Total Synthesis of (±)-Marinopyrrole A and Its Library as Potential Antibiotic and Anticancer Agents

被引：56

作者：

Cheng, Chunwei ^{[2
,3
]}

Pan, Lili ^{[2
,3
]}

Chen, Yi ^{[2
,3
]}

Song, Hao ^{[2
,3
]}

Qin, Yong ^{[2
,3
]}

Li, Rongshi ^{[1
]}

机构：

[1] Univ S Florida, Dept Drug Discovery, H Lee Moffitt Canc Ctr & Res Inst, Tampa, FL 33612 USA

[2] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Minist Educ, W China Sch Pharm,State Key Lab Biotherapy, Chengdu 610041, Peoples R China

[3] Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2010年 / 12卷 / 04期

关键词：

DRUG DISCOVERY; NATURAL-PRODUCTS;

D O I：

10.1021/cc100052j

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The first total synthesis of marine natural product, (+/-)-marinopyrrole A, has been accomplished via a nine-step synthesis in an overall yield of 30%. A small focused library based on marinopyrrole has been designed and synthesized. The scope of chemistry was investigated, and a robust chemistry suitable for library synthesis has been developed in the current study. The method that we have developed has made it possible to generate diverse analogues based on structurally novel marinopyrroles for study of potential antibiotic and anticancer activities.

引用

页码：541 / 547

页数：7

共 13 条

[1] Discovery of Innovative Small Molecule Therapeutics [J].

Abou-Gharbia, Magid .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (01) :2-9

[2] Marine natural product libraries for high-throughput screening and rapid drug discovery [J].

Bugni, Tim S. ;

Richards, Burt ;

Bhoite, Leen ;

Cimbora, Daniel ;

Harper, Mary Kay ;

Ireland, Chris M. .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (06) :1095-1098

[3] Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2007 [J].

Dolle, Roland E. ;

Le Bourdonnec, Bertrand ;

Goodman, Allan J. ;

Morales, Guillermo A. ;

Thomas, Craig J. ;

Zhang, Wei .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (06) :753-802

[4] Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2008 [J].

Dolle, Roland E. ;

Le Bourdonnec, Bertrand ;

Goodman, Allan J. ;

Morales, Guillermo A. ;

Thomas, Craig J. ;

Zhang, Wei .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (05) :739-790

[5] The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp. [J].

Hughes, Chambers C. ;

Prieto-Davo, Alejandra ;

Jensen, Paul R. ;

Fenical, William .

ORGANIC LETTERS, 2008, 10 (04) :629-631

[6] Marinopyrrole A Target Elucidation by Acyl Dye Transfer [J].

Hughes, Chambers C. ;

Yang, Yu-Liang ;

Liu, Wei-Ting ;

Dorrestein, Pieter C. ;

La Clair, James J. ;

Fenical, William .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) :12094-+

[7] The evolving role of natural products in drug discovery [J].

Koehn, FE ;

Carter, GT .

NATURE REVIEWS DRUG DISCOVERY, 2005, 4 (03) :206-220

[8] Drug Discovery and Natural Products: End of an Era or an Endless Frontier? [J].

Li, Jesse W. -H. ;

Vederas, John C. .

SCIENCE, 2009, 325 (5937) :161-165

[9] Drug development from marine natural products [J].

Molinski, Tadeusz F. ;

Dalisay, Doralyn S. ;

Lievens, Sarah L. ;

Saludes, Jonel P. .

NATURE REVIEWS DRUG DISCOVERY, 2009, 8 (01) :69-85

[10] Modern natural products chemistry and drug discovery [J].

Ojima, Iwao .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (09) :2587-2588

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