6138-01-8

Basic information

• Product Name: 4-amino-N-benzothiazol-2-yl-benzenesulfonamide
• Synonyms: 4-amino-N-benzothiazol-2-yl-benzenesulfonamide
• CAS NO: 6138-01-8
• Molecular Formula: C₁₃H₁₁N₃O₂S₂
• Molecular Weight: 305.3753
• Mol File: 6138-01-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 536.2 °C at 760 mmHg
• Flash Point: 278.1 °C
• Appearance: /
• Density: 1.545 g/cm³
• Vapor Pressure: 1.43E-11mmHg at 25°C
• Refractive Index: 1.756
• CAS DataBase Reference: 4-amino-N-benzothiazol-2-yl-benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-N-benzothiazol-2-yl-benzenesulfonamide(6138-01-8)
• EPA Substance Registry System: 4-amino-N-benzothiazol-2-yl-benzenesulfonamide(6138-01-8)

Safety Data

• Hazardous Substances Data: 6138-01-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H11N3O2S2/c14-9-5-7-10(8-6-9)20(17,18)16-13-15-11-3-1-2-4-12(11)19-13/h1-8H,14H2,(H,15,16)

Upstream product

• 103-85-5 monophenylthiourea 
• 304685-30-1 N-acetyl-sulfanilic acid benzothiazol-2-ylamide 
• 136-95-8 2-amino-benzthiazole 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 326901-74-0 N-(benzo[d]thiazol-2-yl)-4-nitrobenzenesulfonamide 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 2651-14-1 Dimethyl N-(4-Aminophenylsulphonyl)dithiocarbonimidate 
• 137-07-5 2-amino-benzenethiol 
• 121-61-9 p-acetylaminobenzenesulfonamide 

Downstream Products

• 1042676-08-3 C₁₉H₁₄N₄O₄S₂ 
• 74322-02-4 N-benzothiazol-2-yl-4-[2-(2-hydroxy-phenyl)-4-oxo-thiazolidin-3-yl]-benzenesulfonamide 
• 74322-09-1 N-benzothiazol-2-yl-4-[3-chloro-2-(4-nitro-phenyl)-4-oxo-azetidin-1-yl]-benzenesulfonamide 
• 74322-08-0 N-benzothiazol-2-yl-4-[3-chloro-2-(3-nitro-phenyl)-4-oxo-azetidin-1-yl]-benzenesulfonamide 
• 74322-00-2 N-benzothiazol-2-yl-4-[2-(4-nitro-phenyl)-4-oxo-thiazolidin-3-yl]-benzenesulfonamide 
• 74321-99-6 N-benzothiazol-2-yl-4-[2-(3-nitro-phenyl)-4-oxo-thiazolidin-3-yl]-benzenesulfonamide 
• 74322-06-8 N-benzothiazol-2-yl-4-(4-oxo-2-styryl-thiazolidin-3-yl)-benzenesulfonamide 
• 74322-07-9 N-benzothiazol-2-yl-4-(3-chloro-2-oxo-4-phenyl-azetidin-1-yl)-benzenesulfonamide 
• 74321-98-5 N-benzothiazol-2-yl-4-(4-oxo-2-phenyl-thiazolidin-3-yl)-benzenesulfonamide 
• 74321-94-1 N-benzothiazol-2-yl-4-(2,4-dihydroxy-benzylideneamino)-benzenesulfonamide 
• 74321-96-3 N-benzothiazol-2-yl-4-(3-phenyl-allylideneamino)-benzenesulfonamide 
• 74321-92-9 N-benzothiazol-2-yl-4-(2-hydroxy-benzylideneamino)-benzenesulfonamide 
• 74321-95-2 N-benzothiazol-2-yl-4-(4-methoxy-benzylideneamino)-benzenesulfonamide 
• 74321-88-3 N-benzothiazol-2-yl-4-benzylideneamino-benzenesulfonamide 

Relevant articles and documents

The optimization and characterization of functionalized sulfonamides derived from sulfaphenazole against Mycobacterium tuberculosis with reduced CYP 2C9 inhibition

In this study, a series of sulfonamide compounds was designed and synthesized through the systematic optimization of the antibacterial agent sulfaphenazole for the treatment of Mycobacterium tuberculosis (M. tuberculosis). Preliminary results indicate that the 4-aminobenzenesulfonamide moiety plays a key role in maintaining antimycobacterial activity. Compounds 10c, 10d, 10f and 10i through the optimization on phenyl ring at the R2 site on the pyrazole displayed promising antimycobacterial activity paired with low cytotoxicity. In particular, compound 10d displayed good activity (MIC = 5.69 μg/mL) with low inhibition of CYP 2C9 (IC50 > 10 μM), consequently low potential risk of drug-drug interaction. These promising results provide new insight into the combination regimen using sulfonamide as one component for the treatment of M. tuberculosis.

Identification of: N -benzothiazolyl-2-benzenesulfonamides as novel ABCA1 expression upregulators

ATP binding cassette transporter A1 (ABCA1) is a critical transporter that mediates cellular cholesterol efflux from macrophages to apolipoprotein A-I (ApoA-I). Therefore, increasing the expression level of ABCA1 is anti-atherogenic and ABCA1 expression upregulators have become novel choices for atherosclerosis treatment. In this study, a series of N-benzothiazolyl-2-benzenesulfonamides, based on the structure of WY06 discovered in our laboratory, were designed and synthesized as novel ABCA1 expression upregulators. Based on an in vitro ABCA1 upregulatory cell model, ABCA1 upregulation of target compounds was evaluated. Compounds 6c, 6d, and 6i have good upregulated ABCA1 expression activities, with EC50 values of 0.97, 0.37, and 0.41 ΜM, respectively. A preliminary structure-activity relationship is summarized. Replacing the methoxy group on the benzothiazole moiety of WY06 with a fluorine or chlorine atom and exchanging the ester group with a cyano group resulted in more potent ABCA1 upregulating activity. Moreover, compound 6i increased ABCA1 mRNA and protein expression and significantly promoted cholesterol efflux in RAW264.7 cells. In conclusion, N-benzothiazolyl-2-benzenesulfonamides were identified as novel ABCA1 expression upregulators.

For ischemia reperfusion injury of the compound and its preparation method (by machine translation)

The present invention provides a compound of formula (I) compound or its pharmaceutically acceptable salt, solvate, or metabolite, can be useful for treating and/or preventing ischemia reperfusion injury and related disorders, acute respiratory distress s