1135797-67-9

Basic information

• Product Name: 2-phenyl-4,5-dihydrothiazole-4-carboxylic acid N-(methoxy)methylamide
• Synonyms: 2-phenyl-4,5-dihydrothiazole-4-carboxylic acid N-(methoxy)methylamide
• CAS NO: 1135797-67-9
• Molecular Weight: 250.321
• Mol File: 1135797-67-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-phenyl-4,5-dihydrothiazole-4-carboxylic acid N-(methoxy)methylamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-4,5-dihydrothiazole-4-carboxylic acid N-(methoxy)methylamide(1135797-67-9)
• EPA Substance Registry System: 2-phenyl-4,5-dihydrothiazole-4-carboxylic acid N-(methoxy)methylamide(1135797-67-9)

Safety Data

• Hazardous Substances Data: 1135797-67-9(Hazardous Substances Data)

Upstream product

• 52-90-4 L-Cysteine 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 100-47-0 benzonitrile 
• 93-97-0 benzoic acid anhydride 
• 65-85-0 benzoic acid 
• 19983-15-4 (4R)-2-phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid 
• 1393377-76-8 (2R,2'R)-3,3'-disulfanediylbis(2-azido-N-methoxy-N-methylpropanamide) 
• 1117-97-1 N,0-dimethylhydroxylamine 

Downstream Products

• 1001669-22-2 2-phenylthiazole-4-carboxylic acid N-(methoxy)methylamide 
• 1135797-91-9 (2-phenylthiazol-4-yl)-(3,4,5-trimethoxyphenyl)methanone 
• 1135797-88-4 (3-methoxyphenyl)(2-phenylthiazol-4-yl)methanone 
• 1135797-97-5 1-(2-phenylthiazol-4-yl)heptadecan-1-one 
• 1135797-95-3 (2-fluorophenyl)(2-phenylthiazol-4-yl)methanone 
• 1135797-96-4 (2-phenylthiazol-4-yl)(pyridin-2-yl)methanone 
• 1135797-90-8 (3,4-dimethoxyphenyl)(2-phenylthiazol-4-yl)methanone 
• 1135797-89-5 (2-methoxyphenyl)(2-phenylthiazol-4-yl)methanone 
• 1135797-85-1 phenyl (2-phenylthiazol-4-yl)-methanone 
• 1135797-86-2 (4-methoxyphenyl)(2-phenylthiazol-4-yl)methanone 
• 1135797-93-1 (3,5-dimethoxyphenyl)(2-phenylthiazol-4-yl)methanone 
• 20949-81-9 2-phenyl-thiazole-4-carbaldehyde 
• 1311195-84-2 N-((2-phenylthiazol-4-yl)(3,4,5-trimethoxyphenyl)methylene)cyanamide 
• 1311195-82-0 N-((2-phenylthiazol-4-yl)(3,4,5-trimethoxyphenyl)methylene)cyanamide 

Relevant articles and documents

Design, synthesis, and biological evaluation of stable colchicine binding site tubulin inhibitors as potential anticancer agents

To block the metabolically labile sites of novel tubulin inhibitors targeting the colchicine binding site based on SMART, ABI, and PAT templates, we have designed, synthesized, and biologically tested three focused sets of new derivatives with modifications at the carbonyl linker, the para-position in the C ring of SMART template, and modification of A ring of the PAT template. Structure-activity relationships of these compounds led to the identification of new benzimidazole and imidazo[4,5-c]pyridine-fused ring templates, represented by compounds 4 and 7, respectively, which showed enhanced antitumor activity and substantially improved the metabolic stability in liver microsomes compared to SMART. MOM group replaced TMP C ring and generated a potent analogue 15, which showed comparable potency to the parent SMART compound. Further modification of PAT template yielded another potent analogue 33 with 5-indolyl substituent at A ring.

One-pot synthesis of 2,4-disubstituted thiazoline from β-azido disulfide and carboxylic acid

A concise and efficient one-pot four-step synthesis of 2,4-disubstituted thiazoline via a cascade disulfide bond cleavage/thiocarbonylation/Staudinger reduction/aza-Wittig reaction is established. Treatment of various carboxylic acids with β-azido disulfides under this one-pot procedure obtained the desired thiazolines in good to excellent isolated yields.

Synthesis, formulation and in vitro evaluation of a novel microtubule destabilizer, SMART-100

A novel microtubule destabilizer, substituted methoxybenzoyl-ary-thiazole (SMART)-100, was synthesized, which showed good anticancer activity in HepG2 cells. SMART-100 was able to circumvent multidrug resistance (MDR) and effectively inhibited the growth of cell lines that overexpress P-glycoprotein (P-gp). SMART-100 inhibited P-gp activity, which may be responsible for its ability to overcome MDR. Since SMART-100 is poorly soluble in water, it was formulated in polyethylene-b-poly(d,l-lactide) (PEG-PLA) micelles. The solubility of SMART-100 was increased by more than 1.1×105 folds. SMART-100 loaded PEG-PLA micelles could effectively inhibit HepG2 cell growth and arrest cell cycle progression at G2/M phase, followed by appearance of a sub-G1 phase, which is indicative of cell apoptosis. Increased Caspase-3 activity was also observed when HepG2 cells were treated with SMART-100. The anticancer activity of SMART-100 loaded PEG-PLA micelles was also evaluated on luciferase expressing C4-2-Luc cell lines by IVIS imaging. Our results suggest that SMART-100 has the potential to treat resistant cancers.