155289-31-9

Basic information

• Product Name: 2-amino-N-{4-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]butyl}benzamide
• Synonyms: benzamide, 2-amino-N-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]-
• CAS NO: 155289-31-9
• Molecular Formula: C₂₂H₂₇N₅OS
• Molecular Weight: 409.5477
• Mol File: 155289-31-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 598.1°C at 760 mmHg
• Flash Point: 315.5°C
• Density: 1.251g/cm³
• Vapor Pressure: 2.88E-14mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: 2-amino-N-{4-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]butyl}benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-N-{4-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]butyl}benzamide(155289-31-9)
• EPA Substance Registry System: 2-amino-N-{4-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]butyl}benzamide(155289-31-9)

Safety Data

• Hazardous Substances Data: 155289-31-9(Hazardous Substances Data)

Usage

Structural Components

Amino Group: NH2
Benzamide Group: C6H5CONH-
Piperazinyl Group: C4H8N2 (from piperazine)
Butyl Chain: C4H9-
Benzothiazole Ring: C7H4NS

Functional Groups

Amino group, benzamide group, piperazinyl group

Linking Bonds

Butyl chain linking amino group, benzamide group, and piperazinyl group

Biological Activities

Anti-cancer
Anti-inflammatory
Antimicrobial
Potential central nervous system agent (due to presence of piperazine ring)

Potential Pharmaceutical Applications

Pharmacological activities make it a target for further research and development in pharmaceuticals.

Upstream product

• 118-48-9 isatoic anhydride 
• 105981-34-8 1-(4-aminobutyl)-4-(1,2-benzisothiazol-3-yl)piperazine 

Relevant articles and documents

Structure-activity relationships of a series of substituted benzamides: Potent D2/5-HT2 antagonists and 5-HT1a agonists as neuroleptic agents

A series of substituted (4-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)butyl)benzamide derivatives was prepared and evaluated as potential atypical antipsychotic agents. The target compounds were readily prepared from their benzoyl chloride, benzoic acid, or isatoic anhydride precursors, and they were evaluated in vitro for their ability to bind to dopamine D2, serotonin 5-HT2, and serotonin 5-HT1a receptors. To assess the potential antipsychotic activity of these compounds, we investigated their ability to inhibit the apomorphine-induced climbing response in mice. Selected compounds were evaluated further to determine their side-effect potentials. Structure-activity relationships of both mono- and polysubstituted benzamides are discussed herein. While several analogues had potent in vitro and in vivo activities indicative of potential atypical antipsychotic activity, anthranilamide 77 (1192U90) demonstrated a superior pharmacological profile. As a result of this investigation, 1192U90 (2-amino-N-(4-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)butyl)benzamide hydrochloride) was selected for further evaluation and is currently in phase I clinical trials as a potential atypical antipsychotic agent.