5319-77-7

Usage

Uses

Used in Pharmaceutical Synthesis:
2-AMINO-5-(METHYLTHIO)-1,3,4-THIADIAZOLE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. One such application is in the synthesis of 9-methylthio-7,7-dioxo-7,7a-dihydro-5-oxo-7λ6,10-dithia-8,11-diaza-cyclopenta[b] phenantren-6-one by reacting with 4-chloro-2-oxo-2H-chromene-3-sulfonyl chloride. 2-AMINO-5-(METHYLTHIO)-1,3,4-THIADIAZOLE may have potential therapeutic applications, contributing to the development of new drugs and treatments in the pharmaceutical industry.

InChI:InChI=1/C3H5N3S2/c1-7-3-6-5-2(4)8-3/h1H3,(H2,4,5)

Upstream product

• 861564-16-1 (bis-methylsulfanyl-methylene)-thiosemicarbazide 
• 871883-24-8 (amino-methylsulfanyl-methylene)-dithiocarbazic acid methyl ester 
• 2349-67-9 2-Amino-5-mercapto-1,3,4-thiadiazole 
• 74-88-4 methyl iodide 
• 2349-67-9 5-amino-2,3-dihydro-1,3,4-thiadiazole-2-thione 
• 74-93-1 methylthiol 
• 74-83-9 methyl bromide 
• 74-87-3 methylene chloride 
• 556-64-9 methyl thiocyanate 
• 79-19-6 thiosemicarbazide 
• 77-78-1 dimethyl sulfate 
• 91679-53-7 1-thiocarbamoyl-S-methyl-iso thiosemicarbazide 

Downstream Products

• 7653-71-6 4-acetylamino-N-(5-methylsulfanyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide 
• 1408325-08-5 C₂₅H₃₃N₃OS₃ 
• 26861-58-5 (5-methylsulfanyl-[1,3,4]thiadiazol-2-yl)-carbamic acid phenyl ester 
• 97109-46-1 2-bromo-5-(methylthio)-1,3,4-thiadiazole 
• 501921-75-1 C₂₀H₁₅ClN₄O₂S₂ 
• 7653-73-8 N-(5-methylsulfanyl-[1,3,4]thiadiazol-2-yl)-4-nitro-benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis and Bioactivity Evaluation of Novel Thiochroman-4-One Derivatives Incorporating Carboxamide and 1, 3, 4-Thiadiazole Thioether Moieties

A series of novel thiochroman-4-one derivatives incorporating carboxamide and 1, 3, 4-thiadiazole thioether moieties were synthesized. Bioassay results indicated that the EC50 values of compound 6-chloro-N-(5-(methylthio)-1, 3, 4-thiadiazol-2-yl)-4-oxothiochromane-2-carboxamide (5a) against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. Citri (Xac) were 24 and 30 μg/mL, respectively, which were even better than those of bismerthiazol and thiadiazole copper. Meanwhile, compound 6-methyl-4-oxo-N-(5-(propylthio)-1, 3, 4-thiadiazol-2-yl)thiochromane-2-carboxamide (5m) showed a better antifungal activity against Botrytis cinerea (B. cinerea), with an inhibition rate of 69%, than carbendazim. As far as we know, this is the first report on the antibacterial and antifungal activities of this series of novel thiochroman-4-one derivatives incorporating carboxamide and 1, 3, 4-thiadiazole thioether moieties.

Design and development of 1,3,4-thiadiazole based potent new nano-fungicides

Being the important organic reaction intermediates and biological scaffolds, a series of 2-alkyl/aralkyl/heterocyclyl sulfanyl-5-amino/methyl-1,3,4-thiadiazoles have been synthesized by suitable synthetic route and characterized by analytical and spectral data. The evaluation of these compounds for their bioefficacy against two phyto-pathogenic fungi revealed their fungicidal potency against Rhizoctonia bataticola (ED50 values, 3.9–300.4 μg/mL) and Rhizoctonia solani (ED50 values, 4.2–228.5 μg/mL). To further augment their fungicidal efficacy, the potent five fungicidal compounds were nano-sized. The protocol for preparing 1,3,4-thiadiazole based nano-fungicide employing polyethylene glycol was developed and standardized. Characterization of nano-forms of 1,3,4-thiadiazole derivatives by particle size analyzer and electron microscopy (TEM) techniques confirmed the 100 nm average particle sizes of all nano-fungicides. The 2–4 times higher fungicidal activity was observed with nano-forms than the corresponding conventional sized 1,3,4-thiadiazole derivatives against phytopathogenic fungi, namely, Rhizoctonia solani and R. bataticola.

Containing 1, 3, 4 - thiadiazole thioether (sulfone) of 2 - (trifluoromethyl) benzamide derivatives, their preparation and use

The invention discloses a containing 1, 3, 4 - thiadiazole thioether (sulfone) of 2 - (trifluoromethyl) benzamide derivatives, their preparation and application, its general formula as follows, wherein: R1 Is methyl, ethyl, 2 - chloroethyl, 2 - fluoro ethyl, 2 - bromo ethyl, propyl, butyl, pentyl, 4 - cyano-benzyl, 4 - benzylic, 2 - fluorobenzyl, cyanomethyl, 2 - cyanoethyl, 3 - cyano-propyl, ; X is S or - S (O)2 -. The invention can control the south-knot nematode and rice [...], tobacco bacterial wilt and citrus canker composite infection.

Design, synthesis and anti-bacterial evaluation of novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety

Novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety were prepared and evaluated for their anti-bacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac) by performing a turbidimetre test. The products were structurally characterised by IR, 1H NMR, 13C NMR, 19F NMR and HRMS. Anti-bacterial testing showed that most of the evaluated compounds (6a-6s) exhibited excellent activity (≥74.19%) against Xoo at a concentration of 200?μg/mL, with 50% effective concentration (EC50) values ranging from 12.21 to 67.20?μg/mL, which were superior to the commercial antibacterial agent bismerthiazol (92.23?μg/mL). Among them, compound 2-((2-chloro-1H-indol-3-yl)methylene)-N-(5-((2-chlorobenzyl)thio)-1,3,4-thiadiazol-2-yl)hydrazine-1-carboxamide (6b) demonstrated good inhibitory activity against Xac (89.46% at 200?μg/mL) and Xoo (EC50 = 18.28?μg/mL); compound 2-((2-chloro-1H-indol-3-yl)methylene)-N-(5-((4-methoxybenzyl)thio)-1,3,4-thiadiazol-2-yl)hydrazine-1-carboxamide (6g) displayed excellent activity against Xoo with EC50 value of 12.21?μg/mL.

Synthesis and in vitro evaluation of west nile virus protease inhibitors based on the 1,3,4,5-tetrasubstituted 1H-Pyrrol-2(5H)-one scaffold

West Nile virus (WNV), a member of the Flaviviridae family, is a mosquito-borne pathogen that causes a large number of human infections each year. There are currently no vaccines or antiviral therapies available for human use against WNV. Therefore, efforts to develop new chemotherapeutics against this virus are highly desired. In this study, a WNV NS2B-NS3 protease inhibitor with a 1,3,4,5-tetrasubstituted 1H-pyrrol-2(5H)-one scaffold was identified by screening a small library of nonpeptidic compounds. Optimization of this initial hit by the synthesis and screening of a focused library of compounds with this scaffold led to the identification of a novel uncompetitive inhibitor ((-)-1a16, IC50=2.2±0.7μM) of the WNV NS2B-NS3 protease. Molecular docking of the chiral compound onto the WNV protease indicates that the Renantiomer of 1a16 interferes with the productive interactions between the NS2B cofactor and the NS3 protease domain and is thus the preferred isomer for inhibition of the WNV NS2B-NS3 protease.

Synthesis and in vitro biological evaluation of farnesylthiosalicylic acid derivatives as anti-tumor carcinoma agents

Novel farnesylthiosalicylic acid (FTA) derivatives 5a-m with different substituted 1,3,4-thiadiazoles were synthesized. Compounds 5b, 5c, 5e and 5f displayed anti-tumor activities superior to FTA in most cancer cells tested. Furthermore, 5e induced tumor cell apoptosis, which was accompanied by lower Bcl-2 expression, but with higher Bax and caspase 3 expression activities in cancer cells.

Synthesis and in vitro antitumor activity of 1,3,4-thiadiazole derivatives based on benzisoselenazolone

A series of novel 1,3,4-thiadiazole derivatives based on benzisoselenazolone were synthesized and evaluated for their cytotoxicity in vitro against human liver cancer cell SSMC-7721, human breast cancer cell MCF-7 and human lung cancer cell A549 by CCK-8 assay. The results showed that compounds 7e, 7f, 7h, 7k, 7l and 7m displayed good cytotoxicity against MCF-7 cell lines. Compound 7l exhibited the most potent antitumor activities among the tested compounds.

Synthesis of 2-alkyl/arylalkyl/phenacylsul-fanyl-1 -thia-3,3, 10-triaza-pentaleno[ 1,2-b]naphthalene-4,9-dione

2,3-Dichloronaphthoquinone is condensed with 5-(alkyl/arylalkyl/ phenacylthio)-1,3,4-thiadiazol-2-amine in acetic acid to furnish a novel and hitherto unknown 2-alkyl/aralkyl/phenacylsulfanyl-1-thia-3,3a,10-triaza- pentaleno[1,2-b]naphthalene-4,9-dione. The structure of the synthesized compound has been confirmed by converting it into the corresponding reductive acetate. The structures of newly prepared compounds have been confirmed by analytical and spectral data.

AZOLYL PIPERAZINYL PHENYL OXAZOLIDINONE ANTIMICROBIALS

Compounds useful in the preparation of pharmaceutical preparations for the treatment of microbial infection where such compounds are of structural Formula I I or pharmaceutically acceptable salts thereof wherein: R1 is -CHO, -COCH3, -COCHCl2, -COCHF2, -CO2CH3, -SO2CH3, or -COCH2OH; X1 and X2 are independently H, F, or Cl; and Q is a five membered ting heterocycle (azolyl ring) of the general form: wherein A, B, and C are independently oxygen (O), nitrogen (N), sulfur (S) or Carbon (C). In all cases, the piperazine nitrogen atom is attached at the carbon atom of the carbon-nitrogen double bond.

Synthesis of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity

Recently a series of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives bearing different substituents were synthesized and screened pharmacologically in order to evaluate their central nervous system activity. The purpose of this study was to evaluate the effects of the title compounds on CNS activity by varying the substituents in the thiadiazole moiety. It was found that some of these compounds possess marked antidepressant and anxiolytic properties comparable in efficiency to the reference drugs Imipramine and Diazepam. The most potent compound 3k was further investigated to complete its pharmacological profile with respect to undesired side effects. Behavioral results showed that 3k is a very promising compound, characterized by a mixed antidepressant-anxiolytic activity accompanied by a therapeutic dose range that is essentially 2 orders of magnitude less than that at which side effects such as sedation and amnesia are evident.