Literature DB >> 12945903

Syntheses and biological evaluation of vinblastine congeners.

Martin E Kuehne1, William G Bornmann, Istvan Markó, Yong Qin, Karen L LeBoulluec, Deborah A Frasier, Feng Xu, Tshilundu Mulamba, Carol L Ensinger, Linda S Borman, Anne E Huot, Christopher Exon, Fred T Bizzarro, Julia B Cheung, Susan L Bane.   

Abstract

Sixty-two congeners of vinblastine (VLB), primarily with modifications of the piperidine ring in the carbomethoxycleavamine moiety of the binary alkaloid, were synthesized and evaluated for cytotoxicity against murine L1210 leukemia and RCC-2 rat colon cancer cells, and for their ability to inhibit polymerization of microtubular protein at < 10(-6) M, and for induction of spiralization of microtubular protein, and for microtubular disassembly at 10(-4) M concentrations. An ID50 range of >10(7) M concentrations was found for L1210 inhibition by these compounds, with the most active 1000x as potent as vinblastine.

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Year:  2003        PMID： 12945903     DOI： 10.1039/b209990j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  11 in total

1.  Synthesis of a Potent Vinblastine: Rationally Designed Added Benign Complexity.

Authors:  Oliver Allemann; Manuela Brutsch; John C Lukesh; Daniel M Brody; Dale L Boger
Journal:  J Am Chem Soc       Date:  2016-07-01       Impact factor: 15.419

2.  10'-Fluorovinblastine and 10'-Fluorovincristine: Synthesis of a Key Series of Modified Vinca Alkaloids.

Authors:  Hiroaki Gotoh; Katharine K Duncan; William M Robertson; Dale L Boger
Journal:  ACS Med Chem Lett       Date:  2011-12-08       Impact factor: 4.345

3.  Key analogs of a uniquely potent synthetic vinblastine that contain modifications of the C20' ethyl substituent.

Authors:  Oliver Allemann; R Matthew Cross; Manuela M Brütsch; Aleksandar Radakovic; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2017-05-18       Impact factor: 2.823

4.  Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues.

Authors:  Annie Tam; Hiroaki Gotoh; William M Robertson; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2010-09-19       Impact factor: 2.823

5.  Total synthesis and evaluation of a key series of C5-substituted vinblastine derivatives.

Authors:  Porino Va; Erica L Campbell; William M Robertson; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

6.  Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues.

Authors:  Hayato Ishikawa; David A Colby; Shigeki Seto; Porino Va; Annie Tam; Hiroyuki Kakei; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-04-08       Impact factor: 15.419

7.  Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: core redesign.

Authors:  Kristin D Schleicher; Yoshikazu Sasaki; Annie Tam; Daisuke Kato; Katharine K Duncan; Dale L Boger
Journal:  J Med Chem       Date:  2013-01-04       Impact factor: 7.446

Review 8.  Total synthesis of vinblastine, related natural products, and key analogues and development of inspired methodology suitable for the systematic study of their structure-function properties.

Authors:  Justin E Sears; Dale L Boger
Journal:  Acc Chem Res       Date:  2015-01-14       Impact factor: 22.384

9.  Ring-expansion synthesis and crystal structure of dimethyl 4-ethyl-1,4,5,6,7,8-hexa-hydro-azonino[5,6-b]indole-2,3-di-carboxyl-ate.

Authors:  Van Tuyen Nguyen; Elena A Sorokina; Anna V Listratova; Leonid G Voskressensky; Nikolai N Lobanov; Pavel V Dorovatovskii; Yan V Zubavichus; Victor N Khrustalev
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2017-02-07

10.  Design of new anti-Alzheimer drugs: ring-expansion synthesis and synchrotron X-ray diffraction study of dimethyl 4-ethyl-11-fluoro-1,4,5,6,7,8-hexa-hydro-azonino[5,6-b]indole-2,3-di-carboxyl-ate.

Authors:  Flavien A A Toze; Anna V Listratova; Leonid G Voskressensky; Natalia Yu Chernikova; Nikolai N Lobanov; Alexey N Bilyachenko; Pavel V Dorovatovskii
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-02-07
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