A study was carried out to identify the mechanism of rearrangement in acetylene-containing oxiranes, leading to the formation of enine hydroxy derivatives, by the NMR method and quantum chemical calculations. Possible conformations and their calculated energy stability, which determine the direction and degree of isomer conversion, are presented. The most active in the rearrangement process are protons that are spatially close to the oxygen atom and have an electron density deficit of +0.247 and +0.234 a.u. In Newman's projections, the relative position of groups in the most probable conformations is considered and their energy stability is calculated. In enine alcohols, which are the products of the oxirane ring opening, the relative content of Z- and E-isomers was determined on the data of their NMR spectra. It has been shown that in the Z-isomer there are intramolecular interactions of the intramolecular hydrogen bond (IHB) type between the π-electron cloud of the acetylene bond and the proton of the OH group in the unstrained six-membered ring. In terms of choleretic activity, enine triols, and their derivatives exceed the activity of dehydrocholic acid by 60-90%, and in terms of the breadth of pharmacological action - more than 2.5 times.
| Mualliflar | Abdullaev, Tohir Kh. |
|---|---|
| Jurnal | Товарлар кимёси ва халқ табобати |
| Nashr sanasi | 2024-05-20 |
| Jild | 3 |
| Son | 1 |
| Betlar | 335-358 |
| Til | O‘zbek |
| DOI | 10.55475/jcgtm/vol3.iss1.2024.250 |
DOI: 10.55475/jcgtm/vol3.iss1.2024.250 · Maqolaning asl sahifasi
ениновые производные, ПМР спектроскопия, внутримолекулярные водородные связи, квантовохимические расчеты, желчегонная активность, enine derivatives, NMR spectroscopy, intramolecular hydrogen bonds, quantum chemical calculations, choleretic activity, Yenin hosilalari, PMR spektroskopiya, molekulyar vodorod bog'lari, kvant kimyoviy hisoblar, xoleretik faollik
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