Polysubstituted pyrazoles, part 5.1. Synthesis of new 1-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents

European Journal of Medicinal Chemistry

Volumn 38, Issue 11-12, 2003, Pages 959-974

  Rostom, Sherif A F ^a   Shalaby, Manal A ^b   El Demellawy, Maha A ^b  

^a KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

^b Universities and Research centers District   (Egypt)

Author keywords

1,2,4 triazolin 3 thiones; 1,3,4 oxadiazoles; 1,3,4 thiadiazole; 1H pyrazoles; Acid hydrazide derivatives; Anti HCV activity; Antitumor activity; RT PCR

Indexed keywords

1 [1 (4 CHLOROPHENYL) 4 HYDROXY 1H PYRAZOLE 3 CARBONYL]THIOSEMICARBAZIDE; 3 (ALKYLIDENEHYDRAZINOCARBONYL) 1 (4 CHLOROPHENYL) 4 HYDROXY 1H PYRAZOLE; 3 ACETYL 5 [4 ACETYLOXY 1 (4 CHLOROPHENYL) 1H PYRAZOL 3 YL] 2 (2,4 DIFLUOROPHENYL) 1,3,4 OXADIAZOLINE; 4 PHENYL 1 [1 (4 CHLOROPHENYL) 4 HYDROXY 1H PYRAZOLE 3 CARBONYL]SEMICARBAZIDE; 5 [1 (4 CHLOROPHENYL) 4 HYDROXY 1H PYRAZOL 3 YL] 1,3,4 OXADIAZOLIN 2 ONE; 5 [1 (4 CHLOROPHENYL) 4 HYDROXY 1H PYRAZOL 3 YL] 1,3,4 OXADIAZOLIN 2 THIONE; 5 [1 (4 CHLOROPHENYL) 4 HYDROXY 1H PYRAZOL 3 YL] 2 PHENYL 1,3,4 OXADIAZOLE; 5 [1 (4 CHLOROPHENYL) 4 HYDROXY 1H PYRAZOL 3 YL] 2 PHENYLAMINO 1,3,4 OXADIAZOLE; 5 [1 (4 CHLOROPHENYL) 4 HYDROXY 1H PYRAZOL 3 YL] 2 PHENYLAMINO 1,3,4 THIADIAZOLE; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; N ACETYL 4 ACETYLOXY 1 (4 CHLOROPHENYL) 1H PYRAZOLE 3 CARBOXYLIC ACID HYDRAZIDE; N FORMYL 1 (4 CHLOROPHENYL) 4 HYDROXY 1H PYRAZOLE 3 CARBOXYLIC ACID HYDRAZIDE; PYRAZOLE DERIVATIVE; THIOSEMICARBAZIDE DERIVATIVE; TRIAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN HEPG2; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFECT; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HEPATITIS C; HEPATITIS C VIRUS; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA CELL; LIVER CELL CARCINOMA; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; TUMOR CELL LINE; VIRUS INFECTION; VIRUS REPLICATION;

EID: 0345306230     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejmech.2003.08.003     Document Type: Article

References (45)

1. Aiello E., Aiello S., Mingoia F., Bacchi A., Pelizzi G., Musiu C., Setzu M.G., Pani A., La Colla P., Marongiu M.E. Bioorg. Med. Chem. 8:2000;2719-2728.
2. El-Gaby M.S.A., Atalla A.A., Gaber A.M., Abd Al-Wahab K.A. Farmaco. 55:2000;596-602.
3. Kocyigit Kaymakcioglu B.K., Rollas S. Farmaco. 57:2002;595-599.
4. Storer R., Ashton C.J., Baxter A.D., Hann M.M., Marr C.L.P., Mason A.M., Mo C.-L., Myers P.L., Noble S.A., Penn H.R., Wier N.G., Niall G., Woods J.M., Coe P.L. Nucleosides Nucleotides. 18:(2):1999;203-216.
5. Genin M.J., Biles C., Keiser B.J., Poppe S.M., Swaney S.M., Tarpley W.G., Yagi Y., Romero D.L. J. Med. Chem. 43:2000;1034-1040.
6. Moukha-chafiq O., Taha M.L., Lazrek H.B., Vasseur J.-J., Pannecouque C., Witvrouw M., De Clercq E. Il Farmaco. 57:2002;27-32.
7. Ishida J., Ohtsu H., Tachibana Y., Nakanishi Y., Bastow K.F., Nagai M., Wang H.-K., Itokawa H., Lee K.-H. Bioorg. Med. Chem. 10:2002;3481-3487.
8. Baraldi P.G., Pavani M.G., Nunez M.d.C., Brigidi P., Vitali B., Gambaric R., Romagnolia R. Bioorg. Med. Chem. 10:2002;449-456.
9. Gamage S.A., Spicer J.A., Rewcastle G.W., Milton J., Sohal S., Dangerfield W., Mistry P., Vicker N., Charlton P.A., Denny W.A. J. Med. Chem. 45:2002;740-743.
10. Goodchild J. Sammes P.G. Topics in Antibiotic Chemistry. 1982;189 Ellis Horwood Limited-John Wiley and Sons, New York.
11. Comber R.N., Gray R.J., Secrist J.A. Carbohydr. Res. 216:1991;441-452.
12. Johansson A., Poliakov A., Kerblom E.A., Lindeberg G., Winiwarter S., Samuelsson B., Danielsonb U.H., Hallberg A. Bioorg. Med. Chem. 2002;3915-3922.
13. Salyers A.A., Whitt D.D. (Eds.), Microbiology Diversity, Disease and the Environment, Fitzgerald Science Press, Bethesda, Maryland, 2001, pp. 356.
14. Goins W.F. McClane B.A., Mietzner T.A. Microbial Pathogenesis: A Principles-Oriented Approach. 1999;395 Fence Creek Publishing, Madison.
15. Bartenschlager R., Lohmann V. Antiviral Res. 52:2001;1-17.
16. Aster J., Kumar V. Cotran R.S., Kumar V., Collins T. Pathologic Basis of Disease. 1999;860-861 W.B. Saunders Company, Philadelphia.
17. Boyer N., Marcellin P. J. Hepatol. 32:2000;98-112.
18. Farghaly A.M., Soliman F.S.G., El Semary M.M., Rostom Sh.A.F. Pharmazie. 56:2001;28-32.
19. Rostom Sh.A.F., Farghaly A.M., Soliman F.S.G., El Semary M.M., Elz S., Lehmann J. Arch. Pharm. Pharm. Med. Chem. 334:2001;241-247.
20. Fahmy H.T.Y., Rostom Sh.A.F., Bekhit A.A. Arch. Pharm. Pharm. Med. Chem. 335:2002;213-222.
21. Bekhit A.A., Fahmy H.T.Y., Rostom Sh.A.F., Baraka A. Eur. J. Med. Chem. 38:2003;27-36.
22. Bekhit A.A., Fahmy H.T.Y., Rostom Sh.A.F., Abdel-Aziem T., XXVIII International Conference of Pharmaceutical Sciences, Cairo, Egypt, 17-19 December 2002, Poster P-81.
23. Silverman R.B. (Ed.), The Organic Chemistry of Drug Design and Drug Action, Academic Press, London, 1992, pp. 263.
24. Al-Obaid A.M., El-Shafie S.F., Al-Mutairi M.S., El-Subbagh H.I. Sci. Pharm. 67:1999;129-147.
25. Hall I.H., Peaty N.J., Henry J.R., Easmon J., Heinisch G., Puerstinger G. Arch. Pharm. Pharm. Med. Chem. 332:1999;115-123.
26. Asis S.E., Bruno A.M., Martinez A.R., Sevilla M.V., Gaozza C.H., Romano A.M., Coussio J.D., Ciccia G. Farmaco. 54:1999;517-523.
27. Castellano S., Stefancich G., Musiu C., La Colla P. Arch. Pharm. Pharm. Med. Chem. 333:2000;299-304.
28. Kucukguzel S.G., Rollas S., Erdeniz H., Kiraz M., Ekinci A.C., Vidin A. Eur. J. Med. Chem. 35:2000;761-771.
29. Turan-Zitouni G., Blache Y., Gueven K. Boll. Chim. Farmac. 140:(6):2001;397-400.
30. Fahmy H.T.Y. Boll. Chim. Farmac. 140:(6):2001;422-427.
31. Demirbas N., Ugurluoglu R., Demirbas A. Bioorg. Med. Chem. 10:2002;3717-3723.
32. Kritsanida M., Mouroutsou A., Marakos P., Pouli N., Papakonstantinou- Garoufalias S., Pannecouque C., Witvrouw M., De Clercq E. Farmaco. 57:2002;253-257.
33. Dogan H.N., Duran A., Rollas S., Sener G., Uysal M.K., Guelen D. Bioorg. Med. Chem. 10:2002;2893-2898.
34. Boiania M., Cerecetto H., Gonzalez M., Risso M., Olea-Azar C., Piro O.E., Castellano E.E., de Cerain A.L., Ezpeleta O., Monge-Vega A. Eur. J. Med. Chem. 36:2001;771-782.
35. Yaday L.D.S., Singh S. Indian J. Chem. Sect. B. 40:2001;440-442.
36. Sahin G., Palaska E., Ekizoglu M., Ozalp M. Farmaco. 57:2002;539-542.
37. Grever M.R., Schepartz S.A., Chabner B.A. Semin. Oncol. 19:1992;622-638.
38. Boyd M.R., Paull K.D. Drug Rev. Res. 34:1995;91-109.
39. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Jangley J., Cronisie P., Viagro-Wolff A., Gray-Goodrich M., Campell H., Boyd M. J. Natl. Cancer Inst. 83:1991;757-766.
40. Acton E.M., Narayanan V.L., Risbood P.A., Shoemaker R.H., Vistica D.T., Boyd M.R. J. Med. Chem. 37:1994;2185-2189.
41. El-Subbagh H.I., El-Naggar W.A., Badria F.A. Med. Chem. Res. 3:1994;503-516.
42. El-Subbagh H.I., Al-Obaid A.M. Eur. J. Med. Chem. 31:1996;1017-1021.
43. Abadi A.H. Arch. Pharm. Pharm. Med. Chem. 331:1998;352-358.
44. Kato N., Ikeda M., Mizutani T., Sugiyama K., Noguchi M., Hirohashi S., Shimotohno K. Jpn J. Cancer Res. 87:1996;787-792.
45. El-Awady M.K., Ismail S.M., El-Sagheer M., Sabour Y.A., Amr K.S., Zaki E.A. Clin. Chim. Acta. 283:1999;1-14.