63698-52-2

Basic information

• Product Name: 5-BENZO[1,3]DIOXOL-5-YL-[1,3,4]OXADIAZOLE-2-THIOL
• Synonyms: 5-Benzo[1,3]dioxol-5-yl-[1,3,4]oxadiazole-2-thiol
• CAS NO: 63698-52-2
• Molecular Formula: C₉H₆N₂O₃S
• Molecular Weight: 222.22
• Mol File: 63698-52-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 313.4°C at 760 mmHg
• Flash Point: 143.3°C
• Appearance: /
• Density: 1.71g/cm³
• Vapor Pressure: 0.000498mmHg at 25°C
• Refractive Index: 1.772
• CAS DataBase Reference: 5-BENZO[1,3]DIOXOL-5-YL-[1,3,4]OXADIAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BENZO[1,3]DIOXOL-5-YL-[1,3,4]OXADIAZOLE-2-THIOL(63698-52-2)
• EPA Substance Registry System: 5-BENZO[1,3]DIOXOL-5-YL-[1,3,4]OXADIAZOLE-2-THIOL(63698-52-2)

Safety Data

• Hazardous Substances Data: 63698-52-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H6N2O3S/c15-9-11-10-8(14-9)5-1-2-6-7(3-5)13-4-12-6/h1-3H,4H2,(H,11,15)

Upstream product

• 6951-08-2 ethyl 1,3-benzodioxole-5-carboxylate 
• 326-56-7 methyl 3,4-methylenedioxybenzoate 
• 94-53-1 Piperonylic acid 
• 75-15-0 carbon disulfide 
• 22026-39-7 benzo[d][1,3]dioxole-5-carbohydrazide 

Downstream Products

• 876552-72-6 2-benzylthio-5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazole 
• 1374671-63-2 4'-((5-(benzo[d][1,3]dioxol-5-yl)-1,3,4-oxadiazol-2-ylthio)methyl)biphenyl-2-carbonitrile 
• 875456-04-5 methyl 4-(5-(benzo[d][1,3]dioxol-5-yl)-1,3,4-oxadiazol-2-ylthio)methyl benzoate 
• 876687-00-2 2-(benzo[d][1,3]dioxol-5-yl)-5-(biphenyl-4-ylmethylthio)-1,3,4-oxadiazole 
• 67572-46-7 2-((ethoxycarbonyl)methylthio)-5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazole 
• 69164-67-6 5-benzo[1,3]dioxol-5-yl-3-(4-methoxy-anilinomethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 70705-13-4 5-benzo[1,3]dioxol-5-yl-3-(4-fluoro-anilinomethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 69164-62-1 5-benzo[1,3]dioxol-5-yl-3-(2-methyl-anilinomethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 70705-11-2 5-benzo[1,3]dioxol-5-yl-3-(2-chloro-anilinomethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 70705-12-3 5-benzo[1,3]dioxol-5-yl-3-(3-chloro-anilinomethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 69164-61-0 3-anilinomethyl-5-benzo[1,3]dioxol-5-yl-3H-[1,3,4]oxadiazole-2-thione 
• 69164-68-7 5-benzo[1,3]dioxol-5-yl-3-(4-chloro-anilinomethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 70705-14-5 5-benzo[1,3]dioxol-5-yl-3-(3-trifluoromethyl-anilinomethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 1417334-78-1 C₂₂H₁₄F₂N₂O₃S 

Relevant articles and documents

Synthesis, characterization and urease inhibiting derivatives of 5-(3,4-Methylenedioxyphenyl)-1,3,4-Oxadiazol-2-thiol

In the present work, the urease inhibition activity of 1,3,4-oxadiazole bearing molecules was evaluated and were found to be potential inhibitors. 3,4-(Methylenedioxy)benzoic acid (1) was employed to synthesize 5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazol-2-thiol (4) via a series of steps. It was further stepped to yield S-substituted-5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazole derivatives (6a-h) on reaction with alkyl/aralkyl halides (5a-h) in DMF using LiH as an activator. All the synthesized compounds were well supported by IR, 1H NMR and EIMS spectral analysis. The enzyme inhibition activity against urease enzyme showed these molecules as potent inhibitors of this enzyme.

Identification of glycogen synthase kinase-3 inhibitors with a selective sting for glycogen synthase kinase-α

The glycogen synthase kinase-3 (GSK-3) has been linked to the pathogenesis of colorectal cancer, diabetes, cardiovascular disease, acute myeloid leukemia (AML), and Alzheimer's disease (AD). The debate on the respective contributions of GSK-α and GSK-3β to AD pathology and AML is ongoing. Thus, the identification of potent GSK-α-selective inhibitors, endowed with favorable pharmacokinetic properties, may elucidate the effect of GSK-α inhibition in AD and AML models. The analysis of all available crystallized GSK-3 structures provided a simplified scheme of the relevant hot spots responsible for ligand binding and potency. This resulted in the identification of novel scorpion shaped GSK-3 inhibitors. It is noteworthy, compounds 14d and 15b showed the highest GSK-α selectivity reported so far. In addition, compound 14d did not display significant inhibition of 48 out of 50 kinases in the test panel. The GSK-3 inhibitors were further profiled for efficacy and toxicity in the wild-type (wt) zebrafish embryo assay.

NOVEL 1,4-DIAZA-BICYCLO[3.2.2]NONYL OXADIAZOLYL DERIVATIVES USEFUL AS MODULATOR OF NICOTINIC ACETYLCHOLINE RECEPTORS

This invention relates to novel N-oxides of a 1,4-diaza-bicyclo[3.2.2]nonyl oxadiazolyl derivative and their use in the manufacture of pharmaceutical compositions. The compounds of the invention are found to be cholinergic ligands at the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.