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Lassalas P, Oukoloff K, Makani V, et al. Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group. ACS Med Chem Lett. 2017;8(8):864-868doi: 10.1021/acsmedchemlett.7b00212.
Lassalas, P., Oukoloff, K., Makani, V., James, M., Tran, V., Yao, Y., Huang, L., Vijayendran, K., Monti, L., Trojanowski, J. Q., Lee, V. M., Kozlowski, M. C., Smith, A. B., Brunden, K. R., & Ballatore, C. (2017). Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group. ACS medicinal chemistry letters, 8(8), 864-868. https://doi.org/10.1021/acsmedchemlett.7b00212
Lassalas, Pierrik, et al. "Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group." ACS medicinal chemistry letters vol. 8,8 (2017): 864-868. doi: https://doi.org/10.1021/acsmedchemlett.7b00212
Lassalas P, Oukoloff K, Makani V, James M, Tran V, Yao Y, Huang L, Vijayendran K, Monti L, Trojanowski JQ, Lee VM, Kozlowski MC, Smith AB, Brunden KR, Ballatore C. Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group. ACS Med Chem Lett. 2017 Jul 05;8(8):864-868. doi: 10.1021/acsmedchemlett.7b00212. eCollection 2017 Aug 10. PMID: 28835803; PMCID: PMC5554911.
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ACS Med Chem Lett. 2017 Jul 05;8(8):864-868. doi: 10.1021/acsmedchemlett.7b00212. eCollection 2017 Aug 10.

Evaluation of Oxetan-3-ol, Thietan-3-ol, and Derivatives Thereof as Bioisosteres of the Carboxylic Acid Functional Group.

ACS medicinal chemistry letters

Pierrik Lassalas, Killian Oukoloff, Vishruti Makani, Michael James, Van Tran, Yuemang Yao, Longchuan Huang, Krishna Vijayendran, Ludovica Monti, John Q Trojanowski, Virginia M-Y Lee, Marisa C Kozlowski, Amos B Smith, Kurt R Brunden, Carlo Ballatore

Affiliations

  1. Department of Chemistry, School of Arts and Sciences, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
  2. Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093, United States.
  3. Center for Neurodegenerative Disease Research, Department of Pathology and Laboratory Medicine, Perelman School of Medicine, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.

PMID: 28835803 PMCID: PMC5554911 DOI: 10.1021/acsmedchemlett.7b00212

Abstract

The oxetane ring serves as an isostere of the carbonyl moiety, suggesting that oxetan-3-ol may be considered as a potential surrogate of the carboxylic acid functional group. To investigate this structural unit, as well as thietan-3-ol and the corresponding sulfoxide and sulfone derivatives, as potential carboxylic acid bioisosteres, a set of model compounds has been designed, synthesized, and evaluated for physicochemical properties. Similar derivatives of the cyclooxygenase inhibitor, ibuprofen, were also synthesized and evaluated for inhibition of eicosanoid biosynthesis in vitro. Collectively, the data suggest that oxetan-3-ol, thietan-3-ol, and related structures hold promise as isosteric replacements of the carboxylic acid moiety.

Keywords: Oxetan-3-ol; carboxylic acid bioisostere; cyclooxygenase; dual inhibitors; lipoxygenase; thietan-3-ol

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