Synthesis and physical chemical properties of CF3O-containg secondary amines—Perspective building blocks for drug discovery
•Ten CF3O-containing cyclic aliphatic secondary amines were prepared using different approaches.•Effect of CF3O group on physico-chemical properties of several aliphatic secondary amines was evaluated. The effect of CF3O-group on the acid/base properties and lipophilicity is rather complex and depen...
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| Published in | Journal of fluorine chemistry Vol. 257-258; pp. 109990 - 110005 |
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| Main Authors | , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
LAUSANNE
Elsevier B.V
01.05.2022
Elsevier Elsevier BV |
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| Abstract | •Ten CF3O-containing cyclic aliphatic secondary amines were prepared using different approaches.•Effect of CF3O group on physico-chemical properties of several aliphatic secondary amines was evaluated. The effect of CF3O-group on the acid/base properties and lipophilicity is rather complex and depends on the substitution position and the conformation of the molecules.•DFT calculations and X-ray data for one of the compounds (trifluoromethoxymethyl)piperidine) show a favored gauche-arrangement with regard to the amino group.
Conformational and electronic effects of the trifluoromethoxy group make it attractive to be introduced in biorelevant structures. A mini-library of CF3O-substituted piperidines, pyrrolidines and azetidines was synthesized in 4-5 steps from commercial amino alcohols. Comparison of the measured pKa- and log D7.4 values of selected regioisomeric CF3O piperidines with the corresponding CF3- and MeO analogues shows that the effect on the acid/base properties and lipophilicity is rather complex and depends of the substitution position and the conformation of the molecules. For the most stable conformers of β-OCF3 compounds 2-(trifluoromethoxymethyl)piperidine (1c) and 3-trifloromethoxypiperidine (1e), DFT calculations and X-ray data (for 1c) show a favored gauche-arrangement with regard to the amino group.
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| AbstractList | Conformational and electronic effects of the trifluoromethoxy group make it attractive to be introduced in biorelevant structures. A mini-library of CF3O-substituted piperidines, pyrrolidines and azetidines was synthesized in 4-5 steps from commercial amino alcohols. Comparison of the measured pKa- and log D7.4 values of selected regioisomeric CF3O piperidines with the corresponding CF3- and MeO analogues shows that the effect on the acid/base properties and lipophilicity is rather complex and depends of the substitution position and the conformation of the molecules. For the most stable conformers of ß-OCF3 compounds 2-(trifluoromethoxymethyl)piperidine (1c) and 3-trifloromethoxypiperidine (1e), DFT calculations and X-ray data (for 1c) show a favored gauche-arrangement with regard to the amino group. Conformational and electronic effects of the trifluoromethoxy group make it attractive to be introduced in biorelevant structures. A mini-library of CF3O-substituted piperidines, pyrrolidines and azetidines was synthesized in 4-5 steps from commercial amino alcohols. Comparison of the measured pKa- and log D7.4 values of selected regioisomeric CF3O piperidines with the corresponding CF3- and MeO analogues shows that the effect on the acid/base properties and lipophilicity is rather complex and depends of the substitution position and the conformation of the molecules. For the most stable conformers of beta-OCF3 compounds 2-(trifluoromethoxymethyl)piperidine (1c) and 3-trifloromethoxypiperidine (1e), DFT calculations and X-ray data (for 1c) show a favored gauche-arrangement with regard to the amino group. •Ten CF3O-containing cyclic aliphatic secondary amines were prepared using different approaches.•Effect of CF3O group on physico-chemical properties of several aliphatic secondary amines was evaluated. The effect of CF3O-group on the acid/base properties and lipophilicity is rather complex and depends on the substitution position and the conformation of the molecules.•DFT calculations and X-ray data for one of the compounds (trifluoromethoxymethyl)piperidine) show a favored gauche-arrangement with regard to the amino group. Conformational and electronic effects of the trifluoromethoxy group make it attractive to be introduced in biorelevant structures. A mini-library of CF3O-substituted piperidines, pyrrolidines and azetidines was synthesized in 4-5 steps from commercial amino alcohols. Comparison of the measured pKa- and log D7.4 values of selected regioisomeric CF3O piperidines with the corresponding CF3- and MeO analogues shows that the effect on the acid/base properties and lipophilicity is rather complex and depends of the substitution position and the conformation of the molecules. For the most stable conformers of β-OCF3 compounds 2-(trifluoromethoxymethyl)piperidine (1c) and 3-trifloromethoxypiperidine (1e), DFT calculations and X-ray data (for 1c) show a favored gauche-arrangement with regard to the amino group. [Display omitted] |
| ArticleNumber | 109990 |
| Author | Stepaniuk, Roman O. Daniliuc, Constantin G. Kondratov, Ivan S. Logvinenko, Ivan G. Morev, Roman N. Mück-Lichtenfeld, Christian Dolovanyuk, Violetta G. Tolmachova, Nataliya A. Trofymchuk, Serhii A. Pridma, Stanislav O. Boretskyi, Andrii L. Haufe, Günter |
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| Keywords | Amines Gauche-conformation Fluorination Trifluoromethoxy group Building blocks DESIGN PHARMACEUTICALS SULFONAMIDES DEPROTECTION TRENDS ALCOHOLS TRIFLUOROMETHYL ETHERS CHEMISTRY ALPHA-FLUORINATED ETHERS THIOETHERS |
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| Snippet | •Ten CF3O-containing cyclic aliphatic secondary amines were prepared using different approaches.•Effect of CF3O group on physico-chemical properties of several... Conformational and electronic effects of the trifluoromethoxy group make it attractive to be introduced in biorelevant structures. A mini-library of... |
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| StartPage | 109990 |
| SubjectTerms | Alcohols Amines Building blocks Chemical properties Chemical synthesis Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Conformation Fluorination Gauche-conformation Physical Sciences Piperidine Science & Technology Trifluoromethoxy group |
| Title | Synthesis and physical chemical properties of CF3O-containg secondary amines—Perspective building blocks for drug discovery |
| URI | https://dx.doi.org/10.1016/j.jfluchem.2022.109990 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000804179800002 https://www.proquest.com/docview/2694491332 |
| Volume | 257-258 |
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