5711-72-8

Usage

Uses

Used in Pharmaceutical Industry:
5-Pyridin-2-yl-1,3,4-oxadiazol-2-ylamine is used as a chemical intermediate for the development of new drugs, given its unique structure and potential interactions with biological targets. Its presence in the class of dialkylarylamines suggests that it may have properties that could be harnessed for therapeutic applications.
Used in Drug Discovery Research:
In the field of drug discovery, 5-Pyridin-2-yl-1,3,4-oxadiazol-2-ylamine is used as a starting material or a building block for the synthesis of more complex molecules with potential medicinal properties. Its structure may allow for the creation of compounds that can target specific receptors or enzymes involved in disease processes.
Used in Chemical Synthesis:
5-Pyridin-2-yl-1,3,4-oxadiazol-2-ylamine is used as a reagent in the synthesis of other organic compounds, particularly those that require the presence of a pyridine or oxadiazole moiety. Its versatility in chemical reactions makes it a valuable component in the creation of a wide range of molecules with diverse applications.

InChI:InChI=1/C7H6N4O/c8-7-11-10-6(12-7)5-3-1-2-4-9-5/h1-4H,(H2,8,11)

Upstream product

• 4923-12-0 (2-picoloylcarbonyl)thiosemicarbazone 
• 98-98-6 2-Picolinic acid 
• 4426-72-6 hydrazine carboxamide 
• 61043-10-5 (E)-2-(pyridin-2-ylmethylene)hydrazinecarbothioamide 
• 1452-63-7 picolinic acid hydrazide 
• 506-68-3 bromocyane 
• 1121-60-4 pyridine-2-carbaldehyde 
• 13370-79-1 2-(pyridin-2-ylmethylidene)hydrazinecarboxamide 

Relevant academic research and scientific papers

New 1,3,4-oxadiazolecopper(II) derivatives obtained from thiosemicarbazone complexes

Pyridine-2-carbaldehyde thiosemicarbazone and pyridine-2-carbaldehyde 4N-methyl thiosemicarbazone ligands (HLI and HLImm respectively) undergo an oxidative cyclization when treated with bromate or iodate, leading to 2-amino-5-pyridin

Ultrapotent Inhibitor of Clostridioides difficile Growth, Which Suppresses Recurrence in Vivo

Clostridioides difficile is the leading cause of healthcare-associated infection in the U.S. and considered an urgent threat by the Centers for Disease Control and Prevention (CDC). Only two antibiotics, vancomycin and fidaxomicin, are FDA-approved for the treatment of C. difficile infection (CDI), but these therapies still suffer from high treatment failure and recurrence. Therefore, new chemical entities to treat CDI are needed. Trifluoromethylthio-containing N-(1,3,4-oxadiazol-2-yl)benzamides displayed very potent activities [sub-μg/mL minimum inhibitory concentration (MIC) values] against Gram-positive bacteria. Here, we report remarkable antibacterial activity enhancement via halogen substitutions, which afforded new anti-C. difficile agents with ultrapotent activities [MICs as low as 0.003 μg/mL (0.007 μM)] that surpassed the activity of vancomycin against C. difficile clinical isolates. The most promising compound in the series, HSGN-218, is nontoxic to mammalian colon cells and is gut-restrictive. In addition, HSGN-218 protected mice from CDI recurrence. Not only does this work provide a potential clinical lead for the development of C. difficile therapeutics but also highlights dramatic drug potency enhancement via halogen substitution.

Synthesis of 2-amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via sequential condensation and I2-mediated oxidative C-O/C-S bond formation

2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I2-mediated oxidative C-O/C-S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.

A green approach for the synthesis of biologically active heterocyclic compounds at the platinum electrode

In the present study, 2-amino-5-substituted-1,3,4-oxadiazoles (4a-k) have been synthesized by the electrochemical oxidation of semicarbazone (3a-k) using platinum anode at room temperature under controlled potential electrolysis in an undivided cell assem

Structure-activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis

A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl) -1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 μM or 0.008 μg/mL in 7H9 media and therapeutic index of nearly ～300. However, 55 is rapidly metabolized by human liver microsomes (t1/2 = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of ～10-5.

Oxidation of 2-amino-5-aryl-1,3,4-oxadiazole by sodium periodate: A kinetic study

Kinetics of oxidation of a few 2-amino-5-aryl-1,3,4-oxadiazoles by sodium periodate in aqueous acetic acid-HClO4 medium have been studied. The reaction follows a first order rate each with respect to oxidant and substrate concentration. A suita