4, 5-Dihydrooxazole-pyrazoline hybrids: Synthesis and their evaluation as potential antimalarial agents

European Journal of Medicinal Chemistry

Volumn 123, Issue , 2016, Pages 476-486

  Pandey, Ashutosh Kumar ^a   Sharma, Supriya ^b   Pandey, Minakshi ^c   Alam, M Mumtaz ^a   Shaquiquzzaman, M ^a   Akhter, Mymoona ^a  

^a HAMDARD UNIVERSITY   (India)

^b NATIONAL INSTITUTE OF MALARIA RESEARCH   (India)

^c BBS Institute of Pharmaceutical and Allied Sciences   (India)

Author keywords

Antimalarial; IC50; Oxazoline; Plasmodium falciparum; Pyrazoline

Indexed keywords

1 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 3 (3 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 3 (4 FLUOROPHENYL)PROP 2 EN 1 ONE; 1 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 3 (4 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 3 (4 NITROPHENYL)PROP 2 EN 1 ONE; 1 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 3 (4 TOLYL)PROP 2 EN 1 ONE; 1 [5 (4 CHLOROPHENYL) 3 [4 [(4,5 DIHYDROOXAZOL 2 YL) METHOXY]PHENYL] 4,5 DIHYDRO 1H PYRAZOL 1 YL]ETHANONE; 2 [[4 [1 PHENYL 5 (4 TOLYL) 4,5 DIHYDRO 1H PYRAZOL 3 YL]PHENOXY]METHYL] 4,5 DIHYDROOXAZOLE; 2 [[4 [5 (1H INDOL 3 YL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 3 YL]PHENOXY]METHYL] 4,5 DIHYDROOXAZOLE; 2 [[4 [5 (1H INDOL 3 YL) 4,5 DIHYDRO 1H PYRAZOL 3 YL]PHENOXY]METHYL] 4,5 DIHYDROOXAZOLE; 2 [[4 [5 (4 CHLOROPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 3 YL]PHENOXY]METHYL] 4,5 DIHYDROOXAZOLE; 2 [[4 [5 (4 FLUOROPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 3 YL]PHENOXY]METHYL] 4,5 DIHYDROOXAZOLE; 2 [[4 [5 (4 METHOXYPHENYL) 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 3 YL]PHENOXY]METHYL] 4,5 DIHYDROOXAZOLE; 2 [[4 [5 (4 METHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 3 Y]PHENOXY]METHYL] 4,5 DIHYDROOXAZOLE; 3 (3 CHLOROPHENYL) 1 [4 [(4, 5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL]PROP 2 EN 1 ONE; 3 (4 CHLOROPHENYL) 1 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL]PROP 2 EN 1 ONE; 4 [3 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 5 (3 METHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [3 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 5 (3 NITROPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [3 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 5 (4 FLUOROPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [3 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 5 (4 METHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [3 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 5 (4 NITROPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [5 (2,3 DIHYDROBENZO[B]DIOXIN 6 YL) 3 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 4,5 DIHYDRO 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [5 (3 CHLOROPHENYL) 3 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 4,5 DIHYDRO 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 4 [5 (4 CHLOROPHENYL) 3 [4 [(4,5 DIHYDROOXAZOL 2 YL)METHOXY]PHENYL] 4,5 DIHYDRO 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 4,5 DIHYDROOXAZOLE PYRAZOLINE; ANTIMALARIAL AGENT; CHALCONE DERIVATIVE; CHLOROQUINE; OXAZOLINE DERIVATIVE; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; PYRAZOLE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIMALARIAL ACTIVITY; ARTICLE; CC50; CONTROLLED STUDY; DRUG BINDING; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HISTOPATHOLOGY; IC50; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PLASMODIUM BERGHEI INFECTION; POLYMERIZATION; RAT; SELECTIVITY INDEX; STOICHIOMETRY; SUBSTITUTION REACTION; ANIMAL; CHEMISTRY; CHLOROCEBUS AETHIOPS; DRUG DESIGN; DRUG EFFECTS; PLASMODIUM BERGHEI; SYNTHESIS; VERO CELL LINE;

ANIMALS; ANTIMALARIALS; CERCOPITHECUS AETHIOPS; CHALCONES; CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG DESIGN; FEMALE; INHIBITORY CONCENTRATION 50; MICE; PLASMODIUM BERGHEI; PYRAZOLES; RATS; VERO CELLS;

EID: 84979936612     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2016.07.055     Document Type: Article

References (27)

1. [1] Leven, M., Held, J., Duffy, S., Tschan, S., Sax, S., Kamber, J., Frank, W., Kuna, K., Geffken, D., Siethoff, C., Barth, S., Avery, V.M., Wittlin, S., Mordmüller, B., Kurz, T., J. Med. Chem. 57 (2014), 7971–7976.
2. [2] Biamonte, M.A., Wanner, J., Roch, K.G.L., Bioorg. Med. Chem. Lett. 23 (2013), 2829–2843.
3. [3] Wanare, G., Aher, R., Kawathekar, N., Ranjan, R., Kaushik, N.K., Sahal, D., Bioorg. Med. Chem. Lett. 20 (2010), 4675–4678.
4. [4] Smit, F.J., N'Da, D.D., Bioorg. Med. Chem. 22 (2014), 1128–1138.
5. [5] Tadigoppula, N., Korthikunta, V., Gupta, S., Kancharla, P., Khaliq, T., Soni, A., Srivastava, R.K., Srivastava, K., Puri, S.K., Raju, K.S.R., Sijwali, P.S., Kumar, V., Mohammad, I.S., J. Med. Chem. 56 (2013), 31–45.
6. [6] Padmavathi, V., Mahesh, K., Dinneswara, G., Padmaja, R.A., Eur. J. Med. Chem. 45 (2010), 3178–3183.
7. [7] Moraski, G.C., Markley, L.D., Chang, M., Cho, S., Franzblau, S.G., Hwang, C.H., Boshoff, H., Miller, M.J., Bioorg. Med. Chem. 20 (2012), 2214–2220.
8. [8] Bashir, R., Ovais, S., Yaseen, S., Hamid, H., Alam, M.S., Samim, M., Singh, S., Javed, K., Bioorg. Med. Chem. Lett. 21 (2011), 4301–4305.
9. [9] Das, N., Dash, B., Dhanawat, M., Shrivastava, S.K., Chem. Pap. 66 (2012), 67–74.
10. [10] Wahab, B.F.A., Latif, E.A., Mohamed, H.A., A Awad, G.E., Eur. J. Med. Chem. 52 (2012), 263–268.
11. [11] Acharya, B.N., Saraswat, D., Tiwari, M., Shrivastava, A.K., Ghorpade, R., Bapna, S., Kaushik, M.P., Eur. J. Med. Chem. 45 (2009), 430–438.
12. [12] Insuasty, B., Montoya, A., Becerra, D., Quiroga, J., Abonia, R., Robledo, S., Vélez, I.D., Upegui, Y., Nogueras, M., Cobo, J., Eur. J. Med. Chem. 67 (2013), 252–262.
13. [13] Marella, A., Shaquiquzzaman, M., Akhter, M., Verma, G., Alam, M.M., Enz, J., Inhib. Med. Chem. 30 (2014), 1–10.
14. [14] Dua, V.K., Sinha, S.N., Biswas, S., Valecha, N., Puri, S.K., Sharma, V.P., Biorg. Med. Chem. Lett. 12 (2002), 3587–3589.
15. [15] Trager, W., Jensen, J.B., Science 193 (1976), 673–675.
16. [16] Shah, N.M., Patel, M.P., Patel, R.G., Eur. J. Med. Chem. 54 (2012), 239–247.
17. [17] Menard, R., (eds.) Methods in Molecular Biology, vol. 923, 2013, © Springer Science + Business media, LLC, 10.1007/978-1-62703-026-7_1.
18. [18] Mosmann, T., J. Immunol. Meth. 65 (1983), 55–63.
19. [19] Devi, C.U., Valecha, N., Atul, P.K., Pillai, C.R., Curr. Sci. 80 (2001), 917–919.
20. [20] Maurya, R., Soni, A., Anand, D., Ravi, M., Raju, K.S.R., Taneja, I., Naikade, N.K., Puri, S.K., Wahajuddin, Kanojiya, S., Yadav, P.P., ACS Med. Chem. Lett. 4 (2013), 165–169.
21. [21] Manohar, S., Rajesh, U.C., Khan, S.I., Tekwani, B.L., Rawat, D.S., ACS Med. Chem. Lett. 3 (2012), 555–559.
22. [22] Romero, A.H., Acosta, M.E., Gamboa, N., Charris, J.E., Salazar, J., López, S.E., Biorg. Med. Chem. 23 (2015), 4755–4762.
23. [23] Pinheiro, L.C.S., Boechat, N., Ferreira, M.L.G., Júnior, C.C.S., Jesus, A.M.L., Leite, M.M.M., Souza, N.B., Krettli, A.U., Biorg. Med. Chem. 23 (2015), 5979–5984.
24. [24] Agbaje, E., Adeneye, A.A., Daramola, A.O., Afr. J. Trad. CAM 6 (2009), 241–254.
25. [25] OECD, OECD No. 423, ‘Acute Oral Toxicity –Acute Class Method’. The Organization for Economic Co-operation and Development (OECD) Guidelines for the Testing of Chemicals, Adopted by the Council on 17th December, 2001. 2001.
26. [26] Singh, K., Kaur, H., Chibale, K., Balzarini, J., Little, S., Bharatam, P.V., Eur. J. Med. Chem. 52 (2012), 82–97.
27. [27] Kumar, D., Khan, S.I., Tekwani, B.L., Ponnan, P., Rawat, D.S., Eur. J. Med. Chem. 89 (2015), 490–502.