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Motilides, Macrolides With Gastrointestinal Motor Stimulating Activity. I. O-substituted and Tertiary N-substituted Derivatives of 8,9-anhydroerythromycin A 6,9-hemiacetal

Motilides, Macrolides With Gastrointestinal Motor Stimulating Activity. I. O-substituted and Tertiary N-substituted Derivatives of 8,9-anhydroerythromycin A 6,9-hemiacetal

K Tsuzuki, T Sunazuka, S Marui, H Toyoda, S Omura, N Inatomi, Z Itoh

Chem Pharm Bull (Tokyo). 1989 Oct;37(10):2687-700.

PMID: 2611928

Abstract:

Chemical modifications of 8,9-anhydroerythromycin A 6,9-hemiacetal (1), which showed gastrointestinal motor stimulating (GMS) activity 10 times more potent than that of erythromycin A (EM-A), were undertaken to search for derivatives having stronger GMS activity and no antimicrobial activity; details are described in this and a subsequent paper. Displacement of a methyl group of the dimethylamino group of 1 with an ethyl group and an isopropyl group provided de(N-methyl-N-ethyl-8,9-anhydroerythromycin A 6,9-hemiacetal (55) and de(N-methyl)-N-isopropyl-8,9-anhydroerythromycin A 6,9-hemiacetal (58), respectively. They showed significant GMS activity and no antibacterial activity. In particular, the GMS activity of 58 was increased to 248 times that of EM-A. EM-A and the derivatives obtained in this study mimic exogenous motilin in the dog. The name "motilide", meaning a motilin-like macrolide, is proposed for this new family of macrolide compounds.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP23893132	Anhydroerythromycin A		23893-13-2	Price

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