SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 10: 2119 - 2123

DOI: https://doi.org/10.6023/cjoc201404031

Notes

Studies of Molecular Structures of 3,17-Androstandiol Derivative

  • Fang Mingfeng ,
  • Chu Gang ,
  • Li Xin ,
  • Lu Guo Yuan
Expand
  • a. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b. Sanhome Pharmaceutical Co., Ltd., Nanjing 210038;
    c. Department of Chemistry, Nanjing University, Nanjing 210093

Received date: 2014-04-17

  Revised date: 2014-06-01

  Online published: 2014-06-18

Supported by

Project supported by the National Natural Science Foundation of China (No. 31200451), the Natural Science Foundation of Jiangsu Province (No. BK2012821) and the Foundation of Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions.

Fold

Abstract

Rocuronium bromide is a new neuromuscular blocking agent in clinical intervention. Its potency, specificity of action and little side effect have been confirmed. The 3,17-androstandiol (1) is a key intermediate for the preparation of rocuronium bromide. In this paper, The 3,17-androstandiol (1) was synthesized from (2α,3α,5α,16β)-2,3-epoxy-16- (1-pyrrolidinyl)-17-oxoandrostane by a reduction with sodium borohydride in methanol and then an epoxy ring opening reaction in morpholine and water. The molecular constitution was confirmed by 1H NMR, 13C NMR, 1H-1H COSY, DEPT, HSQC,HMBC, 2D NOESY and TOF-MS spectra. The single crystal of 3,17-androstandiol (1) was prepared by crystallized from 2-MeTHF and then was subjected to X-ray crystallography analysis that confirmed the stereo configuration of compound 1. And studies of X-ray powder diffractive analysis indicate that the diffractive spectrum of the sample compound 1 is consistent with the diffractive spectrum calculated on the crystal data. Therefore, the compound is (2β,3α,5α,16β,17β)- 2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstan-3,17-diol and its stereochemistry is accordant with that of rocuronium bromide.

Key words： androstandiol; rocuronium bromide; NMR spectra; configuration; crystal structure

Cite this article

Fang Mingfeng , Chu Gang , Li Xin , Lu Guo Yuan . Studies of Molecular Structures of 3,17-Androstandiol Derivative[J]. Chinese Journal of Organic Chemistry, 2014 , 34(10) : 2119 -2123 . DOI: 10.6023/cjoc201404031

References

[1] Sparr, J.; Beaufort, M.; Fuchs-Buder, T. Drugs 2001, 61(7), 919.
[2] Lee, C. Pharmacol. Ther. 2003, 98(2), 143.
[3] European Pharmacopoeia Commission, European Pharmacopoeia 6.0, Strasbourg, 2008, pp. 2835～2837．
[4] Zhang, Y. M.; Guo, J.; Xiong, T. Chin. J. Med. Chem. 2008, 18(6), 434 (in Chinese).
(张永明, 郭佳, 熊涛, 中国药物化学杂志, 2008, 18(6), 434.)
[5] Savage, D. S.; Sleigh, T.; Carlyle, I. G. EP 287150, 1988 [Chem. Abstr. 1989, 110, 115184].
[6] Buckett, W. R.; Hewett, C. L.; Savage, D. S. J. Med. Chem. 1973, 16, 1116.
[7] Yan, H.; Qiu, F.; Diao, Y. Chin. J. Pharm. 2011, 42(6), 472 (in Chinese).
(严慧, 邱飞, 刁勇, 中国医药工业杂志, 2011, 42(6), 472.)
[8] Sleigh, T.; Savage, D. S.; Mearns, N.; Carlyle, I. G. US 4894369, 1990 [Chem. Abstr. 1989, 110, 115184].
[9] Mendez, J. A.; Mora, M. D.; Rodriguez, A. A. US 7569687, 2009 [Chem. Abstr. 2007, 146, 359039].
[10] Mendes, J. A.; Mora, M. D.; Rodriguez, A. A.; Barragan, E. US 2007/0117975, 2007 [Chem. Abstr. 2007, 146, 359039]
[11] Magni, A.; Grisenti, P. US 6090957, 2000 [Chem. Abstr. 1998, 129, 189525].
[12] Magni, A.; Grisenti, P. US 5808051, 1998 [Chem. Abstr. 1998, 129, 189525].
[13] Wang, H, X. Pharm. Clin. Res. 2012, 212, 135 (in Chinese).
(汪会霞, 药学与临床研究, 2012, 212, 135.)

Options
Outlines

/

〈 〉