Journal of Medicinal Chemistry

, volume 59 , issue 16 , pages 7677-7682

1,2,3-Triazoles as Amide Bioisosteres: Discovery of a New Class of Potent HIV-1 Vif Antagonists

Idrees Mohammed ¹

Indrasena Reddy Kummetha ²

Gatikrushna Singh ¹

Natalia Sharova ³

Gianluigi Lichinchi ^{1, 2}

Jason Dang ²

Mario Stevenson ³

Tariq Rana ^{1, 2}

Hide authors affiliations Show authors affiliations: 3 affiliations

Program for RNA Biology, Sanford Burnham Prebys Medical Discovery Institute, La Jolla, California 92037, United States |

Department of Pediatrics, University of California San Diego School of Medicine, 9500 Gilman Drive, MC 0762, La Jolla, California 92093 United States |

Division of Infectious Diseases, Miller School of Medicine, University of Miami, Miami, Florida 33136, United States |

Publication type: Journal Article

Publication date: 2016-08-10

American Chemical Society (ACS)

Journal of Medicinal Chemistry

scimago Q1

wos Q1

SJR: 1.801

CiteScore: 11.5

Impact factor: 6.8

ISSN: 00222623, 15204804

DOI: 10.1021/acs.jmedchem.6b00247

Copy DOI

PubMed ID: 27509004

Drug Discovery

Molecular Medicine

Abstract

RN-18 based viral infectivity factor (Vif), Vif antagonists reduce viral infectivity by rescuing APOBEC3G (A3G) expression and enhancing A3G-dependent Vif degradation. Replacement of amide functionality in RN-18 (IC50 = 6 μM) by isosteric heterocycles resulted in the discovery of a 1,2,3-trizole, 1d (IC50 = 1.2 μM). We identified several potent HIV-1 inhibitors from a 1d based library including 5ax (IC50 = 0.01 μM), 5bx (0.2 μM), 2ey (0.4 μM), 5ey (0.6 μM), and 6bx (0.2 μM).

Found

2 citations

Belyaev Evgeny

🤝

PhD in Chemistry

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h-index: 10

A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences

2 citations

Tsvetkov Vladimir

🤝

PhD in Chemistry

88 publications, 1 272 citations, 1 review

h-index: 19

A.V. Topchiev Institute of Petrochemical Synthesis RAS

Sechenov First Moscow State Medical University

Federal Research and Clinical Center of Physical-Chemical Medicine of Federal Medical Biological Agency

Modelling and Simulations

quadruplexes and i-motifs of DNA and RNA

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Larina Lyudmula

56 publications, 361 citations, 2 reviews

h-index: 10

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Photochemistry Center

Emanuel Institute of Biochemical Physics of the Russian Academy of Sciences

Chungnam National University

1 citation

Tikhonov Andrey

7 publications, 55 citations

h-index: 3

Sechenov First Moscow State Medical University

Peoples' Friendship University of Russia

Targeted drug delivery

Virology

1 citation

Skvortsova Yuliya

23 publications, 272 citations

h-index: 10

Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

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GOST Copy

Mohammed I. et al. 1,2,3-Triazoles as Amide Bioisosteres: Discovery of a New Class of Potent HIV-1 Vif Antagonists // Journal of Medicinal Chemistry. 2016. Vol. 59. No. 16. pp. 7677-7682.

GOST all authors (up to 50) Copy

Mohammed I., Kummetha I. R., Singh G., Sharova N., Lichinchi G., Dang J., Stevenson M., Rana T. 1,2,3-Triazoles as Amide Bioisosteres: Discovery of a New Class of Potent HIV-1 Vif Antagonists // Journal of Medicinal Chemistry. 2016. Vol. 59. No. 16. pp. 7677-7682.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.jmedchem.6b00247

UR - https://doi.org/10.1021/acs.jmedchem.6b00247

TI - 1,2,3-Triazoles as Amide Bioisosteres: Discovery of a New Class of Potent HIV-1 Vif Antagonists

T2 - Journal of Medicinal Chemistry

AU - Mohammed, Idrees

AU - Kummetha, Indrasena Reddy

AU - Singh, Gatikrushna

AU - Sharova, Natalia

AU - Lichinchi, Gianluigi

AU - Dang, Jason

AU - Stevenson, Mario

AU - Rana, Tariq

PY - 2016

DA - 2016/08/10

PB - American Chemical Society (ACS)

SP - 7677-7682

IS - 16

VL - 59

PMID - 27509004

SN - 0022-2623

SN - 1520-4804

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2016_Mohammed,

author = {Idrees Mohammed and Indrasena Reddy Kummetha and Gatikrushna Singh and Natalia Sharova and Gianluigi Lichinchi and Jason Dang and Mario Stevenson and Tariq Rana},

title = {1,2,3-Triazoles as Amide Bioisosteres: Discovery of a New Class of Potent HIV-1 Vif Antagonists},

journal = {Journal of Medicinal Chemistry},

year = {2016},

volume = {59},

publisher = {American Chemical Society (ACS)},

month = {aug},

url = {https://doi.org/10.1021/acs.jmedchem.6b00247},

number = {16},

pages = {7677--7682},

doi = {10.1021/acs.jmedchem.6b00247}

}

MLA

Cite this

MLA Copy

Mohammed, Idrees, et al. “1,2,3-Triazoles as Amide Bioisosteres: Discovery of a New Class of Potent HIV-1 Vif Antagonists.” Journal of Medicinal Chemistry, vol. 59, no. 16, Aug. 2016, pp. 7677-7682. https://doi.org/10.1021/acs.jmedchem.6b00247.

Publisher

American Chemical Society (ACS)

Journal

Journal of Medicinal Chemistry

scimago Q1

wos Q1

SJR

1.801

CiteScore

11.5

Impact factor

6.8

ISSN

00222623 (Print)

15204804 (Electronic)