Synthesis of New Phosphorylated 1,2,4-Triazole-3-thiones. N,S-Functionalization Methods

Structures of a Phosphoryl Derivative of 4-Allyl-2,4-dihydro-3H-1,2,4-triazole-3-thione: An Illustrative Example of Conformational Polymorphism

“…Bulk material (compound 1) was obtained by heterocyclization of the corresponding diphenylphosphorylacetyl thiosemicarbazide by a synthetic method recently developed by some of us [9,15]. Single crystals of first polymorphic modification (1a) suitable for X ray diffraction were obtained upon cooling a hot saturated solution in dimethyl forma mide.…”

“…The title compound of this paper (Scheme 1), N-allyl-2,4-dihydro-3H-1,2,4-triazole 3-thione (1), falls into both categories described above. The synthesis of 1 was recently reported by some of us [9], but its crystal structure was unknown. The molecule is confor mationally flexible and contains fragments that can participate in strong hydrogen bonds It is important that 1 is built from moieties that are frequently used in pharmaceutica applications.…”

Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

“…Treatment of oxadiazole thione 10a with hydrazine hydrate gave 4-amino-triazolethione (11a) which on reacting with various aldehydes gave the Schiff bases of triazolethiones 67a-d. The synthesis of 1,3,4-trisubstituted triazolethiones 69a-d was carried out from the reaction of triazolethiones 67a-d with (2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate (68) in good yields (Scheme 17) [30]. The synthesized compounds were screened for their cytotoxic activity against human malignant cell lines (MCF-7 and Bel-7402).…”

“…In vitro screening of anticancer activity against three different cell lines, i.e., human hepatocellular carcinoma (Hep3B), human breast adenocarcinoma (MCF7), and human cervical carcinoma (HeLa), towards triazolethione and triazolothiadiazines showed that the nature of the long-chain on third position affected the potency of these drugs. Besides, fused triazolothiadiazines 141a-d were found to be potential anticancer agents [68]. The cyclization reaction of longer alkenyl/hydroxyl alkenyl acid hydrazides 9h-k CS 2 /KOH followed by treatment with hydrazine hydrate yielded the corresponding 4-amino-3-substituted-1H-1,2,4-triazole-5(4H)-thiones 11k-n. 1,2,4-Triazolothiadiazines 141a-d were directly obtained from the reaction of amino triazolethiones 11k-n with phenacyl bromide in 62-90% yields (Scheme 38).…”

“…In vitro screening of anticancer activity against three different cell lines, i.e., human hepatocellular carcinoma (Hep3B), human breast adenocarcinoma (MCF7), and human cervical carcinoma (HeLa), towards triazolethione and triazolothiadiazines showed that the nature of the long-chain on third position affected the potency of these drugs. Besides, fused triazolothiadiazines 141a-d were found to be potential anticancer agents [68].…”