94133-71-8

Usage

Chemical structure

1-acetyl-4-[4-(2,3-dihydroxypropoxy)phenyl]piperazine

Family

Piperazine

Core structure

Piperazine

Additional groups

Acetyl group and a phenyl ring

Potential properties

Anti-cancer

Target cancer types

Prostate and breast cancers

Mechanism of action

Inhibits growth of cancer cells by targeting specific biological pathways involved in cancer development and progression

Current status

Undergoing preclinical and clinical studies

Study focus

Evaluating safety, efficacy, and potential as a therapeutic agent for cancer treatment

InChI:InChI=1/C15H22N2O4/c1-12(19)16-6-8-17(9-7-16)13-2-4-15(5-3-13)21-11-14(20)10-18/h2-5,14,18,20H,6-11H2,1H3

Upstream product

• 67914-60-7 N-acetyl-N'-(4-hydroxyphenyl)piperazine 
• 106-89-8 epichlorohydrin 

Relevant academic research and scientific papers

Preparation method of ketoconazole

The invention belongs to the technical field of medicine synthesis and in particular relates to a preparation method of ketoconazole. The preparation method of the ketoconazole, provided by the invention, comprises the following step: S101: enabling a compound shown as a formula I and a compound shown as a formula II to be mixed for reaction in an acidic medium to obtain the ketoconazole. According to the preparation method of the ketoconazole, the steric hindrance of the compound shown as the formula I and the compound shown as the formula II is great, so that the cis-trans selectivity of 1,3-dioxolame formed by reaction of the compound shown as the formula I and the compound shown as the formula II is remarkably improved, and furthermore, a benzoyl removing step is omitted; finally, theproduction period of the ketoconazole is shortened and the cost is reduced; meanwhile, the utilization of dangerous substances including bromine liquid and the like is reduced; the technical defects in the prior art that steps for synthesizing the ketoconazole is more and the yield and the purity are low are overcome.

Stereoselective Syntheses of Both Enantiomers of Ketoconazole from (R)- and (S)-Epichlorohydrin

Stereoselective syntheses of both enantiomers of ketoconazole (1) from commercially available (R)- or (S)-epichlorohydrin has been developed.The key-step of syntheses involves the selective substitution of the methylene chlorine atom by benzoate on a mixture of (2S,4R)-14a and (2R,4R)-15a or of their enentiomers, followed by crystalization of the corresponding cis-benzoates, (2R,4R)-18 or (2S,4S)-18, from which (+)- or (-)-1 were obtained as described for (+/-)-1.The ee's of (+)- and (-)-ketocanazole were determined by HPLC on the CSP Chiracel OD-H.