Synthesis of new 2,5-disubstituted-1,3,4-thiadiazole derivatives and their in vivo anticonvulsant activity

Abstract

A series of 2,5-disubstituted-1,3,4-thiadiazole derivatives were synthesized by the reaction of 3-(2-cyanopropan-2-yl)-N-(5-(piperazine-1-yl)-1,3,4-thiadiazol-2-yl)benzamide with various sulfonyl chlorides and evaluated for their anticonvulsant activity in MES test. Rotorod method was employed to determine the neurotoxicity. The purity of the compounds is confirmed on the basis of their elemental analysis. The structures of all the new compounds are established on the basis of 1H NMR and mass spectral data. Out of fifteen compounds, three were found to be potent anticolvunstants. The same compounds showed no neurotoxicity at the maximum dose administered (100 mg/kg).

Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

“…This simple route to 2-amino 5-substituted-1,3,4-thiadiazole seems to be quite general 18 . In the example shown R may be methyl 18 , norhydnocarpyl 19 , benzyl 20 , cyclopropyl 21 and many others.…”

“…They have known to exhibit diverse biological activities such as in vitro inhibition of cyclooxygenase and 5-lipoxygenase activities 3 . New acylated 5-thio-beta-D-glucopyranosylimino-disusbstituted 1,3,4-thiadiazoles prepared by cycloaddition of the glycosyl isothiocyanate with the reactive intermediates 1-aza-2-azoniaallene hexachloro antimonates, and have been tested in vitro antiviral activity against HIV-1, HIV-2, human cytomegallovirus (HMCV) [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] .…”

Synthesis and Antitumor Activities of Disulfide Derivatives Containing 1,3,4-Thiadiazole Moiety

“…、 抗氧化 [16,20] 、 抗菌 [21～23] 、 抗抑郁 [24,25] 、 抗真菌 [26,27] 、抗癫痫 [28,29] 以及抗炎 [30,31] 等多种生物活 性. 特别是 1,3,4-噻二唑衍生物的"碳氮硫"结构能作 为活性中心螯合生物体内的某些金属离子, 具有较好的 细胞组织通透性, 能够更好地发挥药效.…”

Design, Synthesis and Antiproliferative Evaluation of Novel Disulfides Containing 1,3,4-Thiadiazole Moiety

“…1,3,4-Thiadiazoles are an important class of heterocyclic bioactive compounds with a broad range of biological activities such as antioxidant, 5,6) antibacterial, 7,8) antidepressant, 9,10) antidiabetic, 11,12) antifungal, 13,14) anticonvulsant, 15,16) anti-inflammatory, 17,18) anticholinesterase, 19) antileishmanial, 20) inhibition of human protoporphyrinogen oxidase. 21) In particular, a large number of 1,3,4-thiadiazole derivatives display interesting antitumour activities in vitro and in vivo conditions.…”