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Phenyl Acetate Derivatives, Fluorine-Substituted on the Phenyl Group, as Rapid Recovery Hypnotic Agents With Reflex Depression

Phenyl Acetate Derivatives, Fluorine-Substituted on the Phenyl Group, as Rapid Recovery Hypnotic Agents With Reflex Depression

Heng Zhang, Xiangqing Xu, Yin Chen, Yinli Qiu, Xin Liu, Bi-Feng Liu, Guisen Zhang

Eur J Med Chem. 2015 Jan 7;89:524-39.

PMID: 25462263

Abstract:

We report the synthesis of novel, potentially hypnotic fluorine-substituted phenyl acetate derivatives. We describe the structure-activity relationship that led us to the promising derivative: ethyl 2-(4-(2-(diethylamino)-2-oxoethoxy)-5-ethoxy-2-fluorophenyl) acetate (55). The unique pharmacological features of compound 55 are its relatively high affinity for the GABAA receptor, together with a unique affinity for the NMDA receptor, different to propanidid and AZD3043. In animal models, compound 55 showed stronger hypnotic potency and longer duration of LORR than propanidid and AZD3043, but also maintained a rapid recovery time to walking and behavioral recovery. In particular, compound 55 displayed reflex depression during infusion.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP122792	Phenyl acetate		122-79-2	Price

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