Synthesis and antimalarial activity of novel chiral and achiral benzenesulfonamides bearing 1, 3, 4-oxadiazole moieties

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 22, Issue 3, 2007, Pages 301-308

  Zareef, Muhammad ^a   Iqbal, Rashid ^a   De Dominguez, Neira Gamboa ^b   Rodrigues, Juan ^b   Zaidi, Javid H ^a   Arfan, Muhammad ^a   Supuran, Claudiu T ^c  

^a QUAID I AZAM UNIVERSITY   (Pakistan)

^b UNIVERSIDAD CENTRAL DE VENEZUELA   (Venezuela)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

1,3,4 oxadiazole; Antimalarial activity; Chiral benzenesulfonamides; Electrophoretic analysis; Parasitaemia

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 2 (4 CHLOROPHENYLSULFONAMIDO)BUTANE HYDRAZIDE; 2 (4 CHLOROPHENYLSULFONAMIDO)PROPANE HYDRAZIDE; 2 (4 METHYLPHENYLSULFONAMIDO)BUTANE HYDRAZIDE; 2 [1,5 BIS(4 CHLOROPHENYLSULFONAMIDO)]PENTYL 5 MERCAPTO 1,3,4 OXADIAZOLE; 2 [1,5 BIS(4 METHOXYPHENYLSULFONAMIDO)]PENTYL 5 MERCAPTO 1,3,4 OXADIAZOLE; 2,6 BIS(4 CHLOROPHENYLPHENYLSULFONAMIDO)HEXANE HYDRAZIDE; 2,6 BIS(4 METHYLPHENYLSULFONAMIDO)HEXANE HYDRAZIDE; 4 (4 CHLOROPHENYLSULFONAMIDO)BUTANE HYDRAZIDE; 4 (4 METHYLPHENYLSULFONAMIDO)BUTANE HYDRAZIDE; 4 CHLORO N [1 (5 MERCAPTO 1,3,4 OXADIAZOL 2 YL)ETHYL]BENZENESULFONAMIDE; 4 CHLORO N [1 (5 MERCAPTO 1,3,4 OXADIAZOL 2 YL)PROPYL]BENZENESULFONAMIDE; 4 CHLORO N [3 (5 MERCAPTO 1,3,4 OXADIAZOL 2 YL)PROPYL]BENZENESULFONAMIDE; 4 METHYL N [1 (5 MERCAPTO 1,3,4 OXADIAZOL 2 YL)PROPYL]BENZENESULFONAMIDE; 4 METHYL N [3 (5 MERCAPTO 1,3,4 OXADIAZOL 2 YL)PROPYL]BENZENESULFONAMIDE; AMINO ACID; ANTIMALARIAL AGENT; BENZENESULFONAMIDE; CHLOROQUINE; HEMOGLOBIN; HYDRAZIDE DERIVATIVE; N [1 [5 (4 NITROBENZYLTHIO) 1,3,4 OXADIAZOL 2 YL]ETHYL] 4 CHLOROBENZENESULFONAMIDE; N [1 [5 (4 NITROBENZYLTHIO) 1,3,4 OXADIAZOL 2 YL]PROPYL] 4 CHLOROBENZENESULFONAMIDE; N [1 [5 (BENZYLTHIO) 1,3,4 OXADIAZOL 2 YL]PROPYL] 4 METHYLBENZENESULFONAMIDE; PYRROLE; PYRROLE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ELECTROPHORESIS; MALARIA; MALE; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; POLYMERIZATION; PRIORITY JOURNAL; PROTEIN DEGRADATION;

ANIMALS; ANTIMALARIALS; CRYSTALLIZATION; DRUG EVALUATION, PRECLINICAL; HEMOGLOBINS; MAGNETIC RESONANCE SPECTROSCOPY; MALARIA; MALE; MICE; OXADIAZOLES; PLASMODIUM BERGHEI; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

MUS; PLASMODIUM BERGHEI;

EID: 34547751012     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360601114569     Document Type: Article

References (27)

1. Shenai, BR, Lee, BJ, Hernandez, AA, Chong, PY, Emal, CD, Neitz, RJ, Roush, WR and Rosenthal, PJ (2003) Structure-activity relationships for inhibition of cysteine protease activity and development of plasmodium falciparum by peptidyl vinyl sulfones. Antimicrob Agents Chemother, 47, pp. 154-160.
2. Korolkovas, A. (1988) Essentials of medicinal chemistry 1988, pp. 647-649. John Wiley & Sons, USA
3. Krungkrai, J., Scozzafava, A., Reungprapavut, S., Krungkrai, SR, Rattanajak, R., Kamchonwongpaisan, S. and Supuran, CT (2005) Carbonic anhydrase inhibitors. Inhibition of plasmodium falciparum carbonic anhydrase with aromatic sulfonamides towards antimalarials with a novel mechanism of action. Bioorg Med Chem, 13, pp. 483-489.
4. Supuran, CT, Scozzafava, A. and Casini, A. (2003) Carbonic anhydrase inhibitors. Med Res Rev, 23, pp. 146-189.
5. Clark, WG, Brater, DC and Johnson, AR (1992) Medical pharmacology, p. 637. Mosby Year Book, USA
6. Xia, G., Peng, A., Lai, S., Zhang, S., Shen, J., Liu, Z. and Chen, X. (2005) Synthesis and phosphodiesterase 5 inhibitory activity of novel pyrido[1,2-e] purin-4(3H)-one derivatives. Bioorg Med Chem Lett, 15, pp. 2790-2794.
7. Abbate, F., Casini, A., Owa, T., Scozzafava, A. and Supuran, CT (2004) Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg Med Chem Lett, 14, pp. 217-223.
8. Casini, A., Scozzafava, A., Mastrolorenzo, A. and Supuran, CT (2002) Sulfonamides and sulfonylated derivatives as anticancer agents. Curr Cancer Drug Targets, 2, pp. 55-75.
9. Rahman, A. and Farghaly, AH (2004) Synthesis reactions and antimicrobial activity of some new indolyl-1,3,4- oxadiazole, triazole and pyrazole derivatives. J Chin Chem Soc, 51, pp. 147-156.
10. Khanum, SA, Shashikanth, S., Umesha, S. and Kavitha, R. (2005) Synthesis and antimicrobial study of novel heterocyclic compounds from hydroxybenzophenones. Eur J Med Chem, 40, pp. 1156-1162.
11. Zheng, X., Wang, Y., Chen, W., Huang, Q., Liu, C. and Song, G. (2003) Synthesis and insecticidal activities of novel 2,5- disubstituted 1,3,4- oxadiazoles. J Fluorine Chem, 117, pp. 163-169.
12. Al-Soud, YA, Al-Deeri, MN and Al-Mosoudi, NA (2004) Synthesis, antitumor and antiviral properties of some 1,2,4- triazole derivatives. Il Farmaco, 59, pp. 775-783.
13. El-Emam, AA, Al-Deeb, OA and Al-Omar, M Lehmann (2004) Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl) -2- substituted thio-1,3,4- oxadiazoles and 5-(1-adamantyl) -3- substituted aminomethyl -1,3,4- oxadiazoles -2-thiones. Bioorg Med Chem, 12, pp. 5107-5113.
14. Hutt, MP, ElLger, EF and Werbel, LM (1970) 2-Phenyl-5-(trichloromethyl)-1,3,4- oxadiazoles, a new class of antimalarial substances. J Heterocycl Chem, 7, pp. 511-518.
15. Neamati, N., Mazumder, A., Sunder, S., Owen, JM, Schultz, RJ and Pommier, Y. (1997) 2-Mercaptobenzenesulfonamides as a novel class of human immunodeficiency type 1 (HIV-1) integrase and HIV-1 replication. Antimicrob Agents Chemother, 8, pp. 485-495.
16. Louie, AY and Meade, TJ (1999) Metal complexes as enzyme inhibitors. Chem Rev, 99, pp. 2711-2734.
17. Young, SD, Britcher, SF, Tran, LO, Payne, LS, Lumma, WC, Lyle, TA, Huff, JR, Anderson, PS, Olsen, DB, Carrol, SS, Pettibone, DJ, Obrien, JA, Ball, RG, Ballani, SK, Lin, JH, Chen, WI, Schleif, WA, Sardana, VV, Long, WJ, Byrnes, VW and Emini, EA (1995) L- 743,726 (DMP): A novel, highly potent, nonnucleoside inhibitor of human immunodeficiency virus type 1 reverse transcriptase. Antimicrob Agents Chemother, 39, pp. 2602-2605.
18. Brzozowski, Z., Saczewski, F., Sanchez, T., Kuo, CL, Gdaniec, M. and Neamati, N. (2004) Synthesis, antimicrobial, and anti-HIV-1 integrase activities of 3-aroyl-1,1-dioxo-1,4,2- benzodithiazines. Bioorg Med Chem, 12, pp. 5107-5113.
19. Lai, JYQ, Ferguson, Y. and Jones, M. (2003) Preparation of substituted quinolinyl and isoquinolinyl sulfonyl chlorides for synthesis of novel sulfonamides. Synh Commun, 33, pp. 3427-3433.
20. Furniss, BS, Hannaford, AJ, Rogers, V., Smith, PWG and Tatchell, AR (1978) Vogel textbook of practical organic chemistry, Longmann, London
21. Yousif, MY, Ismail, AM, Elman, AA and El-Kerdawy, MM (1986) Synthesis of substituted mercapto-1,2,4-triazoles and substituted 1,2,4-triazoles-5-ylmercaptomethyl-1,3,4-oxadiazoles as antimicrobal agents. J Chem Soc Pak, 8, p. 183.
22. Ahmad, R., Iqbal, R., Akhtar, H., Haq, ZU, Duddeck, H., Stefaniak, L. and Sitkowski, J. (2001) Synthesis and structure determination of some oxadiazole-2-thione and triazole-3-thione galactosides. Nucleosides, Nucleotides and Nucleic Acids, 20, pp. 1671-1682.
23. Baelmans, R., Deharo, E., Muñoz, V., Sauvain, M. and Ginsburg, H. (2000) Experimental conditions for testing the inhibitory activity of chloroquine on the formation of beta-hematin. Exp Parasitol, 4, pp. 243-248.
24. Mitsuya, H., Weinhold, KJ, Furman, PA, St. Clair, MH, Lehrmann, SN, Gallo, RC, Bolognesi, D., Barry, DW and Border, S. (1985) 3′-Azido-3′-deoxythymidine (BW A509U): An antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. Proc Natl Acad Sci USA, 82, pp. 7096-8000.
25. Deharo, E., Gautret, Ph, Ginsburg, H., Chabaud, AG and Landau, I. (1994) Synchronization of plasmodium yoelii nigeriensis and P.y. killicki infection in the mouse by means of percoll-glucose gradient stage fractionation: Determination of the duration of the schizogonic cycle. Parasitol Res, 80, pp. 159-164.
26. Rosenthal, P. (1995) Plasmodium falciparum: Effects of proteinase inhibitors on globin hydrolysis by cultured malaria parasites. Exp Parasitol, 80, pp. 272-281.
27. Peters, W. (1987) Chemotherapy and drug resistance in malaria, Academic Press, New York