Thiadiazole—a Promising Structure in Medicinal Chemistry

Abstract

Many compounds containing a five-membered heterocyclic ring display exceptional chemical properties and versatile biological activities. In this Minireview, thiadiazoles are summarized according to their therapeutic potential, highlighting the versatility of this scaffold in medicinal chemistry. The unique properties of thiadiazoles are also discussed in relation to their potential effect on activity. Thiadiazole is a bioisostere of pyrimidine and oxadiazole, and given the prevalence of pyrimidine in nature it is unsurprising that thiadiazoles exhibit significant therapeutic potential. The sulfur atom of the thiadiazole imparts improved liposolubility, and the mesoionic nature of thiadiazoles makes these compounds better able to cross cellular membranes. By summarizing the thiadiazole-containing compounds reported in recent decades, we aim to give a brief introduction to their synthesis and diverse biological activities, such as anti-inflammatory, anticancer, antibacterial, antifungal, antiviral, antiparasitic, anticonvulsant, anticoagulant, antidiabetic, and to show the significant utility of the thiadiazole scaffolds in medicinal chemistry.

A continuous flow synthesis and derivatization of 1,2,4-thiadiazoles

“…[1][2][3][4] The presence of these heteroatoms increases both the membrane permeability as well as the ability to act as versatile hydrogen bond acceptors. Due to the spacial similarity of vinyl groups to ring embedded sulfur atoms thiadiazoles can be considered isosteres of diazines 5,6 adding to their potential to serve as fragments of bioactive structures.…”

“…Due to the spacial similarity of vinyl groups to ring embedded sulfur atoms thiadiazoles can be considered isosteres of diazines 5,6 adding to their potential to serve as fragments of bioactive structures. [7][8][9][10] Thiadiazoles can occur in four distinct regioisomeric forms (1)(2)(3)(4) enriching their structural diversity with respect to local polarization and vector space occupied by both carbon bound substituents R 1 and R 2 ( Figure 1). …”

Badania spektroskopowe efektów podwójnej fluorescencji w wybranym związku z grupy 1,3,4-tiadiazoli w rozpuszczalnikach organicznych oraz roztworach wodnych

“…According to the numerous reports, a broad array of biological activity exhibited by 1,3,4-thiadiazoles results from the presence of thioimine moiety, which constitutes the 5-membered core ring [2,3]. Due to this unique structural feature, 1,3,4-thiadiazoles can act as potential antiproliferative, antifungal, antibacterial, antiinflammatory, or antiviral agents, just to name a few [4][5][6][7][8][9][10][11][12][13].…”

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

“…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] .…”