28004-59-3

Basic information

• Product Name: 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine
• Synonyms: 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine
• CAS NO: 28004-59-3
• Molecular Formula: C₁₁H₁₃N₃O₃S
• Molecular Weight: 267.30422
• Mol File: 28004-59-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 447.2°C at 760 mmHg
• Flash Point: 224.3°C
• Appearance: /
• Density: 1.304g/cm³
• Vapor Pressure: 3.42E-08mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine(28004-59-3)
• EPA Substance Registry System: 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine(28004-59-3)

Safety Data

• Hazardous Substances Data: 28004-59-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13N3O3S/c1-15-7-4-6(10-13-14-11(12)18-10)5-8(16-2)9(7)17-3/h4-5H,1-3H3,(H2,12,14)

Upstream product

• 7658-75-5 1-(3,4,5-trimethoxybenzoyl)thiosemicarbazide 
• 79-19-6 thiosemicarbazide 
• 1885-35-4 3,4,5-trimethoxybenzonitrile 
• 3291-03-0 3,4,5-trimethoxybenzohydrazide 
• 847063-15-4 C₁₅H₂₃N₃O₄S 
• 185951-45-5 C₁₈H₂₁N₃O₄S 
• 22043-16-9 2-(3,4,5-trimethoxybenzylidene)hydrazinecarbothioamide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 118-41-2 Eudesmic acid 

Downstream Products

• 116758-60-2 (5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-yl) acetamide D 
• 104830-81-1 2-benzoylamino-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole 
• 116758-65-7 1-Phenyl-3-[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-urea 
• 125766-71-4 1-(4-Methoxy-phenyl)-3-[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-urea 
• 125766-47-4 6-(4-Methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione 
• 154662-32-5 5-(3,4,5-trimethoxyphenyl)-2-(2-chloroacetylamido)-1,3,4-thiadiazole 
• 91918-57-9 6-(4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole 
• 91918-55-7 6-(2-Nitro-phenyl)-2-(3,4,5-trimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazole 
• 1019855-22-1 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-[5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide 
• 1356166-70-5 6-p-tolyl-2-(3,4,5-trimethoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole-6-carbaldehyde 
• 1356166-71-6 6-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole-6-carbaldehyde 
• 125766-38-3 6-(4-Chloro-phenyl)-2-(3,4,5-trimethoxy-phenyl)-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione 
• 125766-53-2 1-(4-Chloro-phenyl)-3-[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-urea 

Relevant articles and documents

Synthesis and antiviral activity of some imidazo[1,2-b][1,3,4]thiadiazole carbohydrate derivatives

Herein we describe the synthesis of imidazo[2,1-b][1,3,4]thiadiazoles from carbohydrates with D-ribo and D-xylo configuration. The antiviral activity of these compounds was tested against Junín virus (the etiological agent of Argentine hemorrhagic fever). The p-chlorophenyl derivatives showed antiviral activity in a range of micromolar concentration.

Synthesis, molecular docking, antimicrobial evaluation, and DNA cleavage assay of new thiadiazole/oxadiazole ciprofloxacin derivatives

Abstract: Herein we report the synthesis of new N-4-piperazinyl thiadiazole and oxadiazole ciprofloxacin derivatives and their antibacterial and antimycobacterial activities. Although thiadiazole ciprofloxacin derivatives compound showed broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative organisms, the oxadiazole derivatives exhibited weaker antibacterial and antimycobacterial activities than thiadiazole derivatives against most of the tested strains compared with the reference ciprofloxacin. Moreover, the antimycobacterial screening revealed that compounds which containing thiadiazole scaffold potently inhibited Mycobacterium smegmatis at MIC of 1.56 and 3.13, respectively, and modestly inhibited the drug-resistant strains. DNA cleavage assay revealed that thiadiazole ciprofloxacin derivatives inhibited supercoil relaxation, albeit to a lesser extent than ciprofloxacin, and it also increased the amount of nicked substrate produced. Graphic abstract: [Figure not available: see fulltext.].

Synthesis, bioevaluation and docking study of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents

Since the first histone deacetylase (HDAC) inhibitor (Zolinza, widely known as suberoylanilide hydroxamic acid; SAHA) was approved by the Food and Drug Administration for the treatment of T-cell lymphoma in 2006, the search for newer HDAC inhibitors has attracted a great deal of interest of medicinal chemists worldwide. As a continuity of our ongoing research in this area, we designed and synthesized a series of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as analogues of SAHA and evaluated their biological activities. A number of compounds in this series, for example, N1-hydroxy-N8-(5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5b), N1-hydroxy-N8-(5-(3-chlorophenyl-1,3,4-thiadiazol-2-yl)octandiamide (5c) and N1-hydroxy-N8-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5d), were found to possess potent anticancer cytotoxicity and HDAC inhibition effects. Compounds 5b-d were generally two- to five-fold more potent in terms of cytotoxicity compared to SAHA against five cancer cell lines tested. Docking studies revealed that these hydroxamic acid displayed higher affinities than SAHA toward HDAC8.