Generic placeholder image

Current Organic Synthesis

Author(s): Preetismita Borah*, Biswa Mohan Sahoo, Vhatkar Dattatraya Shivling and Bimal Krishna Banik

DOI: 10.2174/1570179417666200825164654

DownloadDownload PDF Flyer Cite As
Microwave-Induced Ugi-Four Component Reactions: Synthesis of New Hetero- Steroid-Amino Acid Conjugates

Page: [641 - 647] Pages: 7

  • * (Excluding Mailing and Handling)

Explore Articles
About Journal
For Authors
For Editors
For Reviewers

Abstract

Background: Aza-steroids are an important class of compounds because of their numerous biological activities. The hetero steroids have different hydrogen bonding ability and hydrophobicity in comparison to steroids.

Materials and Methods: Microwave-induced synthesis of a novel type of hybrid hetero-steroid amine conjugates, following Ugi-four component reactions of steroidal amines with alanine and valine methyl esters as amino acid residues is described. Specifically, hetero-steroid-amino acid conjugate based on D-ring fused hetero steroidal amine, hetero-steroid-amino acid conjugate based on A-ring hetero steroidal amine, and hetero-steroidamino acid conjugate based on B-ring hetero steroidal amine are synthesized.

Results and Discussion: The yield of the products under microwave-induced process was considerably higher than that obtained by the conventional method. In contrast to the conventional method for the synthesis of these molecules, microwave-induced method has several advantages.

Conclusion: These include rapid reaction, a superior yield of the product, minimum side reaction, and economical microwave-induced process.

Keywords: Microwave, Ugi-4CR, steroidal amines, amino acids, heterosteroid conjugates, aza-steroids.

Graphical Abstract

[1]
Borah, P.; Borah, J.M.; Chowdhury, P. Microwave (MW) irradiated Ugi four-component reaction (Ugi-4CR): Expedited synthesis of steroid-amino acid conjugates--A novel class of hybrid compounds. Steroids, 2015, 98, 49-57.
[http://dx.doi.org/10.1016/j.steroids.2015.02.012] [PMID: 25701096]
[2]
Borah, P.; Begum, A.; Chowdhury, P. Microwave Energy in Ugi four-Component Reaction (Ugi-4CR): Expedient Synthesis of Steroid-Peptide Conjugates based on Aminosteroids-An important Class of Hybrid Compounds. Curr. Org. Synth., 2016, 13, 1-7.
[http://dx.doi.org/10.2174/1570179413666160204235819]
[3]
(a)Morand, P.; Lyall, J. The steroidal estrogens. Chem. Rev., 1968, 68(1), 85-124.
[http://dx.doi.org/10.1021/cr60251a003] [PMID: 4864944]
(b)Ritzén, E.M.; Nilsson, O.; Grigelioniene, G.; Holst, M.; Sävendahl, L.; Wroblewski, J. Estrogens and human growth. J. Steroid Biochem. Mol. Biol., 2000, 74(5), 383-386.
[http://dx.doi.org/10.1016/S0960-0760(00)00116-3] [PMID: 11162948]
(c)Ganag, F.W. Review of Medical Physiology Prentice Hall International: (UK) Ltd.: London, 1991, 335
[4]
(a)Alauddin, M.; Smith, M.M. Biological activity in steroids possessing nitrogen atoms. Pharm. Pharmacol., 1962, 14, 469.
[http://dx.doi.org/10.1111/j.2042-7158.1962.tb11127.x]
(b)Alauddin, M.; Smith, M.M. Biological activity in steroids possessing nitrogen atoms. Part i. Synthetic nitrogenous steroids. Pharm. Pharmacol., 1962, 14, 325-349.
(c)Alauddin, M.; Smith, M.M. Biological activity in steroids possessing nitrogen atoms: Recent advances. Pharm. Pharmacol., 1962, 16, 569.
(d)Bhide, G.V.; Tikotkar, N.L.; Tilak, B.D. Synthesis of heterocyclic steroids—IV. Tetrahedron, 1960, 10(3-4), 223-229.
[http://dx.doi.org/10.1016/S0040-4020(01)97810-X]]
[5]
Ibrahim-Ouali, M.; Rocheblave, L. Recent advances in azasteroids chemistry. Steroids, 2008, 73(4), 375-407.
[http://dx.doi.org/10.1016/j.steroids.2007.12.013] [PMID: 18249432]
[6]
Ibrahim-Ouali, M. Recent advances in oxasteroids chemistry. Steroids, 2007, 72(6-7), 475-508.
[http://dx.doi.org/10.1016/j.steroids.2007.03.004] [PMID: 17499322]
[7]
(a)Leclercq, G. Antitumor Steroids; Blickenstaff, R.T., Ed.; Academic Press: New York, 1992.
(b)Raus, J. Cytotoxic Estrogens in Hormone Receptive Tumors; Raus, J.; Martens, H.; Leclercq, G., Eds.; Academic Press: London, 1980.
(c)Hirshmann, R.. Steinberg, N.G.; Buchschacher, P.; Fried, J.H.; Kent, G.J.; Tishler, M. J. Am. Chem. Soc.,, 1963, 85, 120..
[http://dx.doi.org/doi.org/10.1021/ja00884a034]
[8]
Zhang, B.L.; Zhang, E.; Pang, L.P.; Song, L.X.; Li, Y.F.; Yu, B.; Liu, H.M. Design and synthesis of novel D-ring fused steroidal heterocycles. Steroids, 2013, 78(12-13), 1200-1208.
[http://dx.doi.org/10.1016/j.steroids.2013.07.006] [PMID: 23911850]
[9]
Borthakur, M.; Boruah, R.C. A microwave promoted and Lewis acid catalysed solventless approach to 4-azasteroids. Steroids, 2008, 73(6), 637-641.
[http://dx.doi.org/10.1016/j.steroids.2008.01.022] [PMID: 18342350]
[10]
Feng-Wu, L.; Hong-Min, Z. Yan-Bing. Z.; Jing- Yu, T. Chlorination of 3beta-hydroxyl-5-Delta steroids with anhydrous ferric chloride. Steroids, 2005, 70, 825.
[11]
(a)Nicoletti, D.; Ghini, A. A.A.; Burton, G. 1-Substituted 2′-deoxyinosine analogues. Chem. Soc. Perkin transion, 1995, 1, 1089.
(b)Duran, F.J.; Ghini, A.A.; Coirinib, H.; Burtona, G. Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone. Tetrahedron, 2006, 62, 4762-4768.
[http://dx.doi.org/10.1016/j.tet.2006.03.025]