Synthesis, antimicrobial and cytotoxic activities of sulfonamidomethane linked heterocycles

Chemical and Pharmaceutical Bulletin

Volumn 61, Issue 7, 2013, Pages 722-730

  Swapna, Mukkara ^a   Premakumari, Chokkappagari ^a   Reddy, Sanapalli Nagi ^a   Padmaja, Adivireddy ^a   Padmavathi, Venkatapuram ^a   Kondaiah, Paturu ^b   Krishna, Narra Siva ^b  

^a SRI VENKATESWARA UNIVERSITY   (India)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

1,3,4 Oxadiazole; 1,3,4 Thiadiazole; Antimicrobial activity; Cytotoxicity; Pyrazole; Pyrrole

Indexed keywords

2 (PARA CHLOROPHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 1H PYRAZOL 3 YL) 1,3,4 OXIDIAZOLE; 2 (PARA CHLOROPHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 1H PYRROLE 3 YL) 1,3,4 OXIDIAZOLE; 2 (PARA CHLOROPHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 1H PYRROLE 3 YL) 1,3,4 THIOXIDIAZOLE; 2 (PARA CHLOROPHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 4,5 DIHYDRO 1H PYRAZOL 3 YL) 1,3,4 THIADIAZOLE; 2 (PARA CHLOROPHENYLSULFONYLAMINOMETHYL) 5 STYRYL 1,3,4 OXADIAZOLE; 2 (PARA CHLOROPHENYLSULFONYLAMINOMETHYL) 5 STYRYL 1,3,4 THIADIAZOLE; 2 (PARA METHYLPHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 1H PYRAZOL 3 YL) 1,3,4 OXIDIAZOLE; 2 (PARA METHYLPHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 1H PYRROLE 3 YL) 1,3,4 OXIDIAZOLE; 2 (PARA METHYLPHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 1H PYRROLE 3 YL) 1,3,4 THIOXIDIAZOLE; 2 (PARA METHYLPHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 4,5 DIHYDRO 1H PYRAZOL 3 YL) 1,3,4 OXADIAZOLE; 2 (PARA METHYLPHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 4,5 DIHYDRO 1H PYRAZOL 3 YL) 1,3,4 THIADIAZOLE; 2 (PARA METHYLPHENYLSULFONYLAMINOMETHYL) 5 STYRYL 1,3,4 OXADIAZOLE; 2 (PARA METHYLPHENYLSULFONYLAMINOMETHYL) 5 STYRYL 1,3,4 THIADIAZOLE; 2 (PHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 1H -PYRAZOL 3 YL) 1,3.4 OXIDIAZOLE; 2 (PHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 1H PYRROLE 3 YL) 1,3,4 OXIDIAZOLE; 2 (PHENYLSULFONYLAMINOMETHYL) 5 (4 PHENYL 4,5 DIHYDRO 1H PYRAZOL 3 YL) 1,3,4 OXADIAZOLE; 2 PHENYLSULFONYLAMINOMETHYL 5 STYRYL 1,3,4 OXADIAZOLE; 2 PHENYLSULFONYLAMINOMETHYL 5 STYRYL 1,3,4 THIADIAZOLE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; CHLORAMPHENICOL; KETOCONAZOLE; OXADIAZOLE DERIVATIVE; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; 2-(P-CHLOROPHENYLSULFONYLAMINOMETHYL)-5-STYRYL-1,3,4-OXADIAZOLE; ANTIINFECTIVE AGENT; HETEROCYCLIC COMPOUND; SULFONAMIDE;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BACILLUS SUBTILIS; CARCINOMA CELL; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; KLEBSIELLA PNEUMONIAE; LUNG CARCINOMA; NONHUMAN; PENICILLIUM CHRYSOGENUM; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; HUMAN; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TOXICITY; TUMOR CELL LINE;

ANTI-INFECTIVE AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; HETEROCYCLIC COMPOUNDS; HUMANS; MICROBIAL SENSITIVITY TESTS; OXADIAZOLES; PENICILLIUM CHRYSOGENUM; PSEUDOMONAS AERUGINOSA; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; THIADIAZOLES;

EID: 84880023195     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.c13-00218     Document Type: Article

References (52)

1. Omar F. A., Mahfouz N., Rahman M. A., Eur. J. Med. Chem., 31, 819-825 (1996).
2. Sahin G., Palaska E., Ekizoglu M., Ozalp M., II Farmaco, 57, 539-542 (2002).
3. Macaev F., Rusu G., Pogrebnoi S., Gudima A., Stingaci E., Vlad L., Shvets N., Kandemirli F., Dimoglo A., Reynolds R., Bioorg. Med. Chem., 13, 4842-4850 (2005).
4. Turan-Zitouni G., Kaplancikli Z. A., Yildiz M. T., Chevallet P., Kaya D., Eur. J. Med. Chem., 40, 607-613 (2005).
5. Amir M., Shikha K., Eur. J. Med. Chem., 39, 535-545 (2004).
6. Narayana B., Vijaya Raj K. K., Ashalatha B. V., Kumari N. S., Arch. Pharm. (Weinheim), 338, 373-377 (2005).
7. Guimarães C. R. W., Boger D. L., Jorgensen W. L., J. Am. Chem. Soc., 127, 17377-17384 (2005).
8. Liras S., Allen M. P., Segelstein B. E., Synth. Commun., 30, 437-443 (2000).
9. Gaonkar S. L., Rai K. M. L., Prabhuswamy B., Eur. J. Med. Chem., 41, 841-846 (2006).
10. Khan K. M., Ullah Z., Rani M., Perveen S., Haider S. M., Choudhary M. I., Rahman A., Voelter W., Lett. Org. Chem., 1, 50-52 (2004).
11. Palaska E., Sahin G., Kelicen P., Durlu N. T., Altinok G., II Farmaco, 57, 101-107 (2002).
12. Schenone S., Brullo C., Bruno O., Bondavalli F., Ranise A., Filippelli W., Rinaldi B., Capuano A., Falcone G., Bioorg. Med. Chem., 14, 1698-1705 (2006).
13. Wang X. X., Li Z., Da Y. X., Chang J. C., Indian J. Chem., 40B, 422-423 (2001).
14. Palaska E., Sahin G., Kelicen P., Durlu N. T., Altinok G., II Farmaco, 57, 101-107 (2002).
15. Kees K. L., Fitzgerald J. J. Jr., Steiner K. E., Mattes J. F., Mihan B., Tosi T., Mondoro D., McCaleb M. L., J. Med. Chem., 39, 3920-3928 (1996).
16. Penning T. D., Talley J. J., Bertenshaw S. R., Carter J. S., Collins P. W., Docter S., Graneto M. J., Lee L. F., Malecha J. W., Miyashiro J. M., Rogers R. S., Rogier D. J., Yu S. S., AndersonGD, Burton E. G., Cogburn J. N., Gregory S. A., Koboldt C. M., Perkins W. E., Seibert K., Veenhuizen A. W., Zhang Y. Y., Isakson P. C., J. Med. Chem., 40, 1347-1365 (1997).
17. Rinaldi-Carmona M., Barth F., Héaulme M., Shire D., Calandra B., Congy C., Martinez S., Maruani J., Néliat G., Caput D., Ferrara P., Soubrie P., Breliere J. C., Fur G. L., FEBS Lett., 350, 240-244 (1994).
18. Kostakis I. K., Magiatis P., Pouli N., Marakos P., Skaltsounis A. L., Pratsinis H., Léonce S., Pierré A., J. Med. Chem., 45, 2599-2609 (2002).
19. Park B. S., El-Deeb I. M., Yoo K. H., Oh C. H., Cho S. J., Han D. K., Lee H. S., Lee J. Y., Lee S. H., Bioorg. Med. Chem. Lett., 19, 4720-4723 (2009).
20. Rostom S. A. F., Bioorg. Med. Chem., 18, 2767-2776 (2010).
21. Castagnolo D., De Logu A., Radi M., Bechi B., Manetti F., Magnani M., Supino S., Meleddu R., Chisu L., Botta M., Bioorg. Med. Chem., 16, 8587-8591 (2008).
22. Conti P., Pinto A., Tamborini L., Rizzo V., Micheli C. D., Tetrahedron, 63, 5554-5560 (2007).
23. Palazzino G., Cecchi L., Melani F., Colotta V., Filacchioni G., Martini C., Lucacchini A., J. Med. Chem., 30, 1737-1742 (1987).
24. Deng X., Mani N. S., Org. Lett., 8, 3505-3508 (2006).
25. Washizuka K. I., Nagai K., Minakata S., Ryu I., Komatsu M., Tetrahedron Lett., 40, 8849-8853 (1999).
26. Komatsu M., Minakata S., Oderaotoshi Y., ARKIVOC, vii, 370-389 (2006).
27. Boger D. L., Boyce C. W., Labroli M. A., Sehon C. A., Jin Q., J. Am. Chem. Soc., 121, 54-62 (1999).
28. Fan H., Peng J., Hamann M. T., Hu J. F., Chem. Rev., 108, 264-287 (2008).
29. Manley J. M., Kalman M. J., Conway B. G., Ball C. C., Havens J. L., Vaidyanathan R., J. Org. Chem., 68, 6447-6450 (2003).
30. Magnus N. A., Staszak M. A., Udodong U. E., Wepsiec J. P., Org. Process Res. Dev., 10, 899-904 (2006).
31. Wang Y. F., Toh K. K., Chiba S., Narasaka K., Org. Lett., 10, 5019-5022 (2008).
32. Chen J., Wu H., Zheng Z., Jin C., Zhang X., Su W., Tetrahedron Lett., 47, 5383-5387 (2006).
33. Surya K. D., Synth. Commun., 38, 2768-2774 (2008).
34. Nishibayashi Y., Yoshikawa M., Inada Y., Milton M. D., Hidai M., Uemura S., Angew. Chem. Int. Ed., 42, 2681-2684 (2003).
35. Balme G., Angew. Chem. Int. Ed., 43, 6238-6241 (2004).
36. Bharadwaj A. R., Scheidt K. A., Org. Lett., 6, 2465-2468 (2004).
37. Tejedor D., González-Cruz D., García-Tellado F., Marrero-Tellado J. J., Rodríguez M. L., J. Am. Chem. Soc., 126, 8390-8391 (2004).
38. Declerck V., Ribiere P., Martinez J., Lamaty F., J. Org. Chem., 69, 8372-8381 (2004).
39. Gorin D. J., Davis N. R., Toste F. D., J. Am. Chem. Soc., 127, 11260-11261 (2005).
40. Kamijo S., Kanazawa C., Yamamoto Y., J. Am. Chem. Soc., 127, 9260-9266 (2005).
41. Larionov O. V., de Meijere A., Angew. Chem. Int. Ed., 44, 5664-5667 (2005).
42. Padmaja A., Muralikrishna A., Rajasekhar C., Padmavathi V., Chem. Pharm. Bull., 59, 1509-1517 (2011).
43. Muralikrishna A., Venkatesh B. C., Padmavathi V., Padmaja A., Kondaiah P., Krishna N. S., Eur. J. Med. Chem., 54, 605-614 (2012).
44. French G. L., J. Antimicrob. Chemother., 58, 1107-1117 (2006).
45. Chung K. T., Thomasson W. R., Wu-Yuan C. D., J. Appl. Bacteriol., 69, 498-503 (1990).
46. Azoro C., World J. Biotechnol., 3, 347-351 (2002).
47. Janovska D., Kubikova K., Kokoska L., Czech J. Food Sci., 21, 107-110 (2003).
48. Bishnu J., Sunil L., Anuja S., J. Science, Engineering and Technol., 5, 143-150 (2009).
49. National Committee for Clinical Laboratory Standards Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, "Approved Standard, NCCLS Publication M7-A3," 3rd ed., Villanova, PA, 1993.
50. National Committee for Clinical Laboratory Standards, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, Proposed Standard, "NCCLS Document M27-P," Villanova, PA, 1992.
51. Mosmann T., J. Immunol. Methods, 65, 55-63 (1983).
52. Hansen M. B., Nielsen S. E., Berg K., J. Immunol. Methods, 119, 203-210 (1989).