Ultrasound-assisted synthesis, anticonvulsant activity, and docking study of indole-appended thiazolidin-4-ones

Archiv der Pharmazie

Volumn 347, Issue 10, 2014, Pages 756-767

  Nikalje, Anna Pratima G ^a   Shaikh, Sameer I ^a   Mulay, Abhineet ^a   Khan, Firoz A K ^a   Sangshetti, Jaiprakash N ^a   Shaikh, Shoaib ^b  

^a Y B CHAVAN COLLEGE OF PHARMACY   (India)

^b Wockhardt Research Centre   (India)

Author keywords

Anticonvulsant activity; Computational study; Docking study; Indolyl thiazolidin 4 ones; Ultrasound irradiation

Indexed keywords

2 (1H INDOL 3 YL) 3 (2 MERCAPTOPHENYL) 5 METHYLTHIAZOLIDIN 4 ONE; 2 (1H INDOL 3 YL) 3 (2 MERCAPTOPHENYL)THIAZOLIDIN 4 ONE; 2 (1H INDOL 3 YL) 3 (4 METHOXYPHENYL) 5 METHYLTHIAZOLIDIN 4 ONE; 2 (1H INDOL 3 YL) 3 (4 METHOXYPHENYL)THIAZOLIDIN 4 ONE; 2 (1H INDOL 3 YL) 3 4 TOLYLTHIAZOLIDIN 4 ONE; 2 (1H INDOL 3 YL) 3 PHENYLTHIAZOLIDIN 4 ONE; 2 (1H INDOL 3 YL) 5 METHYL 3 4 TOLYLTHIAZOLIDIN 4 ONE; 2 (1H INDOL 3 YL) 5 METHYL 3 PHENYLTHIAZOLIDIN 4 ONE; 3 (2 HYDROXYPHENYL) 2 (1H INDOL 3 YL) 5 METHYLTHIAZOLIDIN 4 ONE; 3 (2 HYDROXYPHENYL) 2 (1H INDOL 3 YL)THIAZOLIDIN 4 ONE; 3 (2,4 DICHLOROPHENYL) 2 (1H INDOL 3 YL) 5 METHYLTHIAZOLIDIN 4 ONE; 3 (2,4 DICHLOROPHENYL) 2 (1H INDOL 3 YL)THIAZOLIDIN 4 ONE; 3 (3 CHLOROPHENYL) 2 (1H INDOL 3 YL) 5 METHYLTHIAZOLIDIN 4 ONE; 3 (3 CHLOROPHENYL) 2 (1H INDOL 3 YL)THIAZOLIDIN 4 ONE; 3 (3,5 DIMETHYLPHENYL) 2 (1H INDOL 3 YL) 5 METHYLTHIAZOLIDIN 4 ONE; 3 (3,5 DIMETHYLPHENYL) 2 (1H INDOL 3 YL)THIAZOLIDIN 4 ONE; 3 (4 BROMOPHENYL) 2 (1H INDOL 3 YL) 5 METHYLTHIAZOLIDIN 4 ONE; 3 (4 BROMOPHENYL) 2 (1H INDOL 3 YL)THIAZOLIDIN 4 ONE; 3 (4 CHLOROPHENYL) 2 (1H INDOL 3 YL) 5 METHYLTHIAZOLIDIN 4 ONE; 3 (4 CHLOROPHENYL) 2 (1H INDOL 3 YL)THIAZOLIDIN 4 ONE; 4 THIAZOLIDINONE DERIVATIVE; CARBAMAZEPINE; DIAZEPAM; INDOLE DERIVATIVE; LAMOTRIGINE; PHENYTOIN; UNCLASSIFIED DRUG; ANTICONVULSIVE AGENT; PENTETRAZOLE; THIAZOLIDINE DERIVATIVE;

ANIMAL BEHAVIOR; ANIMAL EXPERIMENT; ANTICONVULSANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG DETERMINATION; DRUG ELIMINATION; DRUG METABOLISM; DRUG SYNTHESIS; IN VIVO STUDY; INFRARED SPECTROSCOPY; LOCOMOTION; MOLECULAR DOCKING; MOUSE; NEUROTOXICITY; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROTAROD TEST; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY; ULTRASOUND; ULTRASOUND ASSISTED SYNTHESIS; ANIMAL; CHEMICAL STRUCTURE; DISEASE MODEL; DRUG DESIGN; DRUG EFFECTS; ELECTRIC SHOCK; MALE; MASS SPECTROMETRY; MOTOR ACTIVITY; NEUROTOXICITY SYNDROMES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PATHOPHYSIOLOGY; PSYCHOLOGY; SEIZURES; SYNTHESIS; TIME;

ANIMALS; ANTICONVULSANTS; BEHAVIOR, ANIMAL; DISEASE MODELS, ANIMAL; DRUG DESIGN; ELECTROSHOCK; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; MICE; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; MOTOR ACTIVITY; NEUROTOXICITY SYNDROMES; PENTYLENETETRAZOLE; ROTAROD PERFORMANCE TEST; SEIZURES; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLIDINES; TIME FACTORS; ULTRASONICS;

EID: 84908027629     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201400148     Document Type: Article

References (50)

1. H. S. White, J. H. Woodhead, M. R. Franklin, E. A. Swinyard, H. Wolf, in: Antiepileptic Drugs (Eds.:, R. H. Levy, R. H. Mattson, B. S. Meldrum,), Raven Press, New York 1995, pp. 99-110.
2. I. E. Leppik, Epilepsia 1994, 35, S29-S40.
3. Media Center, Epilepsy Fact Sheet; World Health Organization: Geneva, 2014; http://www.who.int/mediacentre/factsheets/fs999/en/index.html (June 2014).
4. N. Siddiqui, W. Ahsan, Eur. J. Med. Chem. 2010, 45, 1536-1543.
5. D. Schmidt, W. Loscher, Epilepsia 2005, 46, 858-877.
6. A. V. Delgado-Escueta, Ann. Neurol. 1984, 16, S145.
7. B. Malawska, Mini Rev. Med. Chem. 2003, 3, 341-348.
8. L. Bruno-Blanch, J. Gálvez, R. García-Domenech, Bioorg. Med. Chem. Lett. 2003, 13, 2749-2754.
9. J. R. Dimmock, R. N. Puthucode, J. M. Smith, M. Hetherington, J. W. Quail, U. Pugazhenthi, T. Lechler, J. P. Stables, J. Med. Chem. 1996, 39, 3984-3997.
10. W. J. Houlihan, W. A. Remers, R. K. Brown, Indoles: Part I. Wiley, New York 1992.
11. S. K. Sridhar, S. N. Pandeya, J. P. Stables, A. Ramesh, Eur. J. Pharm. Sci. 2002, 16, 129-132.
12. S. N. Pandeya, I. Ponnilavarasan, A. Pandey, R. Lakhan, J. P. Stables, Pharmazie 1999, 54, 923-926.
13. S. N. Pandeya, D. Sriram, P. Yogeeswari, J. P. Stables, Pharmazie 2001, 56, 875-878.
14. N. Karali, A. Gursoy, Farmaco 1994, 49, 819-822.
15. N. Siddiqui, M. Shamsher Alam, W. Ahsan, Acta Pharm. 2008, 58, 445-454.
16. H. Mandour Adel, E. R. El-Sawy, K. H. Shaker, M. A. Mustafa, Acta Pharm. 2010, 60, 73-88.
17. S. Katayama, N. Ae, T. Kodo, S. Masumoto, S. Hourai, C. Tamamura, H. Tanaka, R. Nagata, J. Med. Chem. 2003, 46, 691-701.
18. J. L. Stanton, M. H. Ackerman, J. Med. Chem. 1983, 26, 986.
19. K. Kaminnski, J. Obniska, Bioorg. Med. Chem. 2008, 16, 4921.
20. J. S. Biradar, S. Y. Manjunath, Indian J. Chem. (b) 2004, 43, 389.
21. J. L. Stanton, M. H. Ackerman, J. Med. Chem. 1983, 26, 986-989.
22. V. K. Agarwal, A. K. Chaturvedi, T. K. Gupta, S. S. Parmar, B. De Boer, J. Med. Chem. 1974, 17, 378-380.
23. V. K. Agarwal, T. K. Gupta, S. S. Parmar, J. Med. Chem. 1972, 15, 1000-1001.
24. H. H. Keasling, R. E. Willette, J. Szmuszkovicz, J. Med. Chem. 1964, 7, 94-96.
25. A. Gursoy, N. Terzioglu, Turk. J. Chem. 2005, 29, 247-254.
26. A. Agarwal, S. Lata, K. K. Saxena, V. K. Srivastava, A. Kumar, Eur. J. Med. Chem. 2006, 41, 1223-1229.
27. H. D. Troutman, L. M. Long, J. Am. Chem. Soc. 1948, 70, 3436-3439.
28. Archana, V. K. Srivastava, A. Kumar, Eur. J. Med. Chem. 2002, 37, 873-882.
29. K. M. Amin, D. E. Rahman Abdel, Y. A. Al-Eryani, Bioorg. Med. Chem. 2008, 16, 5377-5388.
30. C. Dwivedi, T. K. Gupta, S. S. Parmar, J. Med. Chem. 1972, 15, 553-554.
31. H. Kaur, S. Kumar, P. Vishwakarma, M. Sharma, K. K. Saxena, A. Kumar, Eur. J. Med. Chem. 2010, 45, 2777-2783.
32. S. S. Parmar, C. Dwivedi, A. Chaudhari, T. K. Gupta, J. Med. Chem. 1972, 15, 99-101.
33. R. V. Shingalapur, K. M. Hosamani, R. S. Keri, M. H. Hugar, Eur. J. Med. Chem. 2010, 45, 1753-1759.
34. J. J. Bhatt, B. R. Shah, H. P. Shah, P. B. Trivedi, N. K. Undavia, N. C. Desai, Indian J. Chem. (b) 1994, 33, 189-192.
35. A. P. G. Nikalje, F. K. Khan, M. Ghodke, Eur. J. Med. Chem. 2011, 46, 5448-5455.
36. A. P. G. Nikalje, M. Ghodke, A. Girbane, Arch. Pharm. Chem. Life Sci. 2012, 345, 57-64.
37. T. J. Mason, Chem. Soc. Rev. 1997, 26, 443-451.
38. K. Unverferth, J. Engel, N. Hofgen, R. Rostock, R. Gunther, H. J. Lankau, M. Menzer, A. Rolfs, J. Liebscher, B. Muller, H. J. Hofmann, J. Med. Chem. 1998, 41, 63-73.
39. R. R. Reddy, D. S. Iyenger, U. T. Bhalerao, J. Heterocyclic Chem. 1985, 22, 321.
40. C. A. Rohl, F. A. Boeckman, C. Baker, T. Scheuer, W. A. Catterall, R. E. Klevit, Biochemistry 1999, 38, 855-861.
41. G. Saravanan, V. Alagarsamy, C. R. Prakash, Bioorg. Med. Chem. Lett. 2012, 22, 3072-3078.
42. P. N. James, H. R. Synder, Org. Synth. 1959, 39, 30.
43. D. Sinha, A. K. Tiwari, S. Singh, G. Shukla, P. Mishra, H. Chandra, A. K. Mishra, Eur. J. Med. Chem. 2008, 43, 160-165.
44. F. H. Westheimer, K. Taguchi, J. Org. Chem. 1971, 36, 1570-1572.
45. R. I. Krall, J. K. Penry, B. G. White, H. J. Kupferberg, E. A. Swinyard, Epilepsia 1978, 19, 409-417.
46. R. J. Porter, J. J. Cereghino, G. D. Gladding, B. J. Hessei, H. J. Kupferberg, B. Scoville, Cleve Clin. Q 1984, 51, 293-303.
47. VLife Molecular Design Suite 4.3, VLife Sciences Technologies Pvt. Ltd. www.Vlifesciences.com.
48. M. G. Wong, J. A. defina, P. R. Andrews, J. Med. Chem. 1986, 29, 562-572.
49. V. A. Farrar, M. Ciechanowicz-Rutkowska, J. Grochowski, P. Serda, T. Pilati, G. Filippini, C. N. Hinko, A. El-Assadi, J. A. Moore, I. O. Edafiogho, C. W. Andrews, M. Cory, J. M. Nicholson, K. R. Scott, J. Med. Chem. 1993, 36, 3517-3525.
50. Y. Zhao, M. H. Abraham, J. Lee, A. Hersey, N. C. Luscombe, G. Beek, B. Sherborne, I. Cooper, Pharm. Res. 2002, 19, 1446-1457.