Benzamide human PDE4B (phosphodiesterase 4B) inhibitor obtained through condensation of isovanillic acid derivative and saturated small cyclic amine

A technology of isovanillic acid and benzamide, applied in the field of enzyme inhibitor drugs

CN105646399AInactive Publication Date: 2016-06-08CHONGQING MEDICAL UNIVERSITY
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Authority / Receiving Office
CN · China
Current Assignee / Owner
Publication Date
2016-06-08
Estimated Expiration
Not applicable · inactive patent

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Abstract

A benzamide human PDE4B (phosphodiesterase 4B) inhibitor obtained through condensation of an isovanillic acid derivative and saturated small cyclic amine is structurally characterized in that an isovanillic acid mother nucleus comprises 3-(cyclopentyloxy)-4-methoxybenzoic acid and 3-cyclopropylmethoxy-4-difluoromethoxybenzoic acid, and the corresponding saturated small cyclic amine comprises morpholine, tetrahydropyrrole, cyclopentylamine and cyclohexylamine; the isovanillic acid mother nucleus and the corresponding saturated small cyclic amine are combined and subjected to condensation, and an amide compound is formed; in terms of the active characteristic, the amide compound is the human PDE4B inhibitor, and the human PDE4B inhibitor has an inhibition function for inflammatory factors TNF-a released by human monocytes under the stimulation of lipopolysaccharide.
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Description

technical field

[0001] The technical field of the present invention is enzyme inhibitor drugs, and relates to the structure of benzamides obtained by condensation of isovanillic acid derivatives and saturated small cyclic amines and the activity of inhibiting human phosphodiesterase 4B; representative compounds have strong inhibitory activity and anti inflammatory activity. Background technique

[0002] 3,5-cyclic adenosine monophosphate (cAMP) and 3,5-cyclic guanosine monophosphate (cGMP) are key second messengers in mammalian cells, regulating cellular functions; the only pathway for their degradation in vivo is phosphodiesterase ( Cyclicnucleotidephosphodiesterase (PDE)) catalyzed hydrolysis. In inflammatory cells and immune cells, phosphodiesterase isoenzyme 4 (PDE4) is the main one. PDE4 can specifically hydrolyze cAMP and is mainly expressed in neutrophils, monocytes, T cells, and bronchial smooth muscle cells The subtype is PDE4B [ProcNatlSciUSA. 2002, 99(11): 7628-...