Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities

Bioorganic Chemistry

Volumn 52, Issue , 2014, Pages 77-82

  Idhayadhulla, Akber ^a   Xia, Likai ^a   Lee, Yong Rok ^a   Kim, Sung Hong ^b   Wee, Young Jung ^a   Lee, Chong Soon ^a  

^a Yeungnam University   (South Korea)

^b Korea Basic Science Institute (KBSI)   (South Korea)

Author keywords

3,4 Dihydromollugin; Antibacterial activity; Antioxidant activity; Mollugin

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 3,4 DIHYDROMOLLUGIN; 6 HYDROXY 2,2 DIMETHYL 2H BENZO[H]CHROMENE 5 CARBOXYLIC ACID; 6 HYDROXY 2,2 DIMETHYL 3,4 DIHYDRO 2H BENZO[H]CHROMENE 5 CARBOXYLIC ACID; BUTYLCRESOL; CIPROFLOXACIN; METHYL 6 HYDROXY 2 METHYL 2 (4 METHYLPENT 3 EN 1 YL) 2H BENZO[H]CHROMENE 5 CARBOXYLATE; METHYL 6 HYDROXY 2 METHYL 2 (4 METHYLPENTYL) 3,4 DIHYDRO 2H BENZO[H]CHROMENE 5 CARBOXYLATE; METHYL 6 HYDROXY 2 PHENYL 3,4 DIHYDRO 2H BENZO[H]CHROMENE 5 CARBOXYLATE; METHYL 6 HYDROXY 2 PHENYL 4H BENZO[H]CHROMENE 5 CARBOXYLATE; MOLLUGIN; PHENETHYL 6 HYDROXY 2 METHYL 2 (4 METHYLPENT 3 EN 1 YL) 2H BENZO[H]CHROMENE 5 CARBOXYLATE; PHENETHYL 6 HYDROXY 2 METHYL 2 (4 METHYLPENTYL) 3,4 DIHYDRO 2H BENZO[H]CHROMENE 5 CARBOXYLATE; PHENETHYL 6 HYDROXY 2,2 DIMETHYL 2H BENZO[H]CHROMENE 5 CARBOXYLATE; PHENETHYL 6 HYDROXY 2,2 DIMETHYL 3,4 DIHYDRO 2H BENZO[H]CHROMENE 5 CARBOXYLATE; PLANT MEDICINAL PRODUCT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BACTERIAL STRAIN; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS; STRUCTURE ANALYSIS;

3,4-DIHYDROMOLLUGIN; ANTIBACTERIAL ACTIVITY; ANTIOXIDANT ACTIVITY; MOLLUGIN;

ANTI-BACTERIAL AGENTS; ANTIOXIDANTS; DRUG EVALUATION, PRECLINICAL; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PYRANS; STAPHYLOCOCCUS AUREUS;

EID: 84891671091     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2013.11.008     Document Type: Article

References (45)

1. Pharmacopeia of the People's Republic of China; Guangdong Science and Technology Press: Guangzhou, PR China, 1992; p. 179.
2. G.M.A. Hocking Dictionary of Natural Products 1997 Plexus Publishing Medford, NJ p. 679
3. H. Itokawa, T. Mihar, and K. Takeya Chem. Pharm. Bull. 31 1983 2353
4. H. Itokawa, Y. Qiao, and K. Takeya Phytochemistry 28 1989 3465
5. M. Wang, Z. Wang, L. Yue, and J. Cai Xibei Yaoxue Zazhi 27 2012 307
6. K. Wang, W. Sun, M. Shan, and A. Ding Zhongguo Shiyan Fangjixue Zazhi 18 2012 113
7. Z.-Y. Tan, Y. Yao, J.-H. Wang, and Z.-L. You Zhongguo Zhongyiyao Xinxi Zazhi 18 2011 65
8. Z.-L. Zhang, Y. Zhou, and X.-F. Huang Zhongchengyao 29 2007 1803
9. S.-C. Kuo, P.-R. Chen, S.-W. Lee, and Z.-T. Chen J. Chin. Chem. Soc. 42 1995 869
10. J. Koyama, T. Ogura, K. Tagahara, T. Konoshima, and M. Kozuka Phytochemistry 31 1992 2907
11. Y. Liu, and Y. Bai Yaoxue Xuebao 20 1985 53
12. K. Inoue, Y. Shiobara, H. Nayeshiro, H. Inouye, G. Wilson, and M.H. Zenk Phytochemistry 23 1984 307
13. Y. Kawasaki, Y. Goda, and K. Yoshihira Chem. Pharm. Bull. 40 1992 1504
14. F. Marec, I. Kollarova, and A. Jegorov Planta Med. 67 2001 127
15. P.P. Gutpa, R.C. Srimal, N. Verma, and J.S. Tandon Pharm. Biol. 37 1999 46
16. Jpn. Kokai Tokkyo Koho, JP 081s13536, 1996.
17. L.-K. Ho, M.-J. Don, H.-C. Chen, S.-F. Yeh, and J.-M. Chen J. Nat. Prod. 59 1996 330
18. L.C. Chang, D. Chavez, J.J. Gills, H.H.S. Fong, J.M. Pezzuto, and D. Kinghorn Tetrahedron Lett. 41 2000 7157
19. M.I. Chung, S.J. Jou, T.H. Cheng, C.N. Lin, F.N. Ko, and C.M. Teng J. Nat. Prod. 57 1994 313
20. Y.R. Lee, X. Wang, Y.M. Kim, J.J. Shim, B.N. Kim, and D.H. Han Bull. Korean Chem. Soc. 28 2007 1735
21. M.N.V. Sastry, S. Claessens, P. Habonimana, and K.N. De J. Org. Chem. 75 2010 2274
22. P. Habonimana, S. Claessens, and K.N. De Synlett 2006 2472
23. S. Claessens, B. Kesteleyn, V.T. Nguyen, and N. De Kimpe Tetrahedron 62 2006 8419
24. J.-P. Lumb, and D. Trauner Org. Lett. 7 2005 5865
25. L.-K. Ho, H.-J. Yu, C.-T. Ho, and M.-J. Don J. Chin. Chem. Soc. 48 2001 77
26. H.W. Jung, J.S. Oh, S.H. Lee, J.L. Liang, D.H. Kim, A.F.M.M. Rahman, and Y. Jahng Bull. Korean Chem. Soc. 28 2007 1863
27. H. Schildknecht, and F. Straub Justus Liebigs Ann. Chem. 1976 1307
28. L. Heide, and E. Leistner J. Biosci. 37 C 1982 354
29. N.V.S. Mudiganti, S. Claessens, P. Habonimana, and N. De Kimpe J. Org. Chem. 73 2008 3867
30. G. Cefarelli, B. D'Abrosca, A. Fiorentino, A. Izzo, C. Mastellone, S. Pacifico, and V. Piscopo J. Agric. Food Chem. 54 2006 803
31. M. Burits, and F. Bucar Phytother. Res. 14 2000 323
32. O.P. Sharma, and T.K. Bhat Food Chem. 113 2009 1202
33. A.W. Bauer, W.M. Kirby, J.C. Sherris, and M. Turck Am. J. Clin. Pathol. 45 1966 493
34. R.P. Pandit, and Y.R. Lee Synthesis 44 2012 2910
35. B.H. Park, H.J. Lee, and Y.R. Lee J. Nat. Prod. 74 2011 644
36. E.J. Jung, B.H. Park, and Y.R. Lee Green Chem. 12 2010 2003
37. B.H. Park, Y.R. Lee, and W.S. Lyoo Synthesis 2009 2146
38. L. Xia, and Y.R. Lee Synlett 2008 1643
39. Y.R. Lee L. Xia Tetrahedron Lett. 49 2008 3283
40. Y.R. Lee, and J.H. Kim Synlett 2007 2232
41. X. Wang, and Y.R. Lee Tetrahedron Lett. 48 2007 6275
42. Y.R. Lee, and X. Wang Org. Biomol. Chem. 3 2005 3955
43. L.R.C. Barclay, C.D. Edwards, K. Mukai, Y. Egawa, and T. Nishi J. Org. Chem. 60 1995 2739
44. G.W. Burton, T. Doba, E. Gabe, L. Hughes, F.L. Lee, L. Prasad, and K.U. Ingold J. Am. Chem. Soc. 107 1985 7053
45. M. Charton Prog. Phys. Org. Chem. 13 1981 119