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Structure-activity relationship studies of manzamine A: amidation of positions 6 and 8 of the beta-carboline moiety.

Abstract：

:Twenty manzamine amides were synthesized and evaluated for in vitro antimalarial and antimicrobial activities. The amides of manzamine A (1) showed significantly reduced cytotoxicity against Vero cells, although were less active than 1. The structure-activity analysis showed that linear, short alkyl groups adjacent to the amide carbonyl at position 8 are favored for antimalarial activity, while bulky and cyclic groups at position 6 provided the most active amides. Most of the amides showed potent activity against Mycobacterium intracellulare. The antimicrobial activity profile for position 8 series was similar to that for antimalarial activity profile, in which linear, slightly short alkyl groups adjacent to the amide carbonyl showed improved activity. Two amides 14 and 21, which showed potent antimalarial activity in vitro against Plasmodium falciparum were further evaluated in vivo in Plasmodium berghei infected mice. Oral administration of 14 and 21 at the dose of 30mg/kg (once daily for three days) caused parasitemia suppression of 24% and 62%, respectively, with no apparent toxicity.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Wahba AE,Peng J,Kudrimoti S,Tekwani BL,Hamann MT

doi

10.1016/j.bmc.2009.09.026

subject

Has Abstract

pub_date

2009-11-15 00:00:00

pages

7775-82

issue

22

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(09)00878-5

journal_volume

17

pub_type

杂志文章

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