1303709-11-6

Basic information

• Product Name: 1-[4-methyl-2-((1,1′-biphenyl)-4-yl)thiazol-5-yl]ethanone
• Synonyms: 1-[4-methyl-2-((1,1′-biphenyl)-4-yl)thiazol-5-yl]ethanone
• CAS NO: 1303709-11-6
• Molecular Weight: 293.389
• Mol File: 1303709-11-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-[4-methyl-2-((1,1′-biphenyl)-4-yl)thiazol-5-yl]ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-methyl-2-((1,1′-biphenyl)-4-yl)thiazol-5-yl]ethanone(1303709-11-6)
• EPA Substance Registry System: 1-[4-methyl-2-((1,1′-biphenyl)-4-yl)thiazol-5-yl]ethanone(1303709-11-6)

Safety Data

• Hazardous Substances Data: 1303709-11-6(Hazardous Substances Data)

Upstream product

• 92-92-2 biphenyl-4-carboxylic acid 
• 3815-20-1 biphenyl-4-carboxylic acid amide 
• 13363-50-3 4-phenylthiobenzamide 
• 1694-29-7 3-chloropentane-2,4-dione 
• 3218-36-8 4-Phenylbenzaldehyde 

Downstream Products

• 1537168-43-6 2-{1-[2-([1,1′-biphenyl]-4-yl)-4-methylthiazol-5-yl]-ethylidene}hydrazinecarboximidamide 

Relevant articles and documents

Development of Biphenylthiazoles Exhibiting Improved Pharmacokinetics and Potent Activity against Intracellular Staphylococcus aureus

Exploring the structure-activity relationship (SAR) at the cationic part of arylthiazole antibiotics revealed hydrazine as an active moiety. The main objective of the study is to overcome the inherited toxicity associated with the free hydrazine. A series of hydrocarbon bridges was inserted in between the groups, to separate the two amino groups. Hence, the aminomethylpiperidine-containing analog 16 was identified as a new promising antibacterial agent with efficient antibacterial and pharmacokinetic profiles. Briefly, compound 16 outperformed vancomycin in terms of the antibacterial spectrum against vancomycin-resistant staphylococcal and enterococcal strains with minimum inhibitory concentrations (MICs) ranging from 2 to 4 μg/mL, which is a faster bactericidal mode of action, completely eradicating the high staphylococcal burden within 6-8 h, and it has a unique ability to completely clear intracellular staphylococci. In addition, the initial pharmacokinetic assessment confirmed the high metabolic stability of compound 16 (biological half-life >4 h); it had a good extravascular distribution and maintained a plasma concentration higher than the average MIC value for over 12 h. Moreover, compound 16 significantly reduced MRSA burden in an in vivo MRSA skin infection mouse experiment. These attributes collectively suggest that compound 16 is a good therapeutic candidate for invasive staphylococcal and enterococcal infections. From a mechanistic point of view, compound 16 inhibited undecaprenyl diphosphate phosphatase (UppP) with an IC50value of 29 μM.

Discovery and characterization of potent thiazoles versus methicillin- and vancomycin-resistant Staphylococcus aureus

Methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA) infections are growing global health concerns. Structure-activity relationships of phenylthiazoles as a new antimicrobial class have been addressed. We present 10 thiazole derivatives that exhibit strong activity against 18 clinical strains of MRSA and VRSA with acceptable PK profile. Three derivatives revealed an advantage over vancomycin by rapidly eliminating MRSA growth within 6 h, and no derivatives are toxic to HeLa cells at 11 μg/mL.