3690-46-8

Basic information

• Product Name: 5-(3-PYRIDINYL)-1,3,4-OXADIAZOLE-2-THIOL
• Synonyms: 5-(3-PYRIDINYL)-1,3,4-OXADIAZOLE-2-THIOL;5-(PYRIDIN-3-YL)-1,3,4-OXADIAZOLE-2(3H)-THIONE;5-PYRIDIN-3-YL-1,3,4-OXADIAZOLE-2-THIOL;AKOS BC-1866;ASISCHEM D13340;RARECHEM BG FB 0051;5-(3-PYRIDYL)-1,3,4-OXADIAZOLE-2-THIOL;5-(3-Pyridinyl)-1,3,4-oxadiazole-2(3H)-thione
• CAS NO: 3690-46-8
• Molecular Formula: C₇H₅N₃OS
• Molecular Weight: 179.2
• Mol File: 3690-46-8.mol
• Article Data: 35

Chemical Properties

• Melting Point: 231 °C (dec.)
• Boiling Point: 274.9 °C at 760 mmHg
• Flash Point: 120.1 °C
• Appearance: /
• Density: 1.52 g/cm³
• Vapor Pressure: 0.00524mmHg at 25°C
• Refractive Index: 1.744
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-(3-PYRIDINYL)-1,3,4-OXADIAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-PYRIDINYL)-1,3,4-OXADIAZOLE-2-THIOL(3690-46-8)
• EPA Substance Registry System: 5-(3-PYRIDINYL)-1,3,4-OXADIAZOLE-2-THIOL(3690-46-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3690-46-8(Hazardous Substances Data)

Usage

General Description

5-(3-pyridinyl)-1,3,4-oxadiazole-2-thiol is a heterocyclic compound with a unique structure. It consists of a pyridine ring attached to an oxadiazole ring, with a thiol group at the 2 position of the oxadiazole ring. 5-(3-PYRIDINYL)-1,3,4-OXADIAZOLE-2-THIOL has potential applications in the field of medicinal chemistry and drug development, as it is known to exhibit various biological activities, such as antibacterial, antifungal, and anticancer properties. Additionally, its structure makes it a useful building block for the synthesis of more complex organic molecules. Further research and exploration of the properties and potential applications of 5-(3-pyridinyl)-1,3,4-oxadiazole-2-thiol are warranted to fully understand and harness its capabilities.

InChI:InChI=1/C7H5N3OS/c12-7-10-9-6(11-7)5-2-1-3-8-4-5/h1-4H,(H,10,12)

Upstream product

• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 88317-41-3 potassium N-(pyridine-4-carbonyl)-hydrazine carbodithiolate 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 59-67-6 nicotinic acid 
• 553-53-7 Nicotinic acid hydrazide 
• 75-15-0 carbon disulfide 
• 28540-05-8 3-pyridyldithiocarbazoic acid methyl ester 

Downstream Products

• 105491-51-8 3-(5-benzylsulfanyl-[1,3,4]oxadiazol-2-yl)-pyridine 
• 129119-80-8 4-benzyl-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiol 
• 81555-95-5 1-Phenyl-2-(5-pyridin-3-yl-[1,3,4]oxadiazol-2-ylsulfanyl)-ethanone 
• 78027-00-6 4-amino-5-(pyridine-3-yl)-4,5-dihydro-3H-1,2,4-triazole-3-thione 
• 488135-93-9 4-{[1H-indol-3-ylmethylene]amino}-5-pyridin-3-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 78027-00-6 4-amino-5-(3-pyridyl)-4H-1,2,4-triazole-3-thiol 

Relevant articles and documents

Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker

A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.

Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof

The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.

Design, synthesis, and biological evaluation of new challenging thalidomide analogs as potential anticancer immunomodulatory agents

Thalidomide and its analogs are immunomodulatory drugs that inhibit the production of certain inflammatory mediators associated with cancer. In the present work, a new series of thalidomide analogs was designed and synthesized to obtain new effective antitumor immunomodulatory agents. The synthesized compounds were evaluated for their cytotoxic activities against a panel of four cancer cell lines (HepG-2, HCT-116, PC3 and MCF-7). Compounds 33h, 33i, 42f and 42h showed strong potencies against all tested cell lines with IC50 values ranging from 14.63 to 49.90 μM comparable to that of thalidomide (IC50 values ranging from 32.12 to 76.91 μM). The most active compounds were further evaluated for their in vitro immunomodulatory activities via estimation of human tumor necrosis factor alpha (TNF-α), human caspase-8 (CASP8), human vascular endothelial growth factor (VEGF), and nuclear factor kappa-B P65 (NF-κB P65) in HCT-116 cells. Thalidomide was used as a positive control. Compounds 33h and 42f showed a significant reduction in TNF-α. Furthermore, compounds 33i and 42f exhibited significant elevation in CASP8 levels. Compounds 33i and 42f inhibited VEGF. In addition, compound 42f showed significant decrease in levels of NF-κB p65. Moreover, apoptosis and cell cycle tests of the most active compound 42f, were performed. The results indicated that compound 42f significantly induce apoptosis in HCT-116 cells and arrest cell cycle at the G2/M phase.