Reinvestigation of structure-activity relationship of methoxylated chalcones as antimalarials: Synthesis and evaluation of 2,4,5-trimethoxy substituted patterns as lead candidates derived from abundantly available natural β-asarone

European Journal of Medicinal Chemistry

Volumn 45, Issue 11, 2010, Pages 5292-5301

  Kumar, Rakesh ^a   Mohanakrishnan, Dinesh ^b   Sharma, Abhishek ^a   Kaushik, Naveen Kumar ^b   Kalia, Kalpana ^a   Sinha, Arun Kumar ^a   Sahal, Dinkar ^b  

^a CSIR INSTITUTE OF HIMALAYAN BIORESOURCE TECHNOLOGY   (India)

^b INTERNATIONAL CENTRE FOR GENETIC ENGINEERING AND BIOTECHNOLOGY   (Italy)

Author keywords

Asarone; Antimalarial; Chalcones; Structure activity relationship

Indexed keywords

1 ( 2,3,4 TRIMETHOXYPHENYL) 3 ( 2,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 3,4 DICHLOROPHENYL) 3 ( 2,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 3,4 DIOXYMETHYLENE) 3 ( 4 CHLOROPHENYL)PROP 2 EN 1 ONE; 1 ( 4 BROMOPHENYL) 3 ( 2,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 4 BROMOPHENYL) 3 ( 4 CHLOROPHENYL)PROP 2 EN 1 ONE; 1 ( 4 CHLOROPHENYL) 3 ( 2,4 DIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 4 CHLOROPHENYL) 3 ( 2,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 4 CHLOROPHENYL) 3 ( 2,4,6 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 4 CHLOROPHENYL) 3 ( 3,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 4 CHLOROPHENYL) 3 ( 4 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 4 CYNOPHENYL) 3 ( 2,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 4 IODOPHENYL) 3 ( 2,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 4 METHOXYPHENYL) 3 ( 2,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 4 NITROPHENYL) 3 ( 2,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 ( 4 NITROPHENYL) 3 (THIOPHEN 2 YL)PROP 2 EN 1 ONE; 1 [( 4 ( 4 BROMOPHENYL)PHENYL)] 3 ( 2,45 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1,3 BIS( 4 CHLOROPHENYL)PROP 2 EN 1 ONE; 3 ( 3,4 DICHLOROPHENYL) 1 ( 4 METHOXYPHENYL)PROP 2 EN 1 ONE; 3 ( 4 CHLOROPHENYL) 1 ( 4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 3 ( 4 CHLOROPHENYL) 1 ( 4 METHOXYPHENYL)PROP 2 EN 1 ONE; 3 ( 4 CHLOROPHENYL) 1 ( 4 NITROPHENYL)PROP 2 EN 1 ONE; 3 ( 4 CHLOROPHENYL) 1 [ 4 (PROP 2 EN 1 YLOXY)PHENYL]PROP 2 EN 1 ONE; 3 (FURAN 2 YL) 1 ( 4 NITROPHENYL)PROP 2 EN 1 ONE; 4 ( 2,4 DIMETHOXYPHENYL)BUT 3 EN 1 ONE; ACORUS CALAMUS EXTRACT; BETA ASARONE; CHALCONE DERIVATIVE; CHLOROQUINE; HYDROXYL GROUP; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACORUS CALAMUS; ANIMAL CELL; ANTIMALARIAL ACTIVITY; ARTICLE; BIOASSAY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; ELECTRON; FEMALE; HUMAN; HUMAN CELL; IC 50; NONHUMAN; PLASMODIUM FALCIPARUM; RING OPENING; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; ANISOLES; ANTIMALARIALS; CHALCONES; HELA CELLS; HUMANS; INHIBITORY CONCENTRATION 50; PLASMODIUM FALCIPARUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77957832893     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.08.049     Document Type: Article

References (59)

1. M. Wahlgren, and M.T. Bejarano Nature 400 1999 506 507
2. M.L. Go Med. Res. Rev. 23 2003 456 487
3. C. Fattorusso, G. Campiani, G. Kukreja, M. Persico, S. Butini, M.P. Romano, M. Altarelli, S. Ros, M. Brindisi, L. Savini, E. Novellino, V. Nacci, E. Fattorusso, S. Parapini, N. Basilico, D. Taramelli, V. Yardley, S. Croft, M. Borriello, and S. Gemma J. Med. Chem. 51 2008 1333 1343
4. S. Vangapandu, M. Jain, K. Kaur, P. Patil, S.R. Patel, and R. Jain Med. Res. Rev. 27 2007 65 107
5. O.V. Miroshnikova, T.H. Hudson, L. Gerena, D.E. Kyle, and A.J. Lin J. Med. Chem. 50 2007 889 896
6. M.A.V. Agtmael, T.A. Eggette, and C.J.V. Boxtel Trends Pharmacol. Sci. 20 1999 199 205
7. Y. Wu Acc. Chem. Res. 35 2002 255 259
8. V. Kumar, A. Mahajan, and K. Chibale Bioorg. Med. Chem. 17 2009 2236 2275
9. S. Kamchonwongpaisan, P. Mckeever, P. Hossler, H. Ziffer, and S.R. Meshnick Am. J. Trop. Med. Hyg. 56 1997 7 12
10. T.-Y. Wang, and R.-C. Xu J. Tradit. Chin. Med. 5 1985 240 242
11. J.A. Lin, D.L. Klayman, and W.K.J. Milhouse J. Med. Chem. 30 1987 2147 2150
12. Q.C. Yang, W.Z. Shi, R. Li, and J. Gan J. Tradit. Chin. Med. 2 1982 99 103
13. G. Schmidt, and W. Hofheinz J. Am. Chem. Soc. 105 1983 624 625
14. M.A. Avery, W.K.M. Chong, and C.J. White J. Am. Chem. Soc. 114 1992 974 979
15. J.S. Yadav, R.S. Babu, and G. Sabitha Tetrahedron Lett. 44 2003 387 389
16. C. Luxemburger, K. Silamut, F. Nosten, M. van Vugt, F. Gimenez, T. Chongsuphajaisiddhi, and N.J. White Trans. R. Soc. Trop. Med. Hyg. 92 1998 668 669
17. N.J. Gogtay, V.S. Kadam, D.R. Karnad, A. Kanbur, K.D. Kamtekar, and N.A. Kshirsagar Ann. Trop. Med. Parasitol. 94 2000 519 520
18. F. Sahr, V.R. Willoughby, A.A. Gbakima, and M.J. Bockarie Ann. Trop. Med. Parasitol. 95 2001 445 449
19. S.R. Meshnick Int. J. Parasitol. 32 2002 1655 1660
20. A.M. Dondorp, F. Nosten, P. Yi, D. Das, A.P. Phyo, J. Tarning, K.M. Lwin, F. Ariey, W. Hanpithakpong, S.J. Lee, P. Ringwald, K. Silamut, M. Imwong, K. Chotivanich, P. Lim, T. Herdman, S.S. An, S. Yeung, P. Singhasivanon, N.P. Day, N. Lindegardh, D. Socheat, and N.J. White N. Engl. J. Med. 361 2009 455 467
21. Z. Nowakowska Eur. J. Med. Chem. 42 2007 125 137
22. M. Chen, T.G. Theander, S.B. Christensen, L. Hviid, L. Zhai, and A. Kharazmi Antimicrob. Agents Chemother. 38 1994 1470 1475
23. M. Liu, P. Wilairat, S.L. Croft, A.L.C. Tan, and M.L. Go Bioorg. Med. Chem. 11 2003 2729 2738
24. M. Liu, P. Wilairat, and M.L. Go J. Med. Chem. 44 2001 4443 4452
25. R. Li, X. Chen, B. Gong, J.N. Dominguez, E. Davidson, G. Kurzban, R.E. Miller, E.O. Nuzum, P.J. Rosenthal, and J.H. McKerrow J. Med. Chem. 38 1995 5031 5037
26. J.N. Domínguez, J.E. Charris, G. Lobo, N.G. Domínguez, M.M. Moreno, F. Riggione, E. Sanchez, J. Olson, and P.J. Rosenthal Eur. J. Med. Chem. 36 2001 555 560
27. N. Mishra, P. Arora, B. Kumar, L.C. Mishra, A. Bhattacharya, S.K. Awasthi, and V.K. Bhasin Eur. J. Med. Chem. 43 2008 1530 1535
28. J.N. Domýnguez, C. Leon, J. Rodrigues, N.G. Dominguez, J. Gut, and P.J. Rosenthal Il Farmaco 60 2005 307 311
29. J.N. Domýnguez, C. Leon, J. Rodrigues, N.G. Domýnguez, J. Gut, and P.J. Rosenthal J. Med. Chem. 48 2005 3654 3658
30. X. Wu, P. Wilairatb, and M.L. Go Bioorg. Med. Chem. Lett. 12 2002 2299 2302
31. A. Agarwal, K. Srivastava, S.K. Puri, and P.M.S. Chauhan Bioorg. Med. Chem. Lett. 15 2005 3133 3136
32. C.N. Saha, S. Bhattacharya, and D. Chetia Int. J. Chem. Tech. Res. 1 2009 322 328
33. J.P. Dheyongera, W.J. Geldenhuys, T.G. Dekker, M.G. Matsabisa, and C.J.V.D. Schyf Biorg. Med. Chem. 13 2005 1653 1659
34. A. Barazarte, J. Camacho, J. Domínguez, G. Lobo, N. Gamboa, J. Rodrigues, M.V. Capparelli, Á.Á. Larena, S. Andujar, D. Enriz, and J. Charris Biorg. Med. Chem. 16 2008 3661 3674
35. L.F. Tietze Chem. Rev. 96 1996 115 136
36. A.K. Sinha, B.P. Joshi, and R. Acharya Chem. Lett. 32 2003 780 781
37. A.K. Sinha, B.P. Joshi, A. Sharma, H.C. Goel, and J. Prasad Nat. Prod. Res. 18 2004 219 223
38. A.K. Sinha, A. Sharma, B.P. Joshi, and N.P. Singh Nat. Prod. Res. 19 2005 771 776
39. A.K. Sinha, B.P. Joshi, and R. Dogra Nat. Prod. Lett. 15 2007 439 444
40. U.K. Sharma, N. Sharma, R. Kumar, R. Kumar, and A.K. Sinha Org. Lett. 11 2009 4846 4888
41. A. Sharma, R. Kumar, N. Sharma, V. Kumar, and A.K. Sinha Adv. Synth. Catal. 350 2008 2910 2920
42. A. Sharma, N. Sharma, R. Kumar, U.K. Sharma, and A.K. Sinha Chem. Commun. 2009 5299 5301
43. A. Sharma, N. Sharma, R. Kumar, A. Shard, and A.K. Sinha Chem. Commun. 46 2010 3283 3285
44. P.T. Anastas, T.C. Williamson, Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes 1998 Oxford University Press New York
45. F. Dong, C. Jian, F. Zhenghao, G. Kai, and L. Zuliang Catal. Commun. 9 2008 1924 1927
46. B.P. Joshi, A. Sharma, and A.K. Sinha Tetrahedron 62 2006 2590 2593
47. S. Manohar, S.I. Khan, and D.S. Rawat Bioorg. Med. Chem. Lett. 20 2010 322 325
48. S. Fu, and S.-H. Xiao Parasitol. Today 11 1991 310 313
49. S.J. Kesten, M.J. Degnan, J. Hung, D.J. McNamara, D.F. Ortwine, S.E. Uhlendorf, and L. Werbel J. Med. Chem. 35 1992 3429 3447
50. M. Smilkstein, N. Sriwilaijaroen, J.X. Kelly, P. Wilairat, and M. Riscoe Antimicrob. Agents Chemother. 48 2004 1803 1806
51. H. Chandru, A.C. Sharada, B.K. Bettadaiah, C.S.A. Kumar, K.S. Rangappa, and S.K. Jayashree Bioorg. Med. Chem. 15 2007 7696 7703
52. K.H. Lee, F.H.A. Aziz, A. Syahida, F. Abas, K. Shaari, D.A. Israf, and N.H. Lajis Eur. J. Med. Chem. 44 2009 3195 3200
53. D. Batovska, S. Parushev, B. Stamboliyska, I. Tsvetkova, M. Ninova, and H. Najdenski Eur. J. Med. Chem. 44 2009 2211 2218
54. L. Santos, R.C. Pedrosa, R. Correa, V.C. Filho, R.J. Nunes, and R.A. Yunes Arch. Pharm. Chem. Life Sci. 339 2006 541 546
55. 4 provided the chalcone derivatives in optimum yield.
56. P. Patil, and S. Dharmaprakash Mater. Lett. 62 2008 451 453
57. A. Sharma, V. Kumar, and A.K. Sinha Adv. Synth. Catal. 348 2006 354 360
58. A.R. Chamberlin, and J.S. Daniel Comprehensive Organic Synthesis third ed. 1991 Pergamon Press New York pp. 923-927
59. W. Trager, and J.B. Jensen Science 193 1976 673 675