Synthesis of novel N-(2-hydroxy-2-p-tolylethyl)-amide and N-(2-oxo-2-p-tolylethyl)-amide derivatives and their antidyslipidemic and antioxidant activity

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 21, 2011, Pages 6393-6397

  Narender, T ^a   Rajendar, K ^a   Sarkar, S ^a   Singh, V K ^a   Chaturvedi, Upma ^a   Khanna, A K ^a   Bhatia, G ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Aegeline; Aegle marmelos; Antidyslipidemic activity; Phenylethanolamine derivatives; Triton model

Indexed keywords

AEGELINE; ALKALOID DERIVATIVE; AMIDE; ANTILIPEMIC AGENT; ANTIOXIDANT; CHOLESTEROL; GEMFIBROZIL; N (2 HYDROXY 2 P TOLYLETHYL) AMIDE DERIVATIVE; N (2 OXO 2 P TOLYLETHYL) AMIDE DERIVATIVE; NATURAL PRODUCT; PHOSPHOLIPID; TRIACYLGLYCEROL; TYLOXAPOL; UNCLASSIFIED DRUG;

AEGLE MARMELOS; ANIMAL EXPERIMENT; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; IN VIVO STUDY; MALE; NONHUMAN; RAT;

AEGLE MARMELOS;

EID: 80054784309     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.08.099     Document Type: Article

References (33)

1. Eghdamian, E.; Ghose, K. Drugs Today 1998, 34, 943.
2. Christophe, B.; Manteghetti, M.; Gross, R.; Baissac, Y.; Jacob, M.; Petit, P.; Sauvaire, Y.; Ribes, G. Eur. J. Pharm. 2000, 390, 339.
3. Narender, T.; Anju, P.; Shweta; Tanvir, K.; Rashmi, S.; Bhatia, G.; Chander, R. Bioorg. Med. Chem. Lett. 2006, 16, 293.
4. Werner, E. A.; Bell, J. J. Chem. Soc. 1922, 221, 1790
5. Shapiro, S. L.; Parrino, V. A.; Freedman, L. J. Am. Chem. Soc. 1959, 81, 3728.
6. Bailey, C. T. Diabetic Care 1989, 12, 553.
7. Deslypere, J. P. Curr. Ther. Res. 1995, 56, 111.
8. McClellan, K. J. Drugs 1998, 55, 415.
9. Yamamoto, A.; Yamamura, T.; Yokoyama, S.; Sudo, H.; Matsuzara, Y. Int. J. Clin. Pharmacol. Ther. Toxicol. 1984, 22, 493.
10. McCarthy, P. A.; Deivinno, M. P.; Morchouse, L. A. J. Med. Chem. 1996, 39, 1935.
11. Bang, H. O.; Dyerberg, J.; Nielsen, A. B. Lancet 1971, 1, 1143; Bang, H. O.; Dyerberg, J. Acta Med. Scand. 1972, 192, 85; Bang, H. O.; Dyerberg, J.; Hjorne, N. Acta Med. Scand. 1975, 200, 69.
12. Kirtikar, B. D.; Basu, K. R. Indian Med. Plants Part I 1993.
13. Narender, T.; Shweta, S.; Tiwari, P.; Papi Reddy, K.; Khaliq, T.; Prathipati, P.; Puri, A.; Srivastava, A. K.; Chander, R.; Agarwal, S. C.; Raj, K. Bioorg. Med. Chem. Lett. 2007, 17, 1808.
14. Chatterjee, A.; Bose, S. J. Ind. Chem. Soc. 1952, 29, 425.
15. Chatterjee, A.; Bose, S.; Srimay, S. K. J. Org. Chem. 1959, 24, 687.
16. Brown, R. F. C.; Jackson, W. R.; McCarthy, T. D. Tetrahedron: Asymmetry 1993, 4, 205
17. Yadav, J. S.; Reddy, P. T.; Nanda, S.; Rao, A. B. Tetrahedron: Asymmetry 2001, 24, 3381
18. Kamal, A.; Shaik, A. A.; Mahendra, S.; Malik, M. S. Tetrahedron: Asymmetry 2004, 15, 3939
19. Sadyandy, R.; Fernades, A. R.; Kumar, P. ARKIVOC 2005, III, 36.
20. Please see the Supplementary data for procedures for the synthesis of compounds, spectral data, stereochemistry, optical rotation and melting points of synthetic compounds.
21. Deeg, R.; Ziegehorn, J. Clin. Chem. 1983, 29, 1798
22. Buccolo, G.; David, H. Clin. Chem. 1973, 19, 476
23. Zilversmit, D. B.; Davis, A. K.; Memphis, B. S.; Tenn, J. L. Clin. Med. 1950, 35, 155.
24. Data were analyzed using Student's t-test. The hyperlipidemic groups were compared with control drug treated groups. Similarly the generations of oxygen free radicals with different derivatives were compared with that of their formation without compounds. P <0.05 was considered to be significant.
25. Wing, D. R.; Robinson, D. F. Biochem. J. 1968, 109, 841.
26. We previously reported Aegeline's (V) antihyperlipidemic activity in hamster model (Bioorg. Med. Chem. Lett. 2007, 17, 1808).
27. Kaliora, A. C.; Dedoussis, G. V. Z.; Schmidt, H. Atherosclerosis 2006, 18, 1
28. Wattanapitayakul, S. K.; Bauer, J. A. Pharmacol. Ther. 2001, 89, 187
29. Griendling, K. K.; Ushio-Fukai, M. J. Lab. Clin. Med. 1998, 132, 9
30. Hirio, S.; Harada, H.; Nishi, H. Biochem. Biophys. Res. Commun. 1999, 261, 332.
31. Bindoli, A.; Valente, M.; Cavallini, L. Pharmacol. Res. Commun. 1985, 17, 831.
32. Halliwell, B.; Gutteridge, J. M. C.; Arouma, O. Anal. Biochem. 1987, 165, 215.
33. Okhawa, H.; Ohishi, N.; Yagi, K. Anal. Biochem. 1978, 95, 351.