Synthesis of stereochemically diverse cyclic analogs of tubulysins

Yunjeong Park; Song Yi Bae; Jung Mi Hah; Sang Kook Lee; Jae Sang Ryu

doi:10.1016/j.bmc.2015.10.003

Synthesis of stereochemically diverse cyclic analogs of tubulysins

Yunjeong Park, Song Yi Bae, Jung Mi Hah, Sang Kook Lee, Jae Sang Ryu

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

The synthesis of tubulysin analogs containing stereochemically diverse cyclic Tuv moieties is described. A tetrahydropyranyl moiety was incorporated into the Tuv unit by enantioselective hetero Diels-Alder reactions of Danishefsky's diene and thiazole aldehyde. Four different stereoisomers of cyclic Tuv units were used as surrogates for the Tuv moiety. The synthesized stereochemically diverse simplified cyclic analogs were evaluated for the inhibition of tubulin polymerization.

Original language	English
Pages (from-to)	6827-6843
Number of pages	17
Journal	Bioorganic and Medicinal Chemistry
Volume	23
Issue number	21
DOIs	https://doi.org/10.1016/j.bmc.2015.10.003
State	Published - 1 Nov 2015

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Republic of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning ( NRF-2015R1A2A2A01004511 ).

Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.

Keywords

Antitumor agents
Asymmetric catalysis
Hetero Diels-Alder reaction
Peptides
Tubulysin

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10.1016/j.bmc.2015.10.003

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title = "Synthesis of stereochemically diverse cyclic analogs of tubulysins",

abstract = "The synthesis of tubulysin analogs containing stereochemically diverse cyclic Tuv moieties is described. A tetrahydropyranyl moiety was incorporated into the Tuv unit by enantioselective hetero Diels-Alder reactions of Danishefsky's diene and thiazole aldehyde. Four different stereoisomers of cyclic Tuv units were used as surrogates for the Tuv moiety. The synthesized stereochemically diverse simplified cyclic analogs were evaluated for the inhibition of tubulin polymerization.",

keywords = "Antitumor agents, Asymmetric catalysis, Hetero Diels-Alder reaction, Peptides, Tubulysin",

author = "Yunjeong Park and Bae, {Song Yi} and Hah, {Jung Mi} and Lee, {Sang Kook} and Ryu, {Jae Sang}",

note = "Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Republic of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning ( NRF-2015R1A2A2A01004511 ). Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

year = "2015",

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doi = "10.1016/j.bmc.2015.10.003",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry",

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T1 - Synthesis of stereochemically diverse cyclic analogs of tubulysins

AU - Park, Yunjeong

AU - Bae, Song Yi

AU - Hah, Jung Mi

AU - Lee, Sang Kook

AU - Ryu, Jae Sang

N1 - Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Republic of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning ( NRF-2015R1A2A2A01004511 ). Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2015/11/1

Y1 - 2015/11/1

N2 - The synthesis of tubulysin analogs containing stereochemically diverse cyclic Tuv moieties is described. A tetrahydropyranyl moiety was incorporated into the Tuv unit by enantioselective hetero Diels-Alder reactions of Danishefsky's diene and thiazole aldehyde. Four different stereoisomers of cyclic Tuv units were used as surrogates for the Tuv moiety. The synthesized stereochemically diverse simplified cyclic analogs were evaluated for the inhibition of tubulin polymerization.

AB - The synthesis of tubulysin analogs containing stereochemically diverse cyclic Tuv moieties is described. A tetrahydropyranyl moiety was incorporated into the Tuv unit by enantioselective hetero Diels-Alder reactions of Danishefsky's diene and thiazole aldehyde. Four different stereoisomers of cyclic Tuv units were used as surrogates for the Tuv moiety. The synthesized stereochemically diverse simplified cyclic analogs were evaluated for the inhibition of tubulin polymerization.

KW - Antitumor agents

KW - Asymmetric catalysis

KW - Hetero Diels-Alder reaction

KW - Peptides

KW - Tubulysin

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M3 - Article

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SP - 6827

EP - 6843

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 21

ER -

Synthesis of stereochemically diverse cyclic analogs of tubulysins

Abstract

Bibliographical note

Keywords

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