4-Trifluoromethoxy proline: synthesis of stereoisomers and lipophilicity study

Logvinenko, Ivan G.; Sadkova, Iryna V.; Tolmachova, Nataliya A.; Shishkina, Svitlana V.; Daniliuc, Constantin G.; Haufe, Günter; Kondratov, Ivan S.

doi:10.1039/d4ob00688g

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00688g

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4-Trifluoromethoxy proline: synthesis of stereoisomers and lipophilicity study

Ivan G. Logvinenko,

Iryna V. Sadkova,

Nataliya A. Tolmachova

et al.

Abstract: All four stereoisomers of 4-CF3O-proline were synthesized on a gram scale, and their physical–chemical properties were studied.

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Proline Analogues in Drug Design: Current Trends and Future Prospects

Kubyshkin,

Mykhailiuk

2024

J. Med. Chem.

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Proline analogues are versatile chemical building blocks that enable modular construction of small-molecule drugs and pharmaceutical peptides. Over the past 15 years, the FDA has approved over 15 drugs containing proline analogues in their structures, five in the last three years alone (daridorexant, trofinetide, nirmatrelvir, rezafungin, danicopan). This perspective offers an analysis of the most common types of proline analogues currently trending in drug design. We focus on examples of fluoroprolines, α-methylproline, bicyclic proline analogues, and aminoprolines, while also highlighting proline analogues that remain underrepresented. We supplement our analysis with physicochemical information regarding the specific molecular properties of these moieties. Additionally, we discuss several intriguing cases where nonproline residues were replaced with proline analogues as a strategy to eliminate unwanted hydrogen bond donor sites. In conclusion, we present some suggestions for the future exploration of this promising class of molecular entities in drug discovery. ■ SIGNIFICANCEOver 15 drug structures approved in the past 15 years contain proline analogues. The cyclic nature of these analogues provides conformationally restricted 3D scaffolds, enhancing the activity and bioavailability of bioactive molecules and peptides. In this work, we analyze the most prominent proline analogues in current drug discovery, with a focus on fluoroprolines, αmethylproline, aminoprolines, and bicyclic analogues. Additionally, we provide detailed physicochemical data and creative suggestions to guide future research efforts.

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Proline Analogues in Drug Design: Current Trends and Future Prospects

Kubyshkin,

Mykhailiuk

2024

J. Med. Chem.

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4-Trifluoromethoxy proline: synthesis of stereoisomers and lipophilicity study

Abstract: All four stereoisomers of 4-CF3O-proline were synthesized on a gram scale, and their physical–chemical properties were studied.

Cited by 1 publication

References 50 publications

Proline Analogues in Drug Design: Current Trends and Future Prospects

Proline Analogues in Drug Design: Current Trends and Future Prospects

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