ArticleACS medicinal chemistry letters2021
Comprehensive Strategies to Bicyclic Prolines: Applications in the Synthesis of Potent Arginase Inhibitors.
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Article in ACS medicinal chemistry letters, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5citing papers in PubMed
1.0field-weighted citation impact, top 25% of its field
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
5 citing papers in PubMed, 19 citations in OpenAlex.
- Modular diastereoselective synthesis of hindered cyclobutane amino nitriles through triplet nitrene-mediated ring expansion.Nature chemistry · 2026Article
- Diversity-oriented photobiocatalytic synthesis via stereoselective three-component radical coupling.Science (New York, N.Y.) · 2025Article
- Therapeutic potential of natural arginase modulators: mechanisms, challenges, and future directions.Frontiers in pharmacology · 2025Review
- Synthesis of 2-Azanorbornanes via Strain-Release Formal Cycloadditions Initiated by Energy Transfer.Angewandte Chemie (International ed. in English) · 2023Article
- Virus-Induced Membrane Fusion in Neurodegenerative Disorders.Frontiers in cellular and infection microbiology · 2022Review
Corrections and comments
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Authors and funding
25 authors at 2 institutions in 2 countries.
Derun LiDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.ORCID https://orcid.org/0000-0003-0512-6684
Hongjun ZhangDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.ORCID https://orcid.org/0000-0002-1136-6142
Thomas W LyonsDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Min LuDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.ORCID https://orcid.org/0000-0003-0378-9134
Abdelghani AchabDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Qinglin PuDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.ORCID https://orcid.org/0000-0002-7853-4542
Matthew ChildersDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Matthew J MitcheltreeDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.ORCID https://orcid.org/0000-0003-3774-628X
Jialiang WangIDSU, WuXi AppTec Co., Ltd., Shanghai 200131, China.
Theodore A MartinotDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.ORCID https://orcid.org/0000-0003-2290-9621
Spencer E McMinnDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
David L SlomanDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.ORCID https://orcid.org/0000-0003-3404-9382
Anandan PalaniDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Adam BeardDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Lisa NogleDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Symon GathiakaDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Josep SauríDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Hai-Young KimDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.ORCID https://orcid.org/0000-0002-9010-4895
Donovon AdpressaDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Peter SpacciapoliDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
J Richard MillerDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Rachel L PalteDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Charles A LesburgDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.ORCID https://orcid.org/0000-0001-7245-7331
Jared CummingDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Christian FischerDepartment of Discovery Chemistry, Department of Discovery Process Chemistry, Department of In Vitro Pharmacology, Department of Computational and Structural Chemistry, and Department of Analytical Research and Development, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States.
Merck & Co., Inc., Rahway, NJ, USA (United States) · USWuXi AppTec (China) · CN
Funding
No grant is acknowledged in the PubMed record.
Abstract
Comprehensive synthetic strategies afforded a diverse set of structurally unique bicyclic proline-containing arginase inhibitors with a high degree of three-dimensionality. The analogs that favored the Cγ-exo conformation of the proline improved the arginase potency over the initial lead. The novel synthetic strategies reported here not only enable access to previously unknown stereochemically complex proline derivatives but also provide a foundation for the future synthesis of bicyclic proline analogs, which incorporate inherent three-dimensional character into building blocks, medicine, and catalysts and could have a profound impact on the conformation of proline-containing peptides and macrocycles.
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