Synthesis, anti-HSV-1, and cytotoxic activities of some new pyrazole- and isoxazole-based heterocycles

Medicinal Chemistry Research

Volumn 20, Issue 7, 2011, Pages 912-919

  Dawood, Kamal M ^a   Abdel Gawad, Hassan ^b   Mohamed, Hanan A ^b   Badria, Farid A ^c  

^a CAIRO UNIVERSITY   (Egypt)

^b NATIONAL RESEARCH CENTRE   (Egypt)

^c MANSOURA UNIVERSITY   (Egypt)

Author keywords

Anti HSV 1; Cytotoxic activities; Isoxazole; Pyrazole; Thiadiazole; Thiazole

Indexed keywords

1 (2 (4 FLUOROPHENYL)HYDRAZONO) 1 CHLOROPROPAN 2 ONE; 1 [5 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOLE 3 CARBONYL] 4 [2 (4 FLUOROPHENYL) HYDRAZONO] 3 METHYL 1H PYRAZOL 5(4H) ONE; 1 [5 (4 CHLOROPHENYL)ISOXAZOLE 3 CARBONYL] 4 [2 (4 FLUOROPHENYL)HYDRAZONO] 3 METHYL 1H PYRAZOL 5(4H) ONE; 2 [2 [5 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOLE 3 CARBONYL]HYDRAZONO] N' (4 FLUOROPHENYL)PROPANEHYDRAZONOYL CHLORIDE; 2 [2 [5 (4 CHLOROPHENYL)ISOXAZOLE 3 CARBONYL]HYDRAZONO] N' (4 FLUOROPHENYL) PROPANEHYDRAZONOYL CHLORIDE; 2 [5 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOLE 3 CARBONYL] N PHENYLHYDRAZINE CARBOTHIOAMIDE; 2 [5 (4 CHLOROPHENYL)ISOXAZOLE 3 CARBONYL] N PHENYLHYDRAZINECARBOTHIOAMIDE; 4 CHLOROACETOPHENONE; 5 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOLE 3 CARBOHYDRAZIDE; 5 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOLE 3 CARBOXYLATE; 5 (4 CHLOROPHENYL) N (1,3 DIOXOISOINDOLIN 2 YL)ISOXAZOLE 3 CARBOXAMIDE; 5 (4 CHLOROPHENYL) N' (4 (4 CHLOROPHENYL) 3 PHENYLTHIAZOL 2(3H) YLIDENE) 1 PHENYL 1H PYRAZOLE 3 CARBOHYDRAZIDE; 5 (4 CHLOROPHENYL) N' (4 FLUOROBENZYLIDENE) 1 PHENYL 1H PYRAZOLE 3 CARBOHYDRAZIDE; 5 (4 CHLOROPHENYL) N' (4 FLUOROBENZYLIDENE)ISOXAZOLE 3 CARBOHYDRAZIDE; 5 (4 CHLOROPHENYL) N' [4 (4 CHLOROPHENYL) 3 PHENYLTHIAZOL 2(3H) YLIDENE]ISOXAZOLE 3 CARBOHYDRAZIDE; 5 (4 CHLOROPHENYL) N' [5 (4 FLUOROBENZYLIDENE) 4 OXO 3 PHENYLTHIAZOLIDIN 2 YLIDENE] 1 PHENYL 1H PYRAZOLE 3 CARBOHYDRAZIDE; 5 (4 CHLOROPHENYL) N' [5 (4 FLUOROBENZYLIDENE) 4 OXO 3 PHENYLTHIAZOLIDIN 2 YLIDENE] ISOXAZOLE 3 CARBOHYDRAZIDE; 5 (4 CHLOROPHENYL)ISOXAZOLE 3 CARBOHYDRAZIDE; 5 [5 (4 CHLOROPHENYL) 1 PHENYL 1H PYRAZOL 3 YL] N PHENYL 1,3,4 THIADIAZOL 2 AMINE; 5 [5 (4 CHLOROPHENYL)ISOXAZOL 3 YL] N PHENYL 1,3,4 THIADIAZOL 2 AMINE; ETHYL 2 (2 (4 FLUOROPHENYL)HYDRAZONO) 3 OXOBUTANOATE; ETHYL 4 (4 CHLOROPHENYL) 2,4 DIOXOBUTANOATE; ETHYL 5 (4 CHLOROPHENYL)ISOXAZOLE 3 CARBOXYLATE; ISOXAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CYCLIZATION; CYTOTOXICITY; HERPES SIMPLEX VIRUS 1; NONHUMAN; SYNTHESIS; VIRUS PLAQUE;

EID: 80054758800     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9420-4     Document Type: Article

References (37)

1. Abdel-Aziz HA, Mekawey AAI, Dawood KM (2009) Convenient synthesis and antimicrobial evaluation of some novel 2-substituted-3-methylbenzofuran derivatives. Eur J Med Chem 44:3637-3644
2. Abdel-Wahab BF, Abdel-Aziz HA, Ahmed EM (2008) Convenient synthesis and antimicrobial activity of new 3-substituted 5-(benzofuran-2-yl)-pyrazole derivatives. Arch Pharm 341: 734-739
3. Abdel-Wahab BF, Abdel-Aziz HA, Ahmed EM (2009) Synthesis and antimicrobial evaluation of some new 1,3-thiazole; 1,3,4-thiadiazole; 1,2,4-triazole and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine derivatives including 5-(benzofuran-2-yl)-1-phenyl-pyrazole moiety. Monatsh Chem 140:601-605
4. Abou-Karam M, Shier WT (1990) A simplified plaque reduction assay for antiviral agents from plants. Demonstration of frequent occurrence of antiviral activity in higher plants. J Nat Prod 53:340-345
5. Arrieta A, Carrillo JR, Cossío FP, Ortiz AD, Gómez- Escalonilla MJ, de la Hoz A, Langa F, Moreno A (1998) Efficient tautomerization hydrazone-azomethine imine under microwave irradiation. Synthesis of [4,30] and [5,30]bipyrazoles. Tetrahedron 54: 13167-13180 (Pubitemid 28470701)
6. Biere H, Schroeder E, Ahrens H, Kapp JF (1982) Non-steroidal antiinflammatory agents. 5. Antiinflammatory pyrazole acetic acids. I. Eur J Med Chem 17:27-34 (Pubitemid 12145296)
7. Bouabdallah I, M'barek LA, Zyad A, Ramadan A, Zidane I, Melhaoui A (2006) Anticancer effect of three pyrazole derivatives. Nat Prod Res 20:1024-1030 (Pubitemid 44566681)
8. Campagna F, Palluotto F, Carotti A, Maciocco E (2004) Synthesis, central and peripheral benzodiazepine receptor affinity ofpyrazole and pyrazole-containing polycyclic derivatives. Farmaco 59:849-856 (Pubitemid 39488364)
9. Dawood KM (2005) Synthesis of spiro-pyrazole-3, 30-thiopyrano [2,3-b]pyridines and azolo[a]pyrido[20,30:5,6]thiopyrano[3,4-d]pyrimidines as new ring systems with antifungal and antibacterial activities. J Heterocycl Chem 42:221-225 (Pubitemid 40489452)
10. Dawood KM, Farag AM, Abdel-Aziz HA (2005) Synthesis and antimicrobial evaluation of some 1,2,4-triazole, 1,3,4-oxa(thia) diazole, and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives. Heteroat Chem 16:621-627 (Pubitemid 43082174)
11. Dawood KM, Abdel-Gawad H, Ellithey M, Mohamed HA, Hegazi B (2006a) Synthesis, anticonvulsant and anti-inflammatory activities of some new benzofuran-based heterocycles. Arch Pharm 339:133-140
12. Dawood KM, Abdel-Gawad H, Rageb EA, Ellithey M, Mohamed HA (2006b) Synthesis, anticonvulsant, and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. Bioorg Med Chem 14:3672-3680
13. Dickerson FB, Boronow JJ, Stallings C (2004) Infection with herpes simplex virus type 1 is associated with cognitive deficits in bipolar disorder. Biol Psychiatry 55:588-593 (Pubitemid 38315032)
14. Dobson CB, Itzhaki RF (1999) Herpes simplex virus type 1 and Alzheimer's disease. Neurobiol Aging 20:457-465
15. El-Subbagh HI, Abu-Zaid SM, Mahran MA, Badria FA, Al-obaid M (2000) Synthesis and biological evaluation of certain a,bunsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents. J Med Chem 43:2915-2921 (Pubitemid 30599649)
16. Fahmy HTY, Rostom SAF, Bekhit AA (2002) Synthesis and antitumor evaluation of new polysubstituted thiazole and derived thiazolo[4,5-d]pyrimidine systems. Arch Pharm 335:213-222 (Pubitemid 34847514)
17. Gupta R, Warren T, Wald A (2007) Genital herpes. Lancet 370: 2127-2137 (Pubitemid 350296304)
18. Habeeb GA, Rao PNP, Kanus EE (2001) Design and synthesis of 4,5-diphenyl-4-isoxazolines: Novel inhibitors of cyclooxygenase-2 with analgesic and antiinflammatory activity. J Med Chem 44:2921-2927.
19. Hafford LD, Badria FA, Abou-Karam M, Sheir WT, Rogers RD (1991) Preparation, characterization, and antiviral activity of microbial metabolites of stemodin. J Nat Prod 54:1543-1552
20. Itzhaki RF, Lin WR, Shang D, Wilcock GK, Faragher B, Jamieson GA (1997) Herpes simplex virus type 1 in brain and risk of Alzheimer's disease. Lancet 349:241-244 (Pubitemid 27050990)
21. Kimberlin DW (2007) Herpes simplex virus infections of the newborn. Semin Perinatol 31:19-25 (Pubitemid 46273659)
22. Kocan RM, Sabo KM, Landolt ML (1985) Cytotoxicity/genotoxicity: The application of cell culture techniques to the measurement of marine sediment pollution. Aquatic Toxicol 6:165-177 (Pubitemid 15073464)
23. Mahesh VK, Goyal RN, Gupta R, Sharma R (1980) Synthesis of some pyrimidinylpyrazoles and pyrimidinyl-2-pyrazolin-5-ones. J Indian Chem Soc 57:1037-1038
24. Matysiak J, Nasulewicz A, Pelczynska M, Switalska M, Jaroszewicz I, Opolski A (2006) Synthesis and antiproliferative activity of some 5-substituted 2-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles. Eur J Med Chem 41:475-482
25. McGeoch DJ, Rixon FJ, Davison AJ (2006) Topics in herpesvirus genomics and evolution. Virus Res 117:90-104
26. Oh LM, Wang H, Shilcrat SC, Herrmann RE, Patience DB, Spoors P, Sisko J (2007) Development of a scalable synthesis of GSK183390A, a PPAR a/c agonist. Org Process Res Dev 11: 1032-1042
27. Pei Y, Wickham BOS (1993) Regioselective syntheses of 3-aminomethyl-5-substituted isoxazoles: A facile and chemoselective reduction of azide to amine by sodium borohydride using 1,3-propanedithiol as a catalyst. Tetrahedron Lett 34:7509-7512
28. Pommery N, Taverne T, Telliez A, Goossens L, Charlier C, Pommery J, Goossens JF, Houssin R, Durant F, Hénichart JP (2004) New COX-2/5-LOX inhibitors: Apoptosis-inducing agents potentially useful in prostate cancer chemotherapy. J Med Chem 47: 6195-6206 (Pubitemid 39587244)
29. Rashad AE, Hegab MI, Abdel-Megeid RE, Micky JA, Abdel-Megeid FME (2008) Synthesis and antiviral evaluation of some new pyrazole and fused pyrazolopyrimidine derivatives. Biorg Med Chem 16:7102-7106
30. Roizman B, Pellett PE (2001) In: Knipe DM, Howley PM (eds) Fields virology, vol 2. Lippincott Williams and Wilkins, Philadelphia, PA, p 2381
31. Roy AK, Batra S (2003) Facile Baylis-Hillman reaction of substituted 3-isoxazolecarbaldehydes: The impact of a proximal heteroatom within a heterocycle on the acceleration of the reaction. Synthesis 15:2325-2330 (Pubitemid 37409976)
32. Velikorodov AV, Sukhenkol LT (2003) Synthesis and antimicrobial activity of 3,5-disubstituted isoxazolines and isoxazoles with carbamate groups. Pharm Chem J 37:22-24 (Pubitemid 37025249)
33. Wang X, Li Z, Da Y, Ma Y (2002) Synthesis of 5,50-diaryloxymethyl-2,20- (1,4-phenylenedioxydiacetylamido)-bis(1,3,4-thiadiazoles). Synth Commun 32:1121-1127
34. Wei F, Zhao BX, Huang B, Zhang L, Sun CH, Dong WL, Shin DS, Miao JY (2006) Design, synthesis, and preliminary biological evaluation of novel ethyl 1-(20-hydroxy-30-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate. Bioorg Med Chem Lett 16: 6342-6347 (Pubitemid 44712059)
35. Wozniak MA, Mee AP, Itzhaki RF (2009) Herpes simplex virus type 1 DNA is located within Alzheimer's disease amyloid plaques. J Pathol 217:131-138
36. Yar MS, Siddiqui AA, Ali MA (2006) Synthesis and evaluation of phenoxy acetic acid derivatives as anti-mycobacterial agents. Bioorg Med Chem Lett 16:4571-4574 (Pubitemid 44094073)
37. Zaki MEA, Yousef EAA, Hassanien A-ZA (2007) Fatty acid hydrazides in heterocyclic synthesis: Synthesis of 1,2-diazepine and pyridazine derivatives. Heteroat Chem 18:259-264 (Pubitemid 46716663)