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






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.10.4.376-380.1909

Links for Article


| | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 61 times | PDF Article downloaded 26 times

Funding information


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

References

[1]. Mashkovskiy, M. D. Lekarstvennie sredstva, Medicine, Tashkent, 1984. Part 1, pp. 239, [in Russian].

[2]. Gapparov, A. M.; Okhunov, I. I.; Aripova, S. F.; Nabiev, A.; Khuzhaev, V. U. Chem. Nat. Compd. 2011, 47, 608-611.
https://doi.org/10.1007/s10600-011-0007-1

[3]. Xashimova, Z. S.; Aripova, S. F.; Seomashko, N. E.; Terenteva, E. O.; Ohunov, I. I.; Kadirova, D. B.; Azimova, Sh. S. Patent RUz, No IAP 04965; «Sredstvo, proyavlyayushee izbiratelnuyu sitotoksicheskuyu aktivnost po otnosheniyu k kletkam raka gortani» (in Russian).

[4]. Oxford Diffraction, CrysAlis PRO. Version 1.171.37.34. Oxford Diffraction Ltd., Yarnton, Oxfordshire, England.

[5]. Sheldrick, G. M. Acta Cryst. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[6]. Sheldrick, G. M. Acta Cryst. C 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218

[7]. Gapparov, A. M.; Razzakov, N. A.; Aripova, S. F. Chem. Nat. Compd. 2007, 43, 291-292.
https://doi.org/10.1007/s10600-007-0107-0

[8]. Gapparov, A. M.; Aripova, S. F.; Tashkhodzhaev, B.; Levkovich, M. G.; Aripov, O. Chem. Nat. Compd. 2010, 46, 590-592.
https://doi.org/10.1007/s10600-010-9682-6

[9]. Chananont, P.; Hamor, T.A. J. Chem. Res. 1978, 10, 414-415.
https://doi.org/10.1108/eb003699

[10]. Hamor, T.A. J. Chem. Soc., Perkin Trans. 2 1976, 1359-1363.
https://doi.org/10.1039/p29760001359

[11]. Dalpiaz, A.; Ferretti, V.; Gilli, P.; Bertolasi, V. Acta Cryst. B 1996, 52, 509-518.
https://doi.org/10.1107/S0108767396082633

[12]. Zhu, N.; Reynolds, M.; Klein, C. L.; Trudell, M. Acta Cryst. C 1994, 50, 2067-2069.
https://doi.org/10.1107/S0108270194003367

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. 20 Jan. 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

| | | | |

| | | | | |

Save to Zotero Save to Mendeley

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

Refbacks

  • There are currently no refbacks.




Copyright (c) 2019 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).


© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.