Bioorganic and Medicinal Chemistry Letters

, том 6 , издание 10 , страницы 1133-1138

Nonpeptidic HIV protease inhibitors: 3-(S-benzyl substituted)-4-hydroxy-6-(phenyl substituted)-2H-pyran-2-one with an inverse mode of binding

J.V.N Vara Prasad ¹

A. Pavlovsky ¹

Kimberly S Para ¹

Edmund L. Ellsworth ¹

Peter J. Tummino ²

Carolyn Nouhan ²

Donna Ferguson ²

Скрыть аффилиации авторов Показать аффилиации авторов: 2 аффилиации

Department of Chemistry, Division ofWarner-Lambert Company, 2800 Plymouth Road, Ann Arbor, Michigan 48106, U.S.A. |

Department of Biochemistry, Parke-Davis Pharmaceutical Research, Division ofWarner-Lambert Company, 2800 Plymouth Road, Ann Arbor, Michigan 48106, U.S.A. |

Тип публикации: Journal Article

Дата публикации: 1996-05-01

Elsevier

Bioorganic and Medicinal Chemistry Letters

scimago Q2

wos Q2

БС2

SJR: 0.472

CiteScore: 5.1

Impact factor: 2.2

ISSN: 0960894X, 14643405

DOI: 10.1016/0960-894x(96)00185-0

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Organic Chemistry

Drug Discovery

Biochemistry

Molecular Biology

Pharmaceutical Science

Clinical Biochemistry

Molecular Medicine

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Systematic substitutions on 6-phenyl and 3-SCH 2 Ph rings of inhibitor 1 , were carried out to optimize the inhibitory activity against HIV PR. These studies lead to 3-Sbenzyl esters with enhanced potency. The X-ray crystal structure of 32 bound to HIV PR revealed that the 3-SCH 2 phenyl group is occupying the P 2 ′ pocket, which is contrary to the binding mode of 1 (derivative lacking ortho isopropyl ester group). In the latter case, benzyl group occupies the P 1 ′ pocket.

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Vara Prasad J. et al. Nonpeptidic HIV protease inhibitors: 3-(S-benzyl substituted)-4-hydroxy-6-(phenyl substituted)-2H-pyran-2-one with an inverse mode of binding // Bioorganic and Medicinal Chemistry Letters. 1996. Vol. 6. No. 10. pp. 1133-1138.

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Vara Prasad J., Pavlovsky A., Para K. S., Ellsworth E. L., Tummino P., Nouhan C., Ferguson D. Nonpeptidic HIV protease inhibitors: 3-(S-benzyl substituted)-4-hydroxy-6-(phenyl substituted)-2H-pyran-2-one with an inverse mode of binding // Bioorganic and Medicinal Chemistry Letters. 1996. Vol. 6. No. 10. pp. 1133-1138.

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TY - JOUR

DO - 10.1016/0960-894x(96)00185-0

UR - https://doi.org/10.1016/0960-894x(96)00185-0

TI - Nonpeptidic HIV protease inhibitors: 3-(S-benzyl substituted)-4-hydroxy-6-(phenyl substituted)-2H-pyran-2-one with an inverse mode of binding

T2 - Bioorganic and Medicinal Chemistry Letters

AU - Vara Prasad, J.V.N

AU - Pavlovsky, A.

AU - Para, Kimberly S

AU - Ellsworth, Edmund L.

AU - Tummino, Peter J.

AU - Nouhan, Carolyn

AU - Ferguson, Donna

PY - 1996

DA - 1996/05/01

PB - Elsevier

SP - 1133-1138

IS - 10

VL - 6

SN - 0960-894X

SN - 1464-3405

ER -

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@article{1996_Vara Prasad,

author = {J.V.N Vara Prasad and A. Pavlovsky and Kimberly S Para and Edmund L. Ellsworth and Peter J. Tummino and Carolyn Nouhan and Donna Ferguson},

title = {Nonpeptidic HIV protease inhibitors: 3-(S-benzyl substituted)-4-hydroxy-6-(phenyl substituted)-2H-pyran-2-one with an inverse mode of binding},

journal = {Bioorganic and Medicinal Chemistry Letters},

year = {1996},

volume = {6},

publisher = {Elsevier},

month = {may},

url = {https://doi.org/10.1016/0960-894x(96)00185-0},

number = {10},

pages = {1133--1138},

doi = {10.1016/0960-894x(96)00185-0}

}

MLA

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MLA Скопировать

Vara Prasad, J.V.N, et al. “Nonpeptidic HIV protease inhibitors: 3-(S-benzyl substituted)-4-hydroxy-6-(phenyl substituted)-2H-pyran-2-one with an inverse mode of binding.” Bioorganic and Medicinal Chemistry Letters, vol. 6, no. 10, May. 1996, pp. 1133-1138. https://doi.org/10.1016/0960-894x(96)00185-0.

Издатель

Elsevier

Журнал

Bioorganic and Medicinal Chemistry Letters

scimago Q2

wos Q2

БС2

SJR

0.472

CiteScore

5.1

Impact factor

2.2

ISSN

0960894X (Print)

14643405 (Electronic)