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Journal articles on the topic 'Pyrrole compound'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Iqbal, Sarosh, Hina Rasheed, Rabiya Javed Awan, Ramsha Javed Awan, Asma Mukhtar, and Mark G. Moloney. "Recent Advances in the Synthesis of Pyrroles." Current Organic Chemistry 24, no. 11 (2020): 1196–229. http://dx.doi.org/10.2174/1385272824999200528125651.

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: Pyrroles are the most prevalent heterocyclic compounds, which are present as the basic cores in many natural products, such as vitamin B12, bile pigments like bilirubin and biliverdin, the porphyrins of heme, chlorophyll, chlorins, bacteriochlorins, and porphyrinogens. The biological activities of compounds having pyrrole analogs include antimicrobial (antibacterial, antifungal), anti-cancer (anti-cytotoxic, antimitotic), anti-tumor, anti-hyperlipidemic, anti-depressant, anti-inflammatory, antihyperglycemic, antiproliferative, anti-HIV and anti-viral activities. Accordingly, significant atte

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2

Sakamoto, Toshio, Ayaka Nishida, Naoki Wada, et al. "Identification of a Novel Pyrrole Alkaloid from the Edible Mushroom Basidiomycetes-X (Echigoshirayukidake)." Molecules 25, no. 21 (2020): 4879. http://dx.doi.org/10.3390/molecules25214879.

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Three pyrrole alkaloid derivatives were isolated from the edible mushroom Basidiomycetes-X (Echigoshirayukidake) by water extraction followed by ethyl acetate fractionation. The chemical structures determined by MS and NMR were 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanoic acid (compound I), 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanamide (compound II), and 5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde (compound III). Compound I was found to be the major component, followed by compound II, and compound III was the minor component. The dry powder of Basidiomycetes-X contained

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3

Macías, Mario A., Juan-Carlos Castillo, and Jaime Portilla. "A series of (E)-5-(arylideneamino)-1-tert-butyl-1H-pyrrole-3-carbonitriles and their reduction products to secondary amines: syntheses and X-ray structural studies." Acta Crystallographica Section C Structural Chemistry 74, no. 1 (2018): 82–93. http://dx.doi.org/10.1107/s2053229617017260.

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An efficent access to a series of N-(pyrrol-2-yl)amines, namely (E)-1-tert-butyl-5-[(4-chlorobenzylidene)amino]-1H-pyrrole-3-carbonitrile, C16H16ClN3, (7a), (E)-1-tert-butyl-5-[(2,4-dichlorobenzylidene)amino]-1H-pyrrole-3-carbonitrile, C16H15Cl2N3, (7b), (E)-1-tert-butyl-5-[(pyridin-4-ylmethylene)amino]-1H-pyrrole-3-carbonitrile, C15H16N4, (7c), 1-tert-butyl-5-[(4-chlorobenzyl)amino]-1H-pyrrole-3-carbonitrile, C16H18ClN3, (8a), and 1-tert-butyl-5-[(2,4-dichlorobenzyl)amino]-1H-pyrrole-3-carbonitrile, C16H17Cl2N3, (8b), by a two-step synthesis sequence (solvent-free condensation and reduction)

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4

Bray, Brian L., та Joseph M. Muchowski. "α-(Dialkylamino)-α-pyrrolylacetonitriles. A potpourri of useful synthetic transformations". Canadian Journal of Chemistry 68, № 8 (1990): 1305–8. http://dx.doi.org/10.1139/v90-201.

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α-(Dialkylamino)-α-(pyrrol-2-yl)acetonitriles (3) are versatile intermediates that are readily converted into regiochemically pure 2-bromo-6-dialkylamino-1-azafulvenes and 5-bromo-2-acylpyrroles (acyl = CHO, COR). In addition, 3 (R1 = H), 4 (R1 = H), and the β-substituted compound 9 are transformed easily and under mild conditions, via the corresponding α-methylthio compounds (e.g., 7a), into the methyl pyrrole carboxylates 8a, 8b, and 10, respectively. Keywords: α-(dialkylamino)-α-(pyrrol-2-yl)acetonitriles, 5-bromo-2-acylpyrroles, methyl pyrrole carboxylates.

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5

Davis, Rohan A., Anthony R. Carroll, and Ronald J. Quinn. "The Synthesis of Two Combinatorial Libraries Using a 4-(2-Thienyl)-pyrrole Template." Australian Journal of Chemistry 55, no. 12 (2002): 789. http://dx.doi.org/10.1071/ch02110.

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The synthesis of the novel biaryl compound, 4-(2-thienyl)-1H-pyrrole-2-carbaldehyde (1), by Suzuki–Miyaura coupling conditions is reported. Compound (1) was subsequently used as a combinatorial template in the parallel solution-phase synthesis of an amine and imine compound library. The amine library was produced using reductive amination conditions, and purification was achieved by a liquid–liquid partition followed by silica chromatography to afford ten amine analogues. The imine library consisted of five compounds, which were synthesized using volatile primary amines that allowed purificati

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6

Mohamed, Mosaad, Ramdan El-Domany, and Rania Abd El-Hameed. "Synthesis of certain pyrrole derivatives as antimicro-bial agents." Acta Pharmaceutica 59, no. 2 (2009): 145–58. http://dx.doi.org/10.2478/v10007-009-0016-9.

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Synthesis of certain pyrrole derivatives as antimicro-bial agentsIn an effort to establish new pyrroles and pyrrolo[2,3-d] pyrimidines with improved antimicrobial activity we report here the synthesis andin vitromicrobiological evaluation of a series of pyrrole derivatives. A series of new 2-aminopyrrole-3-carbonitriles (1a-d) were synthesized from the reaction of benzoin, primary aromatic amines and malononitrile, from which a number of pyrrole derivatives (2a-dto5a-d) and pyrrolo[2,3-d]pyrimidines (6a-dto10a, d) were synthesized. Thein vitroantimicrobial testing of the synthesized compounds

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7

Martyn, Derek C., та Andrew D. Abell. "The Synthesis and Testing of α-(Hydroxymethyl)pyrroles as DNA Binding Agents". Australian Journal of Chemistry 57, № 11 (2004): 1073. http://dx.doi.org/10.1071/ch04183.

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The α-(hydroxymethyl)pyrroles 16a and 16b were prepared and shown to be cytotoxic against the P388 cancer cell line. Ethyl 5-hydroxymethyl-1H-pyrrole-2-carboxylate 18 was inactive, demonstrating that an α-(hydroxymethyl)pyrrole group alone is not sufficient for activity. Compound 16b has been shown to bind to DNA with reasonable affinity.

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8

Black, DS, and RJ Strauch. "Nitrones and Oxaziridines. XLI. Chromophoric Systems Based on 1-Pyrroline 1-Oxides and 2H-Pyrrole 1-Oxides." Australian Journal of Chemistry 44, no. 9 (1991): 1217. http://dx.doi.org/10.1071/ch9911217.

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1-Pyrroline 1-oxides and 2H-pyrrole 1-oxides have been shown to be suitable compounds for the development of extended chromophoric systems. 1-Pyrroline 1-oxides (31, (5) and (7) have conjugated systems in which a nitrone group is conjugatively linked to a dimethylamino group. The 2H-pyrrole 1-oxides (10), (13), (14) and (19) provide cross-conjugated systems incorporating the same structural features. The most extensive delocalization arises in the distyryl compound (19), which on protonation gives an extended cyanine chromophore. The bis nitrone (21) shows a chromophore with nitrone groups at

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9

Kennedy, Alan R., Abedawn I. Khalaf, Fraser J. Scott, and Colin J. Suckling. "Four pyrrole derivatives used as building blocks in the synthesis of minor-groove binders." Acta Crystallographica Section E Crystallographic Communications 73, no. 2 (2017): 254–59. http://dx.doi.org/10.1107/s2056989017001177.

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The title nitropyrrole-based compounds, C7H8N2O4, (I) (ethyl 4-nitro-1H-pyrrole-2-carboxylate), its derivative C12H14N2O4, (II) [ethyl 4-nitro-1-(4-pentynyl)-1H-pyrrole-2-carboxylate], C15H26N4O3, (III) {N-[3-(dimethyamino)propyl]-1-isopentyl-4-nitro-1H-pyrrole-2-carboxamide}, and C20H27N9O5, (IV) {1-(3-azidopropyl)-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-N-[2-(morpholin-4-yl)ethyl]-1H-pyrrole-2-carboxamide}, are intermediates used in the synthesis of modified DNA minor-groove binders. In all four compounds, the nitro groups lie in the plane of the pyrrole ring. In compounds (I) and (II)

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10

Gajdoš, Peter, Soňa Pavlíková, Filip Bureš, and Alžbeta Krutošíková. "2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions." Open Chemistry 3, no. 2 (2005): 311–25. http://dx.doi.org/10.2478/bf02475999.

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AbstractThe synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By

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11

Kemskyi, Sergiy, Alina Grozav, Vitalii Chornous, et al. "Synthesis, antimicrobial activity, DFT-calculation, and docking of 4-(1,3,4-thiadiazol-2-yl)-containing polysubstituted pyrroles." Current Chemistry Letters 13, no. 4 (2024): 761–76. http://dx.doi.org/10.5267/j.ccl.2024.3.005.

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A series of new 4-(1,3,4-thiadiazol-2-yl)-containing polysubstituted pyrroles 3 a-k has been synthesized by a preparative convenient method from ethyl 5-chloro-4-formyl-1H-pyrrole-3-carboxylates 1 a-e, which were selectively transformed into the corresponding polysubstituted pyrrole-4-carboxylic acids 2 а-е using sodium hypochlorite as an oxidizer. Further, they were transformed into the target compounds with a high yield using the cyclocondensation with N-mono- or N,N-disubstituted thiosemicarbazides in the boiling phosphorus trichloroxide. As seen from the screening of antimicrobial activity

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12

Giordano, Lorenza, Rafael Ballesteros, and Rafael Ballesteros-Garrido. "4,4′-(Pyrrolo[3,2-b]pyrrole-1,4-diyl)dianiline." Molbank 2020, no. 4 (2020): M1169. http://dx.doi.org/10.3390/m1169.

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4,4′-(Pyrrolo[3,2-b]pyrrole-1,4-diyl)dianiline was synthesized in one step from benzene-1,4-diamine and ethylene glycol with Pd/Al2O3 and ZnO. The title compound was characterized by means of NMR techniques and HRMS mass spectrometry.

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13

Antonucci, T., J. S. Warmus, J. C. Hodges, and D. G. Nickell. "Characterization of the Antiviral Activity of Highly Substituted Pyrroles: A Novel Class of Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitor." Antiviral Chemistry and Chemotherapy 6, no. 2 (1995): 98–108. http://dx.doi.org/10.1177/095632029500600204.

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As a result of mass screening of the Parke-Davis Pharmaceutical compound library for inhibitors of HIV-1 reverse transcriptase (RT) activity, a novel class of inhibitor, the pyrroles, was identified. Subsequently, a series of analogues was screened for inhibitory activity against HIV-1 and some structure-activity relationships were identified. Further characterization of the most potent pyrrole involved comparing its effects in peripheral blood lymphocytes (PBLs) with its effects in transformed cell lines; the pyrrole had the same efficacy (EC50 = approximately 2 μM) but was less toxic in PBLs

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14

Axford, Lorraine C., Kate E. Holden, Katrin Hasse, et al. "Attempts to Mimic Key Bond-Forming Events Associated with the Proposed Biogenesis of the Pentacyclic Lamellarins." Australian Journal of Chemistry 61, no. 2 (2008): 80. http://dx.doi.org/10.1071/ch07402.

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The pyrrole-tethered veratroles 16 and 27 each engage in PIFA-induced oxidative cyclization reactions to give compounds 22 and 29, respectively, which incorporate a key tricyclic fragment associated with the title natural products. In contrast, the corresponding catechols 11 and 12 only produce polymeric materials on subjection to analogous reaction conditions. Efforts to study lactone ring formation by the oxidative cyclization of catechol 30 and veratrole 38 have been thwarted by an inability to prepare the former substrate and decomposition of the latter. The reported conversions 44 → 45 an

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15

Kim, Chong-Hyeak, Yea-Sel Jeon, Vincent Lynch, Jonathan L. Sessler, and Kwang-Jin Hwang. "2-[(1H-Pyrrol-2-yl)methyl]-1H-pyrrole." Acta Crystallographica Section E Structure Reports Online 69, no. 11 (2013): o1697. http://dx.doi.org/10.1107/s1600536813028365.

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In the title compound, C9H10N2, the two pyrrole ring planes are twisted by a dihedral angle of 69.07 (16)° and the C—C—C methane angle is 115.1 (2)°. In the crystal, molecules are connected into layers in thebcplane by N—H...π interactions.

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16

Miranda-Sánchez, Diter, Carlos H. Escalante, Dulce Andrade-Pavón, et al. "Pyrrole-Based Enaminones as Building Blocks for the Synthesis of Indolizines and Pyrrolo[1,2-a]pyrazines Showing Potent Antifungal Activity." Molecules 28, no. 20 (2023): 7223. http://dx.doi.org/10.3390/molecules28207223.

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As a new approach, pyrrolo[1,2-a]pyrazines were synthesized through the cyclization of 2-formylpyrrole-based enaminones in the presence of ammonium acetate. The enaminones were prepared with a straightforward method, reacting the corresponding alkyl 2-(2-formyl-1H-pyrrol-1-yl)acetates, 2-(2-formyl-1H-pyrrol-1-yl)acetonitrile, and 2-(2-formyl-1H-pyrrol-1-yl)acetophenones with DMFDMA. Analogous enaminones elaborated from alkyl (E)-3-(1H-pyrrol-2-yl)acrylates were treated with a Lewis acid to afford indolizines. The antifungal activity of the series of substituted pyrroles, pyrrole-based enaminon

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17

Husson, Jérôme. "4′-(N-(2-Cyanoethyl)pyrrol-2-yl)-2,2′:6′,2″-terpyridine." Molbank 2023, no. 3 (2023): M1689. http://dx.doi.org/10.3390/m1689.

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The preparation and characterization of a new multi-functionalized terpyridine molecule featuring a pyrrole heterocycle and a cyano group is described. This new compound was obtained via a KF/alumina-catalyzed Michael addition of 4′-(pyrrol-2-yl)-2,2′:6′,2″-terpyridine into acrylonitrile. The mild reaction conditions leave the nitrile group unaltered. The title compound was fully characterized via NMR spectroscopy (1H and 13C) as well as via high resolution mass spectrometry and infrared spectroscopy.

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18

Journal, Baghdad Science. "Synthesis, Characterization of Poly Heterocyclic Compounds, and Effect on Cancer Cell (Hep-2) In vitro." Baghdad Science Journal 15, no. 4 (2018): 415–524. http://dx.doi.org/10.21123/bsj.15.4.415-524.

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A synthesis series of new heterocyclic derivatives (A2-A7) (pyrrole, pyridazine, oxazine and imidazol) derived from 4-acetyl-2,5-dichloro-1-(3,5-dinitrophenyl)-1H-pyrrole-3-carboxylate(A1) have been synthesised. Synthesis of compound (A2) by the reaction of starting material (A1) with hydroxyl amine hydrochloride in the presence of pyridine. Compound (A2) was reacted with hydrazine hydrate in dry benzene to give (A3) derivative. The compound )A3( deals with sodium nitrite to give diazonium salt, and the reaction diazonium salt with ethyl acetoacetate to produce compound (A4). To a mixture of c

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19

Kamel, Moumen S., Amany Belal, Moustafa O. Aboelez, et al. "Microwave-Assisted Synthesis, Biological Activity Evaluation, Molecular Docking, and ADMET Studies of Some Novel Pyrrolo [2,3-b] Pyrrole Derivatives." Molecules 27, no. 7 (2022): 2061. http://dx.doi.org/10.3390/molecules27072061.

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Novel pyrrolo [2,3-b] pyrrole derivatives were synthesized and their hypolipidemic activity was assessed in hyperlipidemic rats. The chemical structures of the new derivatives were confirmed through spectral analysis. Compounds 5 and 6 were revealed to be the most effective hypolipidemic agents, with considerable hypocholesterolemic and hypotriglyceridemic effects. They appear to be promising candidates for creating new powerful derivatives with anti-atherosclerotic and hypolipidemic properties. As for antimicrobial activity, some of the tested compounds showed moderate activity against Pseudo

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20

Tejeswararao, D., and B. Srikanth. "SnCl2 Catalyzed Direct Synthesis of Pyrroles under Aqueous Conditions." Asian Journal of Chemistry 32, no. 4 (2020): 795–802. http://dx.doi.org/10.14233/ajchem.2020.22454.

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Synthetic substituted pyrroles are related with interesting biological activities, yet they remain inadequately explored within drug discovery. Late years have seen a growing interest in synthetic approaches that can provide access to structurally novel pyrroles so that the biological usefulness of this compound class can be more fully investigated. Herein, an efficient and versatile practical protocol for the pyrroles using stannous(II) chloride dihydrate as catalyst is described under aqueous conditions at 55 ºC in high yields. Also, this method is applicable for the preparation of diversity

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21

Bulatov, Evgeny, Tatiana Chulkova, and Matti Haukka. "5-Imino-3,4-diphenyl-1H-pyrrol-2-one." Acta Crystallographica Section E Structure Reports Online 70, no. 2 (2014): o162. http://dx.doi.org/10.1107/s1600536814001032.

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The title compound, C16H12N2O, exists in the crystalline state as the 5-imino-3,4-diphenyl-1H-pyrrol-2-one tautomer. The dihedral angles between the pyrrole and phenyl rings are 35.3 (2) and 55.3 (2)°. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generate a graph-set motif ofR22(8)viaN—H...N hydrogen bonds.

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22

Ji, Hongzhang, Changyue Wu, Min Ni, et al. "In vitro Antichlamydial Activity of 1,2,3,5-Tetrasubstituted Pyrrole Derivatives." Chemotherapy 63, no. 2 (2018): 95–99. http://dx.doi.org/10.1159/000487880.

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Background: Chlamydia is a group of bacterial pathogens distributed worldwide that can lead to serious reproductive and other health problems. The rise of antibiotic-resistant pathogens promotes the development of novel antichlamydial agents. The aim of this study is to assess in vitro antichlamydial activity of our previously synthesized 1,2,3,5- tetrasubstituted pyrroles. Methods: The derivatives were screened for their antichlamydial activity against three Chlamydia strains by calculating IC50 values using concentration-response inhibition data between 1 and 32 μM. The action of the compoun

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23

WILLIAMS, Carvell H., та Jill LAWSON. "Mechanism-based inhibition of monoamine oxidase by 3-aryl-Δ3-pyrrolines". Biochemical Journal 336, № 1 (1998): 63–67. http://dx.doi.org/10.1042/bj3360063.

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The compound 1-methyl-3-phenyl-Δ3-pyrroline and its 4-chlorophenyl analogue appear to act as irreversible inhibitors of monoamine oxidase B (MAO B) in mitochondria of rat liver. The compounds are metabolized by MAO B and concomitantly inhibit the enzyme in what seems to be a two-step process. The metabolic end product of this process is the corresponding pyrrole. This inhibition process is considered in the light of possible intermediates formed during the enzymic oxidation, and comparisons are made with the structurally analogous neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.

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24

Kondo, Mitsuyo, Makiko Kawamoto, Atsushi Hasuoka, Masahiro Kajino, Nobuhiro Inatomi, and Naoki Tarui. "High-Throughput Screening of Potassium-Competitive Acid Blockers." Journal of Biomolecular Screening 17, no. 2 (2011): 177–82. http://dx.doi.org/10.1177/1087057111421004.

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H+,K+-ATPase is a key enzyme in the process of gastric acid secretion, and proton pump inhibitors (PPIs) have been accepted as one of the most effective treatments for peptic ulcer and gastroesophageal reflux disease. To discover a novel class of PPIs, the authors screened a low-molecular-weight compound library and identified two prospective acid blockers that were pyrrole derivatives. Both compounds inhibited H+,K+-ATPase in a reversible and potassium-competitive manner. These compounds led to the development of TAK-438 (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methyl

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25

Ivan, Beatrice-Cristina, Stefania-Felicia Barbuceanu, Camelia Mia Hotnog, et al. "New Pyrrole Derivatives as Promising Biological Agents: Design, Synthesis, Characterization, In Silico, and Cytotoxicity Evaluation." International Journal of Molecular Sciences 23, no. 16 (2022): 8854. http://dx.doi.org/10.3390/ijms23168854.

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The current study describes the synthesis, physicochemical characterization and cytotoxicity evaluation of a new series of pyrrole derivatives in order to identify new bioactive molecules. The new pyrroles were obtained by reaction of benzimidazolium bromide derivatives with asymmetrical acetylenes in 1,2-epoxybutane under reflux through the Huisgen [3 + 2] cycloaddition of several ylide intermediates to the corresponding dipolarophiles. The intermediates salts were obtained from corresponding benzimidazole with bromoacetonitrile. The structures of the newly synthesized compounds were confirme

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26

Zeng, Yu, Baoxuan Nong, Xiuzhong Xia, et al. "Metabolome and Transcriptome Unveil the Correlated Metabolites and Transcripts with 2-acetyl-1-pyrroline in Fragrant Rice." International Journal of Molecular Sciences 25, no. 15 (2024): 8207. http://dx.doi.org/10.3390/ijms25158207.

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Fragrance is a valuable trait in rice varieties, with its aroma significantly influencing consumer preference. In this study, we conducted comprehensive metabolome and transcriptome analyses to elucidate the genetic and biochemical basis of fragrance in the Shangsixiangnuo (SSXN) variety, a fragrant indica rice cultivated in Guangxi, China. Through sensory evaluation and genetic analysis, we confirmed SSXN as strongly fragrant, with an 806 bp deletion in the BADH2 gene associated with fragrance production. In the metabolome analysis, a total of 238, 233, 105 and 60 metabolic compounds exhibite

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27

Leonardi, Marco, Mercedes Villacampa, and J. Carlos Menéndez. "High-speed vibration-milling-promoted synthesis of symmetrical frameworks containing two or three pyrrole units." Beilstein Journal of Organic Chemistry 13 (September 15, 2017): 1957–62. http://dx.doi.org/10.3762/bjoc.13.190.

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The pseudo-five-component reaction between β-dicarbonyl compounds (2 molecules), diamines and α-iodoketones (2 molecules), prepared in situ from aryl ketones, was performed efficiently under mechanochemical conditions involving high-speed vibration milling with a single zirconium oxide ball. This reaction afforded symmetrical frameworks containing two pyrrole or fused pyrrole units joined by a spacer, which are of interest in the exploration of chemical space for drug discovery purposes. The method was also extended to the synthesis of one compound containing three identical pyrrole fragments

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28

Petrova, Olga V., Igor A. Ushakov, Lyubov N. Sobenina, Victoriya V. Kireeva, and Boris A. Trofimov. "4-Amino-5-benzoyl-1-benzyl-2-(4,5,6,7-tetrahydro-1H-indol-2-yl)-1H-pyrrole-3-carbonitrile." Molbank 2023, no. 1 (2023): M1547. http://dx.doi.org/10.3390/m1547.

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The title compound, 4-amino-5-benzoyl-1-benzyl-2-(4,5,6,7-tetrahydro-1H-indol-2-yl)- 1H-pyrrole-3-carbonitrile, was synthesized for the first time in a 40% yield by the reaction of N-benzyl-3-imino-5,6,7,8-tetrahydro-3H-pyrrolo[1,2-a]indol-1-amine and 1-chloroacetophenone in a K2CO3/MeCN system (reflux, 6 h). The product was characterized by 1H-NMR, 13C-NMR, IR spectroscopy, and elemental analysis.

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29

Raja, R., M. Suresh, R. Raghunathan, and A. SubbiahPandi. "Crystal structures of methyl 3-(4-isopropylphenyl)-1-methyl-1,2,3,3a,4,9b-hexahydrothiochromeno[4,3-b]pyrrole-3a-carboxylate, methyl 1-methyl-3-(o-tolyl)-1,2,3,3a,4,9b-hexahydrothiochromeno[4,3-b]pyrrole-3a-carboxylate and methyl 1-methyl-3-(o-tolyl)-3,3a,4,9b-tetrahydro-1H-thiochromeno[4,3-c]isoxazole-3a-carboxylate." Acta Crystallographica Section E Crystallographic Communications 71, no. 6 (2015): 574–77. http://dx.doi.org/10.1107/s2056989015008063.

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In the title compounds, C23H27NO2S, (I), and C21H23NO2S, (II), the pyrrole rings have envelope conformations with the C atom substituted by the benzene ring as the flap. In the third title compound, C20H21NO3S, (III), the isoxazole ring has a twisted conformation on the C—C bond substituted by the benzene ring and the carboxylate group. In all three compounds, the thiopyran ring has a half-chair conformation. The mean plane of the pyrrole ring is inclined to the mean plane of the thiopyran ring by 57.07 (9), 58.98 (9) and 60.34 (12)° in (I), (II) and (III), respectively. The benzene rings are

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30

Díaz, Jesús G., María A. de Buergo, and David Díaz Díaz. "A New Pyrrole Alkaloid from Capsicum annuum L. var. palmera Grown in La Palma (Canary Islands, Spain)." Molbank 2025, no. 1 (2025): M1950. https://doi.org/10.3390/m1950.

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Capsicum annuum, commonly known as pepper, is a widely cultivated crop valued for its nutritional and economic significance. Among its varieties, the small red bell pepper, locally known as “pimienta palmera”, is a unique cultivar from La Palma in the Canary Islands, renowned for its distinctive flavor and use in traditional dishes. Despite its cultural importance, limited research exists on the chemical composition of this pepper variety. This study investigates the chemical constituents of dichloromethane and n-butanol fractions extracted from the pericarp of Capsicum annuum var. palmera. Is

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Kim, Donghyeon, Jaehyun You, Da Hye Lee, Hojin Hong, Dongwook Kim, and Yoonsu Park. "Photocatalytic furan-to-pyrrole conversion." Science 386, no. 6717 (2024): 99–105. http://dx.doi.org/10.1126/science.adq6245.

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The identity of a heteroatom within an aromatic ring influences the chemical properties of that heterocyclic compound. Systematically evaluating the effect of a single atom, however, poses synthetic challenges, primarily as a result of thermodynamic mismatches in atomic exchange processes. We present a photocatalytic strategy that swaps an oxygen atom of furan with a nitrogen group, directly converting the furan into a pyrrole analog in a single intermolecular reaction. High compatibility was observed with various furan derivatives and nitrogen nucleophiles commonly used in drug discovery, and

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32

Redzicka, Aleksandra, Żaneta Czyżnikowska, Benita Wiatrak, Katarzyna Gębczak, and Andrzej Kochel. "Design and Synthesis of N-Substituted 3,4-Pyrroledicarboximides as Potential Anti-Inflammatory Agents." International Journal of Molecular Sciences 22, no. 3 (2021): 1410. http://dx.doi.org/10.3390/ijms22031410.

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In the present paper, we describe the biological activity of the newly designed and synthesized series N-substituted 3,4-pyrroledicarboximides 2a–2p. The compounds 2a–2p were obtained in good yields by one-pot, three-component condensation of pyrrolo[3,4-c]pyrrole scaffold (1a–c) with secondary amines and an excess of formaldehyde solution in C2H5OH. The structural properties of the compounds were characterized by 1H NMR, 13C NMR FT-IR, MS, and elemental analysis. Moreover, single crystal X-ray diffraction has been recorded for compound 2h. The colorimetric inhibitor screening assay was used t

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33

Barbera, Vincenzina, Andrea Bernardi, Alberto Palazzolo, Alessandro Rosengart, Luigi Brambilla, and Maurizio Galimberti. "Facile and sustainable functionalization of graphene layers with pyrrole compounds." Pure and Applied Chemistry 90, no. 2 (2018): 253–70. http://dx.doi.org/10.1515/pac-2017-0708.

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AbstractA facile and sustainable functionalization of graphene layers was performed with pyrrole compounds (PyC) prepared through the Paal–Knorr reaction of a primary amine with 2,5-hexanedione. A good number of primary amines were used: hexanamine, dodecanamine, octadecanamine, 2-aminoacetic acid, 2-amino-1,3-propanediol, 3-(triethoxysilyl)propan-1-amine. The reactions were characterized by good yield, up to 96%, and indeed satisfactory atom efficiency, up to 80%. The functionalization of graphene layers was obtained by mixing PyC with a high surface area graphite and heating at a temperature

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Hagbani, Turki Al, Afrasim Moin, Talib Hussain, et al. "Anticancer Activity of Anti-Tubercular Compound(s) Designed on Pyrrolyl Benzohydrazine Scaffolds: A Repurposing Study." Processes 11, no. 7 (2023): 1889. http://dx.doi.org/10.3390/pr11071889.

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The present study explored anti-tubercular pyrrole derivatives against cancer targets using different in silico and in vitro approaches. Initially, nineteen anti-tubercular pyrrolyl benzohydrazide derivatives were screened against a potent cancer target PLK1 using an AutoDock Vina approach. Out of the nineteen derivatives, the two most potent derivatives C8 [N′-(4-(1H-pyrrol-1-yl) benzoyl)-3-chlorobenzohydrazide] and C18 [N′-(4-(1H-pyrrol-1-yl) benzoyl)-4-nitrobenzohydrazide], were subjected to molecular simulation analysis for a 100 ns trajectory. Further, these two derivatives were tested ag

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35

Howells, Rachel L., Scott G. Lamont, Thomas M. McGuire, et al. "Synthesis of Novel Pyrazine-Substituted 1H-Pyrrole-2-carboxamides and Related Tethered Heterocycles." Synthesis 54, no. 09 (2022): 2267–81. http://dx.doi.org/10.1055/s-0040-1719873.

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AbstractAs part of a drug discovery program, 4-pyrazin-2-yl-1H-pyrrole-2-carboxamides were accessed along with a number of bicyclic analogues. Routes to these compounds were largely absent from the scientific literature. The synthesis of a 4-(pyrazin-2-yl)-1H-pyrrole-2-carboxamide and several fused bicyclic analogues all using standard procedures (SNAr, borylation, C–C cross couplings, hydrolysis, amide bond formation, cyclisation, halogenation, and alkylation) from readily available starting materials is reported. The synthetic sequences range from 4–12 steps per final compound, with yields o

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36

Dholakia, Sandip P. "Synthesis and anti-inflammatory activity of 2-amino-4,5-diphenyl-1-(substituted)-1H-pyrrole-3- carbonitrile derivatives." Journal of medical pharmaceutical and allied sciences 12, no. 1 (2023): 5613–17. http://dx.doi.org/10.55522/jmpas.v12i1.4452.

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Pyrrole is privileged and active heterocycle with diverse pharmacological activities that specifically serve as a promising scaffold for antiinflammatory, antimalarial, antimicrobial, antiviral, antitubercular, and enzyme-inhibiting drugs. In an attempt to explore this scaffold, a series of 2- amino-4,5-diphenyl-1-(substituted)-1H-pyrrole-3-carbonitrilewere synthesized and screened for anti-inflammatory activity. The structures of synthesized novel compounds were characterized by 1H Nuclear Magnetic Resonance, Mass and Fourier Transfer Infrared spectroscopic data. All the compounds are screene

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37

Pfaff, Ulrike, Marcus Korb та Heinrich Lang. "Crystal structure of 3-ferrocenyl-1-phenyl-1H-pyrrole, [Fe(η5-C5H4cC4H3NPh)(η5-C5H5)]". Acta Crystallographica Section E Crystallographic Communications 72, № 1 (2016): 92–95. http://dx.doi.org/10.1107/s2056989015024214.

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The molecular structure of the title compound, [Fe(C5H5)(C15H12N)], consists of a ferrocene moiety with anN-phenylpyrrole heterocycle bound to one cyclopentadienyl ring. The 1,3-disubstitution of the pyrrole results in an L-shaped arrangement of the molecule with plane intersections of 2.78 (17)° between the pyrrole and theN-bonded phenyl ring and of 8.17 (18)° between the pyrrole and the cyclopentadienyl ring. In the crystal, no remarkable intermolecular interactions are observed

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38

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 tetrahydroa

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Chen, Yuehan, Shuping Wang, and Zhoupeng Li. "A cobalt–pyrrole coordination compound as high performance cathode catalyst for direct borohydride fuel cells." RSC Advances 10, no. 49 (2020): 29119–27. http://dx.doi.org/10.1039/d0ra05143h.

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Aitken, R. Alan, Charles Bloomfield, Liam J. R. McGeachie, and Alexandra M. Z. Slawin. "Diethyl pyrrole-2,5-dicarboxylate." Molbank 2020, no. 1 (2020): M1117. http://dx.doi.org/10.3390/m1117.

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The title compound was obtained in moderate yield by a new and unexpected base-induced ring contraction from a 1,4-thiazine precursor. Its X-ray structure showing hydrogen bonded dimers was compared with those of other crystallographically characterised 2-acylpyrroles.

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Inokuma, Yasuhide. "Calix[3]Pyrrole and Related Macrocycles: Synthesis and Properties." ECS Meeting Abstracts MA2023-01, no. 15 (2023): 1409. http://dx.doi.org/10.1149/ma2023-01151409mtgabs.

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Calix[4]pyrrole is a porphyrinogen-like macrocycle in which four pyrrole units are linked by four sp3-hybridized carbon atoms at the α-positions. While such tetrapyrrolic macrocycles are readily synthesized by acid-catalyzed condensation reactions of pyrrole monomer and carbonyl compound, analogous macrocycles composed of three pyrrole units are always not observed. Calix[3]pyrrole is a ring-contracted analogue of calix[4]pyrrole, and has been missing in porphyrin-related chemistry. In this presentation, the first synthesis of calix[3]pyrrole and its furan-embedded analogues is reported, and t

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42

Zhao, Xinyuan, Xun Zhang, Yan Liu, Siping Pang, and Chunlin He. "Asymmetrical Methylene-Bridge Linked Fully Iodinated Azoles as Energetic Biocidal Materials with Improved Thermal Stability." International Journal of Molecular Sciences 24, no. 13 (2023): 10711. http://dx.doi.org/10.3390/ijms241310711.

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The instability and volatility of iodine is high, however, effective iodine biocidal species can be readily stored in iodinated azoles and then be released upon decomposition or detonation. Iodine azoles with high iodine content and high thermal stability are highly desired. In this work, the strategy of methylene bridging with asymmetric structures of 3,4,5-triiodo-1-H-pyrazole (TIP), 2,4,5-triiodo-1H-imidazol (TIM), and tetraiodo-1H-pyrrole (TIPL) are proposed. Two highly stable fully iodinated methylene-bridged azole compounds 3,4,5-triiodo-1-((2,4,5-triiodo-1H-imidazol-1-yl)methyl)-1H-pyra

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43

Donkeng Dazie, Joel, Jiří Ludvík, Jan Fábry, and Václav Eigner. "Crystal structure of 2-tert-butyl-2,3-dihydro-1H-benzo[c]pyrrol-1-one." Acta Crystallographica Section E Crystallographic Communications 73, no. 8 (2017): 1184–88. http://dx.doi.org/10.1107/s2056989017010337.

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The asymmetric unit of the title compound, C12H15NO, comprises two symmetry-independent molecules which differ mainly in the conformations of the tert-butyl groups. The molecules contain an essentially planar five-membered 3-pyrroline ring incorporating a carbonyl substituent (pyrrolinone) which forms part of an isoindolinone skeleton. The planarity of the pyrrole ring is compared to other structures with isoindolinone. There are only weak intra- and intermolecular C—H...O and C—H...π-electron-ring interactions in the crystal structure.

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44

Al-Matarneh, Maria Cristina, Roxana-Maria Amărandi, Ionel I. Mangalagiu, and Ramona Danac. "Synthesis and Biological Screening of New Cyano-Substituted Pyrrole Fused (Iso)Quinoline Derivatives." Molecules 26, no. 7 (2021): 2066. http://dx.doi.org/10.3390/molecules26072066.

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Several new cyano-substituted derivatives with pyrrolo[1,2-a]quinoline and pyrrolo[2,1-a]isoquinoline scaffolds were synthesized by the [3 + 2] cycloaddition of (iso)quinolinium ylides to fumaronitrile. The cycloimmonium ylides reacted in situ as 1,3-dipoles with fumaronitrile to selectively form distinct final compounds, depending on the structure of the (iso)quinolinium salt. Eleven compounds were evaluated for their anticancer activity against a panel of 60 human cancer cell lines. The most potent compound 9a showed a broad spectrum of antiproliferative activity against cancer cell lines re

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45

Shan, Wei-Guang, Yuan Wang, Lie-Feng Ma, and Zha-Jun Zhan. "A new pyrrole alkaloid from the mycelium of Inonotus obliquus." Journal of Chemical Research 41, no. 7 (2017): 392–93. http://dx.doi.org/10.3184/174751917x14967701766941.

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Inotopyrrole B, a new pyrrole alkaloid, was isolated from the mycelium of Inonotus obliquus together with two known ones, inotopyrrole and 5-(hydroxymethyl)-1 H-pyrrole-2-carboxaldehyde. The structure of the new compound was established via detailed analyses of the spectroscopic data, in particular, 1D and 2D NMR and HRESIMS.

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46

Zemanová, Ivana, and Renata Gašparová. "SYNTHESIS AND REACTIONS OF NEW DERIVATIVES OF FURO[3,2-b]PYRROLE." Nova Biotechnologica et Chimica 12, no. 2 (2013): 100–107. http://dx.doi.org/10.2478/nbec-2013-0012.

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Abstract Synthesis of methyl 4H-furo[3,2-b]pyrrole-5-carboxylate is taken place in two step synthesis. Vilsmeier-Haack reaction of 4H-furo[3,2-b]pyrrole-5-carboxylate 1 led to methyl 2-formyl-4H-furo[3,2- b]pyrrole-5-carboxylate 4, which served as starting compound for synthesis of furo[3,2-b]pyrrole-2- aldoxime 5 and methyl 2-[(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]-4H-furo[3,2-b]pyrrole-5- carboxylate 7. The hydrazinolysis of 1 was prepared by carbohydrazide 2, which subsequently reacted with aldehydes to form of derivatives 3. Pyrazole derivatives 11 were prepared by the reaction

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Panchal, Dhruv, and Purnima Bhanot. "Activity of a Trisubstituted Pyrrole in Inhibiting Sporozoite Invasion and Blocking Malaria Infection." Antimicrobial Agents and Chemotherapy 54, no. 10 (2010): 4269–74. http://dx.doi.org/10.1128/aac.00420-10.

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ABSTRACT Malaria infection is initiated by Plasmodium sporozoites infecting the liver. Preventing sporozoite infection would block the obligatory first step of the infection and perhaps reduce disease severity. In addition, such an approach would decrease P lasmodium vivax hypnozoite formation and therefore disease relapses. Here we describe the activity of a trisubstituted pyrrole, 4-[2-(4-fluorophenyl)-5-(1-methylpiperidine-4-yl)-1H-pyrrol-3-yl] pyridine, in inhibiting motility, invasion, and consequently infection by P. berghei sporozoites. In tissue culture, the compound was effective with

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48

Boyd, Peter D. W., Ali Hosseini, and Clifton E. F. Rickard. "2,8,12,18-Tetrabutyl-3,7,13,17-tetramethyl-5,15-bis(3-nitrophenyl)porphyrinogen methanol disolvate." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (2006): o2883—o2885. http://dx.doi.org/10.1107/s1600536806022288.

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The title compound, C52H66N6O4·2CH3OH, is a 5,15-diaryloctaalkylporphyrinogen. The molecule is centrosymmetric, with the pyrrole rings adopting a 1,2-alternate arrangement. The methanol molecules are included in the tetrapyrrole cavity through hydrogen bonding and O—H...π interactions. The molecules form chains in the crystal structure via phenyl C—H...π-pyrrole stacking.

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Cheng, Ming-Jen, Ming-Der Wu, Tzong-Huei Lee, Jing-Ru Weng, and Jih-Jung Chen. "A New Pyrrole Compound from Monascus ruber." Chemistry of Natural Compounds 55, no. 6 (2019): 1098–100. http://dx.doi.org/10.1007/s10600-019-02903-4.

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Shi, Ting, Yan-Jing Li, Ze-Min Wang, Yi-Fei Wang, Bo Wang, and Da-Yong Shi. "New Pyrroline Isolated from Antarctic Krill-Derived Actinomycetes Nocardiopsis sp. LX-1 Combining with Molecular Networking." Marine Drugs 21, no. 2 (2023): 127. http://dx.doi.org/10.3390/md21020127.

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Antarctic krill (Euphausia superba) of the Euphausiidae family comprise one of the largest biomasses in the world and play a key role in the Antarctic marine ecosystem. However, the study of E. superba-derived microbes and their secondary metabolites has been limited. Chemical investigation of the secondary metabolites of the actinomycetes Nocardiopsis sp. LX-1 (in the family of Nocardiopsaceae), isolated from E. superba, combined with molecular networking, led to the identification of 16 compounds a–p (purple nodes in the molecular network) and the isolation of one new pyrroline, nocarpyrroli

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