14269-45-5

Basic information

• Product Name: Benzamide, N-(4-phenyl-2-thiazolyl)-
• CAS NO: 14269-45-5
• Molecular Formula: C16H12N2OS
• Molecular Weight: 280.35
• Mol File: 14269-45-5.mol

Chemical Properties

• CAS DataBase Reference: Benzamide, N-(4-phenyl-2-thiazolyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-(4-phenyl-2-thiazolyl)-(14269-45-5)
• EPA Substance Registry System: Benzamide, N-(4-phenyl-2-thiazolyl)-(14269-45-5)

Safety Data

• Hazardous Substances Data: 14269-45-5(Hazardous Substances Data)

Upstream product

• 2010-06-2 2-Amino-4-phenylthiazole 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 65-85-0 benzoic acid 
• 98-86-2 acetophenone 
• 34161-31-4 2-amino-4-phenyl-thiazole hydrobromide 
• 17356-08-0 thiourea 
• 728-84-7 2-bromo-1,3-diphenylpropane-1,3-dione 

Downstream Products

• 64343-56-2 N-(4-phenylthiazole-2-yl)phenylimidoyl chloride 
• 72886-36-3 N-(3-methyl-4-phenylthiazol-2(3H)-ylidene)benzamide 
• 14269-44-4 N-methyl-N-(4-phenyl-thiazol-2-yl)-benzamide 
• 26542-70-1 2-phenyl-5-phenylthiazolo-<3,2-b>-s-triazole 
• 103966-08-1 1-(4-phenylthiazol-2-yl)-5-phenyltetrazole 

Relevant articles and documents

Molecular properties prediction, synthesis, and antimicrobial activity of bis(azolyl)sulfonamidoacetamides

A library of bis(azolyl)sulfonamidoacetamides was prepared by the reaction of azolylsulfonylamines with azolylchloroacetamides in the presence of pyridine/4-(dimethylamino)pyridine (DMAP) under ultrasonication. The reaction proceeded well with DMAP, resulting in a higher yield of the products. The antimicrobial activity of the compounds indicated that N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl)amino}-2-oxoethyl)sulfamoyl]-4-phenylthiazol-2-yl}benzamide (22a), N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl]amino}-2-oxoethyl)sulfamoyl]-4-(4-chlorophenyl)thiazol-2-yl}benzamide (22c), and N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl]amino}-2-oxoethyl)sulfamoyl]-4-(4-chloro-phenyl)-1H-imidazol-2-yl}benzamide (24c) exhibited a low minimal inhibitory concentration (MIC) against Bacillus subtilis, equal to the standard drug, chloramphenicol. Compounds 22c and 24c also showed low MICs against Aspergillus niger, equal to the standard drug, ketoconazole. The molecular properties of the synthesized molecules were studied to identify druglikeness properties of the target compounds. On the basis of molecular properties prediction, 19a, 19b, 20b, 20c, 21a–c, 22b, 22c, and 23a–c can be treated as drug candidates.

Synthesis and antimicrobial activity of bisazolylsulfonyl amines

A variety of bisazolylsulfonyl amines have been prepared from azolylsulfonyl chlorides and azolylsulfonamides and their antimicrobial activity studied. The chloro substituted bisthiazolylsulfonyl amines exhibit pronounced antibacterial activity against B.

2-amino-4-arylthiazole derivatives as anti-giardial agents: Synthesis, biological evaluation and QSAR studies

A series of seven 2-amino-4-arylthiazoles were prepared following Hantzsch's modified method under microwave irradiation. A set of 50 derivatives was obtained and the in vitro activity against Giardia intestinalis was evaluated. The results on the biological activity revealed that, in general, the N-(5-bromo-4-aryl-thiazol-2-yl)-acetamide scaffold showed high bioactivity. In particular, compounds 6e (IC50= 0.39 μM) and 6b (IC50= 0.87 μM) were found to be more potent than the positive control metronidazole. Citoxicity and acute toxicity tests performed showed low toxicity and high selectivity of the most active compounds (6e SI = 139, 6b SI = 52.3). A QSAR analysis was applied to a data set of 37 obtained 2-amino-4-arylthiazoles derivatives and the best model described a strongly correlation between the anti-giardiasic activity and molecular descriptors as E2M, RDF115m, F10, MATS6v, and Hypnotic-80, with high statistical quality. This finding indicates that N-substituted aminothiazole scaffold should be investigated for the development of highly selective anti-giardial agent.

Design and synthesis of thiazole derivatives as potent FabH inhibitors with antibacterial activity

Components of fatty acid biosynthetic pathway have been identified as attractive targets for the development of new antibacterial agents. Compounds of series A (4a-4g) and series B (5a-5g) were synthesized by the formation of an amine bond between aromati

Structure-activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis

A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl) -1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 μM or 0.008 μg/mL in 7H9 media and therapeutic index of nearly ～300. However, 55 is rapidly metabolized by human liver microsomes (t1/2 = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of ～10-5.

Discovery of a series of thiazole derivatives as novel inhibitors of metastatic cancer cell migration and invasion

Effective inhibitors of cancer cell migration and invasion can potentially lead to clinical applications as a therapy to block tumor metastasis, the primary cause of death in cancer patients. To this end, we have designed and synthesized a series of thiazole derivatives that showed potent efficacy against cell migration and invasion in metastatic cancer cells. The most effective compound, 5k, was found to have an IC50 value of 176 nM in the dose-dependent transwell migration assays in MDA-MB-231cells. At a dose of 10 μM, 5k also blocked about 80% of migration in HeLa and A549 cells and 60% of invasion of MDA-MB-231 cells. Importantly, the majority of the derivatives exhibited no apparent cytotoxicity in the clonogenic assays. The low to negligible inhibition of cell proliferation is a desirable property of these antimigration derivatives because they hold promise of low toxicity to healthy cells as potential therapeutic agents. Mechanistic studies analyzing the actin cytoskeleton by microscopy demonstrate that compound 5k substantially reduced cellular f-actin and prevented localization of fascin to actin-rich membrane protrusions. These results suggest that the antimigration activity may result from impaired actin structures in protrusions that are necessary to drive migration.

Design, synthesis and antibacterial activity studies of thiazole derivatives as potent ecKAS III inhibitors

Two series of thiazole derivatives containing amide skeleton were synthesized and developed as potent Escherichia coli β-ketoacyl-(acyl- carrier-protein) synthase III (ecKAS III) inhibitors. All the 24 new synthesized compounds were assayed for antibacterial activity against the respective Gram-negative and Gram-positive bacterial strains, including E. coli, Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus. In which, 10 compounds with broad-spectrum antibacterial activities were further tested for their ecKAS III inhibitory activity. Last, we have successfully found that compound 4e showed both the promising broad antibacterial activity with MIC of 1.56-6.25 μg/mL against the representative bacterial stains, and also processed the most potent ecKAS III inhibitory activity with IC50 of 5.3 μM. In addition, docking simulation also carried out in this study to give a potent prediction binding mode between the small molecule and ecKAS III (PDB code: 1hnj) protein.

PhCOCI-Py/basic alumina as a versatile reagent for benzoylation in solvent-free conditions

A solvent-free procedure using PhCOCl-Py/basic alumina under microwave irradiation has been developed for N-, O- and S-benzoylation.

Substituted 4-Phenyl-2-(phenylcarboxamido)-1,3-thiazole derivatives as antagonists for the adenosine A1 receptor

The synthesis and receptor binding of novel adenosine receptor antagonists is described. We found that non-xanthine 4-phenyl-2-(phenylcarboxamido)-1,3-thiazole derivatives may have high affinity and substantial selectivity for the adenosine A1