134812-30-9

Basic information

• Product Name: N-[4-(3-AMinophenyl)-2-thiazolyl]acetaMide
• Synonyms: N-[4-(3-AMinophenyl)-2-thiazolyl]acetaMide;N-(4-(3-Aminophenyl)thiazol-2-yl)acetamide
• CAS NO: 134812-30-9
• Molecular Formula: C₁₁H₁₁N₃OS
• Molecular Weight: 233.28954
• Mol File: 134812-30-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-[4-(3-AMinophenyl)-2-thiazolyl]acetaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-(3-AMinophenyl)-2-thiazolyl]acetaMide(134812-30-9)
• EPA Substance Registry System: N-[4-(3-AMinophenyl)-2-thiazolyl]acetaMide(134812-30-9)

Safety Data

• Hazardous Substances Data: 134812-30-9(Hazardous Substances Data)

Upstream product

• 15473-81-1 3'-amino-2-bromoacetophenone hydrobromide 
• 591-08-2 acetylthiourea 
• 53173-92-5 N-(4-(3'-nitrophenyl)thiazol-2-yl)acetamide 
• 99-03-6 1-(3-aminophenyl)ethanone 
• 72801-78-6 1-(3-formylaminophenyl)ethanone 
• 2227-64-7 3'-nitro-2-bromoacetophenone 
• 121-89-1 3-Nitroacetophenone 

Downstream Products

• 1609402-34-7 N-(4-(3-(phenylsulfonamido)phenyl)thiazol-2-yl)acetamide 
• 1609402-27-8 N-(4-(3-((4-methylphenyl)sulfonamido)phenyl)thiazol-2-yl)acetamide 
• 1609402-09-6 N-(4-(3-(naphthalene-2-sulfonamido)phenyl)thiazol-2-yl)acetamide 

Relevant articles and documents

Structure activity relationship and optimization of N-(3-(2-aminothiazol-4-yl)aryl)benzenesulfonamides as anti-cancer compounds against sensitive and resistant cells

We recently described a new family of bioactive molecules with interesting anti-cancer activities: the N-(4-(3-aminophenyl)thiazol-2-yl)acetamides. The lead compound of the series (1) displays significant anti-proliferative and cytotoxic activities against a panel of cancer cell lines, either sensitive or resistant to standard treatments. This molecule also shows a good pharmacological profile and high in vivo potency towards mice xenografts, without signs of toxicity on the animals. In the present article, we disclose the structure-activity relationships of this lead compound, which have provided clear information about the replacement of the acetamide function and the substitution pattern of the benzenesulfonamide ring. An improved high-yielding synthetic procedure towards these compounds has also been developed. Our drug design resulted in potency enhancement of 1, our new optimized lead compound being 19. These findings are of great interest to further improve this scaffold for the development of future clinical candidates.

SUBSTITUTED HYDROPHOBIC BENZENE SULFONAMIDE THIAZOLE COMPOUNDS FOR USE IN TREATING CANCER

The present invention relates to compound of general formula (I) R1 is selected from H, aryl and alkyl, R2 is selected from H, alkyl, aryl and CO-R6; R3 is selected from H, halogen, alkyl, alkenyl, alkynyl, aryl, NHR7, NR7R8, OR7 and SR7; R4 is selected from(C6-C12) alkyl, (C2-C12) alkenyl, (C2-C12) alkynyl and (C6-C10) aryl, R5 represents H, R6, aryl, OH, OR6, O-aryl, SH, SR6, S-aryl, CN, NO2, CF3, COOR6, SO2NR6R7, CONR6R7, NH2, NHR6, NH-aryl, NR6R7, NHCOR6 or aminoacyl; R6 is alkyl optionally substituted with halogen, OH, SH, NH2, O-alkyl, S-alkyl, NH- alkyl or NH-di(alkyl); R7 and R8 identical or different are H or alkyl optionally substituted with halogen, OH, SH, NH2, O-alkyl, S-alkyl, NH-alkyl or NH-di (alkyl), their pharmaceutically acceptable salts and/or isomers, tautomers, solvates or isotopic variations thereof. The compounds are useful for the treatment of cancers.

NEW BENZENE SULFONAMIDE THIAZOLE COMPOUNDS

The present invention relates to compound of general formula (1) wherein R1 represents C6-C10 aryl comprising one or two fused rings, wherein from 2 to 5 carbon atoms may be replaced with a heteroatom selected from O, S and NR6, and eventually substituted with from 5 to 11 substituants selected from R6, halo, CN, NO2, CF3, OCF3, COOR6, OCOR6, SO2NR6R7, CONR6R7, NR6R7, NR6COR7, (CH2)P- NR6R7, (CH2)P- OR6 and (CH2)PSR6, as well as, if appropriate, their pharmaceutically acceptable salts and/or isomers, tautomers, solvates or isotopic variations thereof. The compounds are useful for the treatment of cancers.