1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure−Antituberculosis Activity Relationship Investigation

Abstract

A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl)-1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.

[5-(4-Bromophenoxymethyl)-1,3,4-thiadiazole-2-thiolato]triphenyltin(IV)

“…For the biological activity of 1,3,4-thiadiazole compounds, see: Oruc et al (2004); Sawhney & Sharma (1993); Srivastava & Pandey (1993). For the biological activity of organotin(IV) compounds, see: Jimenez-Perez et al (2000).…”

Eosin Y Catalyzed Visible-light-promoted One –Pot Facile Synthesis of 1,3,4- Thiadiazole

“…Many drugs containing thiadiazole nucleus are available in the market such as acetazolamide, methazolamide, sulfamethazole, etc. 1,3,4-thiadiazoles are associated with diverse pharmacological activities such as analgesic, 25 antidepressant, anxiolytic, 26 anticonvulsant, 27−28 anti-inflammatory, 29 antimicrobial, 30 anti-tubercular, 31 antitumor, 32 and anti-viral activities. 33 The synthesis of 1,3,4-thiadiazole have not been reported by photooxidation reaction so far.…”

The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5-one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety

“…In our previous papers, we have reported that isoxazolinones (11) possess antifungal activity and 1,3,4-thiadiazoles including compounds, isoxazolinones and hydrazones (7)(8)(9)(26)(27)(28) possess antitubercular and cytotoxic activities. Pyrazolinones (6) which are isosters of isoxazolidinones have also shown antitubercular activity.…”