3274-63-3Relevant academic research and scientific papers
Pyrrole derivative as well as preparation method and application thereof
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Paragraph 0081; 0089-0093, (2020/09/12)
The invention belongs to the field of medical chemistry, and relates to a pyrrole derivativex as well as a preparation method and application thereof. A compound with a structure shown as a general formula (I), or one or a mixture of more of a tautomer, a
Design, synthesis and molecular docking study of novel pyrrole-based α-amylase and α-glucosidase inhibitors
Jadhav, Nikhil C.,Pahelkar, Akshata R.,Desai, Neha V.,Telvekar, Vikas N.
, p. 2675 - 2691 (2017/10/05)
Abstract: In an effort to design and synthesize a new class of α-glucosidase and α-amylase inhibitors, we have synthesized novel pyrrole based molecules using molecular hybridization approach. These novel analogs were synthesized by the novel methodology developed in our lab which comprises of the multi-component direct synthesis route using hypervalent iodine reagent. The compounds were characterized by infrared, 1H nuclear magnetic resonance (NMR), 13C NMR and Mass Spectroscopy. These compounds were screened for their α-amylase and α- glucosidase activity. They showed a varying degree of inhibition with IC50 values ranging between 0.4 to 4.14 μmol/mL and 0.8 to 4.14 μmol/mL for α-amylase and α-glucosidase respectively. Compounds 3, 7, 12, and 18 showed excellent activity as compared to standard acarbose. This has identified a new class of α-amylase and α-glucosidase inhibitor which can be further developed as antihyperglycemic agents. The molecular docking analysis was carried out to better understand of interaction between α-amylase and α-glucosidase target and inhibitors in this series. We also generated a homology model for human α-glucosidase enzyme and identified the key residues at the binding site. The outcome of the study could be used for the rational design of potent and selective α-amylase and α-glucosidase inhibitors, respectively. Graphical abstract: [InlineMediaObject not available: see fulltext.].
Synthesis of multisubstituted 1H-pyrrole: Selenium-catalyzed reaction of γ-nitro substituted carbonyl compounds and carbon monoxide
Umeda, Rui,Mashino, Tsukasa,Nishiyama, Yutaka
, p. 4395 - 4399 (2014/06/10)
The novel and efficient selenium-catalyzed reductive N-heterocyclization of γ-nitro substituted carbonyl compounds with carbon monoxide has been developed. Various multisubstituted 1H-pyrroles can be easily prepared by this protocol. The one-pot synthesis
Ambivalent role of metal chlorides in ring opening reactions of 2H-azirines: Synthesis of imidazoles, pyrroles and pyrrolinones
Auricchio, Sergio,Truscello, Ada M.,Lauria, Mirvana,Meille, Stefano V.
experimental part, p. 7441 - 7449 (2012/09/22)
2H-Azirines were found to react with imines, enaminones and enaminoesters in the presence of metal salts. Imidazoles, pyrroles and new pyrrolinones derivatives are isolated in good overall yields. The role of metal salts was investigated as they can act as Lewis acids or electron donors. Mechanisms are proposed suggesting that imidazoles arise from addition of azirine to imines via radical or ionic mechanism; pyrroles and pyrrolinones are obtained from azirines with enamino derivatives when the salt acts as a Lewis acid. In the latter case the properties of the metallic compound influence the reaction regioselectivity.
Efficient synthesis of pyrroles and 4,5,6,7-tetrahydroindoles via palladium-catalyzed oxidation of hydroxy-enamines
Aoyagi, Yutaka,Mizusaki, Toshihiko,Shishikura, Masahiro,Komine, Takashi,Yoshinaga, Tokuji,Inaba, Haruko,Ohta, Akihiro,Takeya, Koichi
, p. 8533 - 8538 (2007/10/03)
Facile and one-pot synthetic route of poly-substituted pyrroles and 4-oxo-4,5,6,7-tetrahydroindoles is established, which consists of three steps: (1) palladium-catalyzed oxidation of hydroxy-enamines by using tetrakis(triphenylphosphine)palladium and mesityl bromide oxidation system, (2) intramolecular cyclization, and (3) dehydration.
Versatility of Weinreb amides in the Knorr pyrrole synthesis
Alberola, Angel,Ortega, Alfonso Gonzalez,Sadaba, M. Luisa,Sanudo, Carmen
, p. 6555 - 6566 (2007/10/03)
N-Methoxy-N-methyl-α-enaminocarboxamides were prepared starting from enamines and Weinreb α-aminoamides. Their reaction with oganometallic compounds and subsequent cyclization constitute a versatile alternative in the Knorr pyrrole synthesis.
Facile and efficient synthesis of pyrroles and indoles via palladium-catalyzed oxidation of hydroxy-enamines and -amines
Aoyagi, Yutaka,Mizusaki, Toshihiko,Ohta, Akihiro
, p. 9203 - 9206 (2007/10/03)
The palladium-catalyzed oxidation of hydroxy-enamines, which were obtained by the condensation of β-aminoalcohols and carbonyl compounds, proceeded to give the corresponding polysubstituted pyrroles and 4,5,6,7-tetrahydroindoles in good yields. The treatment of o-(2-hydroxyethyl)aniline with the palladium catalyst also gave indole in 78% yield.
Unusual Michael Reaction of Acyclic 1,3-Dicarbonyl Compounds with Nitro-olefins. A Novel Pyrrole Synthesis
Gomez-Sanchez, Antonio,Stiefel, Berta Marco,Fernandez-Fernandez, Rosario,Pascual, Conrado,Bellanato, Juana
, p. 441 - 447 (2007/10/02)
Acetoacetic esters and pentane-2,4-dione undergo unusual Michael reactions with β-nitrostyrene in methanol-sodium methoxide to form the (2R,3R,2'S,3'S)-bis-(4-acyl-2,3-dihydro-5-methyl-3-phenyl-2)-furylhydroxylamines (5) in high yields.The normal adducts
Base-Induced Cycloaddition of N-(Tosylmethyl)imino Compounds to Michael Acceptors. Synthesis of 2,3,4-Trisubstituted Pyrroles
Houwing, Hendrik A.,van Leusen, Albert M.
, p. 1127 - 1132 (2007/10/02)
A series of N-(tosylmethyl)imino compounds has been prepared, and applied to a new, base induced, one operational synthesis of otherwise more difficulty accesible 2,3,4-trisubstituted pyrroles from electron deficient olefins.This regiospec
