Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 9
Submit an article Journal homepage
152
Views
0
CrossRef citations to date
0
Altmetric
Articles

Efficient and stereoselective synthesis of thiosulfinates from disulfide using cumene hydroperoxide in the presence of titanium-based catalyst systems

Pengju SunXiangya School of Pharmaceutical Sciences, Central South University, Changsha, China; View further author information
,
Jiansheng HuangDrug Research Institute, Hisun Group, Taizhou, ChinaView further author information
,
Jinyi XuDrug Research Institute, Hisun Group, Taizhou, ChinaView further author information
&
Niefang YuXiangya School of Pharmaceutical Sciences, Central South University, Changsha, China; ;Drug Research Institute, Hisun Group, Taizhou, ChinaCorrespondence[email protected]
View further author information
Pages 1165-1172 | Received 19 Jan 2019, Published online: 02 Apr 2019

References

  • Kim, K.-H.; Cho, S.-J.; Kim, B.-O.; Pyo, S. Differential Pro-Apoptotic Effect of Allicin in Oestrogen Receptor-Positive or -Negative Human Breast Cancer Cells. J. Funct. Foods 2016, 25, 341-353. DOI: 10.1016/j.jff.2016.06.019.
  • Chu, Y.-L.; Ho, C.-T.; Chung, J.-G.; Rajasekaran, R.; Sheen, L.-Y. Allicin Induces p53-Mediated Autophagy in Hep G2 Human Liver Cancer Cells. J. Agric. Food Chem. 2012, 60, 8363-8371. DOI: 10.1021/jf301298y.
  • Roseblade, A.; Ung, A.; Bebawy, M. Synthesis and In Vitro Biological Evaluation of Thiosulfinate Derivatives for the Treatment of Human Multidrug-Resistant Breast Cancer. Acta Pharmacol. Sin. 2017, 220, 1353-1368. DOI: 10.1038/aps.2016.170.
  • Zhu, G.; Luo, Y.; Xue, M.; Zhou, F.; Zhao, H.; Ji, G.; Liu, F. Resistance of Garlic Cultivars to Bradysia Odoriphaga and Its Correlation with Garlic Thiosulfinates. Sci. Rep. 2017, 7, 3249. DOI: 10.1038/s41598-017-03617-9.
  • Leontiev, R.; Hohaus, N.; Jacob, C.; Gruhlke, M. C. H.; Slusarenko, A. J. A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin. Sci. Rep. 2018, 8, 6763.DOI: 10.1038/s41598-018-25154-9.
  • Filipovic, M. R.; Zivanovic, J.; Alvarez, B.; Banerjee, R. Chemical Biology of H2S Signaling through Persulfidation. Chem. Rev. 2018, 118, 1253-1337. DOI: 10.1021/acs.chemrev.7b00205.
  • Silva, F.; Baker, A.; Stansall, J.; Michalska, W.; Yusubov, M. S.; Graz, M.; Saunders, R.; Evans, G. J. S.; Wirth, T. Selective Oxidation of Sulfides in Flow Chemistry. Eur. J. Org. Chem. 2018, 2018, 2134-2137. DOI: 10.1002/ejoc.201800339.
  • Harrison, S. J.; Bishton, M.; Bates, S. E.; Grant, S.; Piekarz, R. L.; Johnstone, R. W.; Dai, Y.; Lee, B.; Araujo, M. E.; Prince, H. M.; et al. A Focus on the Preclinical Development and Clinical Status of the Histone Deacetylase Inhibitor, Romidepsin (Depsipeptide, Istodax). Epigenomics 2012, 4, 571-589. DOI: 10.2217/epi.12.52.
  • Narita, K.; Matsuhara, K.; Itoh, J.; Akiyama, Y.; Dan, S.; Yamori, T.; Ito, A.; Yoshida, M.; Katoh, T. Synthesis and Biological Evaluation of Novel FK228 Analogues as Potential Isoform Selective HDAC Inhibitors. Eur. J. Med. Chem. 2016, 121, 592-609. DOI: 10.1016/j.ejmech.2016.05.031.
  • Ni, M.; Esposito, E.; Raj, V. P.; Muzi, L.; Zunino, F.; Zuco, V.; Cominetti, D.; Penco, S.; Dal Pozzo, A. New Macrocyclic Analogs of the Natural Histone Deacetylase Inhibitor FK228; Design, Synthesis and Preliminary Biological Evaluation. Bioorg. Med. Chem. 2015, 23, 6785-6793. DOI: 10.1016/j.bmc.2015.10.004.
  • Maro, S. D.; Pong, R. C.; Hsieh, J. T.; Ahn, J. M. Efficient Solid-Phase Synthesis of FK228 Analogues as Potent Antitumoral Agents. J. Med. Chem. 2008, 51, 6639-6641. DOI: 10.1021/jm800959f.
  • Seenivasaperumal, M.; Federsel, H. J.; Szabó, K. J. Mechanism of the Asymmetric Sulfoxidation in the Esomeprazole Process: Effects of the Imidazole Backbone for the Enantioselection. Adv. Synth. Catal. 2009, 351, 903-919. DOI: 10.1002/adsc.200800753.
  • Seenivasaperumal, M.; Federsel, H. J.; Ertan, A.; Szabó, K. J. Factors Influencing the Selectivity in Asymmetric Oxidation of Sulfides Attached to Nitrogen Containing Heterocycles. Chem. Commun. 2007, 38, 2187-2189. DOI: 10.1039/b700860k.
  • Boche, G.; Möbus, K.; Harms, K.; Marsch, M. [((è2-tert-Butylperoxo)Titanatrane)2.3 Dichloromethane]: X-Ray Crystal Structure and Oxidation Reactions. J. Am. Chem. Soc. 1996, 118, 2770-2771. DOI: 10.1021/ja954308f.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.