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Literature DB >> 14611838

Synthesis and antimycobacterial activity of capuramycin analogues. Part 1: substitution of the azepan-2-one moiety of capuramycin.

Hitoshi Hotoda¹, Miyuki Furukawa, Makiko Daigo, Kazuhiro Murayama, Masakatsu Kaneko, Yasunori Muramatsu, Michiko Miyazawa Ishii, Shun-ichi Miyakoshi, Toshio Takatsu, Masatoshi Inukai, Masayo Kakuta, Tomomi Abe, Tamako Harasaki, Takashi Fukuoka, Yukio Utsui, Satoshi Ohya.

Abstract

Capuramycin analogues with a variety of substituents in place of the azepan-2-one moiety were synthesized from A-500359E and were tested for their translocase I inhibitory activity and in vitro antimycobacterial activity. Phenyl-type moieties were found to be effective substituents for capuramycin analogues.

Entities: Chemical

Mesh：

Substances：

Year: 2003 PMID： 14611838 DOI： 10.1016/s0960-894x(03)00596-1

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

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Cited

15 in total

1. Chemical modification of capuramycins to enhance antibacterial activity.

Authors: Elena Bogatcheva; Tia Dubuisson; Marina Protopopova; Leo Einck; Carol A Nacy; Venkata M Reddy
Journal: J Antimicrob Chemother Date: 2010-12-23 Impact factor: 5.790

2. A biocatalytic approach to capuramycin analogues by exploiting a substrate permissive N-transacylase CapW.

Authors: Xiaodong Liu; Yuanyuan Jin; Wenlong Cai; Keith D Green; Anwesha Goswami; Sylvie Garneau-Tsodikova; Koichi Nonaka; Satoshi Baba; Masanori Funabashi; Zhaoyong Yang; Steven G Van Lanen
Journal: Org Biomol Chem Date: 2016-04-06 Impact factor: 3.876

Review 3. Molecule Property Analyses of Active Compounds for Mycobacterium tuberculosis.

Authors: Vadim Makarov; Elena Salina; Robert C Reynolds; Phyo Phyo Kyaw Zin; Sean Ekins
Journal: J Med Chem Date: 2020-04-20 Impact factor: 7.446

Review 4. Targeting the Achilles' Heel of Bacteria: Different Mechanisms To Break Down the Peptidoglycan Cell Wall during Bacterial Warfare.

Authors: Stephanie Sibinelli-Sousa; Julia Takuno Hespanhol; Ethel Bayer-Santos
Journal: J Bacteriol Date: 2021-03-08 Impact factor: 3.490

5. The Biosynthesis of Capuramycin-type Antibiotics: IDENTIFICATION OF THE A-102395 BIOSYNTHETIC GENE CLUSTER, MECHANISM OF SELF-RESISTANCE, AND FORMATION OF URIDINE-5'-CARBOXAMIDE.

Authors: Wenlong Cai; Anwesha Goswami; Zhaoyong Yang; Xiaodong Liu; Keith D Green; Sandra Barnard-Britson; Satoshi Baba; Masanori Funabashi; Koichi Nonaka; Manjula Sunkara; Andrew J Morris; Anatol P Spork; Christian Ducho; Sylvie Garneau-Tsodikova; Jon S Thorson; Steven G Van Lanen
Journal: J Biol Chem Date: 2015-04-08 Impact factor: 5.157

Synthesis and antimycobacterial activity of capuramycin analogues. Part 1: substitution of the azepan-2-one moiety of capuramycin.

1. Chemical modification of capuramycins to enhance antibacterial activity.

2. A biocatalytic approach to capuramycin analogues by exploiting a substrate permissive N-transacylase CapW.

Review 3. Molecule Property Analyses of Active Compounds for Mycobacterium tuberculosis.

Review 4. Targeting the Achilles' Heel of Bacteria: Different Mechanisms To Break Down the Peptidoglycan Cell Wall during Bacterial Warfare.

5. The Biosynthesis of Capuramycin-type Antibiotics: IDENTIFICATION OF THE A-102395 BIOSYNTHETIC GENE CLUSTER, MECHANISM OF SELF-RESISTANCE, AND FORMATION OF URIDINE-5'-CARBOXAMIDE.

6. DPAGT1 Inhibitors of Capuramycin Analogues and Their Antimigratory Activities of Solid Tumors.

7. A reliable Pd-mediated hydrogenolytic deprotection of BOM group of uridine ureido nitrogen.

Review 8. Structures of Bacterial MraY and Human GPT Provide Insights into Rational Antibiotic Design.

9. Therapeutic efficacy of SQ641-NE against Mycobacterium tuberculosis.

10. Activity of SQ641, a capuramycin analog, in a murine model of tuberculosis.