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Design and Synthesis of P1-P3 Macrocyclic Tertiary-Alcohol-Comprising HIV-1 Protease Inhibitors

Joshi, Advait ; Veron, Jean-Baptiste ; Unge, Johan LU ; Rosenquist, Asa ; Wallberg, Hans ; Samuelsson, Bertil ; Hallberg, Anders and Larhed, Mats (2013) In Journal of Medicinal Chemistry 56(22). p.8999-9007
Abstract
To study P1-P3 macrocyclizations of previously reported tertiary-alcohol-comprising HIV-1 protease inhibitors (PIs), three new 14- and 15-member macrocyclic PIs were designed, synthesized by ring-closing metathesis, and evaluated alongside with 10 novel linear PIs. Cocrystallized complexes of the macrocyclic PIs and the HIV-1 protease are presented, analyzed, and discussed. The macrocyclic structures exhibited higher activities than the linear precursors with K-i and EC50 values down to 3.1 nM and 0.37 mu M, respectively.
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author
; ; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Medicinal Chemistry
volume
56
issue
22
pages
8999 - 9007
publisher
The American Chemical Society (ACS)
external identifiers
  • wos:000327812600004
  • scopus:84889261380
  • pmid:24160253
ISSN
1520-4804
DOI
10.1021/jm400811d
language
English
LU publication?
yes
id
737fcf4f-7588-45cb-9d20-75c6960b8959 (old id 4272923)
date added to LUP
2016-04-01 10:02:22
date last changed
2022-03-19 08:48:50
@article{737fcf4f-7588-45cb-9d20-75c6960b8959,
  abstract     = {{To study P1-P3 macrocyclizations of previously reported tertiary-alcohol-comprising HIV-1 protease inhibitors (PIs), three new 14- and 15-member macrocyclic PIs were designed, synthesized by ring-closing metathesis, and evaluated alongside with 10 novel linear PIs. Cocrystallized complexes of the macrocyclic PIs and the HIV-1 protease are presented, analyzed, and discussed. The macrocyclic structures exhibited higher activities than the linear precursors with K-i and EC50 values down to 3.1 nM and 0.37 mu M, respectively.}},
  author       = {{Joshi, Advait and Veron, Jean-Baptiste and Unge, Johan and Rosenquist, Asa and Wallberg, Hans and Samuelsson, Bertil and Hallberg, Anders and Larhed, Mats}},
  issn         = {{1520-4804}},
  language     = {{eng}},
  number       = {{22}},
  pages        = {{8999--9007}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of Medicinal Chemistry}},
  title        = {{Design and Synthesis of P1-P3 Macrocyclic Tertiary-Alcohol-Comprising HIV-1 Protease Inhibitors}},
  url          = {{http://dx.doi.org/10.1021/jm400811d}},
  doi          = {{10.1021/jm400811d}},
  volume       = {{56}},
  year         = {{2013}},
}