25660-71-3

Basic information

• Product Name: 2-AMINO-5-BENZYLTHIO-1,3,4-THIADIAZOLE
• Synonyms: 2-BENZYLTHIO-5-AMINO-1,3,4-THIADIAZOLE;2-AMINO-5-BENZYLTHIO-1,3,4-THIADIAZOLE;1,3,4-thiadiazol-2-amine, 5-[(phenylmethyl)thio]-;[5-(benzylthio)-1,3,4-thiadiazol-2-yl]amine;5-((Phenylmethyl)thio)-1,3,4-thiadiazol-2-amine;5-(phenylmethylsulfanyl)-1,3,4-thiadiazol-2-amine;5-(phenylmethylthio)-1,3,4-thiadiazol-2-amine;5-benzylsulfanyl-1,3,4-thiadiazol-2-amine
• CAS NO: 25660-71-3
• Molecular Formula: C₉H₉N₃S₂
• Molecular Weight: 223.32
• Mol File: 25660-71-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 157.0 to 161.0 °C
• Boiling Point: 416.2 °C at 760 mmHg
• Flash Point: 205.5 °C
• Appearance: /
• Density: 1.39 g/cm³
• Vapor Pressure: 3.89E-07mmHg at 25°C
• Refractive Index: 1.693
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.46±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-5-BENZYLTHIO-1,3,4-THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-BENZYLTHIO-1,3,4-THIADIAZOLE(25660-71-3)
• EPA Substance Registry System: 2-AMINO-5-BENZYLTHIO-1,3,4-THIADIAZOLE(25660-71-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 36/37/39
• RTECS: XI2898500
• HazardClass: IRRITANT
• Hazardous Substances Data: 25660-71-3(Hazardous Substances Data)

Usage

Uses

2-Benzylthio-5-amino-1,3,4-thiadiazole is used to study and investigate its antitumor activities against human cervix adenocarcinoma(HeLa), human liver cancer cell(SMMC-7721), human breast cancer cell(MCF-7) and human lung cancer cell(A549) lines that isfurther evaluated by CCK-8 assay.

InChI:InChI=1/C9H9N3S2/c10-8-11-12-9(14-8)13-6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,10,11)

Upstream product

• 100-44-7 benzyl chloride 
• 2349-67-9 5-amino-2,3-dihydro-1,3,4-thiadiazole-2-thione 
• 2349-67-9 2-Amino-5-mercapto-1,3,4-thiadiazole 
• 100-39-0 benzyl bromide 
• 100-53-8 phenylmethanethiol 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 3012-37-1 benzyl thiocyanate 
• 79-19-6 thiosemicarbazide 
• 861564-19-4 3-thiocarbamoyl-thiocarbazic acid benzyl ester 

Downstream Products

• 64387-67-3 2-acetylamino-5-benzylmercapto-1,3,4-thiadiazole 
• 187744-63-4 2-Benzylsulfanyl-5-chloro-[1,3,4]thiadiazole 
• 140833-97-2 5-((5-chlorovaleryl)amino)-2-(benzylthio)-1,3,4-thiadiazole 
• 112807-06-4 2-benzylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one 
• 112807-05-3 2-benzylthio-6-cyano-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one 
• 1408325-15-4 C₃₁H₃₇N₃OS₃ 
• 187744-71-4 2-Benzylsulfanyl-5-(4-methoxy-benzenesulfonyl)-[1,3,4]thiadiazole 

Relevant articles and documents

SINGLE-REACTOR SYNTHESIS OF 2R-THIO-5,7-DIMETHYL-1,3,4-THIADIAZOLOPYRIMIDINIUM PERCHLORATES

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Synthesis, characterization and biological evaluation of thiadiazole amide derivatives as nucleoside triphosphate diphosphohydrolases (NTPDases) inhibitors

Importance of extracellular nucleotides is widely understood. These nucleotides act as ligand for P2X and P2Y receptors and modulate a variety of biological functions. However, their extracellular concentration is maintained by a chain of enzymes termed as ecto-nucleotidases. Amongst them, nucleoside triphosphate diphosphohydrolases (NTPDases) is an important enzyme family responsible for the dephosphorylation of these nucleotides. Overexpression of NTPDases leads to many pathological conditions such as cancer and thrombosis. So far, only a few NTPDase inhibitors have been reported. Considering this scarcity of (NTPDase) inhibitors, a number of thiadiazole amide derivatives were synthesized and screened against human (h)-NTPDases. Several compounds showed promising inhibitory activity; compound 5a (IC50 (μM); 0.05 ± 0.008) and 5g (IC50 (μM); 0.04 ± 0.006) appeared to be the most distinguished molecules corresponding to h-NTPDase1 and -2. However, h-NTPDase3 was the least susceptible isozyme and only three compounds (5d, 5e, 5j) strongly inhibited h-NTPDase3. Interestingly, compound 5e was recognized as the most active compound that showed dual inhibition against h-NTPDase3 as well as against h-NTPDase8. For better comprehension of binding mode of these inhibitors, most potent inhibitors were docked with their respective isozyme.

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.