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

Downstream Products

• 64387-67-3 2-acetylamino-5-benzylmercapto-1,3,4-thiadiazole 
• 54508-99-5 (5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-dithiocarbamic acid butyl ester 
• 54509-00-1 (5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-dithiocarbamic acid allyl ester 
• 55217-82-8 N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-4-iodo-benzamide 
• 55217-81-7 N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-4-bromo-benzamide 
• 55217-78-2 N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-2,4,6-trimethoxy-benzamide 
• 69395-68-2 2-benzylsulfanyl-[1,3,4]thiadiazolo[3,2-a]pyrimidine-5,7-dione 
• 69395-70-6 6-benzyl-2-benzylsulfanyl-[1,3,4]thiadiazolo[3,2-a]pyrimidine-5,7-dione 
• 55217-79-3 N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-2,4,5-trimethoxy-benzamide 
• 69395-69-3 2-benzylsulfanyl-6-ethyl-[1,3,4]thiadiazolo[3,2-a]pyrimidine-5,7-dione 
• 54509-02-3 (5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-dithiocarbamic acid benzyl ester 
• 54508-97-3 (5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-dithiocarbamic acid ethyl ester 
• 54508-98-4 (5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-dithiocarbamic acid propyl ester 
• 69949-74-2 phenyl-(6-phenylmethanesulfinyl-[1,3,4]thiadiazolo[2,3-c][1,2,4]thiadiazol-3-ylidene)-amine 

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.

Synthesis and radioligand-binding assay of 2,5-disubstituted thiadiazoles and evaluation of their anticonvulsant activities

In this study, a number of 2,5-disubstituted 1,3,4-thiadiazoles were synthesized using an appropriate synthetic route, and their anticonvulsant activity was determined by the maximal electroshock seizure (MES) test and their neurotoxicity was evaluated by the rotarod test. Additionally, their hypnotic activity was tested using the pentobarbital-induced sleep test. Compounds 7 (ED50 = 1.14 and 2.72 μmol/kg in the MES and sleep tests, respectively) and 11 (ED50 = 0.65 and 2.70 μmol/kg in the MES and sleep tests, respectively) were the most potent ones in the sleep test and anticonvulsant test, showing a comparable activity with diazepam as the reference drug. The results of in vivo studies, especially the antagonistic effects of flumazenil, and also the radioligand-binding assay confirmed the involvement of benzodiazepine (BZD) receptors in the anticonvulsant and hypnotic activity of compounds 7 and 11. Finally, the docking study of compound 11 in the BZD-binding site of the GABAA (gamma-aminobutyric acid) receptor confirmed the possible binding of the compound to the BZD receptors. We concluded that the novel 1,3,4-thiadiazole derivatives with appropriate substitution at positions 2 and 5 of the heterocyclic ring had a good affinity to BZD receptors and showed significant efficacy in the pharmacological tests.