The Role of S-bond in Tenoxicam Keto–Enolic Tautomerization | Sciact - CRIS-система Института катализа

The Role of S-bond in Tenoxicam Keto–Enolic Tautomerization Научная публикация

Журнал

CrystEngComm
ISSN: 1466-8033

Вых. Данные

Год: 2019, Том: 21, Номер: 36, Страницы: 5392–5401 Страниц : 10 DOI: 10.1039/C9CE00874H

Ключевые слова

CRYSTAL-STRUCTURE; CO-CRYSTALS; MELOXICAM; COCRYSTALS; PHARMACOKINETICS; SOLUBILITY

Авторы

Arkhipov Sergey G. ^1,2,3 , Sherin Peter S. ^1,4 , Kiryutin Alexey S. ^1,4 , Lazarenko Vladimir A. ⁵ , Tantardini Christian ⁶

Организации

1	Novosibirsk State University
2	Boreskov Institute of Catalysis SB RAS
3	Institute of Solid State Chemistry and Mechanochemistry SB RAS
4	International Tomography Center
5	National Research Center “Kurchatov Institute”
6	Center for Energy Science and Technology, Skoltech Skolkovo Institute of Science and Technology

Информация о финансировании (2)

1	Министерство науки и высшего образования Российской Федерации (с 15 мая 2018)	0239-2019-0003
2	Федеральное агентство научных организаций России	0333-2016-0002 (АААА-А16-116121510087-5)

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

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 CAPlus OpenAlex

Поступила в редакцию:	5 июн. 2019 г.
Принята к публикации:	10 июл. 2019 г.
Опубликована online:	18 июл. 2019 г.
Опубликована в печати:	28 сент. 2019 г.

Web of science:	WOS:000486311800020
Scopus:	2-s2.0-85072305090
РИНЦ:	41633218
Chemical Abstracts:	2019:1393430
OpenAlex:	W2957377973

БД	Цитирований
Scopus	15
Web of science	14
РИНЦ	11
OpenAlex	14