22090-27-3

Basic information

• Product Name: 4-(1-PYRROLIDINYL)BENZOIC ACID
• Synonyms: OTAVA-BB BB7018780042;RARECHEM AL BE 1489;TIMTEC-BB SBB009596;4-(1-PYRROLIDINYL)BENZOIC ACID;4-PYRROLIDIN-1-YL-BENZOIC ACID;AKOS BB-8746;AKOS B022048;BUTTPARK 99\06-02
• CAS NO: 22090-27-3
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• Product Categories: Acids and Derivatives;Heterocycles;Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 22090-27-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 262-296 °C (D)
• Boiling Point: 376.9 °C at 760 mmHg
• Flash Point: 181.8 °C
• Appearance: /
• Density: 1.221g/cm³
• Vapor Pressure: 2.37E-06mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: 2-8°C
• PKA: 4.94±0.10(Predicted)
• CAS DataBase Reference: 4-(1-PYRROLIDINYL)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1-PYRROLIDINYL)BENZOIC ACID(22090-27-3)
• EPA Substance Registry System: 4-(1-PYRROLIDINYL)BENZOIC ACID(22090-27-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 22090-27-3(Hazardous Substances Data)

Usage

Chemical Properties

Solid

InChI:InChI=1/C11H13NO2/c13-11(14)9-3-5-10(6-4-9)12-7-1-2-8-12/h3-6H,1-2,7-8H2,(H,13,14)

Upstream product

• 22090-26-2 1-(4-bromo-phenyl)-pyrrolidine 
• 150-13-0 4-amino-benzoic acid 
• 619-45-4 4-methoxycarbonyl aniline 
• 129414-26-2 4-pyrrolidin-1-yl-benzoic acid methyl ester 
• 51980-54-2 4-(pyrrolidin-1-yl)benzaldehyde 
• 124-38-9 carbon dioxide 
• 4096-21-3 N-phenylpyrrolidine 
• 679809-11-1 4-(pyrrolidin-1-yl)benzoyl chloride 

Downstream Products

• 617691-17-5 N-(4-formyl-benzyl)-4-pyrrolidin-1-yl-benzamide 
• 617691-16-4 3-{4-[(4-pyrrolidin-1-ylbenzoylamino)methyl]phenyl}acrylic acid ethyl ester 
• 1400093-67-5 2-methyl-8-(4-(pyrrolidin-1-yl)phenyl)chromeno[7,8-d]imidazol-6(1H)-one 
• 1616960-77-0 N-(2-(2-methyl-1H-indol-1-yl)ethyl)-4-(pyrrolidin-1-yl)benzamide 
• 129414-26-2 4-pyrrolidin-1-yl-benzoic acid methyl ester 
• 1247828-74-5 methyl 5-chloro-2-({[4-(pyrrolidin-1-yl)phenyl]carbonyl}amino)benzoate 
• 1247823-96-6 5-chloro-2-({[4-(pyrrolidin-1-yl)phenyl]carbonyl}amino)benzoic acid hydrochloride 

Relevant articles and documents

Convenient Synthesis of p-Aminobenzoic Acids and their Methyl Esters

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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.