Synthesis of dehydroabietane-derived sulfonamides with fragments of L-amino acid esters and hydrazides

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

Ethyl ester of 12-chlorosulfodehydroabietic acid, when reacted with the methyl esters of glycine, methionine, leucine, glutamic acid, tyrosine, proline, histidine, for the first time yielded the corresponding sulfonamides, the ester group (-COOMe) of which was selectively transferred to the hydrazide (-COONHNH2) without affecting the ethyl group bounded with the dehydroabietic acid fragment. In the case of glutamic acid, the corresponding dihydrazides were obtained. The reaction of 12-chlorosulfodehydroabietic acid ethyl ester with cystine dimethyl ester led to the selective formation of bis-sulfonamide, while carrying out the same reaction in an acetone-contained solution was accompanied by the cleavage of the disulfide bond of the cystine fragment to give thioketal. The obtained bis-sulfonamide and thioketal were oxidized with chlorine dioxide to afford in both cases sulfochloride.

作者简介

E. Izmest'ev

Institute of Chemistry, Komi Scientific Center, Ural Branch of the Russian Academy of Sciences

Email: evgeniyizmestev@rambler.ru

D. Petukhov

Vyatka State University

Email: evgeniyizmestev@rambler.ru

S. Pestova

Institute of Chemistry, Komi Scientific Center, Ural Branch of the Russian Academy of Sciences

Email: evgeniyizmestev@rambler.ru

S. Rubtsova

Institute of Chemistry, Komi Scientific Center, Ural Branch of the Russian Academy of Sciences

Email: evgeniyizmestev@rambler.ru

参考

  1. Gu W., Miao T.-T., Hua D.-W., Jin X.-Y., Tao X.-B., Huang Ch.-B., Wang Sh.-F. Bioorg. Med. Chem. Lett. 2017, 27, 1296-1300. doi: 10.1016/j.bmcl.2017.01.028
  2. Gonzalez M.A. Nat. Prod. Rep. 2015, 32, 684-704. doi: 10.1039/C4NP00110A
  3. Gonzalez M.A. Eur. J. Med. Chem. 2014, 87, 834-842. doi: 10.1016/j.ejmech.2014.10.023
  4. Pertino M.W., Verdugo V., Theoduloz C., Schmeda-Hirschmann G. Molecules. 2014, 19, 2523-2535. doi: 10.3390/molecules19022523
  5. Huang X.-Ch., Wang M., Pan Y.-M., Yao G.-Y., Wang H.-Sh., Tian X.-Y., Qin J.-K., Zhang Y. Eur. J. Med. Chem. 2013, 69, 508-520. doi: 10.1016/j.ejmech.2013.08.055
  6. Huang X.-Ch., Jin L., Wang M., Liang D., Chen Zh.-F., Zhang Y., Pan Y.-M., Wang H.-Sh. Eur. J. Med. Chem. 2015, 89, 370-385. doi: 10.1016/j.ejmech.2014.10.060
  7. Huang X., Huang R., Liao Zh., Pan Y., Gou Sh., Wang H. Eur. J. Med. Chem. 2016, 108, 381-391. doi: 10.1016/j.ejmech.2015.12.008
  8. Huang R.-Zh., Liang G.-B., Huang X.-Ch., Zhang B., Zhou M.-M., Liao Zh.-X., Wang H.-Sh. Eur. J. Med. Chem. 2017, 138, 979-992. doi: 10.1016/j.ejmech.2017.07.020
  9. Zareef M., Iqbal R., Al-Masoudi N.A., Zaidi J.H., Arfan M., Shahzad S.A. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 281-298. doi: 10.1080/10426500600919074
  10. Zareef M., Iqbal R., De Dominguez N.G., Rodrigues J., Zaidi J.H., Arfan M., Supuran C.T. J. Enzyme Inhib. Med. Chem. 2007, 22, 301-308. doi: 10.1080/14756360601114569
  11. Izmest'ev Ye.S., Pestova S.V., Lezina O.M., Rubtsova S.A., Kutchin A.V. ChemistrySelect. 2019, 4, 11034-11037. doi: 10.1002/slct.201902600
  12. Пестова С.В., Петухов Д.В., Изместьев Е.С., Рубцова С.А. ЖОрХ. 2022, 58, 897-905. doi: 10.31857/S0514749222080134
  13. Райхардт К. Растворители и эффекты среды в органической химии. М.: Мир, 1991.
  14. Li J., Sha Y. Molecules. 2008, 13, 1111-1119. doi: 10.3390/molecules13051111

补充文件

附件文件
动作
1. JATS XML
下载

版权所有 © Russian Academy of Sciences, 2023