1219-77-8

Usage

InChI:InChI=1/C12H14N2O2S2/c15-11(16)7-13-8-14(12(17)18-9-13)6-10-4-2-1-3-5-10/h1-5H,6-9H2,(H,15,16)

Upstream product

• 1950-25-0 potassium benzylcarbamodithioate 
• 50-00-0 formaldehyd 
• 56-40-6 glycine 
• 100-46-9 benzylamine 
• 1027986-95-3 Benzyl-hydroxymethyl-dithiocarbamic acid hydroxymethyl ester 
• 75-15-0 carbon disulfide 

Relevant academic research and scientific papers

A versatile approach to hybrid thiadiazine-based molecules by the Ugi four-component reaction

Aiming at developing a versatile method for the generation of hybrid heterocyclic molecules, we describe a sequential approach comprising the formation of carboxy-functionalized 1,3,5-thiadiazines followed by the Ugi reaction with variation of the amino and the isonitrile components. The method enables the generation of structurally diverse molecular hybrids including peptide, lipid, steroidal and sugar moieties linked to the 1,3,5-thiadiazine scaffold.

Novel 1,3,5-thiadiazine-2-thione derivatives containing a hydrazide moiety: Design, synthesis and bioactive evaluation against phytopathogenic fungi in vitro and in vivo

A series of novel 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety were designed, synthesized and evaluated for their antifungal activities against Rhizoctonia solani (Rs), Fusarium graminearum (Fg), Botrytis cinerea (Bc) and Colletotrichum capsici (Cc). The in vitro antifungal bioassays indicated that most of title compounds displayed good selectivity and specificity aganist Rs relative to Fg, Bc and Cc. Strikingly, the title compound N'-(4-chlorophenyl)-2-(5-phenyl-6-thioxo-1,3,5-thiadiazinan-3-yl)acethydrazide (5b) obviously inhibited the Rs growth in vitro with the EC50 value of 0.24 μg/mL, which is approximately 2-folds more effective than the commercialized fungicide carbendazim (0.55 μg/mL). The in vivo anti-Rs effects of title compound 5b were further evaluated on rice leaves with control efficacies of 98.58% at 200 μg/mL and 61.27% at 100 μg/mL. The above researches provide a significant reference for the further structural optimization of 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety as potential fungicides.

Synthesis, in vitro urease inhibitory activity and molecular docking of 3,5-disubstituted thiadiazine-2-thiones

A series of 3,5-disubstituted-tetrahydro-thiadiazine-2-thione (1-16) have been synthesized, characterized by elemental analysis, infrared (IR), UV-visible, 1H NMR, 13C NMR, and MS spectroscopic techniques, and screened against jack bean urease. Among 16 compounds, compounds (1), (2), (3), (4), (6), (7), and (9) demonstrated excellent urease inhibitory activity with IC50 values (9.8?±?0.5, 11.0?±?0.6, 16.0?±?1.5, 17.2?±?0.5, 15.4?±?0.5, 19.7?±?0.4, and 15.8?±?0.2μM), respectively, even better than the standard thiourea (IC50?=?21?±?0.01μM). However, compound (8) shows an almost same level of inhibition (IC50?=?22.9?±?0.3μM), as like standard. In this work, we reported for the first time urease inhibitory activity of thiadiazine thiones and its molecular docking studies.

New prodrug approach for amino acids and amino-acid-like drugs

A series of disubstituted tetrahydro-2H-1,3,5-thiadiazine-2-thione (THTT) derivatives 4a-g were prepared and found to be promising prodrugs for amino acids and similar compounds. The pH profile for the degradation of the THTT derivatives in aqueous buffer solutions was determined using HPLC and was accounted for in terms of specific base-catalyzed reactions. The compounds, however, showed high acid stability. Enzymatic hydrolysis (human serum) of the derivatives offered an advantageous range of t( 1/2 ) values, which may be useful in controlling the onset and the duration of action of drugs.