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 and Evaluation of Some Novel Pregnane Derivatives as Anti-Hyperlipidemic and Anti-Oxidant Agents

Author(s): Arun Sethi*, Akriti Bhatia, Ranvijay Pratap Singh and Atul Srivastava

Volume 16, Issue 1, 2019

Page: [40 - 49] Pages: 10

DOI: 10.2174/1570178615666180806123719

Price: $65

Abstract

In the present paper, synthesis of few novel pregnane derivatives and their evaluation as potential anti-hyperlipidemic and anti-oxidant agents has been reported. The synthesis of 3β-hydroxy- 16α-methoxy pregn-5-en-20-one (4) was achieved by reaction of 3β-hydroxy-5,16-pregnadiene-20-one (3) with KOH/MeOH under reflux. Compound 4 on treatment with succinic and phthalic anhydride afforded compound 6 and 7, respectively. The reaction of the C-20-oxime-pregnadiene (8) with 1,5- dibromohexane yielded 20-(O-6-bromo hexyl)-oximino-3β-hydroxy-pregn-5, 16-diene (9). A novel heterocyclic derivative 3β-hydroxy-androst-5-en [17,16-c]-2′-methyl-7′ bromo-3′,4′-dihydro quinoline (16) was synthesized by reaction of 3 with 3-bromoaniline. However, attempted synthesis of other heterocyclic derivatives by reaction of (3) with other halogenated amine led to Aza-Michael addition products (10-14). The synthesized compounds were also evaluated for their anti-hyperlipidemic and anti-oxidant activities. Compounds 6 and 14 were found to exhibit more lipid lowering and antioxidant activities in comparison to other compounds.

Keywords: Pregnane, Aza-Michael addition, intramolecular condensation, anti-hyperlipidemic, anti-oxidant, steroid.

« Previous Next »
Graphical Abstract

[1]
Sethi, A.; Maurya, A.; Tewari, V.; Srivastava, S.; Faridi, S.; Bhatia, G.; Khan, M.M.; Khanna, A.K.; Saxena, J.K. Bioorg. Med. Chem., 2007, 15, 4520-4527.
[2]
Zaichuk, T.; Ivancic, D.; Scholtens, D.; Schiller, C.; Khan, S.A. J. Steroid Biochem. Mol. Biol., 2007, 105, 76-84.
[3]
Pasqualini, J.R. J. Steroid Biochem. Mol. Biol., 2005, 97, 401-415.
[4]
Levinaa, I.S.; Pokrovskayab, E.V.; Kulikova, L.E.; Kamernitzky, A.V.; Kachala, V.V.; Smirnov, A.N. Steroids, 2008, 73, 815-827.
[5]
Boonananwong, S.; Kongkathip, B.; Kongkathip, B. Steroids, 2008, 73, 1123-1127.
[6]
Romanoa, D.; Ferrarioa, V. Steroids, 2008, 73, 112-115.
[7]
Rafat, M. Mohareb; Nahed, N.E.; Sayed, E.I.; Rafat M.M.; Nahed N.E.E.S.; Mahmoud A.A. Steroids, 2013, 78, 1209-1219.
[8]
Higasio, Y.S.; Shoji, T. Appl. Catal. A Gen., 2001, 221, 197-207.
[9]
Xing, X.; Zhu, X. Li, H.; Jiang, Y.; Ni, J. Chemosphere, 2012, 86, 368-375.
[10]
Verkade, J.M.M.; Van Hemert, L.J.C. Chem. Soc. Rev., 2008, 37, 29-41.
[11]
Ishimaru, K.J.; Kojima, T.J. J. Org. Chem., 2000, 65, 8395-8398.
[12]
Gaunt, M.J.; Johansson, C.C.C. Vo. N.T. Drug Discov. Today, 2007, 12, 8-27.
[13]
Verkade, J.M.M.; Van Hemert, L.J.C. Chem. Soc. Rev., 2008, 37, 29-41.
[14]
Bhadury, P.S.; Song, B.A. Curr. Org. Chem., 2010, 14, 1989-2006.
[15]
Wabnitz, T.C.; Spencer, J.B. Org. Lett., 2003, 5, 2141-2144.
[16]
Sethi, A.; Bhatia, G. Chem. Res., 2011, 20, 36-46.
[17]
Ruotolo, G.; Howard, B.V. Curr. Cardiol. Rep., 2002, 4, 494-500.
[18]
Alexander, C.M.; Londsman, P.B.; Teatsch, S.M. Am. J. Cardiol., 2002, 86, 897-902.
[19]
Parthasarathy, S.; Steinbert, D.; Swiztum, J.L. Annu. Rev. Med., 1992, 43, 219.
[20]
Chander, R.; Khanna, A.K.; Kapoor, N.K. Phytother. Res., 1996, 10, 508-511.
[21]
Muller, G.P.; Norton, L.L. J. Am. Chem. Soc., 1955, 77, 143.
[22]
Kaneko, K.; Watanabbe, M.; Mitsuhashi, K. Phytochemistry, 1973, 12, 1509-1510.
[23]
Muller, G.P. Nature, 1958, 76, 771.
[24]
Zemplen, G. Berichte der deutschen chemischen Gesellschaft, 1926, 59, 1254.
[25]
Harvey, R.A.; Champe, P.C. Lippincott Illustrated Reviews: Pharmacology, 3rd ed; Lippincott Williams and Wilkins: Philadelphia, 2006.
[26]
Katzung, B.G. Basic and Clinical Pharmacology, 9th ed; Mc-Graw-Hill: New York, 2004.
[27]
Laporte, J.R.; Carne, X.; Vidal, X.; Mareno, V.; Juan, J. Lancet, 1991, 337, 85-89.
[28]
Weber, P.; Weitkamp, K.D. Food Res. Int., 2002, 35, 177.
[29]
Halliwell, B.; Gutteridge, J.M.C.; Arouma, O.I. Anal. Biochem., 1987, 165, 215-219.
[30]
Rizvi, F.; Puri, A.; Bhatia, G.; Khanna, A.K.; Wulff, E.M.; Rastogi, A.K. Biochem. Biophys. Res. Commun., 2003, 305, 215-222.
[31]
Bindoli, A.; Valente, M.; Cavallim, L. Pharmacol. Res. Commun., 1985, 17, 831-839.
[32]
Richmond, R.; Halliwell, R.; Chauhan, J.; Darbre, A. Anal. Biochem., 1981, 118, 320-335.

Rights & Permissions Print Cite
Article Metrics
27
3
© 2024 Bentham Science Publishers | Privacy Policy