Facile stereoslective synthesis of spiro[indole-oxiranes] by combination of phase transfer catalyst and ultrasound irradiation and their bioassay

Ultrasonics Sonochemistry

Volumn 18, Issue 5, 2011, Pages 1113-1117

  Dandia, Anshu ^a   Singh, Ruby ^a   Bhaskaran, Sumit ^a  

^a UNIVERSITY OF RAJASTHAN   (India)

Author keywords

Antimicrobial activity; Antioxidant; Spiro indole 3,2 oxiranes ; Ultrasound irradiation

Indexed keywords

ANTIOXIDANTS; BIOASSAY; IRRADIATION; LEAD COMPOUNDS; MICROORGANISMS; POLYCYCLIC AROMATIC HYDROCARBONS; ULTRASONICS;

ANTI-MICROBIAL ACTIVITY; ANTIOXIDANT PROPERTIES; CETYL TRIMETHYL AMMONIUM BROMIDES; ENVIRONMENTALLY BENIGN; OXIRANES; PHASE TRANSFER CATALYSTS; ULTRASOUND IRRADIATION;

CATALYSTS;

3 AROYLMETHYLENE INDOLE 2 ONE; CETRIMIDE; ETHYLENE OXIDE DERIVATIVE; HYDROGEN PEROXIDE; SPIRO[INDOLE 3,2' OXIRANE] 3' BENZOYL 2 (1H) ONE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ANTIOXIDANT ACTIVITY; AQUEOUS SOLUTION; ARTICLE; BIOASSAY; CATALYST; DRUG SYNTHESIS; EPOXIDATION; FLUORINATION; IRRADIATION; PRIORITY JOURNAL; ULTRASOUND;

EID: 79956366029     PISSN: 13504177     EISSN: 18732828     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2010.12.010     Document Type: Article

References (64)

1. K.S. Suslick (Ed.), Ultrasound: Its Chemical, Physical and Biological Effects, VCH, New York, 1988.
2. C. Petrier, J.L. Luche, in: J.L. Luche (Ed.), Synthetic Organic Sonochemistry, Plenum Press, New York, 1998 (Chapter 2).
3. G. Cravotto, P. Cintas, Chem. Soc. Rev. 35 (2006) 180-196.
4. (a) K. Miiller, C. Faeh, F. Diederich, Science 317 (2007) 1881-1888;
5. (b) M. Shimizu, T. Hiyama, Angew. Chem. Int. Ed. 44 (2005) 214-231;
6. (c) X. Ren, W. Wan, H. Jiang, J. Hao, Mini-Rev. Org. Chem. 4 (2007) 330-337;
7. (d) S. Purser, P.R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 37 (2008) 320-330.
8. (a) A.J. Elliott, Chemistry of organic fluorine compounds II: a critical review, in: M. Hudlicky, A.E. Pavlath (Eds.), ACS Monograph, vol. 187, American Chemical Society, Washington, DC, 1995, p. 1119;
9. (b) W.K. Hagmann, J. Med. Chem. 51 (2008) 4359-4369.
10. A.I. Meyers, D.L. Comins, D.M. Roland, R. Henning, K. Shimizu, J. Am. Chem. Soc. 101 (1979) 7104-7105.
11. Y. Sato, H. Watable, T. Nakazawa, T. Shomura, H. Yamamoto, M. Sezaki, S.J. Kondo, Antibiotics 42 (1989) 149-152.
12. T.K.M. Shing, M. Aloui, J. Chem. Soc., Chem. Common. 126 (1988) 1525-1526.
13. A.P. Kozikowski, R.J. Schwiesing, K.L. Sorgi, J. Am. Chem. Soc. 102 (1980) 6577-6580.
14. H.P. Sigg, H.P. Weber, Helv. Chim. Acta 51 (1968) 1395-1408.
15. A. Lattanzi, A. Russo, Tetrahedron 62 (2006) 12264-12269.
16. B.M. Adger, J.V. Barkley, S. Bergeron, M.W. Cappi, B.E. Flowerdew, M.P. Jackson, R. McCague, T.C. Nugent, S.M. Rorberts, J. Chem. Soc. Perkin Trans. 1 (1997) 3501-3507.
17. (a) M.J. Porter, J. Skidmore, Chem. Commun. (2000) 1215-1225;
18. (b) Q.H. Xia, H.Q. Ge, C.P. Ye, Z.M. Liu, K.X. Su, Chem. Rev. 105 (2005) 1603-1662.
19. G. Grigoropoulou, J.H. Clark, Tetrahedron Lett. 47 (2006) 4461-4463.
20. E.V. Dehmlow, S.S. Dehmlow, Phase Transfer Catalysis, Second ed., Verlag Chemei, Weinheim, 1993.
21. S. Arai, H. Tsuge, T. Shioiri, Tetrahedron Lett. 39 (1998) 7563-7566.
22. G. Fioroni, F. Fringuelli, F. Pizzo, L. Vaccaro, Green Chem. 5 (2003) 425-428.
23. J.-T. Li, X.-F. Liu, Y. Yin, C. Du, Org. Commun. 2:1 (2009) 1-6.
24. M.Q. LI, X.G. Jian, G.M. Wang, Y. Yu, Chin. Chem. Lett. 15 (2004) 350-352.
25. M.L. Wang, V. Rajendran, Ultrason. Sonochem. 14 (2007) 46-54.
26. M.H. Entezari, A.A. Keshavarzi, Ultrason. Sonochem. 8 (2001) 213-216.
27. R.J. Sundberg, The Chemistry of Indoles, Academic, New York, NY, 1996.
28. (a) A.H. Abdul-Rahman, E.M. Keshk, M.A. Hanna, Sh.M. El-Bady, Biorg. Med. Chem. 12 (2004) 2483-2488;
29. (b) R.M. Williams, R.J. Cox, Acc. Chem. Res. 36 (2003) 127-139;
30. (c) J.F.M. Da Silva, S.J. Garden, A.C. Pinto, J. Braz. Chem. Soc. 12 (2001) 273-324.
31. (a) Upjohnco, French Patent 1, 445, 824, Chem. Abstr. 66 (1967) 75921x.;
32. (b) Upjohnco, Netherland Appl., 6, 505, 845, 1996;
33. Chem. Abstr. 67 (1967) 21850e.;
34. (c) W.E. Anthony, US Patent, 3413, 299, 1968, Chem. Abstr. 70 (1969) 47294j.;
35. (d) K. Kikugawa, M. Ichino, Chem. Pharm. Bull. 21 (1973) 1151-1155.
36. K.A. Marx, P. O'Neil, P. Hoffman, M.L. Ujwal, J. Chem. Inf. Comput. Sci. 43 (2003) 1652-1667.
37. (a) F. Arndt, B. Eistert, W. Ender, Ber. Dtsch. Chem. Ges. 62B (1929) 44-56;
38. (b) A. Schoenberg, K. Junghans, Chem. Ber. 96 (1963) 3328-3337;
39. (c) L. Capuano, M. Welter, Chem. Ber. 101 (1968) 3671-3678;
40. (d) P.D. Kennewell, D.J. Miller, R.M. Scrowston, R. Westwood, J. Chem. Res., Synop. (1995) 396;
41. (e) S. Muthusamy, C. Gunanathan, M. Nethaji, Synlett (2004) 639.
42. (a) A.D. Ainley, R. Robinson, J. Chem. Soc. (1934) 1508-1520;
43. (b) R. Kikumoto, T. Kobayashi, Tetrahedron 22 (1966) 3337-3343;
44. (c) L. Baiocchi, M. Giannangeli, J. Heterocycl. Chem. 25 (1988) 1905-1909;
45. (d) N. Nishizono, K. Oda, Y. Kato, K. Ohno, M. Minami, M. Machida, Heterocycles 63 (2004) 1083-1091.
46. (a) J.W. Ager Jr., F.A. Eastwood, R. Robinson, Tetrahedron, Suppl. 7 (1966) 277-280;
47. (b) W.C. Anthony, J. Org. Chem. 31 (1966) 77-81;
48. (c) G. Kobayashi, Y. Matsuda, Y. Tominaga, M. Ohkuma, H. Shinoda, M. Kohno, D. Mizuno, Yakugaku Zasshi 97 (1977) 1033-1039;
49. (d) S.A. Brunton, K. Jones, J. Chem. Soc., Perkin Trans. 1 (2000) 763-766.
50. V. Schulz, M. Davoust, M. Lemarie, J.-F. Lohier, J.S. de Oliverira Santos, P. Metzner, J.-F. Brière, Org. Lett. 9 (2007) 1745-1748.
51. (a) A. Dandia, K. Arya, Bioorg. Med. Chem. Lett. 18 (2008) 114-119;
52. (b) A. Dandia, R. Singh, S. Khaturia, J. Fluorine Chem. 128 (2007) 524-529;
53. (c) A. Dandia, R. Singh, S. Khaturia, Bioorg. Med. Chem. 14 (2006) 1303-1308;
54. (d) A. Dandia, R. Singh, P. Sarawgi, Org. Prep. Proc. Int. 37 (2005) 397-402;
55. (e) A. Dandia, K. Arya, M. Sati, S. Gautam, Tetrahedron 60 (2004) 5253-5258;
56. (f) A. Dandia, R. Singh, P. Sarawgi, J. Fluorine Chem. 125 (2004) 1835-1840;
57. (g) A. Dandia, M. Sati, K. Arya, A. Loupy, Green Chem. 4 (2002) 599-602.
58. L.M. Prescott, J.P. Harley, D.A. Klein, Microbiology, fifth ed., McGraw-Hill Companies, Inc., NY, 2002. pp. 805-825.
59. NCCLs, Methods for Dilution Antimicrobial Susceptibility Test for Bacteria, which Grow Aerobically, fifth ed., Approved Standard M7-A5, Nccls, Villanova, PA, 2000.
60. (a) A. Shirwaiker, K. Rajendran, C. Dinesh Kumar, Indian J. Exp. Biol. 42 (2004) 803-807;
61. (b) B.H. Babu, B.S. Shailesh, J. Paddikala Fitotherapia 72 (2001) 272-279.
62. K. Kato, S. Terao, N. Shimamoto, M. Hirata, J. Med. Chem. 31 (1988) 793-798.
63. K.C. Joshi, R. Jain, S. Garg, J. Heterocyclic Chem 21 (1984) 977-979.
64. A. Dandia, R. Singh, M. Saha, A. Shivpuri, Pharmazie 57 (2002) 602-605.