77771-64-3Relevant articles and documents
Structure-activity relationship study and optimisation of 2-aminopyrrole-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile as a broad spectrum metallo-β-lactamase inhibitor
McGeary, Ross P.,Tan, Daniel T.C.,Selleck, Christopher,Monteiro Pedroso, Marcelo,Sidjabat, Hanna E.,Schenk, Gerhard
, p. 351 - 364 (2017/06/19)
A SAR study on derivatives of 2-amino-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile 5a revealed that the 3-carbonitrile group, vicinal 4,5-diphenyl and N-benzyl side chains of the pyrrole are important for the inhibitory potencies of these compounds against members representing the three main subclasses of metallo-β-lactamases (MBLs), i.e. IMP-1 (representing the B1 subgroup), CphA (B2) and AIM-1 (B3). Coupling of 5a with a series of acyl chlorides and anhydrides led to the discovery of two N-acylamide derivatives, 10 and 11, as the two most potent IMP-1 inhibitors in this series. However, these compounds are less effective towards CphA and AIM-1. The N-benzoyl derivative of 5a retained potent in vitro activity against each of MBLs tested (with inhibition constants in the low μM range). Importantly, this compound also significantly enhanced the sensitivity of IMP-1, CphA- or AIM-1-producing cell cultures towards meropenem. This compound presents a promising starting point for the development of a universal MBL inhibitor, targeting members of each of the major subgroups of this family of enzymes.
Synthesis and rearrangements of 7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]-and 7h-pyrrolo[3,2-e][1,2,4]triazolo[4,3-c]pyrimidines
Vorob'ev,Kurbatov,Krasnikov,Mezheritskii,Usova
, p. 1492 - 1497 (2007/10/03)
7H-Pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines were synthesized by the reactions of 2-ethoxymethyleneamino-1H-pyrrole-3-carbonitriles with acid hydrazides and by the reactions of aminoiminopyrimidines (prepared based on the above-mentioned carbonitriles) with acid chlorides.
CYCLOADDITIONS OF 1-SUBSTITUTED CIS- AND TRANS-2,3-DIPHENYLAZIRIDINES VIA AZOMETHINE YLIDES
Huisgen, Rolf,Matsumoto, Kiyoshi,Ross, Carl Heinz
, p. 1131 - 1136 (2007/10/02)
1-Benzyl-cis- and -trans-2,3-diphenylaziridines combine at 110 deg C with olefinic dipolarophiles to produce pyrrolidine derivatives in high yields.Stereospecific conrotation for the ring opening of the aziridines to azomethine ylides was deduced from the structure of the cycloadducts.The rate contstants of adduct formation with diethyl fumarate do not depend on the concentration of the dipolarophile.In contrast, ethyl cis- and trans-2,3-diphenylaziridine-1-carboxylate produce with dimethyl fumarate at 145 deg C the same mixture of diastereomeric pyrrolidines both of which are derived from the exo, endo- diphenyl substituted azomethine ylide.