Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis of Indole and Benzimidazole Substituted Novel 16-Arylidene Steroid Derivatives

Author(s): Semra Karataş, İrfan Çapan and Süleyman Servi*

Volume 16, Issue 11, 2019

Page: [884 - 890] Pages: 7

DOI: 10.2174/1570178616666190305130217

Price: $65

Abstract

Novel aza-heterocyclic substituted dehydroepiandrosterone derivatives were synthesized through a three-step reaction sequence. Some new O-alkylated 4-hydroxybenzaldehydes were synthesized from the reaction of substituted benzaldehydes with dihalogen compounds which have different chain lengths. 16-Arylidene steroids were synthesized from the base-catalyzed aldol condensation of O-alkylated 4-hydroxybenzaldehydes and dehydroepiandrosterone. New indolyl and benzimidazolyl substituted steroid derivatives as hybrid molecules were obtained from the reaction of 16-arylidene steroids with indole or benzimidazole.

Keywords: Dehydroepiandrosterone, indole, benzimidazole, 16-arylidene steroids, O-alkylated 4-hydroxybenzaldehydes, Aldol condensation.

« Previous Next »
Graphical Abstract

[1]
Bhatti, H.N.; Khera, R.A. Steroids, 2012, 77, 1267-1290.
[2]
Guo, H.; Wu, H.; Yang, J.; Xiao, Y.H.; Altenbach, J.; Qiu, G.; Hu, H.; Wu, Z.; He, X.; Zhou, D.; Hu, X. Steroids, 2011, 76, 709-723.
[3]
Kolo, A.M.; Ipek, E.; Capan, I.; Servi, S. J. Het. Chem., 2018, 55, 492-497.
[4]
Mo, Q.; Lu, S.; Simon, F.N.G. J. Steroid Biochem. Mol. Biol., 2006, 99, 50-58.
[5]
Li, Y.; Huang, J.; Liu, J.; Yan, P.; Liu, H.; Sun, Q.; Wang, X.; Wang, C. Steroids, 2011, 76, 1615-1620.
[6]
Singh, R.; Bansal, R. ACS Chem. Neurosci., 2017, 8, 186-200.
[7]
Chattopadhyay, R.; Jindal, D.P.; Maninder, M.; Gupta, R. Arzneim. Forsch. Drug Res., 2004, 54, 551-556.
[8]
El Rashedy, A.A.; Aboul-Enein, H.Y. Mini Rev. Med. Chem., 2013, 13, 399-407.
[9]
Garrido, M.; Cabeza, M.; Cortés, F.; Gutiérrez, J.; Bratoeff, E. Eur. J. Med. Chem., 2013, 68, 301-311.
[10]
Kaushik, N.K.; Kaushik, N.; Attri, P.; Kumar, N.; Kim, C.H.; Verma, A.K.; Choi, E.H. Molecules, 2013, 18, 6620-6662.
[11]
Bansal, R.; Guleria, S.; Thota, S.; Hartmann, R.W.; Zimmer, C. Med. Chem. Res., 2013, 22, 692-698.
[12]
Ali, A.; Asif, M.; Khanam, H.; Mashrai, A.; Sherwani, M.A.; Owais, M. Shamsuzzaman. RSC Adv, 2015, 5, 75964-75984.
[13]
Zammit, S.C.; Cox, A.J.; Gow, R.M.; Zhang, Y.; Gilbert, R.E.; Krum, H.; Kelly, D.J.; Williams, S. J. Bioorg. Med. Chem. Lett., 2009, 19, 7003-7006.
[14]
Patel, M.R.; Bhatt, A.; Steffen, J.D.; Chergui, A.; Murai, J.; Pommier, Y.; Pascal, J.M.; Trombetta, L.D.; Fronczek, F.R.; Talele, T.T. J. Med. Chem., 2014, 57, 5579-5601.
[15]
Pirat, C.; Dacquet, C.; Leclerc, V.; Hennuyer, N.; Beucher-Gaudin, M.; Zanirato, G.; Giants, A.; Staels, B.; Ktorza, A.; Farce, A.; Caignard, D-H.; Berthelot, P.; Lebegue, N. Eur. J. Med. Chem., 2017, 137, 310-326.
[16]
Amomboa, G.M.O.; Kramer, T.; Monte, F.L.; Göring, S.; Fach, M.; Smith, S.; Kolb, S.; Schubenel, R.; Baumann, K.; Schmidt, B. Bioorg. Med. Chem. Lett., 2012, 22, 7634-7640.
[17]
Bansal, R.; Guleria, S.; Thota, S.; Hartmann, R.W.; Zimmer, C. Chem. Pharm. Bull., 2011, 59, 327-331.
[18]
Thamotharan, S.; Parthasarathi, V.; Gupta, R.; Sheetal, G.; Jindalb, D.P.; Lindenc, A. Acta Cryst., 2004, C60, o110-o112.
[19]
Thamotharan, S.; Parthasarathi, V.; Gupta, R.; Guleria, S.; Jindalb, D.P.; Lindenc, A. Acta Cryst., 2002, C58, o727-o729.

Rights & Permissions Print Cite
Article Metrics
29
2
1
© 2024 Bentham Science Publishers | Privacy Policy