Monoamine Oxidase Inhibitory Activity of Ferulic Acid Amides: Curcumin-Based Design and Synthesis

Archiv der Pharmazie

Volumn 349, Issue 1, 2016, Pages 9-19

  Badavath, Vishnu N ^a   Baysal, Ipek ^b   Uçar, Gülberk ^b   Mondal, Susanta K ^c   Sinha, Barij N ^a   Jayaprakash, Venkatesan ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY   (India)

^b HACETTEPE UNIVERSITY   (Turkey)

^c Molecular Modeling Section   (India)

Author keywords

Ferulic acid amides; hMAO inhibitors; Metabolic stability studies; Molecular docking; Permeability studies

Indexed keywords

3 (4 HYDROXY 3 METHOXYPHENYL) 1 (PYRROLIDIN 1 YL)PROP 2 EN 1 ONE; 3 (4 HYDROXY 3 METHOXYPHENYL) 1 MORPHOLINOPROP 2 EN 1 ONE; 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLAMIDE; AMIDE; AMINE OXIDASE (FLAVIN CONTAINING); CARBON; CURCUMIN; FERULIC ACID; MONOAMINE OXIDASE B INHIBITOR; MONOAMINE OXIDASE INHIBITOR; N BENZYL 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLAMIDE; N BUTYL 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLAMIDE; N CYCLOHEXY 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLAMIDE; N ETHYL 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLAMIDE; N ISOPROPYL 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLAMIDE; N METHYL 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLAMIDE; N PHENETHYL 3 (3 HYDROXY 4 METHOXYPHENYL)ACRYLAMIDE; N PHENETHYL 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLAMIDE; N PHENYL 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLAMIDE; N PROPYL 3 (4 HYDROXY 3 METHOXYPHENYL)ACRYLAMIDE; SELEGILINE; UNCLASSIFIED DRUG; COUMARIC ACID; ISOENZYME;

AMINO TERMINAL SEQUENCE; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOCHEMISTRY; CHEMICAL INTERACTION; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; FEMALE; HUMAN; HUMAN CELL; IN VITRO STUDY; MEMBRANE PERMEABILITY; METABOLIC STABILITY; MOLECULAR DOCKING; NONHUMAN; PRIORITY JOURNAL; ANALOGS AND DERIVATIVES; ANIMAL; ANTAGONISTS AND INHIBITORS; CELL MEMBRANE PERMEABILITY; CHEMISTRY; DOG; LIVER MICROSOME; MDCK CELL LINE; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMIDES; ANIMALS; CELL MEMBRANE PERMEABILITY; COUMARIC ACIDS; CURCUMIN; DOGS; HUMANS; ISOENZYMES; MADIN DARBY CANINE KIDNEY CELLS; MICROSOMES, LIVER; MOLECULAR DOCKING SIMULATION; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84955328643     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201500317     Document Type: Article

References (45)

1. M. B. H. Youdim, M. Weinstock, Neuro Toxicol. 2004, 25, 243-250.
2. G. Lavian, J. P. Finberg, M. B. Youdim, Clin. Neuropharmacol. 1993, 16 (Suppl 2), S1-S7.
3. M. Da Prada, H. H. Keller, R. Kettler, Psychiatr. Prax. 1989, 16 (Suppl 1), 18-24.
4. Y. Xu, B. S. Ku, H. Y. Yao, Y. H. Lin, X. Ma, Y. H. Zhang, X. Li, J. Pharmacol. Biochem. Behav. 2005, 82, 200-206.
5. S. K. Kulkarni, M. K. Bhutani, M. Bishnoi, Psychopharmacology 2008, 201, 435-442.
6. A. Rajeswari, M. Sabesan, Inflammopharmacology 2008, 16, 96-99.
7. L. Zhang, J. Luo, M. Zhang, W. Yao, X. Ma, S. Y. Yu, Int. J. Neuropsychopharmacol. 2014, 17, 793-806.
8. R. Wang, Y. Xu, H. L. Wu, Y. B. Li, Y. H. Li, J. B. Guo, X. Li, Eur. J. Pharmacol. 2008, 578, 43-50.
9. Y. Xu, B. S. Ku, H. Y. Yao, Y. H. Lin, X. Ma, Y. H. Zhang, X. Li, Eur. J. Pharmacol. 2005, 518, 40-46.
10. S. Carradori, M. D. Ascenzio, P. Chimenti, D. Secci, A. Bolasco, Mol. Divers. 2014, 18, 219-243.
11. H. H. Tonnesen, M. Masson, T. Loftsson, Int. J. Pharm. 2002, 244, 127-135.
12. M. L. Salum, C. J. Robles, R. Erra-Balsells, Org. Lett. 2010, 12, 4808-4811.
13. B. Galey Jean, E. Terranova, U.S. Patent 5536500, July 16, 1996.
14. H. R. Arthur, W. H. Hui, C. N. Ma, J. Chem. Soc. 1956, 632-635.
15. M. B. H. Youdim, Y. S. Bakhle, Br. J. Pharmacol. 2006, 147, S287-S296.
16. E. H. Kerns, L. Di, S. Petusky, M. Farris, R. Ley, P. Jupp, J. Pharm. Sci. 2004, 93, 1440-1453.
17. L. Kellard, M. Engelstein, J. Assoc. Lab. Autom. 2007, 12, 104-109.
18. P. V. Kaplita, H. Hu, L. Liu, T. M. Farrell, H. Grbic, D. M. Spero, JALA-J. Assoc. Lab. Autom. 2005, 10, 140-148.
19. P. V. Balimane, Y.-H. Han, S. Chong, AAPS J. 2006, 8, E1-E13.
20. P. V. Balimane, S. Chong, Drug Discov. Today 2005, 10, 335-343.
21. L. Di, E. H. Kerns, Y. Hong, T. A. Kleintop, O. J. McConnell, D. M. Huryn, J. Biomol. Screen. Off. J. Soc. Biomol. Screen. 2003, 8, 453-462.
22. K. M. Jenkins, R. Angeles, M. T. Quintos, R. Xu, D. B. Kassel, R. A. Rourick, J. Pharm. Biomed. Anal. 2004, 34, 989-1004.
23. S. K. Mondal, U. K. Mazumdar, N. B. Mondal, S. Banerjee, J. Biol. Sci. 2008, 6, 1110-1114.
24. B. Wahlang, Y. B. Pawar, A. K. Bansal, Eur. J. Pharm. Biopharm. 2011, 77, 275-282.
25. K. Y. Yang, L. C. Lin, T. Y. Tseng, S. C. Wang, T. H. Tsai, J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2007, 853, 183-189.
26. R. A. Sharma, S. A. Euden, S. L. Platton, D. N. Cooke, A. Shafayat, H. R. Hewitt, T. H. Marczylo, B. Morgan, D. Hemingway, S. M. Plummer, M. Pirmohamed, A. J. Gescher, W. P. Steward, Clin. Cancer Res. 2004, 10, 6847-6854.
27. Y. J. Wang, M. H. Pan, A. L. Cheng, L. I. Lin, Y. S. Ho, C. Y. Hsieh, J. K. Lin, J. Pharm. Biomed. Anal. 1997, 15, 1867-1876.
28. M. Mayersohn, T. W. Guentert, Clin. Pharmacokinet. 1995, 29, 292-332.
29. J. Raaflaub, P. Haefelfinger, K. H. Trautmann, Arzneimittelforschung 1984, 34, 80-82.
30. N. P. V. Nair, S. K. Ahmed, N. M. K. Ng Ying Kin, J. Psychiatry Neurosci. 1993, 18, 214-225.
31. J. S. Barrett, P. Szego, S. Rohatagi, R. J. Morales, K. E. DeWitt, G. Rajewski, Ireland J. Pharm. Res. 1996, 13, 1535-1540.
32. K. Laine, M. Anttila, A. Helminen, H. Karnani, R. Huupponen, Br. J. Clin. Pharmacol. 1999, 47, 249-254.
33. G. M. Morris, R. Huey, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, A. J. Olson, J. Comput. Chem. 2009, 30, 2785-2791.
34. C. N. Xia, H. B. Li, F. Liu, W. X. Hu, Bioorg. Med. Chem. Lett. 2008, 18, 6553-6557.
35. B. C. Ergun, T. Coban, F. K. Onurdag, E. Banoglu, Arch. Pharm. Res. 2011, 34, 1251-1261.
36. E. Nomura, A. Kashiwada, A. Hosoda, K. Nakamura, H. Morishita, T. Tsuno, H. Taniguchi, Bioorg. Med. Chem. 2003, 11, 3807-3813.
37. Y.-Y. Lai, L.-J. Huang, H.-C. Lin, T. Wu, C.-M. Teng, S.-C. Kuo, Chin. Pharm. J. 2002, 54, 41-52.
38. K. Freudenberg, R. Dillenburg, Chem. Ber. 1951, 84, 67-70.
39. E. A. Correa, E. D. Högestätt, O. Sterner, F. Echeverri, P. M. Zygmunt, Bioorg. Med. Chem. 2010, 18, 3299-3306.
40. M. M. Bradford, Anal. Biochem. 1976, 72, 248-254.
41. F. Chimenti, S. Carradori, D. Secci, A. Bolasco, B. Bizzarri, P. Chimenti, A. Granese, M. Yáñez, F. Orallo, Eur. J. Med. Chem. 2010, 45, 800-804.
42. S. K. Mondal, N. B. Mondal, S. Banerjee, U. K. Mazumder, Indian J. Pharmacol. 2009, 41, 176-181.
43. B. Vishnu Nayak, S. Ciftci-Yabanoglu, S. S. Jadav, M. Jagrat, B. N. Sinha, G. Ucar, V. Jayaprakash, Eur. J. Med. Chem. 2013, 69, 762-767.
44. A. Sahoo, S. Yabanoglu, B. N. Sinha, G. Ucar, A. Basu, V. Jayaprakash, Bioorg. Med. Chem. Lett. 2010, 20, 132-136.
45. M. Jagrat, J. Behera, S. Yabanoglu, A. Ercan, G. Ucar, B. N. Sinha, V. Sankaran, A. Basu, V. Jayaprakash, Bioorg. Med. Chem. Lett. 2011, 21, 4296-4300.