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Literature DB >> 18975929

Alteration of the bis-tetrahydrofuran core stereochemistries in asimicin can affect the cytotoxicity.

Subhash C Sinha¹, Zhiyong Chen, Zheng-Zheng Huang, Eiko Nakamaru-Ogiso, Halina Pietraszkiewicz, Matthew Edelstein, Frederick Valeriote.

Abstract

A systematic analysis using 10 synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound.

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Year: 2008 PMID： 18975929 PMCID： PMC2670474 DOI： 10.1021/jm801028c

Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446

29 in total

1. A metal-oxo mediated approach to the synthesis of 21,22-diepi-membrarollin.

Authors: Yulai Hu; Richard C D Brown
Journal: Chem Commun (Camb) Date: 2005-10-21 Impact factor: 6.222

Review 2. Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action.

Authors: Almudena Bermejo; Bruno Figadere; Maria-Carmen Zafra-Polo; Isabel Barrachina; Ernesto Estornell; Diego Cortes
Journal: Nat Prod Rep Date: 2005-03-15 Impact factor: 13.423

3. Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells.

Authors: N H Oberlies; C J Chang; J L McLaughlin
Journal: J Med Chem Date: 1997-06-20 Impact factor: 7.446

4. Total synthesis of asimicin and bullatacin.

Authors: H Avedissian; S C Sinha; A Yazbak; A Sinha; P Neogi; S C Sinha; E Keinan
Journal: J Org Chem Date: 2000-09-22 Impact factor: 4.354

5. In vitro antitumor structure-activity relationships of threo/trans/threo/trans/erythro bis-tetrahydrofuranic acetogenins: correlations with their inhibition of mitochondrial complex I.

Authors: José R Tormo; Nuria DePedro; Inmaculada Royo; Isabel Barrachina; M Carmen Zafra-Polo; Cristina Cuadrillero; Pilar Hernández; Diego Cortes; Fernando Peláez
Journal: Oncol Res Date: 2005 Impact factor: 5.574

6. Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin.

Authors: Hongda Zhao; Jeffrey S T Gorman; Brian L Pagenkopf
Journal: Org Lett Date: 2006-09-14 Impact factor: 6.005

3. Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin-Chatenaytrienin-1.

Authors: Vladimir A D'yakonov; Regina A Tuktarova; Usein M Dzhemilev
Journal: ACS Omega Date: 2019-08-16

3 in total

Alteration of the bis-tetrahydrofuran core stereochemistries in asimicin can affect the cytotoxicity.

1. A metal-oxo mediated approach to the synthesis of 21,22-diepi-membrarollin.

Review 2. Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action.

3. Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells.

4. Total synthesis of asimicin and bullatacin.

5. In vitro antitumor structure-activity relationships of threo/trans/threo/trans/erythro bis-tetrahydrofuranic acetogenins: correlations with their inhibition of mitochondrial complex I.

6. Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin.

7. Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.

8. Total synthesis of a 28-member stereoisomer library of murisolins.

9. A modular synthesis of annonaceous acetogenins.

10. Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF rings.

1. Studies toward a library of tetrahydrofurans: click and MCR products of mono- and bis-tetrahydrofurans.

2. Activation of respiratory Complex I from Escherichia coli studied by fluorescent probes.

3. Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin-Chatenaytrienin-1.