325850-28-0

Basic information

• Product Name: (4-(3-NITROPHENYL)(2,5-THIAZOLYL))PHENYLAMINE
• Synonyms: (4-(3-NITROPHENYL)(2,5-THIAZOLYL))PHENYLAMINE;4-(3-nitrophenyl)-N-phenyl-1,3-thiazol-2-amine
• CAS NO: 325850-28-0
• Molecular Formula: C₁₅H₁₁N₃O₂S
• Molecular Weight: 297.33
• Mol File: 325850-28-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4-(3-NITROPHENYL)(2,5-THIAZOLYL))PHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-(3-NITROPHENYL)(2,5-THIAZOLYL))PHENYLAMINE(325850-28-0)
• EPA Substance Registry System: (4-(3-NITROPHENYL)(2,5-THIAZOLYL))PHENYLAMINE(325850-28-0)

Safety Data

• Hazardous Substances Data: 325850-28-0(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 103-72-0 phenyl isothiocyanate 
• 121-89-1 3-Nitroacetophenone 
• 92554-40-0 α-tosyloxy-m-nitroacetophenone 
• 103-85-5 monophenylthiourea 
• 2227-64-7 3'-nitro-2-bromoacetophenone 

Relevant articles and documents

2-Aminothiazole Derivatives as Selective Allosteric Modulators of the Protein Kinase CK2. 2. Structure-Based Optimization and Investigation of Effects Specific to the Allosteric Mode of Action

Protein CK2 has gained much interest as an anticancer drug target in the past decade. We had previously described the identification of a new allosteric site on the catalytic α-subunit, along with first small molecule ligands based on the 4-(4-phenylthiazol-2-ylamino)benzoic acid scaffold. In the present work, structure optimizations guided by a binding model led to the identification of the lead compound 2-hydroxy-4-((4-(naphthalen-2-yl)thiazol-2-yl)amino)benzoic acid (27), showing a submicromolar potency against purified CK2α (IC50 = 0.6 μM). Furthermore, 27 induced apoptosis and cell death in 786-O renal cell carcinoma cells (EC50 = 5 μM) and inhibited STAT3 activation even more potently than the ATP-competitive drug candidate CX-4945 (EC50 of 1.6 μM vs 5.3 μM). Notably, the potencies of our allosteric ligands to inhibit CK2 varied depending on the individual substrate. Altogether, the novel allosteric pocket was proved a druggable site, offering an excellent perspective to develop efficient and selective allosteric CK2 inhibitors.

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.

Effect of substituents on the regioselectivity of the reaction of α-tosyloxyketones with thioureas in acidic medium: Access to 2-aminothiazoles and 2-imino-2,3-dihydrothiazoles

Regioselective condensation of α-tosyloxyacetophenones 1 and N-substituted thioureas 2 in acidic medium to give regioisomers 2-aminothiazoles I and 2-imino-2,3-dihydrothiazoles II is largely influenced by the substituents present on 1 and 2. A mechanism,