Synthesis and activity of N-Benzyl pseudopeptides HIV protease inhibitors

Mauro Marastoni; Martina Bazzaro; Fabrizio Bortolotti; Roberto Tomatis

doi:10.1016/S0968-0896(02)00563-1

Synthesis and activity of N-Benzyl pseudopeptides HIV protease inhibitors

Mauro Marastoni
, Martina Bazzaro
, Fabrizio Bortolotti
, Roberto Tomatis

Obstetrics, Gynecology and Women's Health - Gynecologic Oncology

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

4 Scopus citations

Abstract

A series of N-benzyl pseudopeptides was designed, synthesized and tested as HIV-1 protease inhibitors. The ability of the new compounds containing N-benzyl hydroxyalkylamino acid core structure to inhibit HIV replication in cell culture is comparable to their capacity to inhibit the isolated enzyme, a result compatible with good pharmacokinetic properties of these derivatives. The pseudotripeptide Fmoc-Leu-N(Bzl)Hse-Met-NH-tBu was the best inhibitor of the series (IC₅₀=170 nM) showing promising inhibition of viral replication (ED₅₀=52 nM). All new compounds exhibit high enzymatic resistance and stability against cell cultures and plasma enzymes.

Original language	English (US)
Pages (from-to)	2477-2483
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	11
Issue number	11
DOIs	https://doi.org/10.1016/S0968-0896(02)00563-1
State	Published - May 29 2003

Bibliographical note

Funding Information:
Financial support of this work by University of Ferrara and by Ministero dell'Università e della Ricerca Scientifica e Tecnologica (MURST) is gratefully acknowledged.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Publisher link

10.1016/S0968-0896(02)00563-1

Find It

Find It at U of M Libraries

Cite this

@article{9b949f684a8b47089b3335cca02149fe,

title = "Synthesis and activity of N-Benzyl pseudopeptides HIV protease inhibitors",

abstract = "A series of N-benzyl pseudopeptides was designed, synthesized and tested as HIV-1 protease inhibitors. The ability of the new compounds containing N-benzyl hydroxyalkylamino acid core structure to inhibit HIV replication in cell culture is comparable to their capacity to inhibit the isolated enzyme, a result compatible with good pharmacokinetic properties of these derivatives. The pseudotripeptide Fmoc-Leu-N(Bzl)Hse-Met-NH-tBu was the best inhibitor of the series (IC50=170 nM) showing promising inhibition of viral replication (ED50=52 nM). All new compounds exhibit high enzymatic resistance and stability against cell cultures and plasma enzymes.",

author = "Mauro Marastoni and Martina Bazzaro and Fabrizio Bortolotti and Roberto Tomatis",

note = "Funding Information: Financial support of this work by University of Ferrara and by Ministero dell'Universit{\`a} e della Ricerca Scientifica e Tecnologica (MURST) is gratefully acknowledged.",

year = "2003",

month = may,

day = "29",

doi = "10.1016/S0968-0896(02)00563-1",

language = "English (US)",

volume = "11",

pages = "2477--2483",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd",

number = "11",

}

TY - JOUR

T1 - Synthesis and activity of N-Benzyl pseudopeptides HIV protease inhibitors

AU - Marastoni, Mauro

AU - Bazzaro, Martina

AU - Bortolotti, Fabrizio

AU - Tomatis, Roberto

N1 - Funding Information: Financial support of this work by University of Ferrara and by Ministero dell'Università e della Ricerca Scientifica e Tecnologica (MURST) is gratefully acknowledged.

PY - 2003/5/29

Y1 - 2003/5/29

N2 - A series of N-benzyl pseudopeptides was designed, synthesized and tested as HIV-1 protease inhibitors. The ability of the new compounds containing N-benzyl hydroxyalkylamino acid core structure to inhibit HIV replication in cell culture is comparable to their capacity to inhibit the isolated enzyme, a result compatible with good pharmacokinetic properties of these derivatives. The pseudotripeptide Fmoc-Leu-N(Bzl)Hse-Met-NH-tBu was the best inhibitor of the series (IC50=170 nM) showing promising inhibition of viral replication (ED50=52 nM). All new compounds exhibit high enzymatic resistance and stability against cell cultures and plasma enzymes.

AB - A series of N-benzyl pseudopeptides was designed, synthesized and tested as HIV-1 protease inhibitors. The ability of the new compounds containing N-benzyl hydroxyalkylamino acid core structure to inhibit HIV replication in cell culture is comparable to their capacity to inhibit the isolated enzyme, a result compatible with good pharmacokinetic properties of these derivatives. The pseudotripeptide Fmoc-Leu-N(Bzl)Hse-Met-NH-tBu was the best inhibitor of the series (IC50=170 nM) showing promising inhibition of viral replication (ED50=52 nM). All new compounds exhibit high enzymatic resistance and stability against cell cultures and plasma enzymes.

UR - https://www.scopus.com/pages/publications/0037624750

UR - https://www.scopus.com/pages/publications/0037624750#tab=citedBy

U2 - 10.1016/S0968-0896(02)00563-1

DO - 10.1016/S0968-0896(02)00563-1

M3 - Article

C2 - 12735995

AN - SCOPUS:0037624750

SN - 0968-0896

VL - 11

SP - 2477

EP - 2483

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 11

ER -

Synthesis and activity of N-Benzyl pseudopeptides HIV protease inhibitors

Abstract

Bibliographical note

UN SDGs

Publisher link

Find It

Other files and links

Fingerprint

Cite this