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

Description

2-AMINO-5-BENZYLTHIO-1,3,4-THIADIAZOLE is a chemical compound with potential applications in various fields, particularly in the pharmaceutical industry. It is characterized by its unique molecular structure, which includes a thiadiazole ring with an amino group at the 2nd position and a benzylthio group at the 5th position.

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-BENZYLTHIO-1,3,4-THIADIAZOLE is used as a compound for studying its antitumor activities. It is particularly effective against various types of cancer cells, including human cervix adenocarcinoma (HeLa), human liver cancer cell (SMMC-7721), human breast cancer cell (MCF-7), and human lung cancer cell (A549) lines. The compound's antitumor potential is further evaluated using the CCK-8 assay, a method for assessing cell viability and proliferation.

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 
• 100-53-8 phenylmethanethiol 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 100-39-0 benzyl bromide 
• 3012-37-1 benzyl thiocyanate 
• 79-19-6 thiosemicarbazide 
• 861564-19-4 3-thiocarbamoyl-thiocarbazic acid benzyl ester 

Downstream Products

• 312523-97-0 C₁₆H₁₂FN₃OS₂ 
• 393566-15-9 C₁₆H₁₂ClN₃OS₂ 
• 55217-80-6 N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-4-chloro-benzamide 
• 1220687-92-2 7-hydroxy-2-(benzylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione 
• 42062-03-3 N-(5-(benzylthio)-1,3,4-thiadiazol-2-yl)-4-methylbenzenesulfonamide 
• 73218-27-6 2-Benzolsulfonamino-5-benzylmercapto-1.3.4-thiadiazol 

Relevant articles and documents

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

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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, carbonic anhydrase enzyme inhibition evaluations, and anticancer studies of sulfonamide based thiadiazole derivatives

The sulfonamide-based thiadiazole derivatives (STDs) with different hydrophobic/hydrophilic substitutions were synthesized to investigate their potentials in carbonic anhydrase inhibition (CAI). The CAI activity of the STDs (4a-4h) and the mechanism of the inhibition kinetics were determined. STD 4f contained both methoxy and Cl groups at benzene ring in STD 4f showed the lowest IC50 value. The molecular docking study confirmed that STDs bind strongly with the active sites of the target protein PDBID 1V9E. With the help of Lineweaver-Burk plots, inhibition kinetics of PDBIR 1V9E protein with STDs were determined. Cytotoxicity was checked against human keratinocyte cell lines and the anticancer properties were determined against MCF-7 cell lines. The electrochemical method was used to investigate the binding study with DNA and CA enzymes. Anticancer studies showed that STDs have weak bonding ability to DNA and strong binding ability with CA. It is concluded that anticancer activity is through CAI rather than by DNA binding.

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.