20460-58-6

Basic information

• Product Name: 2-Chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-acetamide
• Synonyms: 2-Chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-acetamide;2-chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)ethanamide;IVK/0028655
• CAS NO: 20460-58-6
• Molecular Formula: C₁₀H₈ClN₃OS
• Molecular Weight: 253.70802
• Mol File: 20460-58-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: 218-220 °C
• Appearance: /
• Density: 1.448±0.06 g/cm3(Predicted)
• PKA: 7.22±0.50(Predicted)
• CAS DataBase Reference: 2-Chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-acetamide(20460-58-6)
• EPA Substance Registry System: 2-Chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-acetamide(20460-58-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 20460-58-6(Hazardous Substances Data)

Upstream product

• 2002-03-1 2-amino-5-phenyl-1,3,4-thiadiazole 
• 79-04-9 chloroacetyl chloride 
• 94794-26-0 (2E)-2-benzylidenehydrazinecarbothioamide 
• 65-85-0 benzoic acid 
• 100-52-7 benzaldehyde 
• 5351-66-6 C₈H₉N₃OS 

Downstream Products

• 111750-54-0 N,N-diethyl-glycine 5-phenyl-[1,3,4]thiadiazol-2-ylamide 
• 313670-35-8 C₁₄H₁₆N₄O₂S 
• 857261-67-7 C₁₈H₂₆N₄OS 
• 857261-66-6 C₁₈H₂₆N₄OS 
• 89335-27-3 5-benzylidene-2-[{5-phenyl-[1,3,4]-thiadiazol-2-yl}imino]-1,3-thiazolidin-4-one 
• 1248828-34-3 2-[{5-phenyl-[1,3,4]-thiadiazol-2-yl}imino]-5-(3,4-dimethoxybenzylidene)-1,3-thiazolidin-4-one 
• 89335-17-1 2-[{5-phenyl-[1,3,4]-thiadiazol-2-yl}imino]-1,3-thiazolidin-4-one 

Relevant articles and documents

Synthesis and Biological Evaluation of Oxadiazole Clubbed Thiadiazole Derivatives as Antimicrobial Agents

A series of 1,3,4-oxadiazole clubbed 1,3,4-thiadiazole derivatives were synthesized and assessed in vitro for their activity as antimicrobial agents. The target compounds 2-(5-(substituted aryl)-1, 3, 4-oxadiazol-2-ylthio)-N-(5-(substituted aryl)-1, 3, 4-thiadiazol-2-yl) acetamides (5a-5s) were synthesized using a basic condensation reaction between 5-(substituted aryl)-1,3,4-oxadiazole-2-thiol and 2-chloro-N-(5-(substituted aryl)-1,3,4-thiadiazol-2-yl)acetamide in presence of K2CO3 as a scavenging agent and acetone as reaction solvent. The titled compounds synthesized here, exhibited excellent to moderate antimicrobial activity against a broad panel of antibacterial strains of Gram-positive and Gram-negative bacteria and fungi.

Benzoxazole/benzothiazole-derived VEGFR-2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluations

A novel series of benzoxazole/benzothiazole derivatives 4a–c–11a–e were designed, synthesized, and evaluated for anticancer activity against HepG2, HCT-116, and MCF-7 cells. HCT-116 was the most sensitive cell line to the influence of the new derivatives. In particular, compound 4c was found to be the most potent derivative against HepG2, HCT-116, and MCF-7 cells, with IC50 values = 9.45 ± 0.8, 5.76 ± 0.4, and 7.36 ± 0.5 μM, respectively. Compounds 4b, 9f, and 9c showed the highest anticancer activities against HepG2 cells with IC50 values of 9.97 ± 0.8, 9.99 ± 0.8, and 11.02 ± 1.0 μM, respectively, HCT-116 cells with IC50 values of 6.99 ± 0.5, 7.44 ± 0.4, and 8.15 ± 0.8 μM, respectively, and MCF-7 cells with IC50 values of 7.89 ± 0.7, 8.24 ± 0.7, and 9.32 ± 0.7 μM, respectively, in comparison with sorafenib as reference drug with IC50 values of 9.18 ± 0.6, 5.47 ± 0.3, and 7.26 ± 0.3 μM, respectively. The most active compounds 4a–c, 9b,c,e,f,h, and 11c,e were further evaluated for their VEGFR-2 inhibition. Compounds 4c and 4b potently inhibited VEGFR-2 at IC50 values of 0.12 ± 0.01 and 0.13 ± 0.02 μM, respectively, which are nearly equipotent to the sorafenib IC50 value (0.10 ± 0.02 μM). Furthermore, molecular docking studies were performed for all synthesized compounds to assess their binding pattern and affinity toward the VEGFR-2 active site.

COMPOUNDS FOR MODULATING AQUAPORINS

The invention relates to compounds of formula (I) pharmaceutical compositions thereof and methods for modulating aquaporin 9.