Ultrasound-assisted convenient synthesis of hypolipidemic active natural methoxylated (E)-arylalkenes and arylalkanones

Tetrahedron

Volumn 61, Issue 12, 2005, Pages 3075-3080

  Joshi, Bhupendra P ^a   Sharma, Anuj ^a   Sinha, Arun K ^a  

^a CSIR INSTITUTE OF HIMALAYAN BIORESOURCE TECHNOLOGY   (India)

Author keywords

(E) Arylalkenes; Arylalkanones; DDQ; Hypolipidemic; Ultrasound

Indexed keywords

1 (2',4',5' TRIMETHOXYPHENYL) 1 BUTENE; 1 (2',4',5' TRIMETHOXYPHENYL)PROP 1 ENE; 1 (3',4' DIMETHOXYPHENYL) 1 BUTENE; 1 (3',4' DIMETHOXYPHENYL)PROP 1 ENE; 1 (3',4' DIOXYMETHYLENEPHENYL)PROP 1 ENE; 1 (3',4',5' TRIMETHOXYPHENYL)PROP 1 ENE; 1 (4' METHOXYPHENYL)PROP 1 ENE; ALKENE DERIVATIVE; AMMONIUM FORMATE; ANTILIPEMIC AGENT; DIOXANE DERIVATIVE; KETONE DERIVATIVE; SILICA GEL; UNCLASSIFIED DRUG; WATER;

ADDITION REACTION; ARTICLE; CIS ISOMER; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; QUANTUM YIELD; TRANS ISOMER;

STAPHYLOCOCCUS PHAGE 3A;

EID: 14644394294     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.071     Document Type: Article

References (59)

1. H.A. Neil, D. Mant, L. Jones, B. Morgan, and J.I. Mann Br. Med. J. 301 1990 584
2. K.S. McCully Nat. Med. 2 1996 386
3. M.C. Chrysselis, E.A. Rekka, and P.N. Kourounakis J. Med. Chem. 43 2000 609
4. G. Mantell, M.T. Burke, and J. Staggers Am. J. Cardiol. 66 1990 B11
5. R. Ceska, V. Melenovsky, J. Malik, E. Kralikova, T. Stulc, and M. Vrablik Int. Congress Ser. 1262 2004 458
6. C.C. Chen, J.D. Hsu, S.F. Wang, H.C. Chiang, M.Y. Yang, E.S. Kao, Y.C. Ho, and C.J. Wang J. Agric. Food Chem. 51 2003 5472
7. K.G.D. Allen, S.J. Bristow, and L. Yu J. Agric. Food Chem. 52 2004 4998
8. M.C. Ramírez-Tortosa, M.D. Mesa, M.C. Aguilera, J.L. Quiles, L. Baro, C.L. Ramírez-Tortosa, E. Martinez-Victoria, and A. Gil Atherosclerosis 147 1999 371
9. K.C. Huang The Pharmacology of Chinese Herbs 1999 CRC New York pp 117-127
10. B.M. Winklhofer-Roob, E. Rock, J. Ribalta, D.H. Shmerling, and J.M. Roob Mol. Aspects Med. 24 2003 391
11. B.C. Vastano, Y. Chen, N. Zhu, C.T. Ho, Z. Zhou, and R.T. Rosen J. Agric. Food. Chem. 48 2000 253
12. R.G. Enqiquez, M.A. Chávez, and F. Jáuregui Phytochemistry 19 1980 2024
13. J.B. Harborne, and H. Baxter Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants 1993 Taylor & Francis Washington, DC
14. P. Tuntiwachwuttikul, O. Pancharoen, T. Jaipetch, and V. Reutrakul Phytochemistry 20 1981 1164
15. U. Bhandari, J.N. Sharma, and R. Zafar J. Ethnopharmacol. 61 1998 167
16. D. Francisco, C. Leticia, F. Rosa, T. Joaquin, L. Fernando, C. German, and M. Heber Org. Prep. Proced. Int. 23 1991 133
17. P. Janusz, L. Bozena, T.D. Alina, L. Barbara, W. Stanislaw, S. Danuta, P. Jacek, K. Roman, C. Jacek, S. Malgorzata, and C. Zdzislaw J. Med. Chem. 43 2000 3671
18. A. Cruz, L. Garduňo, M. Salazar, E. Martínez, F. Diaz, G. Chamorro, and J. Tamariz Med. Chem. Res. 10 2001 587
19. A. Cruz, L. Garduňo, M. Salazar, E. Martínez, H.A. Jiménez-Vázquez, F. Diaz, G. Chamorro, and J. Tamariz Arzneim. Forsch. Drug Res. 51 2001 535
20. Z. Chilmonczyk, D. Siluk, R. Kaliszan, B. Łozowicka, J. Popławski, and S. Filipek Pure Appl. Chem. 73 2001 1445
21. C. Gomez, G. Chamorro, M.A. Chav'ez, G. Martinez, M. Salazar, and N. Pages Plant Med. Phytother. 21 1987 279
22. A. Hernandez, M.L. Lopez, G. Chamorro, and F.T. Mendoza Planta Med. 59 1993 121
23. W.N. Bambang, S. Brunhilde, W. Victor, and P. Peter Phytochemistry 41 1996 129
24. M. Krause, X. Ligneau, H. Stark, M. Garbarg, J.C. Schwartz, and W. Schunack J. Med. Chem. 41 1998 417
25. A.Z. Susana, N.L. Silvia, D.P. Germán, L.F. Ricardo, B.S. Carina, M.F. Lorena, A.G. Fernando, M.R. Ana, and D.E. Ricardo J. Nat. Prod. 62 1999 1353
26. P.K. Sharma, and P.C. Dandiya Ind. J. Appl. Chem. 32 1969 236
27. I. Mori, and Y. Nakachi Tetrahedron Lett. 26 1978 2297
28. A.D. Buss, R. Mason, and S. Warren Tetrahedron Lett. 24 1983 5293
29. G.W. Kabalka, N. Li, D. Tejedor, R.R. Malladi, and S. Trotman J. Org. Chem. 64 1999 3157
30. A. Ohno, Y. Ohnishi, and G. Tsuchihashi Tetrahedron Lett. 8 1969 643
31. E.C. Miller, A.B. Swanson, D.H. Phillips, T.L. Fletcher, A. Liem, and J.A. Miller Cancer Res. 43 1983 1124
32. S.C. Kim, A. Liem, B.C. Stewart, and J.A. Miller Carcinogenesis 20 1999 1303
33. 14 which overall restrict the market potential of an essential oil rich in cis-isomer. Therefore, utilization of an isomeric mixture of arylalkenes via arylalkanes is an added benefit towards formation of useful products including (E)-arylalkenes (3a-3g) and arylalkanones (3h-3j).
34. B.D. Gates, and J.S. Swenton Tetrahedron Lett. 33 1992 2127
35. A. Sen, and T.W. Lai Inorg. Chem. 20 1981 4036
36. M.R. Reddy, and M. Periasamy J. Organomet. Chem. 491 1995 263
37. I.R. Baxendale, A.L. Lee, and S.V. Ley Synlett 3 2002 516
38. J. Yu, M.J. Gaunt, and J.B. Spencer J. Org. Chem. 67 2002 4627
39. Y. Tamaru, H. Ochiai, Y. Ymada, and Z. Yoshida Tetrahedron Lett. 24 1983 3869
40. J.S. Henk, J.M.V. Frank, A.F. Jim, and B.P.A.W. Joannes J. Nat. Prod. 61 1998 1110
41. S.R. Soudagar, and S.D. Samant Ultrason. Sonochem. 2 1995 S15
42. L.H. Thompson, and L.K. Doraiswamy Ind. Eng. Chem. Res. 38 1999 1215
43. A.K. Sinha, B.P. Joshi, A. Sharma, H.C. Goel, and J. Prasad Nat. Prod. Res. 18 2003 219
44. A. Sharma, B.P. Joshi, and A.K. Sinha Chem. Lett. 32 2003 1186
45. (b) Sinha, A. K.; Joshi, B. P.; Dogra, R. U.S. Patent 6566557, 2003.
46. (c) Sinha, A. K.; Joshi, B. P.; Dogra, R. U.S. Patent 6590127, 2003.
47. S. Ram, and R.E. Ehrenkaufer Synthesis 1988 91
48. A. Patra, and A.K. Mitra J. Nat. Prod. 44 1981 668
49. (b) Sinha, A. K. U.S. Patent 6528041, 2003.
50. P.P. Fu, and R.G. Harvey Chem. Rev. 78 1978 317
51. D. Walker, and J.D. Hiebert Chem. Rev. 67 1967 153
52. B. Lal, R.M. Gidwani, J. Reden, and N.J. de Souza Tetrahedron Lett. 25 1984 2901
53. A.G. Gonzalez, Z.E. Aguiar, J.G. Luis, and A.G. Ravelo J. Nat. Prod. 52 1989 1231
54. F.D. Ramdayal, D.J. Kiemle, and R.T. Lalonde J. Org. Chem. 64 1999 4607
55. T. Iliefski, S. Li, and K. Lundquist Tetrahedron Lett. 39 1998 2413
56. A.K. Sinha, R. Acharya, and B.P. Joshi J. Nat. Prod. 65 2002 764
57. R.S. Davidson, A. Safdar, J.D. Spencer, and R. Robinson Ultrasonics 25 1987 35
58. (a) Buckingham, J. Dictionary of Organic Compounds, Chapman & Hall, Mack Printing Company, Eastern Pennsylvania, New York, 1982.
59. (b) Buckingham, J. Dictionary of Natural Products, Chapman & Hall Chemical Database, 2-6 Boundary Row, London SE18HN, 1994.