while deep-frozen ones are applied in orthopedics. The aim of the study was to compare the pyrolytic pattern, as an indirect means of the analysis of organic composition of deep-frozen and lyophilized compact part of the human bone.Methods. Samples of preserved bone tissue were subjected to thermolysis and tetrahydroammonium-hydroxide- (TMAH-) associated thermochemolysis coupled with gas chromatography and mass spectrometry (Py-GC/MS).Results. Derivatives of benzene, pyridine, pyrrole, phenol, sulfur compounds, nitriles, saturated and unsaturated aliphatic hydrocarbons, and fatty acids (C12–C20) were identified in the pyrolytic pattern. The pyrolyzates were the most abundant in derivatives of pyrrole and nitriles originated from proteins. The predominant product in pyrolytic pattern of the investigated bone was pyrrolo[1,2-α]piperazine-3,6-dione derived from collagen. The content of this compound significantly differentiated the lyophilized graft from the deep-frozen one. Oleic and palmitic acid were predominant among fatty acids of the investigated samples. The deep-frozen implants were characterized by higher percentage of long-chain fatty acids than lyophilized grafts.

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13

Choi, Se-Hwa, Ga-Hye Kil, Na-Rim Kim, Chun Yoon, Jae-Pil Kim, and Jae-Hong Choi. "Preparation of Thermally Stable Red Dyes Derived from Diketo-Pyrrolo-Pyrrole Pigment for LCD Color Filter." Molecular Crystals and Liquid Crystals 550, no. 1 (October 18, 2011): 76–82. http://dx.doi.org/10.1080/15421406.2011.600222.

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14

Banfield, JE, GD Fallon, and BM Gatehouse. "Heterocyclic-Derivatives of Guanidine. VI. Formation and X-Ray Structure Determination of 2-Dimethylamino-7,8-diphenyl-4,6-dihydropyrrolo[1,2-a]pyrimidine-4,6-dione." Australian Journal of Chemistry 40, no. 5 (1987): 1003. http://dx.doi.org/10.1071/ch9871003.

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The structure N-(2-dimethylamino-4-oxo-7,8-diphenyl-4,6-dihydropyrrolo [l,2-a]pyrimidi n-6-yl-idene)acetamide (3) is proposed for a compound derived from the action of ketene on 2-(2-imino- 3,4-diphenyl-2H-pyrrol-5-yl)-1,1,3-trimethylguanidine (1; R1 = R2 = R3 = Me) on the basis of the crystal structure of its hydrolysis product, the oxo-compound 2-dimethylamino-7,8-diphenyl-4,6-dihydropyrrolo[l,2-a]pyrimidine-4,6-dione (4), the structure of which was determined by X-ray analysis. A lower homologue of (3), N-(2-methylamino-4-oxo-7,8-diphenyl-4,6-dihydro- pyrrolo[l,2-a]pyrimidin-6-ylidene)acetamide (2), and some related compounds are described.

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15

Choi, Se-Hwa, Oh-Tak Kwon, Na-Rim Kim, Chun Yoon, Jae-Pil Kim, and Jae-Hong Choi. "Preparation of Solvent Soluble Dyes Derived from Diketo-pyrrolo-pyrrole Pigment by Introducing an N-Alkyl group." Bulletin of the Korean Chemical Society 31, no. 4 (April 20, 2010): 1073–76. http://dx.doi.org/10.5012/bkcs.2010.31.04.1073.

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16

Barker, David, Stephanie Lee, Kyriakos G. Varnava, Kevin Sparrow, Michelle van Rensburg, Rebecca C. Deed, Melissa M. Cadelis, et al. "Synthesis and Antibacterial Analysis of Analogues of the Marine Alkaloid Pseudoceratidine." Molecules 25, no. 11 (June 11, 2020): 2713. http://dx.doi.org/10.3390/molecules25112713.

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In an effort to gain more understanding on the structure activity relationship of pseudoceratidine 1, a di-bromo pyrrole spermidine alkaloid derived from the marine sponge Pseudoceratina purpurea that has been shown to exhibit potent biofouling, anti-fungal, antibacterial, and anti-malarial activities, a large series of 65 compounds that incorporated several aspects of structural variation has been synthesised through an efficient, divergent method that allowed for a number of analogues to be generated from common precursors. Subsequently, all analogues were assessed for their antibacterial activity against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Overall, several compounds exhibited comparable or better activity than that of pseudoceratidine 1, and it was found that this class of compounds is generally more effective against Gram-positive than Gram-negative bacteria. Furthermore, altering several structural features allowed for the establishment of a comprehensive structure activity relationship (SAR), where it was concluded that several structural features are critical for potent anti-bacterial activity, including di-halogenation (preferable bromine, but chlorine is also effective) on the pyrrole ring, two pyrrolic units in the structure and with one or more secondary amines in the chain adjoining these units, with longer chains giving rise to better activities.

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17

Choi, Se-Hwa, Ga-Hye Kil, Na-Rim Kim, Chun Yoon, Jae-Pil Kim, and Jae-Hong Choi. "Preparation of Red Dyes Derived from Diketo-pyrrolo-pyrrole Based Pigment and Their Properties for LCD Color Filters." Bulletin of the Korean Chemical Society 31, no. 11 (November 20, 2010): 3427–30. http://dx.doi.org/10.5012/bkcs.2010.31.11.3427.

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18

Hung, Chen-Hsiung, Chia-Chi Liaw, Wei-Ming Chin, Gao-Fong Chang, and Chuan-Hung Chuang. "Nitric acid promoted formation of an N-confused porphyrin-derived porphodimethene and a violinoid." Journal of Porphyrins and Phthalocyanines 10, no. 07 (July 2006): 953–61. http://dx.doi.org/10.1142/s1088424606000284.

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The nitration of free-base N -confused porphyrin led to a novel 5,10-meso-dihydroxy- N -confused porphodimethene and an open-ring N -confused violinoid. The results support nitration occurring first, followed by nucleophilic addition of a hydroxyl group and a parallel reaction of oxygenolysis to cause the ring-opening. The nitro group substituted at the inner carbon of the inverted pyrrole ring is located on both the porphodimethene and violinoid. In the case of the porphodimethene, two dihydroxyl groups with υ( OH ) at 3404 cm−1 are arranged in a syn conformation at the same side with the nitro group. The violinoid exhibits υ( C = O ) at 1659 cm−1. NMR and structure determination suggest that oxygenolysis occurs selectively at the C=C bond between the α-pyrrole and meso carbon closest to the amino NH of the inverted pyrrole ring. The single crystal structure of porphodimethene gave a 50% disorder between the peripheral nitrogen and carbon atom on the inverted pyrrole ring, while a dimeric structure assembled through hydrogen bonding interactions was observed in the crystal lattice of the violinoid.

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19

Pinho e Melo, Teresa M. V. D., Maria I. L. Soares, António M. d'A Rocha Gonsalves, and Hamish McNab. "Reactivity of azafulvenium methides derived from pyrrolo[1,2-c]thiazole-2,2-dioxides: synthesis of functionalised pyrroles." Tetrahedron Letters 45, no. 20 (May 2004): 3889–93. http://dx.doi.org/10.1016/j.tetlet.2004.03.111.

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20

Cox, Matthew, Michael Dixon, Troy Lister, and Rolf H. Prager. "Intramolecular Interactions in Carbenes Derived During the Pyrolysis of N-Alkenylisoxazolones." Australian Journal of Chemistry 57, no. 5 (2004): 455. http://dx.doi.org/10.1071/ch03154.

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Flash vacuum pyrolysis of ethyl 3-(3-methyl-5-oxo-2,5-dihydroisoxazole-2-yl)-3-phenylpropenoate yields 4-ethoxy-3-hydroxy-2-methyl-5-phenylpyridine in addition to the expected pyrrole. The structure assignment is based on two-dimensional NMR and computational evidence. The pyrolysis of the corresponding dimethyl amide gives a mixture of three 3-hydroxypyridines, in addition to the pyrrole. Evidence is presented for the formation of intermediate 1,4-oxazepines by a six-electron electrocyclic reaction of a carbene with ester or amide carbonyl groups.

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21

Wang, Keliang, Yuhe Cao, Zhengrong Gu, Phil Ahrenkiel, Joun Lee, and Qi Hua Fan. "Nitrogen-modified biomass-derived cheese-like porous carbon for electric double layer capacitors." RSC Advances 6, no. 32 (2016): 26738–44. http://dx.doi.org/10.1039/c6ra02748b.

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22

Choi, Se-Hwa, Ga-hye Kil, Na-rim Kim, Chun Yoon, Jae-Pil Kim, and Jae-Hong Choi. "ChemInform Abstract: Preparation of Red Dyes Derived from Diketo-pyrrolo-pyrrole Based Pigment and Their Properties for LCD Color Filters." ChemInform 42, no. 12 (February 24, 2011): no. http://dx.doi.org/10.1002/chin.201112189.

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23

Bello, A., F. Barzegar, M. J. Madito, D. Y. Momodu, A. A. Khaleed, T. M. Masikhwa, J. K. Dangbegnon, and N. Manyala. "Electrochemical performance of polypyrrole derived porous activated carbon-based symmetric supercapacitors in various electrolytes." RSC Advances 6, no. 72 (2016): 68141–49. http://dx.doi.org/10.1039/c6ra12690a.

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24

Fathi, Parinaz, and Dipanjan Pan. "Current trends in pyrrole and porphyrin-derived nanoscale materials for biomedical applications." Nanomedicine 15, no. 25 (October 2020): 2493–515. http://dx.doi.org/10.2217/nnm-2020-0125.

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This article is written to provide an up-to-date review of pyrrole-based biomedical materials. Porphyrins and other tetrapyrrolic molecules possess unique magnetic, optical and other photophysical properties that make them useful for bioimaging and therapy. This review touches briefly on some of the synthetic strategies to obtain porphyrin- and tetrapyrrole-based nanoparticles, as well as the variety of applications in which crosslinked, self-assembled, porphyrin-coated and other nanoparticles are utilized. We explore examples of these nanoparticles’ applications in photothermal therapy, drug delivery, photodynamic therapy, stimuli response, fluorescence imaging, photoacoustic imaging, magnetic resonance imaging, computed tomography and positron emission tomography. We anticipate that this review will provide a comprehensive summary of pyrrole-derived nanoparticles and provide a guideline for their further development.

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25

Alabadi, Akram, Xinjia Yang, Zehua Dong, Zhen Li, and Bien Tan. "Nitrogen-doped activated carbons derived from a co-polymer for high supercapacitor performance." J. Mater. Chem. A 2, no. 30 (2014): 11697–705. http://dx.doi.org/10.1039/c4ta01215a.

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26

Abramyan, Ara, Zhiwei Liu, and Vojislava Pophristic. "An ab-initio study of pyrrole and imidazole arylamides." Journal of the Serbian Chemical Society 78, no. 11 (2013): 1789–95. http://dx.doi.org/10.2298/jsc130929104a.

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Arylamide foldamers have been shown to have a number of biological and medicinal applications. For example, a class of pyrrole-imidazole polyamide foldamers is capable of binding specific DNA sequences and preventing development of various gene disorders, most importantly cancer. Molecular dynamics (MD) simulations can provide crucial details in understanding the atomic level events related to foldamer/DNA binding. An important first step in the accurate simulation of these foldamer/DNA systems is the reparametrization of force field parameters for torsion around the aryl-amide bonds. Here we highlight our Density Functional Theory (DFT) potential energy profiles and derived force field parameters for four aryl-amide bond types for the pyrrole and imidazole building blocks extensively used in foldamer design for the DNA-binding polyamides. These results contribute to developing of computational tools for an appropriate molecular modeling of pyrrole-imidazole polyamide/DNA binding, and provide an insight into the chemical factors that influence the flexibility of the pyrrole-imidazole polyamides, and their binding to DNA.

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27

Wijesekera, Tilak P. "5-Perfluoroalkyldipyrromethanes and porphyrins derived therefrom." Canadian Journal of Chemistry 74, no. 10 (October 1, 1996): 1868–71. http://dx.doi.org/10.1139/v96-209.

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Acid-catalyzed condensation of pyrrole and perfluoroalkyl aldehydes produced, in a single step, α,β-unsubstituted 5-perfluoroalkyldipyrromethanes, which were isolated and characterized for the first time. These dipyrromethanes were used as the key intermediates in the synthesis of trans-perfluroalkylporphyrins as well as meso-tetrakis(perfluoroalkyl)porphyrins. The two-step procedure described here provides access to a wide variety of porphyrins with trans perfluoroalkyl groups. Key words: 5-perfluoroalkyldipyrromethanes, perfluoroalkylporphyrins, electron-deficient porphyrins.

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28

Deans, Richard M., Vanampally Chandrashaker, Masahiko Taniguchi, and Jonathan S. Lindsey. "Complexity in structure-directed prebiotic chemistry. Effect of a defective competing reactant in tetrapyrrole formation." New Journal of Chemistry 39, no. 11 (2015): 8273–81. http://dx.doi.org/10.1039/c5nj01474c.

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29

Ourari, Ali, Djouhra Aggoun, and Lahcène Ouahab. "Poly(pyrrole) films efficiently electrodeposited using new monomers derived from 3-bromopropyl-N-pyrrol and dihydroxyacetophenone—Electrocatalytic reduction ability towards bromocyclopentane." Colloids and Surfaces A: Physicochemical and Engineering Aspects 446 (April 2014): 190–98. http://dx.doi.org/10.1016/j.colsurfa.2014.01.047.

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30

Galenko, Ekaterina E., Firuza M. Shakirova, Vladimir A. Bodunov, Mikhail S. Novikov, and Alexander F. Khlebnikov. "1-(2H-Azirine-2-carbonyl)benzotriazoles: building blocks for the synthesis of pyrrole-containing heterocycles." Organic & Biomolecular Chemistry 18, no. 12 (2020): 2283–96. http://dx.doi.org/10.1039/d0ob00206b.

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31

Fomina, Lioudmila, Jorge Godínez Sánchez, J. A. Olivares, F. L. S. Cuppo, L. Enrique Sansores, and Roberto Salcedo. "Electronic properties of hyperbranched compounds derived by pyrrole." Journal of Molecular Structure 1074 (September 2014): 534–41. http://dx.doi.org/10.1016/j.molstruc.2014.06.031.

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32

Iwata, Makoto, Yuko Kamijoh, and Kazuo Nagasawa. "Synthetic Studies of Oroidin-derived Pyrrole-imidazole Alkaloids." Journal of Synthetic Organic Chemistry, Japan 73, no. 11 (2015): 1092–98. http://dx.doi.org/10.5059/yukigoseikyokaishi.73.1092.

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33

Leonardi, Marco, Mercedes Villacampa, and J. Carlos Menéndez. "Mild and General Synthesis of Pyrrolo[2,1-a]isoquinolines and Related Polyheterocyclic Frameworks from Pyrrole Precursors Derived from a Mechanochemical Multicomponent Reaction." Journal of Organic Chemistry 82, no. 5 (February 22, 2017): 2570–78. http://dx.doi.org/10.1021/acs.joc.6b02995.

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34

Zhang, Yulong, Na Yang, Xiaohua Liu, Jing Guo, Xiying Zhang, Lili Lin, Changwei Hu, and Xiaoming Feng. "Reversal of enantioselective Friedel–Crafts C3-alkylation of pyrrole by slightly tuning the amide units of N,N′-dioxide ligands." Chemical Communications 51, no. 40 (2015): 8432–35. http://dx.doi.org/10.1039/c4cc10055g.

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35

Liu, Xu, Chang Liu, and Xu Cheng. "Ring-contraction of hantzsch esters and their derivatives to pyrroles via electrochemical extrusion of ethyl acetate out of aromatic rings." Green Chemistry 23, no. 9 (2021): 3468–73. http://dx.doi.org/10.1039/d1gc00487e.

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Cut an acetate ester out of a Hantzsch ester. With a 4-electron electrochemical reduction, the Hantzsch-ester-derived pyridine was converted to a polysubstituted pyrrole in one step by dearomatization, ring-contraction, and rearomatization process.

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36

Sar, Saibal, Ranajit Das, Dhiraj Barman, Pikaso Latua, Souvik Guha, Ludovic Gremaud, and Subhabrata Sen. "A sustainable C–H functionalization of indoles, pyrroles and furans under a blue LED with iodonium ylides." Organic & Biomolecular Chemistry 19, no. 35 (2021): 7627–32. http://dx.doi.org/10.1039/d1ob01219c.

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Pyrrole and indole derivatives are functionalized with the dimethyl malonate derived phenyl iodonium ylide in the presence of a blue LED via C–H functionalization of the respective heterocycles in methanol to generate the desired compounds.

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37

Fan, Hui, Jiangnan Peng, Mark T. Hamann, and Jin-Feng Hu. "Lamellarins and Related Pyrrole-Derived Alkaloids from Marine Organisms." Chemical Reviews 108, no. 1 (January 2008): 264–87. http://dx.doi.org/10.1021/cr078199m.

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38

Lipson, Victoria V., Tetiana L. Pavlovska, Nataliya V. Svetlichnaya, Anna A. Poryvai, Nikolay Yu Gorobets, Erik V. Van der Eycken, Irina S. Konovalova, et al. "Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds." Beilstein Journal of Organic Chemistry 15 (May 6, 2019): 1032–45. http://dx.doi.org/10.3762/bjoc.15.101.

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The unexpectedly uncatalyzed reaction between 2-amino-4-arylimidazoles, aromatic aldehydes and Meldrum’s acid has selectively led to the corresponding Knoevenagel–Michael adducts containing a free amino group in the imidazole fragment. The adducts derived from Meldrum’s acid have been smoothly converted into 1,7-diaryl-3-amino-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-ones and 3-(2-amino-4-aryl-1H-imidazol-5-yl)-3-arylpropanoic acids. The interaction of 2-amino-4-arylimidazoles with aromatic aldehydes or isatins and acyclic methylene active compounds has led to the formation of pyrrolo[1,2-c]imidazole-6-carbonitriles, pyrrolo[1,2-с]imidazole-6-carboxylates and spiro[indoline-3,7'-pyrrolo[1,2-c]imidazoles], which can be considered as the analogues of both 3,3’-spirooxindole and 2-aminoimidazole marine sponge alkaloids.

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39

Rawat, Poonam, and R. N. Singh. "Experimental and theoretical study of 4-formyl pyrrole derived aroylhydrazones." Journal of Molecular Structure 1084 (March 2015): 326–39. http://dx.doi.org/10.1016/j.molstruc.2014.12.045.

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40

Zaitsev, A. B., A. M. Vasil'tsov, E. Yu Shmidt, A. I. Mikhaleva, A. V. Afonin, and L. N. Il'icheva. "Trofimov Reaction with Oximes Derived from Ketosteroids: Steroid-Pyrrole Structures." Russian Journal of Organic Chemistry 39, no. 10 (October 2003): 1406–11. http://dx.doi.org/10.1023/b:rujo.0000010554.30452.01.

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41

Tsukamoto, Sachiko, Kazuhiro Tane, Tomihisa Ohta, Shigeki Matsunaga, Nobuhiro Fusetani, and Rob W. M. van Soest. "Four New Bioactive Pyrrole-Derived Alkaloids from the Marine SpongeAxinellabrevistyla." Journal of Natural Products 64, no. 12 (December 2001): 1576–78. http://dx.doi.org/10.1021/np010280b.

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42

Biava, Mariangela, Giulio Cesare Porretta, Giovanna Poce, Claudio Battilocchio, Salvatore Alfonso, Alessandro de Logu, Fabrizio Manetti, and Maurizio Botta. "Developing Pyrrole-Derived Antimycobacterial Agents: a Rational Lead Optimization Approach." ChemMedChem 6, no. 4 (February 21, 2011): 593–99. http://dx.doi.org/10.1002/cmdc.201000526.

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43

Jones, R. Alan, Gloria Quintanilla-López, Orhan Õztürk, Sayed Ali Nagdi Taheri, Gülan Berber Karatepe, and Richard O. Jones. "Pyrrole studies, Part 48.^{1 13}C NMR characterisation of imines and related compounds derived from pyrrole-2-carboxaldehydes and pyrrole-2,5-dicarboxaldehydes." Journal of Chemical Research 2001, no. 8 (August 1, 2001): 309–10. http://dx.doi.org/10.3184/030823401103170052.

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44

Agarwal, Anshu, Meenakshi Sharma, Meenakshi Agrawal, and D. Kishore. "Expedient Protocols for the Installation of Pyrimidine Based Privileged Templates on 2-Position of Pyrrolo[2,1-c][1,4]-benzodiazepine Nucleus Linked Through a p-phenoxyl Spacer." E-Journal of Chemistry 9, no. 3 (2012): 1305–12. http://dx.doi.org/10.1155/2012/629414.

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Exceedingly facile single step expedient protocols based on the versatility and reactivity of corresponding intermediates : [2-(dimethylaminomethylene) ketone] (5) and chalcone (6), derived from 2-(p-acetyl phenoxyl) substituted analogue of pyrrolo[2,1-c][1,4]-benzodiazepine (4), have been developed to provide an easy installation of the pyrimidine based privileged templates at 2-position of pyrrolo[2,1-c][1,4]-benzodiazepine through a p-phenoxyl spacer, by utilizing the synthetic strategy depicted in schemes-1and2.

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45

Becher, J., K. Nielsen, and J. O. Jeppesen. "Supramolecular systems derived from pyrrolo-tetrathiafulvalene building blocks." Journal de Physique IV (Proceedings) 114 (April 2004): 445–48. http://dx.doi.org/10.1051/jp4:2004114104.

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46

Alonso, Ruben, Elena Bermejo, Rosa Carballo, Alfonso Castiñeiras, and Teresa Pérez. "The supramolecular chemistry of thiosemicarbazones derived from pyrrole: a structural view." Journal of Molecular Structure 606, no. 1-3 (March 2002): 155–73. http://dx.doi.org/10.1016/s0022-2860(01)00875-4.

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47

Kozaki, Masatoshi, James P. Parakka, and Michael P. Cava. "New Thiophene−Pyrrole-Derived Annulenes Containing 6 and 10 Heterocyclic Units." Journal of Organic Chemistry 61, no. 11 (January 1996): 3657–61. http://dx.doi.org/10.1021/jo960214s.

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48

Qi, Bowen, Wanqing Yang, Ning Ding, Yuan Luo, Fangfang Jia, Xiao Liu, Juan Wang, Xiaohui Wang, Pengfei Tu, and Shepo Shi. "Pyrrole 2-carbaldehyde derived alkaloids from the roots of Angelica dahurica." Journal of Natural Medicines 73, no. 4 (June 17, 2019): 769–76. http://dx.doi.org/10.1007/s11418-019-01328-1.

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49

Pennetta, Chiara, Giuseppe Floresta, Adriana Carol Eleonora Graziano, Venera Cardile, Lucia Rubino, Maurizio Galimberti, Antonio Rescifina, and Vincenzina Barbera. "Functionalization of Single and Multi-Walled Carbon Nanotubes with Polypropylene Glycol Decorated Pyrrole for the Development of Doxorubicin Nano-Conveyors for Cancer Drug Delivery." Nanomaterials 10, no. 6 (May 31, 2020): 1073. http://dx.doi.org/10.3390/nano10061073.

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A recently reported functionalization of single and multi-walled carbon nanotubes, based on a cycloaddition reaction between carbon nanotubes and a pyrrole derived compound, was exploited for the formation of a doxorubicin (DOX) stacked drug delivery system. The obtained supramolecular nano-conveyors were characterized by wide-angle X-ray diffraction (WAXD), thermogravimetric analysis (TGA), high-resolution transmission electron microscopy (HR-TEM), and Fourier transform infrared (FT-IR) spectroscopy. The supramolecular interactions were studied by molecular dynamics simulations and by monitoring the emission and the absorption spectra of DOX. Biological studies revealed that two of the synthesized nano-vectors are effectively able to get the drug into the studied cell lines and also to enhance the cell mortality of DOX at a much lower effective dose. This work reports the facile functionalization of carbon nanotubes exploiting the “pyrrole methodology” for the development of novel technological carbon-based drug delivery systems.

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50

Mphahlele, Malose J., and Mmakwena M. Mmonwa. "Vilsmeier–Haack reaction of 7-acetyl-2-arylindoles: a convenient method for the synthesis of 6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-1,5-dicarbaldehydes." Organic & Biomolecular Chemistry 17, no. 8 (2019): 2204–11. http://dx.doi.org/10.1039/c8ob03040e.

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