Bioorganic and Medicinal Chemistry Letters

, volume 25 , issue 14 , pages 2763-2767

Heteroaromatic analogs of the resveratrol analog DMU-212 as potent anti-cancer agents

Narsimha R. Penthala ^{1, 2, 3}

Shraddha Thakkar ^{1, 2, 3}

Peter A. Crooks ^{1, 2, 3}

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of Pharmaceutical Sciences, College of Pharmacy

UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES |

Little Rock AR 72205 United States |

Publication type: Journal Article

Publication date: 2015-07-01

Elsevier

Bioorganic and Medicinal Chemistry Letters

scimago Q2

wos Q2

SJR: 0.472

CiteScore: 5.1

Impact factor: 2.2

ISSN: 0960894X, 14643405

DOI: 10.1016/j.bmcl.2015.05.019

Copy DOI

PubMed ID: 26022840

Organic Chemistry

Drug Discovery

Biochemistry

Molecular Biology

Pharmaceutical Science

Clinical Biochemistry

Molecular Medicine

Abstract

Heteroaromatic analogs of DMU-212 (8-15) have been synthesized and evaluated for their anti-cancer activity against a panel of 60 human cancer cell lines. These novel analogs contain a trans-3,4,5-trimethoxystyryl moiety attached to the C2 position of indole, benzofuran, benzothiazole or benzothiophene ring (8, 11, 13 and 14, respectively) and showed potent growth inhibition in 85% of the cancer cell lines examined, with GI50 values <1 μM. Interestingly, trans-3,4- and trans-3,5-dimethoxystyryl DMU-212 analogs 9, 10, 12 and 15 exhibited significantly less growth inhibition than their 3,4,5-trimethoxystyryl counterparts, suggesting that the trans-3,4,5-trimethoxystyryl moiety is an essential structural element for the potent anti-cancer activity of these heterocyclic DMU-212 analogs. Molecular modeling studies showed that the four most active compounds (8, 11, 13 and 14) all bind to the colchicine binding site on tubulin, and that their binding modes are similar to that of DMU-212.

Found

1 citation

Tokarev Sergey

🥼

PhD in Chemistry

24 publications, 227 citations

h-index: 8

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Research interests

Coordination Chemistry

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Penthala N. R. et al. Heteroaromatic analogs of the resveratrol analog DMU-212 as potent anti-cancer agents // Bioorganic and Medicinal Chemistry Letters. 2015. Vol. 25. No. 14. pp. 2763-2767.

GOST all authors (up to 50) Copy

Penthala N. R., Thakkar S., Crooks P. A. Heteroaromatic analogs of the resveratrol analog DMU-212 as potent anti-cancer agents // Bioorganic and Medicinal Chemistry Letters. 2015. Vol. 25. No. 14. pp. 2763-2767.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.bmcl.2015.05.019

UR - https://doi.org/10.1016/j.bmcl.2015.05.019

TI - Heteroaromatic analogs of the resveratrol analog DMU-212 as potent anti-cancer agents

T2 - Bioorganic and Medicinal Chemistry Letters

AU - Penthala, Narsimha R.

AU - Thakkar, Shraddha

AU - Crooks, Peter A.

PY - 2015

DA - 2015/07/01

PB - Elsevier

SP - 2763-2767

IS - 14

VL - 25

PMID - 26022840

SN - 0960-894X

SN - 1464-3405

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2015_Penthala,

author = {Narsimha R. Penthala and Shraddha Thakkar and Peter A. Crooks},

title = {Heteroaromatic analogs of the resveratrol analog DMU-212 as potent anti-cancer agents},

journal = {Bioorganic and Medicinal Chemistry Letters},

year = {2015},

volume = {25},

publisher = {Elsevier},

month = {jul},

url = {https://doi.org/10.1016/j.bmcl.2015.05.019},

number = {14},

pages = {2763--2767},

doi = {10.1016/j.bmcl.2015.05.019}

}

MLA

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MLA Copy

Penthala, Narsimha R., et al. “Heteroaromatic analogs of the resveratrol analog DMU-212 as potent anti-cancer agents.” Bioorganic and Medicinal Chemistry Letters, vol. 25, no. 14, Jul. 2015, pp. 2763-2767. https://doi.org/10.1016/j.bmcl.2015.05.019.

Publisher

Elsevier

Journal

Bioorganic and Medicinal Chemistry Letters

scimago Q2

wos Q2

SJR

0.472

CiteScore

5.1

Impact factor

2.2

ISSN

0960894X (Print)

14643405 (Electronic)