Design, synthesis, X-ray studies, and biological evaluation of novel macrocyclic HIV-1 protease inhibitors involving the P1′-P2′ ligands
[Display omitted] Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1′-P2′ tethers are reported. Inhibitor 5a with a pyrrolidinone-derived macrocycle exhibited favorable enzyme inhibitory and antiviral activity (Ki=13.2nM, IC50=22n...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 27; no. 21; pp. 4925 - 4931 |
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| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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Elsevier Ltd
01.11.2017
Elsevier |
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| Abstract | [Display omitted]
Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1′-P2′ tethers are reported. Inhibitor 5a with a pyrrolidinone-derived macrocycle exhibited favorable enzyme inhibitory and antiviral activity (Ki=13.2nM, IC50=22nM). Further incorporation of heteroatoms in the macrocyclic skeleton provided macrocyclic inhibitors 5m and 5o. These compounds showed excellent HIV-1 protease inhibitory (Ki=62pM and 14pM, respectively) and antiviral activity (IC50=5.3nM and 2.0nM, respectively). Inhibitor 5o also remained highly potent against a DRV-resistant HIV-1 variant. |
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| AbstractList | Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1'-P2' tethers are reported. Inhibitor 5a with a pyrrolidinone-derived macrocycle exhibited favorable enzyme inhibitory and antiviral activity (K
=13.2nM, IC
=22nM). Further incorporation of heteroatoms in the macrocyclic skeleton provided macrocyclic inhibitors 5m and 5o. These compounds showed excellent HIV-1 protease inhibitory (K
=62pM and 14pM, respectively) and antiviral activity (IC
=5.3nM and 2.0nM, respectively). Inhibitor 5o also remained highly potent against a DRV-resistant HIV-1 variant. Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1'-P2' tethers are reported. Inhibitor 5a with a pyrrolidinone-derived macrocycle exhibited favorable enzyme inhibitory and antiviral activity (Ki = 13.2 nM, IC50 = 22 nM). Further incorporation of heteroatoms in the macrocyclic skeleton provided macrocyclic inhibitors 5m and 5o. Lastly, these compounds showed excellent HIV-1 protease inhibitory (Ki = 62 pM and 14 pM, respectively) and antiviral activity (IC50 = 5.3 nM and 2.0 nM, respectively). Inhibitor 5o also remained highly potent against a DRV-resistant HIV-1 variant. Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1′–P2′ tethers are reported. Inhibitor 5a with a pyrrolidinone-derived macrocycle exhibited favorable enzyme inhibitory and antiviral activity ( K i = 13.2 nM, IC 50 = 22 nM). Further incorporation of heteroatoms in the macrocyclic skeleton provided macrocyclic inhibitors 5m and 5o . These compounds showed excellent HIV-1 protease inhibitory ( K i = 62 pM and 14 pM, respectively) and antiviral activity (IC 50 = 5.3 nM and 2.0 nM, respectively). Inhibitor 5o also remained highly potent against a DRV-resistant HIV-1 variant. Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1'-P2' tethers are reported. Inhibitor 5a with a pyrrolidinone-derived macrocycle exhibited favorable enzyme inhibitory and antiviral activity (Ki=13.2nM, IC50=22nM). Further incorporation of heteroatoms in the macrocyclic skeleton provided macrocyclic inhibitors 5m and 5o. These compounds showed excellent HIV-1 protease inhibitory (Ki=62pM and 14pM, respectively) and antiviral activity (IC50=5.3nM and 2.0nM, respectively). Inhibitor 5o also remained highly potent against a DRV-resistant HIV-1 variant. [Display omitted] Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1′-P2′ tethers are reported. Inhibitor 5a with a pyrrolidinone-derived macrocycle exhibited favorable enzyme inhibitory and antiviral activity (Ki=13.2nM, IC50=22nM). Further incorporation of heteroatoms in the macrocyclic skeleton provided macrocyclic inhibitors 5m and 5o. These compounds showed excellent HIV-1 protease inhibitory (Ki=62pM and 14pM, respectively) and antiviral activity (IC50=5.3nM and 2.0nM, respectively). Inhibitor 5o also remained highly potent against a DRV-resistant HIV-1 variant. Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1'-P2' tethers are reported. Inhibitor 5a with a pyrrolidinone-derived macrocycle exhibited favorable enzyme inhibitory and antiviral activity (K-i = 13.2 nM, IC50 = 22 nM). Further incorporation of heteroatoms in the macrocyclic skeleton provided macrocyclic inhibitors 5m and 5o. These compounds showed excellent HIV-1 protease inhibitory (K-i = 62 pM and 14 pM, respectively) and antiviral activity (IC50 = 5.3 nM and 2.0 nM, respectively). Inhibitor 5o also remained highly potent against a DRV-resistant HIV-1 variant. (C) 2017 Elsevier Ltd. All rights reserved. |
| Author | Steffey, Melinda Agniswamy, Johnson Brindisi, Margherita Sean Fyvie, W. Aoki, Manabu Weber, Irene T. Amano, Masayuki Mitsuya, Hiroaki Ghosh, Arun K. Wang, Yuan-Fang |
| AuthorAffiliation | b Department of Medicinal Chemistry, Purdue University, West Lafayette, IN 47907 (USA) d Departments of Hematology and Infectious Diseases, Kumamoto University of Medicine, Kumamoto 860-8556 (Japan) f Center for Clinical Sciences, National Center for Global Health and Medicine, Shinjuku, Tokyo 162-8655 (Japan) a Department of Chemistry, Purdue University, West Lafayette, IN 47907 e Experimental Retrovirology Section, HIV and AIDS Malignancy Branch National Cancer Institute, Bethesda, MD 20892 (USA) c Departments of Biology and Chemistry, Georgia State University, Atlanta, GA 30303 (USA) |
| AuthorAffiliation_xml | – name: a Department of Chemistry, Purdue University, West Lafayette, IN 47907 – name: e Experimental Retrovirology Section, HIV and AIDS Malignancy Branch National Cancer Institute, Bethesda, MD 20892 (USA) – name: b Department of Medicinal Chemistry, Purdue University, West Lafayette, IN 47907 (USA) – name: d Departments of Hematology and Infectious Diseases, Kumamoto University of Medicine, Kumamoto 860-8556 (Japan) – name: f Center for Clinical Sciences, National Center for Global Health and Medicine, Shinjuku, Tokyo 162-8655 (Japan) – name: c Departments of Biology and Chemistry, Georgia State University, Atlanta, GA 30303 (USA) |
| Author_xml | – sequence: 1 givenname: Arun K. surname: Ghosh fullname: Ghosh, Arun K. email: akghosh@purdue.edu organization: Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA – sequence: 2 givenname: W. surname: Sean Fyvie fullname: Sean Fyvie, W. organization: Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA – sequence: 3 givenname: Margherita surname: Brindisi fullname: Brindisi, Margherita organization: Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA – sequence: 4 givenname: Melinda surname: Steffey fullname: Steffey, Melinda organization: Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA – sequence: 5 givenname: Johnson surname: Agniswamy fullname: Agniswamy, Johnson organization: Departments of Biology and Chemistry, Georgia State University, Atlanta, GA 30303, USA – sequence: 6 givenname: Yuan-Fang surname: Wang fullname: Wang, Yuan-Fang organization: Departments of Biology and Chemistry, Georgia State University, Atlanta, GA 30303, USA – sequence: 7 givenname: Manabu surname: Aoki fullname: Aoki, Manabu organization: Departments of Hematology and Infectious Diseases, Kumamoto University of Medicine, Kumamoto 860-8556, Japan – sequence: 8 givenname: Masayuki surname: Amano fullname: Amano, Masayuki organization: Departments of Hematology and Infectious Diseases, Kumamoto University of Medicine, Kumamoto 860-8556, Japan – sequence: 9 givenname: Irene T. surname: Weber fullname: Weber, Irene T. organization: Departments of Biology and Chemistry, Georgia State University, Atlanta, GA 30303, USA – sequence: 10 givenname: Hiroaki surname: Mitsuya fullname: Mitsuya, Hiroaki organization: Departments of Hematology and Infectious Diseases, Kumamoto University of Medicine, Kumamoto 860-8556, Japan |
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| CitedBy_id | crossref_primary_10_1016_j_chemolab_2019_103888 crossref_primary_10_1021_acsinfecdis_1c00237 crossref_primary_10_1016_j_virusres_2020_198289 crossref_primary_10_1002_cbic_201800247 |
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| Keywords | P1′-P2′ ligands Drug resistance HIV protease Macrocyclic inhibitors Structure-based design P1 '-P2 ' ligands POTENT ACTIVE ANTIRETROVIRAL THERAPY TMC114 PI INFECTION DRUG-RESISTANCE BACKBONE |
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Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1′-P2′ tethers are... Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1'-P2' tethers are reported. Inhibitor... Design, synthesis, and evaluation of a new class of HIV-1 protease inhibitors containing diverse flexible macrocyclic P1′–P2′ tethers are reported. Inhibitor... |
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| SubjectTerms | 60 APPLIED LIFE SCIENCES Binding Sites Chemistry Chemistry, Medicinal Chemistry, Organic Crystallography, X-Ray Drug Design Drug resistance HIV protease HIV Protease - chemistry HIV Protease - genetics HIV Protease - metabolism HIV Protease Inhibitors - chemical synthesis HIV Protease Inhibitors - chemistry HIV Protease Inhibitors - metabolism HIV-1 - enzymology Inhibitory Concentration 50 Life Sciences & Biomedicine Ligands Macrocyclic Compounds - chemical synthesis Macrocyclic Compounds - chemistry Macrocyclic Compounds - metabolism Macrocyclic inhibitors Molecular Dynamics Simulation Mutation P1′-P2′ ligands Pharmacology & Pharmacy Physical Sciences Protein Structure, Tertiary Pyrrolidinones - chemistry Science & Technology Structure-Activity Relationship Structure-based design |
| Title | Design, synthesis, X-ray studies, and biological evaluation of novel macrocyclic HIV-1 protease inhibitors involving the P1′-P2′ ligands |
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