38425-26-2

Usage

Chemical Properties

ORANGE-BROWN CRYSTALLINE SOLID

Upstream product

• 108-88-3 toluene 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 5142-75-6 tri(p-tolyl)bismuth 
• 106-38-7 para-bromotoluene 
• 29480-08-8 1-(4-methylphenyl)cyclobutan-1-ol 
• 64214-66-0 N-Methyl-N-methoxy-4-chlorobutanamide 
• 4294-57-9 para-methylphenylmagnesium bromide 

Downstream Products

• 7143-76-2 cyclopropyl-p-tolyl-methanone 
• 75343-35-0 1-Phenyl-3-p-tolyl-1,4,5,6-tetrahydro-pyridazine 
• 38425-22-8 1-(1-Benzyl-4-chloro-butyl)-4-methyl-benzene 
• 104271-52-5 5,6-dihydro-8-(4-methylphenyl)imidazo<1,2-a>pyridine 
• 107454-19-3 5,6-dihydro-3-methyl-8-(4-methylphenyl)imidazo<1,5-a>pyridine 
• 649569-55-1 thioacetic acid S-(4-oxo-4-p-tolyl-butyl) ester 
• 173306-53-1 4-(4'-(hydroxy(diphenyl)methyl)piperidin-1-yl)-1-(4-methylphenyl)butan-1-one 
• 111756-77-5 1-bromo-3-chloropropyl 4-methylphenyl ketone 
• 357443-51-7 R-α-(3-Chloropropyl)-4-methyl-benzenemethanol 
• 3309-03-3 1-chloro-4-(p-methylphenyl)-4,4-ethylenedioxy-butane 
• 1227798-50-6 C₁₅H₂₂ClNOS 
• 1227798-67-5 C₁₅H₂₂ClNOS 
• 1227798-57-3 C₁₅H₂₃NOS 
• 1207729-68-7 (S)-1-((S)-2-methyl-propane-2-sulfinyl)-2-(4-methylphenyl)-pyrrolidine 

Relevant academic research and scientific papers

Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from: Mycobacterium tuberculosis to overcome kanamycin resistance

Tuberculosis (TB), caused by Mycobacterium tuberculosis (Mtb), is a deadly bacterial disease. Drug-resistant strains of Mtb make eradication of TB a daunting task. Overexpression of the enhanced intracellular survival (Eis) protein by Mtb confers resistance to the second-line antibiotic kanamycin (KAN). Eis is an acetyltransferase that acetylates KAN, inactivating its antimicrobial function. Development of Eis inhibitors as KAN adjuvant therapeutics is an attractive path to forestall and overcome KAN resistance. We discovered that an antipsychotic drug, haloperidol (HPD, 1), was a potent Eis inhibitor with IC50 = 0.39 ± 0.08 μM. We determined the crystal structure of the Eis-haloperidol (1) complex, which guided synthesis of 34 analogues. The structure-activity relationship study showed that in addition to haloperidol (1), eight analogues, some of which were smaller than 1, potently inhibited Eis (IC50 ≤ 1 μM). Crystal structures of Eis in complexes with three potent analogues and droperidol (DPD), an antiemetic and antipsychotic, were determined. Three compounds partially restored KAN sensitivity of a KAN-resistant Mtb strain K204 overexpressing Eis. The Eis inhibitors generally did not exhibit cytotoxicity against mammalian cells. All tested compounds were modestly metabolically stable in human liver microsomes, exhibiting 30-60% metabolism over the course of the assay. While direct repurposing of haloperidol as an anti-TB agent is unlikely due to its neurotoxicity, this study reveals potential approaches to modifying this chemical scaffold to minimize toxicity and improve metabolic stability, while preserving potent Eis inhibition. This journal is

Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals

A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful β- and γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale.

Regioselective Synthesis of Carbonyl-Containing Alkyl Chlorides via Silver-Catalyzed Ring-Opening Chlorination of Cycloalkanols

A novel and regioselective approach to carbonyl-containing alkyl chlorides via silver-catalyzed ring-opening chlorination of cycloalkanols is reported. Concurrent C(sp3)-C(sp3) bond cleavage and C(sp3)-Cl bond formation efficiently occur with good yields under mild conditions, and the chlorinated products are readily transformed into other useful synthetic intermediates and drugs. The reaction features complete regioselectivity, high efficiency, and excellent practicality. (Chemical Equation Presented).

Synthetic method of gamma-chlorobutanone derivatives

The invention discloses a synthetic method of gamma-chlorobutanone derivatives, and relates to a production method of inner-end and distal-end chlorinated aliphatic ketones in the technical field of chemical synthesis. Acetonitrile is taken as a solvent, manganese chloride is taken as a catalyst, tert-cyclobutanol, TMSCI (trimethylchlorosilane) and IBX (2-iodoxybenzoic acid) are subjected to a reaction, and a crude product is obtained; an organic solvent is removed through reduced-pressure concentration; the crude product is subjected to chromatography on a silica gel column with an organic solvent, and a refined product can be obtained. A synthetic route is shown in the specification, wherein R is aryl or alkyl. The raw materials used in the whole reaction process are cheap and easily available, a substrate adopted in the method has wide application range, and the whole reaction is simple and easy to operate and higher in yield; the reaction cost is reduced greatly.

The synthesis of ω-(2-aryl-1,3-dioxolan-2-yl)alkyl purine derivatives and their activity towards HIV reverse transcriptase

Novel derivatives of 6-substituted purines were synthesized by alkylation of 6-substituted purines with various 2-(chloroalkyl)-2-aryl-1,3-dioxolanes and related compounds. Their inhibitory properties toward HIV reverse transcriptase were studied. The structure-activity relationship within the synthesized compounds was found.

Synthesis of nitrogenated heterocycles by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)haloimines

Highly optically enriched, protected, nitrogenated heterocycles with different ring sizes have been synthesized by a very efficient methodology consisting of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl) haloimines followed by treatment with a base to promote an intramolecular nucleophilic substitution process. N-Protected aziridines, pyrrolidines, piperidines, and azepanes bearing aromatic, heteroaromatic, and aliphatic substituents have been obtained in very high yields and diastereomeric ratios up to >99:1. The free heterocycles can be easily obtained by a simple and mild desulfinylation procedure. Both enantiomers of the free heterocycles can be prepared with the same good results by changing the absolute configuration of the sulfur atom of the sulfinyl group.

Azido carbonyl compounds as DNA cleaving agents

Irradiation of azido carbonyl compounds using UV light (≥310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (≥350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode.

Atom-efficient cross-coupling reactions of triarylbismuths with acyl chlorides under Pd(0) catalysis

The atom-efficient cross-coupling reaction of triarylbismuths with a variety of aliphatic, aromatic, and hetero-aromatic acyl chlorides was demonstrated to afford high yields of cross-coupled ketones under palladium catalysis. The corresponding cross-coupling reaction with diacid chlorides also furnished bis-coupled ketones in good yields.

One-step preparation of α-chlorostyrenes

α-Chlorostyrenes were prepared via a one-step method involving Friedel-Crafts reaction of various aromatic substrates with acid chlorides in the presence of a heterogeneous Si-Fe catalyst.

Design and synthesis of selective, high-affinity inhibitors of human cytochrome P450 2J2

The active site topology, substrate specificity, and biological roles of the human cytochrome P450 CYP2J2, which is mainly expressed in the cardiovascular system, are poorly known even though recent data suggest that it could be a novel biomarker and potential target for therapy of human cancer. This paper reports a first series of high-affinity, selective CYP2J2 inhibitors that are related to terfenadine, with Ki values as low as 160 nM, that should be useful tools to determine the biological roles of CYP2J2.