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Motilides, Macrolides With Gastrointestinal Motor Stimulating Activity. II. Quaternary N-substituted Derivatives of 8,9-anhydroerythromycin A 6,9-hemiacetal and 9,9-dihydroerythromycin A 6,9-epoxide

Motilides, Macrolides With Gastrointestinal Motor Stimulating Activity. II. Quaternary N-substituted Derivatives of 8,9-anhydroerythromycin A 6,9-hemiacetal and 9,9-dihydroerythromycin A 6,9-epoxide

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

Chem Pharm Bull (Tokyo). 1989 Oct;37(10):2701-9.

PMID: 2611929

Abstract:

A series of quaternary ammonium derivatives of 8,9-anhydroerythromycin A 6,9-hemiacetal (1) and 9,9-dihydroerythromycin A 6,9-epoxide (2) has been prepared and tested for antimicrobial activity and gastrointestinal motor stimulating (GMS) activity in the dog (in vivo). The GMS activity is enhanced markedly when small alkyl halides and unsaturated alkyl halides such as allyl bromide and propargyl bromide are added to the dimethylamino group of 1. Among them, N-propargyl-8,9-anhydroerythromycin A 6,9-hemiacetal bromide (3) exhibits GMS activity 2890 times stronger than that of erythromycin A and is completely devoid of antimicrobial activity. The potency of 3 is comparable to that of synthetic motilin both in vitro and in vivo.

Chemicals Related in the Paper:

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

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