European Journal of Chemistry 2019, 10(4), 376-380 | doi: https://doi.org/10.5155/eurjchem.10.4.376-380.1909 | Get rights and content






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Stereochemistry of tropane alkaloid of convolvine and their derivatives


Kambarali Kuchkarovich Turgunov (1,*) orcid , Dilfuza Kadirova (2) orcid , Rasul Okmanov (3) orcid , Salima Fazilovna Aripova (4) orcid , Bakhodir Tashkhodjaev (5) orcid

(1) Institute of Chemistry of Plant Substances, Tashkent, 100170, Uzbekistan
(2) Institute of Chemistry of Plant Substances, Tashkent, 100170, Uzbekistan
(3) Institute of Chemistry of Plant Substances, Tashkent, 100170, Uzbekistan
(4) Institute of Chemistry of Plant Substances, Tashkent, 100170, Uzbekistan
(5) Institute of Chemistry of Plant Substances, Tashkent, 100170, Uzbekistan
(*) Corresponding Author

Received: 27 Jun 2019 | Revised: 13 Oct 2019 | Accepted: 17 Oct 2019 | Published: 31 Dec 2019 | Issue Date: December 2019

Abstract


Structures of alkaloid convolvine (1) isolated from Convolvulus subhirsutus and its derivatives-convolamine(N-methylconvolvine) (2) and hydrochloride of N-benzylconvolvine (3) have been determined by single crystal X-ray diffraction technique. Compounds were crystallized in monoclinic space groups having four molecules in unit cell. All compounds contain a bicyclic ring system of tropane, where piperidine rings in all case adopt chair conformation. Hydrogen atom and methyl- and benzyl-substituents located in nitrogen atom of studied compounds occupy equatorial positions. The substituent of tropane core- the veratroyloxy group containing in all compound molecules is an α-axial oriented relative to the tropane core. In crystal structures of compound 1 and 2, the molecules are located in the distance of van der Waals interactions. The H-bond between the anion Cl and the proton of the N atom is observed in the crystal of N-benzylconvolvine hydrochloride (Cl···N 3.337 Å, Cl···H 2.42 Å and Cl-H-N 175°).


Keywords


Convolvine; Convolamine; Tropane alkaloids; N-Benzylconvolvine; X‐ray crystallography; Convolvulus subhirsutus

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DOI: 10.5155/eurjchem.10.4.376-380.1909

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Funding information


The project is supported by the Academy of Sciences of the Republic of Uzbekistan, (Grant no: VA-FA-F-6-010).

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How to cite


Turgunov, K.; Kadirova, D.; Okmanov, R.; Aripova, S.; Tashkhodjaev, B. Eur. J. Chem. 2019, 10(4), 376-380. doi:10.5155/eurjchem.10.4.376-380.1909
Turgunov, K.; Kadirova, D.; Okmanov, R.; Aripova, S.; Tashkhodjaev, B. Stereochemistry of tropane alkaloid of convolvine and their derivatives. Eur. J. Chem. 2019, 10(4), 376-380. doi:10.5155/eurjchem.10.4.376-380.1909
Turgunov, K., Kadirova, D., Okmanov, R., Aripova, S., & Tashkhodjaev, B. (2019). Stereochemistry of tropane alkaloid of convolvine and their derivatives. European Journal of Chemistry, 10(4), 376-380. doi:10.5155/eurjchem.10.4.376-380.1909
Turgunov, Kambarali, Dilfuza Kadirova, Rasul Okmanov, Salima Fazilovna Aripova, & Bakhodir Tashkhodjaev. "Stereochemistry of tropane alkaloid of convolvine and their derivatives." European Journal of Chemistry [Online], 10.4 (2019): 376-380. Web. 8 Apr. 2020
Turgunov, Kambarali, Kadirova, Dilfuza, Okmanov, Rasul, Aripova, Salima, AND Tashkhodjaev, Bakhodir. "Stereochemistry of tropane alkaloid of convolvine and their derivatives" European Journal of Chemistry [Online], Volume 10 Number 4 (31 December 2019)

DOI Link: https://doi.org/10.5155/eurjchem.10.4.376-380.1909

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