85103-36-2

Upstream product

• 121-92-6 3-nitrobenzoic acid 
• 833-47-6 5-(3-nitrophenyl)-1,3,4-thiadiazol-2-amine 
• 88541-06-4 2-Chloro-5-(3-nitrophenyl)-1,3,4-thiadiazole 
• 618-95-1 methyl 3-nitrobenzoate 
• 618-94-0 3-nitrobenzoic acid hydrazide 

Downstream Products

• 1374831-11-4 C₁₅H₆F₃N₅O₂S₃ 
• 207236-14-4 2-ethylsulfanyl-5-(3-nitro-phenyl)-[1,3,4]thiadiazole 
• 1041361-29-8 C₁₂H₁₃N₃O₂S₃ 
• 1041361-47-0 C₁₂H₁₃N₃O₄S₃ 
• 21125-34-8 2-methylsulfanyl-5-(3-nitro-phenyl)-[1,3,4]thiadiazole 

Relevant academic research and scientific papers

Azolylthioacetamides as a potent scaffold for the development of metallo-β-lactamase inhibitors

In an effort to develop new inhibitors of metallo-β-lactamases (MβLs), twenty-eight azolylthioacetamides were synthesized and assayed against MβLs. The obtained benzimidazolyl and benzioxazolyl substituted 1–19 specifically inhibited the enzyme ImiS, and 10 was found to be the most potent inhibitor of ImiS with an IC50 value of 15 nM. The nitrobenzimidazolyl substituted 20–28 specifically inhibited NDM-1, with 27 being the most potent inhibitor with an IC50 value of 170 nM. Further studies with 10, 11, and 27 revealed a mixed inhibition mode with competitive and uncompetitive inhibition constants in a similar range as the IC50 values. These inhibitors resulted in a 2–4-fold decrease in imipenem MIC values using E. coli cells producing ImiS or NDM-1. While the source of uncompetitive (possibly allosteric) inhibition remains unclear, docking studies indicate that 10 and 11 may interact orthosterically with Zn2 in the active site of CphA, while 27 could bridge the two Zn(II) ions in the active site of NDM-1 via its nitro group.

Development of 3,5-Dinitrobenzylsulfanyl-1,3,4-oxadiazoles and Thiadiazoles as Selective Antitubercular Agents Active Against Replicating and Nonreplicating Mycobacterium tuberculosis

Herein, we report the discovery and structure-activity relationships of 5-substituted-2-[(3,5-dinitrobenzyl)sulfanyl]-1,3,4-oxadiazoles and 1,3,4-thiadiazoles as a new class of antituberculosis agents. The majority of these compounds exhibited outstanding in vitro activity against Mycobacterium tuberculosis CNCTC My 331/88 and six multidrug-resistant clinically isolated strains of M. tuberculosis, with minimum inhibitory concentration values as low as 0.03 μM (0.011-0.026 μg/mL). The investigated compounds had a highly selective antimycobacterial effect because they showed no activity against the other bacteria or fungi tested in this study. Furthermore, the investigated compounds exhibited low in vitro toxicities in four proliferating mammalian cell lines and in isolated primary human hepatocytes. Several in vitro genotoxicity assays indicated that the selected compounds have no mutagenic activity. The oxadiazole and thiadiazole derivatives with the most favorable activity/toxicity profiles also showed potency comparable to that of rifampicin against the nonreplicating streptomycin-starved M. tuberculosis 18b-Lux strain, and therefore, these derivatives, are of particular interest.

Synthesis and antifungal activity of 2-aryl-1,3,4-thiadiazole-5-sulphides, sulphoxides and sulphones

2-Aryl-1,3,4-thiadiazole-5-sulphides, sulphoxides and sulphones were synthesized and tested against a variety of fungal strains, Miconazole and fluconazole were used as reference drugs. The most active compounds against Candida albicans, Candida spp., Cryptococcus neoformans and Aspergillus niger were 2-(1-methyl-5-nitro-2-imidazolyl)-5-methylsulphonyl-1 ,3,4-thiadiazole (8h) and 2-(5-nitro-2-furyl)-5-methylsulphonyl-1,3,4-thiadiazole (8f). Our results showed that compounds 8h and 8f were several times more active than fluconazole in most fungal strains.