Synthesis and antifungal activity of 3,3'-ethylenebis(5-alkyl-1,3,5-thiadiazine-2-thiones)

Abstract

In a search for promising antifungal compounds, nine new 3,3'‐ethylenebis(5‐alkyl‐1,3,5‐thiadiazine‐2‐thiones) were synthesized by the reaction of ethylene diamine, carbon disulfide, formaldehyde, and the appropriate alkyl amine. The title compounds were tested for their antifungal activity in vitro against pathogenic (Trichophyton rubrum and Candida albicans), phytopathogenic (Penicillum expansum, Trichoderma hazianum, and Fasarium oxysporum), and aflatoxin producing (Aspergillus flavus) fungi. These compounds exhibited varied inhibitory effects on growth or sporulation of some tested fungal species.

Thiourea, triazole and thiadiazine compounds and their metal complexes as antifungal agents

“…Antifungal compounds with a 1,3,5-thiadiazine core Compounds containing a 1,3,5-thiadiazine core have been demonstrated to possess antifungal properties. It has become well established that the 1,3,5-thiadiazine-2-thione moiety exhibits antifungal activity through the production of isothiocyanate and dithiocarbamic acids [69][70][71][72][73][74][75][76][77][78] In 2001, Hussein et al [79] reported on several new derivatives of the 1,3,5-thiadiazine-2-thione core. The study was based on introduction of two moieties of 1,3,5-thiadiazine-2-thione through an ethylene bridge and investigation of the antifungal activity of these structural analogues.…”

“…Synthesis of 3-3 0 -ethylenebis(5-alkyl-1,3,5-thiadiazine-2-thiones) (Compounds 69a-i). The data included in this scheme are taken from [79]. 100 28 22 12 -19 16 50 -19 16 --10 25 --14 ---69b 100 --10 7 13 7 50 --10 --7 25 -----9 compounds not only showed no inhibitory effects on growth or sporulation of the tested fungal species, but also appeared to give rise to a dense mycelial growth.…”

“…''-'' no inhibition zone. T.r = Trichophyton rubrum, C.a = Candida albicans, P.e = Penicillium expansum, T.h = Trichoderma hazianum, F.o = Fusarium oxysporum, A.f = Aspergillus flavus.The data included in this table are taken from[79]. Average of three observations.…”

One-pot synthesis and antimicrobial activity of new 4,6-disubstituted-3,4-dihydropyrimidine-2(1H)-thiones

“…Heterocyclic compounds containing thiones have shown a wide range of pharmacological activities, such as antimicrobial [1][2][3][4], antidepressant [5], antitubercular [6], antihistamines [7], anti-HIV [8], and others [9][10][11][12]. Pyrimidine rings, on the other hand, are important substructures in natural products like nucleic acids and vitamin B1 [13,14].…”

Monolayers of the lipid derivatives of isoniazid at the air/water interface and the formation of self-assembled nanostructures in water

“…Some lipid derivatives of INH were synthesized, but their amphiphilicity and self-assembling property were not investigated [9,11]. The derivatives from tetrahydro-2H-1,3,5-thiadiazine-2-thione (THTT) attracted attention because of their potential antimicrobial activity [12][13][14][15], and especially anti-tubercular activity [16]. In this study, we exploited the monolayers of five synthesized lipid derivatives of INH at the air/water interface and revealed the rule of molecular self-assembly in water.…”