679809-11-1

Basic information

• Product Name: Benzoyl chloride, 4-(1-pyrrolidinyl)- (9CI)
• Synonyms: Benzoyl chloride, 4-(1-pyrrolidinyl)- (9CI)
• CAS NO: 679809-11-1
• Molecular Formula: C₁₁H₁₂ClNO
• Molecular Weight: 209.67208
• Product Categories: ACIDHALIDE
• Mol File: 679809-11-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoyl chloride, 4-(1-pyrrolidinyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoyl chloride, 4-(1-pyrrolidinyl)- (9CI)(679809-11-1)
• EPA Substance Registry System: Benzoyl chloride, 4-(1-pyrrolidinyl)- (9CI)(679809-11-1)

Safety Data

• Hazardous Substances Data: 679809-11-1(Hazardous Substances Data)

Upstream product

• 22090-27-3 4-(pyrrolidine-1-yl)benzoic acid 
• 129414-26-2 4-pyrrolidin-1-yl-benzoic acid methyl ester 
• 619-45-4 4-methoxycarbonyl aniline 
• 150-13-0 4-amino-benzoic acid 
• 75-44-5 phosgene 
• 4096-21-3 N-phenylpyrrolidine 

Downstream Products

• 22090-27-3 4-(pyrrolidine-1-yl)benzoic acid 
• 1379480-09-7 S-3-oxoprop-1-en-2-yl 4-(pyrrolidin-1-yl)benzothioate 
• 1400093-67-5 2-methyl-8-(4-(pyrrolidin-1-yl)phenyl)chromeno[7,8-d]imidazol-6(1H)-one 
• 1400093-72-2 C₂₁H₂₁N₃O₆ 
• 1400093-66-4 8-(4-(pyrrolidin-1-yl)phenyl)chromeno[7,8-d]imidazol-6(1H)-one 
• 1350722-65-4 5-(2,4-dihydroxy-5-isopropylphenyl)-4-(4-pyrrolidin-1-yl-benzoylamino)isoxazole-3-carboxylic acid ethylamide 

Relevant articles and documents

Discovery of N-(3-(5-((3-acrylamido-4-(morpholine-4-carbonyl)phenyl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4-(tert-butyl)benzamide (CHMFL-BTK-01) as a highly selective irreversible Bruton's tyrosine kinase (BTK) inhibitor

Currently there are several irreversible BTK inhibitors targeting Cys481 residue under preclinical or clinical development. However, most of these inhibitors also targeted other kinases such as BMX, JAK3, and EGFR that bear the highly similar active cysteine residues. Through a structure-based drug design approach, we discovered a highly potent (IC50: 7?nM) irreversible BTK inhibitor compound 9 (CHMFL-BTK-01), which displayed a high selectivity profile in KINOMEscan (S score (35)?=?0.00) among 468 kinases/mutants at the concentration of 1?μM. Compound 9 completely abolished BMX, JAK3 and EGFR's activity. Both X-ray crystal structure and cysteine-serine mutation mediated rescue experiment confirmed 9's irreversible binding mode. 9 also potently inhibited BTK Y223 auto-phosphorylation (EC50: 30?nM), arrested cell cycle in G0/G1 phase and induced apoptosis in U2932 and Pfeiffer cells. We believe these features would make 9 a good pharmacological tool to study the BTK related pathology.

Optimization of a small tropomyosin-related kinase B (TrkB) agonist 7,8-dihydroxyflavone active in mouse models of depression

Structure-activity relationship study shows that the catechol group in 7,8-dihdyroxyflavone, a selective small TrkB receptor agonist, is critical for agonistic activity. To improve the poor pharmacokinetic profiles intrinsic to catechol-containing molecules and to elevate the agonistic effect of the lead compound, we initiated the lead optimization campaign by synthesizing various bioisosteric derivatives. Here we show that the optimized 2-methyl-8-(4′- (pyrrolidin-1-yl)phenyl)chromeno[7,8-d]imidazol-6(1H)-one derivative possesses enhanced TrkB stimulatory activity. Chronic oral administration of this compound significantly reduces the immobility in forced swim test and tail suspension test, two classical antidepressant behavioral animal models, which is accompanied by robust TrkB activation in hippocampus of mouse brain. Further, in vitro ADMET studies demonstrate that this compound possesses the improved features compared to the previous lead compound. Hence, this optimized compound may act as a promising lead candidate for in-depth drug development for treating various neurological disorders including depression.