683-58-9

Usage

InChI:InChI=1/C2H4ClNO/c1-2(3)4-5/h5H,1H3/b4-2+

Upstream product

• 107-29-9 Acetaldehyde oxime 
• 598-46-9 acethydroximic acid chloride 
• 75-04-7 ethylamine 
• 677-58-7 2-chloro-3,3-dimethyl-2-nitroso-butane 
• 3121-50-4 (2-chloro-2-nitrosopropan-1-yl)benzene 
• 7647-01-0 hydrogenchloride 
• 3354-65-2 N-(1-nitroso-ethylidene)-hydroxylamine 
• 5780-37-0 (E)-acetaldoxime 
• 7063-95-8 acetonitrile-N-oxide 
• 5775-72-4 Z-acetaldoxime 

Downstream Products

• 143593-81-1 (1-<(1-Chloroethylidene)aminooxy>ethylidene)anilinium Hexachloroantimonate 
• 2518-42-5 3,4-dimethylfurazan-2-oxide 
• 59562-64-0 5-(4-chloro-phenyl)-3-methyl-[1,2,4]oxadiazole 4-oxide 
• 59562-61-7 3-methyl-5-(4-nitro-phenyl)-[1,2,4]oxadiazole 4-oxide 
• 14716-89-3 3-methyl-5-isoxazolemethanol 
• 1017581-53-1 C₁₈H₁₈N₂O₃S 
• 1017581-52-0 C₁₃H₁₂N₂O₃ 
• 70753-36-5 3-methylisoxazole-5-carbaldehyde 
• 677-23-6 1,1-dichloro-1-nitrosoethane 
• 40340-41-8 5-chloromethyl-3-methylisoxazole 
• 6926-36-9 acetohydroximic acid-(N'-phenyl-hydrazide) 
• 7063-93-6 3-methyl-5-vinylisoxazole 
• 7063-94-7 5-ethynyl-3-methyl-4,5-dihydro-isoxazole 
• 21262-81-7 (3-methyl-4,5-dihydro-isoxazol-5-yl)-p-tolyl-methanone 

Relevant academic research and scientific papers

New analogues of epiboxidine incorporating the 4,5-dihydroisoxazole nucleus: Synthesis, binding affinity at neuronal nicotinic acetylcholine receptors, and molecular modeling investigations

A group of novel 4,5-dihydro-3-methylisoxazolyl derivatives, structurally related to epiboxidine (= 1R,4S,6S)-6-(3-methylisoxazol-5-yl)-7-azabicyclo[2.2.1]heptane), was prepared via 1,3-dipolar cyclo-addition of acetonitrile oxide to different olefins. Target compounds 1a and 1b, 2a and 2b, 3, 4, and 5 were tested for affinity at neuronal nicotinic heteromeric (α4β2) and homomeric (α7) acetylcholine receptors. Notably, diastereoisomers 1a and 1b were characterized by a massive drop of the affinity at the α4β2 subtypes (Ki values spanning the range 4.3-126 μM), when compared with that of epiboxidine (Ki= 0.6 nM). Therefore, the replacement of the 3-methylisoxazole ring of epiboxidine with the 4,5-dihydro-3-methylisoxazole nucleus is detrimental for the affinity at α4β2 receptors. A comparable lack of affinity/selectivity for the two nAChR subtypes under study was evidenced for the remaining epiboxidine-related dihydroisoxazole derivatives 2a and 2b, and 3-5. Diastereoisomers 1a and 1b, and spirocyclic derivative 3 were docked into molecular models of the receptor subtypes under study, and their binding mode was compared with that of reference ligands endowed with high binding affinity.

Practical and Regioselective Synthesis of C-4-Alkylated Pyridines

The direct position-selective C-4 alkylation of pyridines has been a long-standing challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using prefunctionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C-4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple and scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci chemistry as a late-stage functionalization technique.

Discovery and preclinical development of AR453588 as an anti-diabetic glucokinase activator

Glucose flux through glucokinase (GK) controls insulin release from the pancreas in response to high levels of glucose. Flux through GK is also responsible for reducing hepatic glucose output. Since many individuals with type 2 diabetes appear to have an inadequacy or defect in one or both of these processes, identifying compounds that can activate GK could provide a therapeutic benefit. Herein we report the further structure activity studies of a novel series of glucokinase activators (GKA). These studies led to the identification of pyridine 72 as a potent GKA that lowered post-prandial glucose in normal C57BL/6J mice, and after 14d dosing in ob/ob mice.

Nitro-, cyano-, and methylfuroxans, and their bis-derivatives: From green primary to melt-cast explosives

In the present work, we studied in detail the thermochemistry, thermal stability, mechanical sensitivity, and detonation performance for 20 nitro-, cyano-, and methyl derivatives of 1,2,5-oxadiazole-2-oxide (furoxan), along with their bis-derivatives. For all species studied, we also determined the reliable values of the gas-phase formation enthalpies using highly accurate multilevel procedures W2-F12 and/or W1-F12 in conjunction with the atomization energy approach and isodesmic reactions with the domain-based local pair natural orbital (DLPNO) modifications of the coupled-cluster techniques. Apart from this, we proposed reliable benchmark values of the formation enthalpies of furoxan and a number of its (azo)bis-derivatives. Additionally, we reported the previously unknown crystal structure of 3-cyano-4-nitrofuroxan. Among the monocyclic compounds, 3-nitro-4-cyclopropyl and dicyano derivatives of furoxan outperformed trinitrotoluene, a benchmark melt-cast explosive, exhibited decent thermal stability (decomposition temperature >200 ?C) and insensitivity to mechanical stimuli while having notable volatility and low melting points. In turn, 4,40-azobis-dicarbamoyl furoxan is proposed as a substitute of pentaerythritol tetranitrate, a benchmark brisant high explosive. Finally, the application prospects of 3,30-azobis-dinitro furoxan, one of the most powerful energetic materials synthesized up to date, are limited due to the tremendously high mechanical sensitivity of this compound. Overall, the investigated derivatives of furoxan comprise multipurpose green energetic materials, including primary, secondary, melt-cast, low-sensitive explosives, and an energetic liquid.

BRIDGED TRICYCLIC CARBAMOYLPYRIDONE COMPOUNDS AND THEIR PHARMACEUTICAL USE

Compounds for use in treating or preventing human immunodeficiency virus (HIV) infection are disclosed. The compounds have the following formula (I): including stereoisomers and pharmaceutically acceptable salts thereof, wherein R1, R2, L, W1, W2, X, Y, and Z are as defined herein. Methods associated with the preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

N -Oxide-Controlled Chemoselective Reduction of Nitrofuroxans

A facile and chemoselective SnCl 2 -mediated mild reduction of regioisomeric 3- and 4-nitrofuroxans for the synthesis of aminofurazans and aminofuroxans in good yields is developed. Reduction of 4-nitrofuroxans results in the selective formation of 4-aminofuroxans, while analogous reduction of 3-nitrofuroxans affords 3-aminofurazans as a result of simultaneous reduction of the nitro group and exocyclic N-O bond.

Simple one-pot synthesis of 5-(chloromethyl)isoxazoles from aldoximes and 2,3-dichloro-1-propene

[Figure not available: see fulltext.] A one-pot synthesis of 3-substituted 5-chloromethylisoxazoles from available starting aldoximes and 2,3-dichloro-1-propene, serving both as a solvent and reagent, is proposed. Excess 2,3-dichloro-1-propene is recovered after the reaction. The synthesis is effective for oximes of both aromatic and aliphatic aldehydes.

NOVEL COMPOUNDS

The invention relates to compounds of Formula (I) and their use in therapy, for example in the treatment of mycobacterial infections or in the treatment of diseases caused by mycobacterium, such as tuberculosis.

BIARYL DERIVATIVE AND MEDICINE CONTAINING SAME

Provided is a compound showing excellent antifungal activity against Trichophyton fungus, which is a major causative microorganism of superficial mycosis, and high effectiveness on diseases caused by Trichophyton fungi. A biaryl derivative represented by the formula (I) or a salt thereof: wherein ring A is an optionally substituted phenyl, or an optionally substituted 5- or 6-membered ring heteroaryl (ring A may be further condensed to form an optionally substituted fused ring); Q is CH2, C=O, NH, O, S or the like; X1, X2 and X3 are CR1 or N; Y is CH or N; Z is CR2b or N; R2a and R2b are each a hydrogen atom, a halogen atom, an optionally substituted C1-C6 alkyl group, a C1-C6 haloalkyl group or the like; R2a and R2b may form, together with carbon atoms bonded thereto, an optionally substituted carbocycle, or an optionally substituted heterocycle.

PHARMACEUTICALS COMPRISING BIARYL DERIVATIVES OR SALTS THEREOF

PROBLEM TO BE SOLVED: To provide compounds with excellent antimycotic activity against Trichophyton. SOLUTION: The invention provides pharmaceuticals comprising biaryl derivatives represented by general formula (I) or salts thereof, where ring A is optionally substituted phenyl or the like; Q is CH2 or the like; X1, X2 and X3 are CR1 or the like; and Y is CH or N. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT