The Role of S-bond in Tenoxicam Keto–Enolic Tautomerization Full article
| Journal |
CrystEngComm
ISSN: 1466-8033 |
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| Output data | Year: 2019, Volume: 21, Number: 36, Pages: 5392–5401 Pages count : 10 DOI: 10.1039/C9CE00874H | ||||||||||||
| Tags | CRYSTAL-STRUCTURE; CO-CRYSTALS; MELOXICAM; COCRYSTALS; PHARMACOKINETICS; SOLUBILITY | ||||||||||||
| Authors |
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| Affiliations |
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Funding (2)
| 1 | Ministry of Science and Higher Education of the Russian Federation | 0239-2019-0003 |
| 2 | Federal Agency for Scientific Organizations | 0333-2016-0002 (АААА-А16-116121510087-5) |
Abstract:
A non-steroidal anti-inflammatory drug, 4-hydroxy-2-methyl-N-2-pyridyl-2H-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide, called tenoxicam (TXM), with important implications in cancer treatment, has a peculiarity with respect to other molecules from the oxicam family. TXM is predominantly found in the zwitterionic form (ZWC) within the crystal structures of pure compounds and their solvates; however, it can be present in the β-keto–enolic form (BKE) or β-diketone (BDK) form. To understand this phenomenon, the combined effects of environment (solvent) and intra-molecular non-covalent interactions on the TXM keto–enol tautomerization were investigated through a combined experimental and computational study. We found that the polarity of a solvent had a minor influence on the crystallization process; this allowed to us synthesize and solve six new solvates with TXM in the ZWC form. Careful investigation of the non-covalent interactions between the sulphur atom of thiophenyl moiety and oxygen of the carbonyl group (S-bond) through a computational approach with the natural bond orbital (NBO) theory has shown that TXM crystallization is modulated by the S-bond. This study further confirms the importance of the S-bond in the drug design; however, nowadays, it is still underestimated
Cite:
Arkhipov S.G.
, Sherin P.S.
, Kiryutin A.S.
, Lazarenko V.A.
, Tantardini C.
The Role of S-bond in Tenoxicam Keto–Enolic Tautomerization
CrystEngComm. 2019. V.21. N36. P.5392–5401. DOI: 10.1039/C9CE00874H WOS Scopus РИНЦ AN OpenAlex
The Role of S-bond in Tenoxicam Keto–Enolic Tautomerization
CrystEngComm. 2019. V.21. N36. P.5392–5401. DOI: 10.1039/C9CE00874H WOS Scopus РИНЦ AN OpenAlex
Dates:
| Submitted: | Jun 5, 2019 |
| Accepted: | Jul 10, 2019 |
| Published online: | Jul 18, 2019 |
| Published print: | Sep 28, 2019 |
Identifiers:
| Web of science: | WOS:000486311800020 |
| Scopus: | 2-s2.0-85072305090 |
| Elibrary: | 41633218 |
| Chemical Abstracts: | 2019:1393430 |
| OpenAlex: | W2957377973 |