Use of a Conformational-Switching Mechanism to Modulate Exposed Polarity: Discovery of CCR2 Antagonist BMS-741672 Article Swipe
Michael G. Yang
,
Zili Xiao
,
Robert J. Cherney
,
Andrew J. Tebben
,
Douglas G. Batt
,
Gregory D. Brown
,
Jing Chen
,
Mary Ellen Cvijic
,
Marta Dabros
,
John V. Duncia
,
Michael A. Galella
,
Daniel S. Gardner
,
Purnima Khandelwal
,
Soo S. Ko
,
Mary F. Malley
,
Ruowei Mo
,
Jian Pang
,
Anne Rose
,
Joseph B. Santella
,
Hong Shi
,
Anurag Srivastava
,
Sarah C. Traeger
,
Bei Wang
,
Songmei Xu
,
Rui-Lin Zhao
,
Joel C. Barrish
,
Sandhya Mandlekar
,
Qihong Zhao
,
Percy H. Carter
·
YOU?
·
· 2019
· Open Access
·
· DOI: https://doi.org/10.1021/acsmedchemlett.8b00439
YOU?
·
· 2019
· Open Access
·
· DOI: https://doi.org/10.1021/acsmedchemlett.8b00439
We encountered a dilemma in the course of studying a series of antagonists of the G-protein coupled receptor CC chemokine receptor-2 (CCR2): compounds with polar C3 side chains exhibited good ion channel selectivity but poor oral bioavailability, whereas compounds with lipophilic C3 side chains exhibited good oral bioavailability in preclinical species but poor ion channel selectivity. Attempts to solve this through the direct modulation of physicochemical properties failed. However, the installation of a protonation-dependent conformational switching mechanism resolved the problem because it enabled a highly selective and relatively polar molecule to access a small population of a conformer with lower polar surface area and higher membrane permeability. Optimization of the overall properties in this series yielded the CCR2 antagonist BMS-741672 (7), which embodied properties suitable for study in human clinical trials.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acsmedchemlett.8b00439
- OA Status
- green
- Cited By
- 17
- References
- 26
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W2909199334
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W2909199334Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.1021/acsmedchemlett.8b00439Digital Object Identifier
- Title
-
Use of a Conformational-Switching Mechanism to Modulate Exposed Polarity: Discovery of CCR2 Antagonist BMS-741672Work title
- Type
-
articleOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2019Year of publication
- Publication date
-
2019-01-16Full publication date if available
- Authors
-
Michael G. Yang, Zili Xiao, Robert J. Cherney, Andrew J. Tebben, Douglas G. Batt, Gregory D. Brown, Jing Chen, Mary Ellen Cvijic, Marta Dabros, John V. Duncia, Michael A. Galella, Daniel S. Gardner, Purnima Khandelwal, Soo S. Ko, Mary F. Malley, Ruowei Mo, Jian Pang, Anne Rose, Joseph B. Santella, Hong Shi, Anurag Srivastava, Sarah C. Traeger, Bei Wang, Songmei Xu, Rui-Lin Zhao, Joel C. Barrish, Sandhya Mandlekar, Qihong Zhao, Percy H. CarterList of authors in order
- Landing page
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https://doi.org/10.1021/acsmedchemlett.8b00439Publisher landing page
- Open access
-
YesWhether a free full text is available
- OA status
-
greenOpen access status per OpenAlex
- OA URL
-
https://doi.org/10.7270/q22r3w0qDirect OA link when available
- Concepts
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Chemistry, Protonation, Antagonist, Bioavailability, Biophysics, Conformational isomerism, Ion channel, Small molecule, Selectivity, Conformational change, Pharmacology, Stereochemistry, Molecule, Receptor, Biochemistry, Ion, Medicine, Biology, Organic chemistry, CatalysisTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
17Total citation count in OpenAlex
- Citations by year (recent)
-
2025: 1, 2024: 1, 2023: 5, 2022: 2, 2021: 3Per-year citation counts (last 5 years)
- References (count)
-
26Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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