15857-68-8

Usage

General Description

2,3-dihydro-4H-1-benzothiopyran-4-one oxime is a chemical compound with the molecular formula C11H11NO2S. It is a heterocyclic compound with a nitrogen and sulfur atom in its ring structure. 2,3-dihydro-4H-1-benzothiopyran-4-one oxime is also known as Trolox, a water-soluble analog of vitamin E with antioxidant properties. It has been studied for its potential therapeutic and protective effects in various diseases and conditions, including cancer, cardiovascular disease, and neurological disorders. 2,3-dihydro-4H-1-benzothiopyran-4-one oxime has shown promising results in reducing oxidative stress and inflammation in the body, making it a subject of interest in pharmaceutical and medical research.

InChI:InChI=1/C9H9NOS/c11-10-8-5-6-12-9-4-2-1-3-7(8)9/h1-4,11H,5-6H2

Upstream product

• 3528-17-4 2,3-dihydro-4H-[1]benzothiopyran-4-one 
• 3055-87-6 3-(phenylthio)propionitrile 
• 108-98-5 thiophenol 
• 5219-65-8 acide phenylthio-3 propanoique 

Downstream Products

• 1010079-97-6 (E)-thiochroman-4-one O-benzyl oxime 
• 58121-91-8 2,3,4,5-Tetrahydro-1,5-benzothiazepin hydrochloride 
• 40358-33-6 2,3,4,5-tetrahydro-benzo[b][1,4]thiazepine 
• 93192-72-4 3,4-dihydro-2H-thiochromen-4-ylamine 

Relevant academic research and scientific papers

New class of benzothiophene morpholine analogues with high selectivity and affinity were designed and evaluated for anti-drug addiction

To probe the mechanism of dopamine receptors in drug addiction and look for potential new methods for treating this disease, we have designed and synthesized benzothiophene morpholine analogues that were considered as dopamine D3 receptor-selective ligands. Radioligand binding assay was used to determine the binding affinity of target compounds. Members of this class have great selectivity and binding affinity in D3 receptor. In addition, the ability of these compounds to mitigate the symptoms of addiction from opioids was investigated in animal behavior patterns, and we have found that two compounds (18a and 18d) have good affinity in the D3R and exhibit the efficacy of anti-drug addiction in morphine-dependent mice induced by naloxone.

Design, synthesis and biological evaluation of brain penetrant benzazepine-based histone deacetylase 6 inhibitors for alleviating stroke-induced brain infarction

Histone deacetylase 6 (HDAC6) has become a promising therapeutic target for central nervous system diseases due to its more complex protein structure and biological functions. However, low brain penetration of reported HDAC6 inhibitors limits its clinical application in neurological disorders. Therefore, the benzazepine, a brain-penetrant rigid fragment, was utilized to design a series of selective HDAC6 inhibitors to improve brain bioavailability. Various synthetic strategies were applied to assemble the tetrahydro-benzazepine ring, and 22 compounds were synthesized. Among them, compound 5 showed low nanomolar potency and strong isozyme selectivity for the inhibition of HDAC6 (IC50 = 1.8 nM, 141-fold selectivity over HDAC1) with efficient binding patterns like coordination with the zinc ion and π-π stacking effect. Western blot results showed it could efficiently transport into SH-SY5Y cells and selectively enhance the acetylation level of α-tubulin with a moderate effect on Histone H3. Notably, pharmacokinetic studies demonstrated that compound 5 (brain/plasma ratio of 2.30) had an excellent ability to penetrate the blood-brain barrier of C57 mice. In male rats with transient middle cerebral artery occlusion (MCAO), compound 5 significantly reduced the cerebral infarction from 21.22% to 11.47% and alleviated neurobehavioral deficits in post-ischemic treatment, which provided a strong rationale for pursuing HDAC6-based therapies for ischemic stroke.

Directing group assisted nucleophilic substitution of propargylic alcohols via o -quinone methide intermediates: Br??nsted acid catalyzed, highly enantio- and diastereoselective synthesis of 7-alkynyl-12a-acetamido-substituted benzoxanthenes

BINOL-based, chiral phosphoric acids catalyze the substitution of 1-(o-hydroxyphenyl)propargylic alcohols with enamides to furnish 7-alkynyl-12a-acetamido-substituted benzo[c]xanthenes and related heterocycles in a one-pot operation with excellent diastereo- and enantioselectivity. Ambient reaction temperature, operationally simple reaction conditions, low catalyst loading, high yields, and excellent stereocontrol are attractive features of this process and make it a highly practical and versatile transformation.

Regioselective synthesis of heterocycles containing nitrogen neighboring an aromatic ring by reductive ring expansion using diisobutylaluminum hydride and studies on the reaction mechanism

(Chemical Equation Presented) A systematic investigation of the reductive ring-expansion reaction of cyclic ketoximes fused to aromatic ringswith diisobutylaluminum hydride (DIBALH) is described. This reaction regioselectively afforded a variety of five- to eight-membered bicyclic heterocycles or tricyclic heterocycles containing nitrogen neighboring an aromatic ring, including indoline, 1,2,3,4,5,6-hexahydrobenz[b]azocine, 3,4-dihydro-2H-benzo[b] [1,4]oxazine, 2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine, 1,2,3,4,5,6- hexahydroazepino[3,2-b]-indole, 2,3,4,5-tetrahydro-1H-benzothieno[2,3-b]azepine, 2,3,4,5-tetrahydro-1H-benzothieno[3,2-b]-azepine, 5,6-dihydrophenanthridine, and 5,6,11,12-tetrahydrodibenz[b, f]azocine. The reaction mechanism leading to the rearrangement was investigated on the basis of the restricted Becke three-parameter plus Lee-Yang-Parr (B3LYP) density functional theory (DFT) with the 6-31G (d) basis set. It was found that the reaction proceeds through a three-centered transition state via a stepwise mechanism because the potential energy curve along the intrinsic reaction coordinate (IRC) had twomaxima (saddle points; TS1 and TS2) and the partial phenonium cation intermediate C. In addition to cyclic ketoximes fused to aromatic rings, the reactions of various cyclic and acyclic ketoximeswere examined to investigate preference of migrating group. It was found that themore electron-rich group migrated preferentially to give the corresponding secondary amines.

Regiospecific synthesis of unsubstituted basic skeletons of heterocycles containing nitrogen neighboring an aromatic ring by the reductive ring expansion reaction using diisobutylaluminum hydride

A systematic investigation of reductive ring expansion reaction of oximes with diisobutylaluminum hydride (DIBAH) was performed. The reaction regiospecifically provided a variety of unsubstituted bicyclic heterocycles 3a-3g or tricyclic heterocycles 3h, 3j-3l that contained nitrogen attached to an aromatic ring.

Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: Application to the synthesis of nicotine analogues

(Chemical Equation Presented) An asymmetric synthesis for the preparation of nonracemic amines bearing heterocyclic and heteroaromatic rings is described. A variety of important enantiopure thionyl and arylalkyl primary amines were afforded by the borane-mediated enantioselective reduction of O-benzyl ketoximes using 10% of catalyst 10 derived from (S)-diphenylvalinol and ethylene glycol with excellent enantioselectivity, in up to 99% ee. The optimal condition for the first asymmetric reduction of 3- and 4-pyridyl-derived O-benzyl ketoxime ethers was achieved using 30% of catalytic loading in dioxane at 10°C. (S)-N-ethylnornicotine (3) was also successfully synthesized from the TIPS-protected (S)-2-amino-2-pyridylethanol in 97% ee.