80549-59-3

Basic information

• Product Name: 5-(1-naphthylmethyl)-1,3,4-oxadiazol-2-yl hydrosulfide
• Synonyms: 5-(1-naphthylmethyl)-1,3,4-oxadiazol-2-yl hydrosulfide
• CAS NO: 80549-59-3
• Molecular Formula: C₁₃H₁₀N₂OS
• Molecular Weight: 242.2963
• Mol File: 80549-59-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(1-naphthylmethyl)-1,3,4-oxadiazol-2-yl hydrosulfide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(1-naphthylmethyl)-1,3,4-oxadiazol-2-yl hydrosulfide(80549-59-3)
• EPA Substance Registry System: 5-(1-naphthylmethyl)-1,3,4-oxadiazol-2-yl hydrosulfide(80549-59-3)

Safety Data

• Hazardous Substances Data: 80549-59-3(Hazardous Substances Data)

Upstream product

• 75-15-0 carbon disulfide 
• 34800-90-3 naphthalen-1-yl-acetic acid hydrazide 
• 86-87-3 naphth-1-yl acetic acid 
• 2876-78-0 methyl 1-naphthylacetate 
• 2122-70-5 ethyl 2-(1-naphthyl)acetate 

Relevant articles and documents

Synthesis and pharmacological screening: Sulfa derivatives of 2-pipecoline-bearing 1,3,4-oxadiazole core

An electrophile, 1-(4-(bromomethylbenzenesulfonyl)-2-methylpiperidine, was synthesized by the reaction of 2-methylpiperidine (2-pipecoline) and 4-bromomethylbenzenesulfonyl chloride in a weak basic medium under pH control. A series of nucleophiles, 5-aryl/aralkyl-1,3,4-oxadiazol-2-thiols, were synthesized from corresponding carboxylic acids in three steps. The title molecules were synthesized by coupling the electrophile to nucleophiles in an aprotic medium using LiH as an activator. The structures of all synthesized compounds were corroborated through IR, 1H NMR, and EI-MS techniques. All the compounds were screened for their pharmacological behavior, particularly, antibacterial and enzyme inhibitory activities. Notably efficient results were obtained against both gram-positive and gram-negative bacterial strains. Regarding enzyme inhibition, compounds were efficient against acetylcholinesterase and butyrylcholinesterase.

Synthesis and biological activity of oxadiazole and triazolothiadiazole derivatives as tyrosinase inhibitors

A series of 16 oxadiazole and triazolothiadiazole derivatives were designed, synthesized and evaluated as mushroom tyrosinase inhibitors. Five derivatives were found to display high inhibition on the tyrosinase activity ranging from 0.87 to 1.49 μM. Compound 5 exhibited highest tyrosinase inhibitory activity with an IC50 value of 0.87 ± 0.16 μM. The in silico protein-ligand docking using autodock 4.1 was successfully performed on compound 5 with significant binding energy value of -5.58 kcal/mol. The docking results also showed that the tyrosinase inhibition might be due to the metal chelating effect by the presence of thione functionality in compounds 1-5. Further studies revealed that the presence of hydrophobic group such as cycloamine derivatives played a major role in the inhibition. Piperazine moiety in compound 5 appeared to be involved in an extensive hydrophobic contact and a 2.9 hydrogen bonding with residue Glu 182 in the active site.