23269-92-3

Basic information

• Product Name: 5-(3,4,5-TRIMETHOXY-PHENYL)-[1,3,4]OXADIAZOLE-2-THIOL
• Synonyms: 5-(3,4,5-TRIMETHOXY-PHENYL)-[1,3,4]OXADIAZOLE-2-THIOL;RARECHEM BG FB 0089;1,3,4-Oxadiazole-2-thiol, 5-(3,4,5-trimethoxyphenyl)-;5-(3,4,5-trimethoxyphenyl)-3H-1,3,4-oxadiazole-2-thione
• CAS NO: 23269-92-3
• Molecular Formula: C₁₁H₁₂N₂O₄S
• Molecular Weight: 268.29
• Mol File: 23269-92-3.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 358.5°Cat760mmHg
• Flash Point: 170.6°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 2.53E-05mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: 5-(3,4,5-TRIMETHOXY-PHENYL)-[1,3,4]OXADIAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3,4,5-TRIMETHOXY-PHENYL)-[1,3,4]OXADIAZOLE-2-THIOL(23269-92-3)
• EPA Substance Registry System: 5-(3,4,5-TRIMETHOXY-PHENYL)-[1,3,4]OXADIAZOLE-2-THIOL(23269-92-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 23269-92-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H12N2O4S/c1-14-7-4-6(10-12-13-11(18)17-10)5-8(15-2)9(7)16-3/h4-5H,1-3H3,(H,13,18)

Upstream product

• 137-26-8 Thiram 
• 3291-03-0 3,4,5-trimethoxybenzohydrazide 
• 118-41-2 Eudesmic acid 
• 6178-44-5 ethyl 3,4,5-trimethoxybenzoate 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 75-15-0 carbon disulfide 

Downstream Products

• 67572-44-5 2-[(ethoxycarbonyl)methylthio]-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 522626-31-9 2-(2-chlorobenzylthio)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 943228-68-0 2-(2-methoxybenzylthio)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 938989-13-0 2-(3-fluorobenzylthio)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 923924-94-1 2-(3-methoxybenzylthio)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 879429-36-4 2-(3-nitrobenzylthio)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 571924-48-6 2-(4-chlorobenzylthio)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 937970-25-7 2-(4-methoxybenzylthio)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 923924-93-0 2-(4-nitrobenzylthio)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 340818-69-1 2-(allylthio)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 336181-28-3 2-benzylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 340818-71-5 2-ethylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 
• 23767-44-4 2-methylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 

Relevant articles and documents

Synthesis, thymidine phosphorylase inhibition and molecular modeling studies of 1,3,4-oxadiazole-2-thione derivatives

Thymidine phosphorylase (TP) inhibitors have attracted great attention due to their ability to suppress the tumors formation. In our ongoing research, a series of 1,3,4-oxadiazole-2-thione (1-12) has been synthesized under simple reaction conditions in good to excellent yields (86-98%) and their TP inhibition potential has also been evaluated. The majority of synthesized compounds showed moderate thymidine phosphorylase inhibitory activity with IC50 values ranging from 38.24 ± 1.28 to 258.43 ± 0.43 μM, and 7-deazaxanthine (7DX) was used as a reference compound (IC50 38.68 ± 4.42). The TP activity was very much dependent on the C-5 substituents; among this series the compound 6 bearing 4-hydroxyphenyl group was found to be the most active with IC50 38.24 ± 1.28 μM. Molecular docking studies revealed their binding mode.

Synthesis of novel indole derivatives containing double 1,3,4-oxadiazole moiety as efficient bactericides against phytopathogenic bacterium Xanthomonas oryzae

Abstract: A series of novel indole derivatives containing double 1,3,4-oxadiazole moiety was designed, synthesized and evaluated for their antibacterial activities in vitro. These compounds were fully characterized by 1H NMR, 13C NMR, and HRMS. Bioassay results indicated that most of title compounds exhibited excellent antibacterial activities against rice bacterial pathogen Xanthomonas oryzae (Xoo). For example, compounds 7d, 7h, 7i, 7j, 7k, 7l and 7m had the half-maximal effective concentration (EC50) values of 52.31, 54.12, 40.65, 38.80, 51.13, 52.75 and 50.66?μg/mL, respectively, which was better than that of commercial product bismerthiazol (BMT) (85.18?μg/mL). The experimental results proved that indole derivatives bearing double 1,3,4-oxadiazole unit are promising candidates for the development of new agricultural bactericides against pathogenic bacterium Xoo. Graphical abstract: [Figure not available: see fulltext.].

1,3,4-oxadiazole/chalcone hybrids: Design, synthesis, and inhibition of leukemia cell growth and EGFR, Src, IL-6 and STAT3 activities

A new series of 1,3,4-oxadiazole/chalcone hybrids was designed, synthesized, identified with different spectroscopic techniques and biologically evaluated as inhibitors of EGFR, Src, and IL-6. The synthesized compounds showed promising anticancer activity, particularly against leukemia, with 8v being the most potent. The synthesized compounds exhibited strong to moderate cytotoxic activities against K-562, KG-1a, and Jurkat leukemia cell lines in MTT assays. Compound 8v showed the strongest cytotoxic activity with IC50 of 1.95 μM, 2.36 μM and 3.45 μM against K-562, Jurkat and KG-1a leukemia cell lines, respectively. Moreover; the synthesized compounds inhibited EGFR, Src, and IL-6. Compound 8v was most effective at inhibiting EGFR (IC50 = 0.24 μM), Src (IC50 = 0.96 μM), and IL-6 (% of control = 20%). Additionally, most of the compounds decreased STAT3 activation.