53370-51-7

Basic information

• Product Name: N'-HYDROXY-2-THIOPHENECARBOXIMIDAMIDE
• Synonyms: N'-HYDROXY-2-THIOPHENECARBOXIMIDAMIDE;THIOPHENE-2-AMIDOXIME;BUTTPARK 37\11-65;2-Thiophenecarboximidamide,N-hydroxy-;2-Thiophenecarboximidamide,N-hydroxy-(9CI);Thiophene-2-amidoxime ,97%;N'-Hydroxy-2-thiophenecarbimide amide;N'-hydroxy-2-thiophenecarboximidamide (en)
• CAS NO: 53370-51-7
• Molecular Formula: C₅H₆N₂OS
• Molecular Weight: 142.18
• Product Categories: OXIME;AMIDINE;Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks;Thiophenes
• Mol File: 53370-51-7.mol
• Article Data: 31

Chemical Properties

• Melting Point: 94-97°
• Boiling Point: 330.2 °C at 760 mmHg
• Flash Point: 153.5 °C
• Appearance: /
• Density: 1.45 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: N'-HYDROXY-2-THIOPHENECARBOXIMIDAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N'-HYDROXY-2-THIOPHENECARBOXIMIDAMIDE(53370-51-7)
• EPA Substance Registry System: N'-HYDROXY-2-THIOPHENECARBOXIMIDAMIDE(53370-51-7)

Safety Data

• Hazard Codes: T
• Statements: 25-37/38-41-36/37/38
• Safety Statements: 26-39-45-36
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 53370-51-7(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

Upstream product

• 1003-31-2 thiophene-2-carbonitrile 

Downstream Products

• 391680-92-5 methyl 5,6-dihydroxy-2-thien-2-ylpyrimidine-4-carboxylate 
• 823195-13-7 5-(3-thiophen-2-yl-[1,2,4]oxadiazol-5-yl)-isophthalic acid diethyl ester 
• 823195-12-6 3-(3-thiophen-2-yl-[1,2,4]oxadiazol-5-yl)-benzoic acid ethyl ester 
• 96898-91-8 5-(4-aminophenyl)-3-(thien-2-yl)-1,2,4-oxadiazole 
• 96898-65-6 5-(4-isothiocyanophenyl)-3-(2-thienyl)-1,2,4-oxadiazole 

Relevant articles and documents

Development of Potent 3-Br-isoxazoline-Based Antimalarial and Antileishmanial Compounds

Starting from the structure of previously reported 3-Br-isoxazoline-based covalent inhibitors of P. falciparum glyceraldehyde 3-phosphate dehydrogenase, and with the intent to improve their metabolic stability and antimalarial activity, we designed and synthesized a series of simplified analogues that are characterized by the insertion of the oxadiazole ring as a bioisosteric replacement for the metabolically labile ester/amide function. We then further replaced the oxadiazole ring with a series of five-membered heterocycles and finally combined the most promising structural features. All the new derivatives were tested in vitro for antimalarial as well as antileishmanial activity. We identified two very promising new lead compounds, endowed with submicromolar antileishmanial activity and nanomolar antiplasmodial activity, respectively, and a very high selectivity index with respect to mammalian cells.

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Design, synthesis and biological activities of piperidine-spirooxadiazole derivatives as α7 nicotinic receptor antagonists

α: 7 nicotinic acetylcholine receptors (nAChRs) expressed in the nervous and immune systems have been suggested to play important roles in the control of inflammation. However, the lack of antagonist tools specifically inhibiting α7 nAChR impedes the validation of the channel as therapeutic target. To discover a selective α7 antagonist, we started a pharmacophore-based virtual screening and identified a piperidine-spirooxadiazole derivative T761–0184 that acts as a α7 antagonist. A series of novel piperidine-spirooxadiazole derivatives were subsequently synthesized and evaluated using two-electrode voltage clamp (TEVC) assay in Xenopus oocytes. Lead compounds from two series inhibited α7 with their IC50 values ranging from 3.3 μM to 13.7 μM. Compound B10 exhibited α7 selectivity over other α4β2 and α3β4 nAChR subtypes. The analysis of structure-activity relationship (SAR) provides valuable insights for further development of selective α7 nAChR antagonists.