58756-26-6

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 4-PHENYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is used as a building block for the preparation of pharmaceutical compounds and bioactive molecules due to its diverse biological activities.
Used in Drug Discovery and Development:
ETHYL 4-PHENYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is used as a potential candidate in drug discovery and development because of its anticancer, antifungal, and antibacterial properties.
Used in Organic Synthesis:
ETHYL 4-PHENYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is used as a chemical compound in organic synthesis for creating various molecules.
Used in Medicinal Chemistry:
ETHYL 4-PHENYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is used in medicinal chemistry for the development of new pharmaceutical compounds and bioactive molecules.
ETHYL 4-PHENYL-1,2,3-THIADIAZOLE-5-CARBOXYLATE is commercially available for research and industrial purposes, making it accessible for further exploration and application in these fields.

InChI:InChI=1/C11H10N2O2S/c1-2-15-11(14)10-9(12-13-16-10)8-6-4-3-5-7-8/h3-7H,2H2,1H3

Upstream product

• 58756-33-5 3-phenyl-3-semicarbazono-propionic acid ethyl ester 
• 100138-74-7 C₁₂H₁₅N₃O₃ 
• 29969-65-1 3,3-diethoxy-2-phenyl-propionic acid ethyl ester 
• 17838-69-6 ethyl 3-oxo-2-phenylpropanoate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Downstream Products

• 58756-27-7 4-phenyl-[1,2,3]thiadiazole-5-carboxylic acid hydrazide 
• 78875-63-5 4-phenyl-[1,2,3]thiadiazole-5-carboxylic acid 
• 23806-17-9 ethyl 3,5-diphenylthiophene-2-carboxylate 
• 58756-07-3 (4-phenyl-[1,2,3]thiadiazol-5-yl)-carbamic acid butyl ester 
• 58756-10-8 (4-phenyl-[1,2,3]thiadiazol-5-yl)-carbamic acid isobutyl ester 
• 58756-01-7 (4-phenyl-[1,2,3]thiadiazol-5-yl)-carbamic acid propyl ester 
• 58756-04-0 (4-phenyl-[1,2,3]thiadiazol-5-yl)-carbamic acid isopropyl ester 
• 58755-98-9 5-ethoxycarbonylamino-4-phenyl-1,2,3-thiadiazole 
• 58755-96-7 (4-phenyl-[1,2,3]thiadiazol-5-yl)-carbamic acid methyl ester 
• 58756-28-8 4-phenyl-[1,2,3]thiadiazole-5-carbonyl azide 
• 58756-13-1 (4-phenyl-[1,2,3]thiadiazol-5-yl)-carbamic acid benzyl ester 
• 78875-62-4 (4-Chloro-phenyl)-(4-phenyl-[1,2,3]thiadiazol-5-yl)-methanol 
• 78875-70-4 5-[Chloro-(4-chloro-phenyl)-methyl]-4-phenyl-[1,2,3]thiadiazole 
• 78875-69-1 5-(Chloro-p-tolyl-methyl)-4-phenyl-[1,2,3]thiadiazole 

Relevant academic research and scientific papers

Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes

The rhodium-catalyzed transannulation reaction between 1,2,3-thiadiazoles and alkynes, proceeding via intermediacy of the previously unknown Rh thiavinyl carbene, toward a highly efficient and regioselective synthesis of up to fully substituted thiophenes is described.

1,2,3-Thiadiazole substituted pyrazolones as potent KDR/VEGFR-2 kinase inhibitors

KDR kinase inhibition is considered to play an important role in regulating angiogenesis, which is vital for the survival and proliferation of tumor cells. Recently we disclosed a structure-based kinase inhibitor design strategy which led to the identification of a new class of VEGFR-2/KDR kinase inhibitors bearing heterocyclic substituted pyrazolones as the core template. Instability in a rat S9 preparation and poor iv PK profiles for most of these inhibitors necessitated exploration of new pyrazolones to identify new analogs with improved metabolic stability. Optimization of the heterocyclic moiety led to the identification of the thiadiazole series of pyrazolones (D) as potent VEGFR-2/KDR kinase inhibitors. SAR modifications, kinase selectivity profiling, and structural elements for improved PK properties were explored. Oral bioavailability up to 29% was achieved in the rat. Modeling results based on the Glide XP docking approach supported our postulation regarding the interaction of the lactam segment of the pyrazolones with the hinge region of the KDR kinase.