77651-26-4

Upstream product

• 55817-67-9 (1-benzyl-3-cyano-4,5-diphenyl-1H-pyrrol-2-yl)carbonohydrazonoyl dicyanide 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 100-46-9 benzylamine 
• 77771-64-3 N-benzyldesylamine 

Downstream Products

• 1221899-15-5 7-benzyl-2-(4-methylphenyl)-5,6-diphenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 1221899-13-3 7-benzyl-2-(4-chlorophenyl)-5,6-diphenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 1221899-16-6 7-benzyl-2-(4-methoxyphenyl)-5,6-diphenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 1221899-12-2 7-benzyl-2-(3-chlorophenyl)-5,6-diphenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 1221899-14-4 7-benzyl-2-(3-methylphenyl)-5,6-diphenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 1242317-66-3 7-benzyl-2-methyl-5,6-diphenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 1354047-23-6 7-benzyl-2-(ethylthio)-5,6-diphenyl-3H-pyrrolo[2,3-d]pyrimidine-4(7H)-one 
• 1354047-26-9 7-benzyl-2-hydrazinyl-5,6-diphenyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one 
• 1354047-29-2 7-benzyl-2-(3,5-dimethyl-1H-pyrazol-1-yl)-5,6-diphenyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one 
• 1354047-34-9 8-benzyl-3-methyl-6,7-diphenyl-1H-pyrrolo[2,3-d]-[1,2,4]triazolo[4,3-a]pyrimidin-5(8H)-one 
• 1354047-20-3 7-benzyl-5,6-diphenyl-2-thioxo-2,3-dihydro-1H-pyrrolo[2,3-d]pyrimidine-4(7H)-one 
• 77651-41-3 C₂₄H₁₇N₃OS 

Relevant academic research and scientific papers

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

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 Kinetic Testing of Tetrahydropyrimidine-2-thione and Pyrrole Derivatives as Inhibitors of the Metallo-β-lactamase from Klebsiella pneumonia and Pseudomonas aeruginosa

Metallo-β-lactamases (MBLs), produced by an increasing number of bacterial pathogens, facilitate the hydrolysis of many commonly used β-lactam antibiotics. There are no clinically useful antagonists against MBLs. Two sets of tetrahydropyrimidine-2-thione and pyrrole derivatives were synthesized and assayed for their inhibitory effects on the catalytic activity of the IMP-1 MBL from Pseudomonas aeruginosa and Klebsiella pneumoniae. Nine compounds tested (1a, 3b, 5c, 6b, 7a, 8a, 11c, 13a, and 16a) showed micromolar inhibition constants (Ki values range from ~20-80μm). Compounds 1c, 2b, and 15a showed only weak inhibition. In silico docking was employed to investigate the binding mode of each enantiomer of the strongest inhibitor, 5c (Ki=19±9μm), as well as 7a (Ki=21±10μm), the strongest inhibitor of the pyrrole series, in the active site of IMP-1.

Synthesis of new pyrroles of potential anti-inflammatory activity

We herein disclose a series of novel pyrrole derivatives 1-4 and pyrrolo[2,3-d]pyrimidine derivatives 6-11 as novel potent anti-inflammatory compounds. The structures were confirmed by IR, 1H-NMR, and MS. Some newly synthesized compounds were e