Abstract
We report herein an efficient enantioselective synthesis of SPF32629A and SPF32629B through one-pot enantioselective reduction and protecting-group-free regioselective O-acylation strategy. The absolute configuration of the enantiomerically pure isomers was established by Mosher ester analysis. The inhibitory potencies of the synthesized compounds were assayed in vitro against a panel of microorganisms and against A549 human lung adenocarcinoma cell line. Compounds 2, 11 and 12 displayed moderate to potent antibacterial activity against all the tested strains and compounds 7, 8, 2, 11 and 12 exhibited significant cytotoxicity in a dose-dependent manner with an IC50 values ranging from 2.92 to 4.14 μg/ml and 8-11 μM.
Copyright © 2011 Elsevier Masson SAS. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Bacterial Agents / chemical synthesis
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology*
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Bacteria / drug effects*
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Cell Proliferation / drug effects
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Dose-Response Relationship, Drug
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Drug Screening Assays, Antitumor
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Humans
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Microbial Sensitivity Tests
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Molecular Structure
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Niacin / analogs & derivatives*
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Niacin / chemical synthesis
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Niacin / chemistry
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Niacin / pharmacology
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Pyridones / chemical synthesis
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Pyridones / chemistry
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Pyridones / pharmacology*
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Stereoisomerism
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Structure-Activity Relationship
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Tumor Cells, Cultured
Substances
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Anti-Bacterial Agents
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Antineoplastic Agents
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Pyridones
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SPF 32629 A
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SPF 32629 B
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Niacin