P-Toluenesulfonic acid-catalyzed solvent-free synthesis and biological evaluation of new 1-(4′,6′-dimethylpyrimidin-2′-yl)-5-amino- 4H-3-arylpyrazole derivatives

Medicinal Chemistry Research

Volumn 23, Issue 3, 2014, Pages 1454-1464

  Aggarwal, Ranjana ^a   Bansal, Anshul ^a   Rozas, Isabel ^b   Diez Cecilia, Elena ^b   Kaur, Amanjot ^a   Mahajan, Ritu ^a   Sharma, Jitender ^a  

^a KURUKSHETRA UNIVERSITY   (India)

^b TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

1 (4 ,6 Dimethylpyrimidin 2 yl) 5 amino 4H 3 arylpyrazoles; Antibacterial activity; Cytotoxicity; N acetamide trifluoroacetamide derivatives; p Toluenesulfonic acid; Solvent free synthesis

Indexed keywords

EID: 84893759037     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0751-9     Document Type: Article

References (46)

1. Abdel-Aziz M, Abuo-Rahma G, El-Din A, Hassan AA (2009) Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. Eur J Med Chem 44:3480-3487
2. Abu Almaati TM, El-Taweel FM (2004) New trends in the chemistry of 5-aminopyrazoles. J Heterocycl Chem 41:109-134
3. Aggarwal R, Kumar V, Kumar R (2007) A facile and rapid one-pot synthesis of 1,4-diaryl-2-mercaptoimidazoles under solvent-free conditions. J Sulfur Chem 28:617-623
4. Aggarwal R, Kumar V, Kumar R, Singh SP (2011) Approaches towards the synthesis of 5-aminopyrazoles. Beilstein J Org Chem 7:179-197
5. An H, Eum S, Koh M, Lee SK, Park SB (2008) Diversity-oriented synthesis of privileged benzopyranyl heterocycles from s-cis-Enones. J Org Chem 73:1752-1761
6. Banks JW, Batsanov AS, Howard JAK, O'Hagan D, Rzepa HS, Santamaria SM (1999) The preferred conformation of α-fluoroamides. J Chem Soc Perkin Trans 2:2409-2411
7. Barril X, Beswick MC, Collier A, Drysdale MJ, Dymock BW, Fink A, Grant K, Howes R, Jordan AM, Massey A, Wayne AS, Workman JP, Wright L (2006) 4-Amino derivatives of the Hsp90 inhibitor CCT018159. Bioorg Med Chem Lett 16:2543-2548
8. Benaamane N, Nedjar-Kolli B, Bentarzi Y, Hammal L, Geronikaki A, Eleftheriou P, Langunin A (2008) Synthesis and in silico biological activity evaluation of new N-substituted pyrazolo-oxazin-2-one systems. Bioorg Med Chem 6:3059-3066
9. Burley SK, Petsko GA (1988) Weakly polar interactions in proteins: advances in protein chemistry. Academic Press, New York, pp 125-189
10. Danagulyan GG, Balasanyan NG, Terent'ev PB, Zalinyan MG (1989) Chemistry of heterocyclic compounds. Kluwer, New York, pp 1369-1373
11. Das J, Moquin RV, Dyckman AJ, Li T, Pitt S, Zhang R, Shen DR, McIntyre KW, Gillooly K, Doweyko AM, Newitt JA, Sack JS, Zhang H, Kiefer SE, Kish K, McKinnon M, Barrish JC, Dodd JH, Schieven GL, Leftheris K (2010) 5-Amino-pyrazoles as potent and selective p38a inhibitors. Bioorg Med Chem Lett 20:6886-6889
12. Dymock BW, Barril X, Brough PA, Cansfield JE, Massey A, McDonald E, Hubbard RE, Surgenor A, Roughley SD, Webb P, Workman P, Wright L, Drysdale MJ (2005) Novel, potent small-molecule inhibitors of the molecular chaperone Hsp90 discovered through structure-based design. J Med Chem 48:4212-4215
13. El-gazzar ABA, Hussein HAR, Hafez HN (2007) Synthesis and biological evaluation of thieno[2,3-d]pyrimidine derivatives for anti-inflammatory, analgesic and ulcerogenic activity. Acta Pharm 57:395-411
14. Farag AM, Mayhoub AS, Barakat SE, Bayomi AH (2008) Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives. Bioorg Med Chem 16:881-889
15. Gakhar HK, Gill GS, Multani JS (1971) Thiopegan derivatives part XLIX. J Indian Chem Soc 48:953-956
16. Gilbert AM, Failli A, Shumsky J, Yang Y, Severin A, Singh G, Hu W, Keeney D, Petersen PJ, Katz AH (2006) Pyrazolidine-3,5-diones and 5-hydroxy-1H- pyrazol-3(2H)-ones, inhibitors of UDP-N-acetylenolpyruvyl glucosamine reductase. J Med Chem 49:6027-6036
17. Goldstein DM, Kuglstatter YL, Soth MJ (2009) Selective p38r inhibitors clinically evaluated for the treatment of chronic inflammatory disorders. J Med Chem 53:2345-2353
18. Gopalsamy A, Yang H, Ellingboe JW, Tsou HR, Zhang N, Honores E, Powell D, Miranda M, McGinnis JP, Rabindran SK (2005) Pyrazolo[1,5-a]pyrimidin-7-yl phenyl amides as novel anti-proliferative agents: parallel synthesis for lead optimization of amide region. Bioorg Med Chem Lett 15:1591-1594
19. Hayakawa M, Kaizawa H, Moritomo H, Koizumi T, Ohishi T, Okada M, Ohta M, Tsukamoto S, Parker P, Workman P, Waterfield M (2006) Synthesis and biological evaluation of 4-morpholino-2-phenylquinazolines and related derivatives as novel PI3 kinase p110α inhibitors. Bioorg Med Chem 14:6847-6858
20. Heffron TP, Berry M, Castanedo G et al (2010) Identification of GNE-477, a potent and efficacious dual PI3 K/mTOR inhibitor. Bioorg Med Chem Lett 20:2408-2411
21. Hiraku Y, Oikawa S, Kawanishi S (2002) Distamycin A, a minor groove binder, changes enediyne-induced DNA cleavage sites and enhances apoptosis. Nucl Acids Res Suppl 2:95-96
22. Jung JC, Walkins EB, Avery MA (2002) Synthesis of 3-substituted and 3,4-disubstituted pyrazolin-5-ones. Tetrahedron 58:3639-3646
23. Junttila TT, Akita RW, Parsons K, Fields C, Lewis Phillips GD, Friedman LS, Sampath D, Sliwkowski MX (2009) Ligand-independent HER2/HER3/PI3 K complex is disrupted by trastuzumab and is effectively inhibited by the PI3 K inhibitor GDC-0941. Cancer Cell 15:429-440
24. Kaiko RF, Wallenstein SL, Rogers AG, Grabinski PY, Houde RW (1981) Analgesic and mood effects of heroin and morphine in cancer patients with postoperative pain. N Engl J Med 304:1501-1505
25. Kane JL, Hirth BH, Laing O, Gourlie BB, Nahill S, Barsomiam G (2003) Ureas of 5-aminopyrazole and 2-aminothiazole inhibit growth of gram-positive bacteria. Bioorg Med Chem Lett 13:4463-4466
26. Kordik CP, Luo C, Zanoni BC, Dax SL, McNally JJ, Lovenberg TW, Wilson SJ, Reitz AB (2001) Aminopyrazoles with high affinity for the human neuropeptide Y5 receptor. Bioorg Med Chem Lett 11:2283-2286
27. Kumar V, Aggarwal R, Tyagi P, Singh SP (2005) Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-4-phenyl-3-trifluoromethylpyrazoles. Eur J Med Chem 40:922-927
28. Kumar V, Aggarwal R, Tyagi P, Singh SP (2006) Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-3H/methyl-4-phenylpyrazoles. Bioorg Med Chem 14:1785-1791
29. Lee KY, Kim JM, Kim JN (2003) Regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles from Baylis-Hillman adducts. Tetrahedron Lett 44:6737-6740
30. Lindvall M, McBride C, McKenna M, Gesner TG, Yabannavar A, Wong K, Lin S, Walter A, Shafer CM (2011) 3D pharmacophore model-assisted discovery of novel CDC7 inhibitors. Med Chem Lett 2:720-723
31. Liu XH, Cui P, Song BA, Bhadury PS, Zhu HL, Wang SF (2008) Synthesis, structure and antibacterial activity of novel 1-(5-substituted-3-substituted-4, 5-dihydropyrazol-1-yl)ethanone oxime ester derivatives. Bioorg Med Chem 16:4075-4082
32. Manetti F, Brullo C, Magnani M, Mosci F, Chelli B, Crespan E, Schenone S, Naldini A, Bruno O, Trincavelli ML, Maga G, Carraro F, Martini C, Bondavalli F, Botta M (2008) Structure-based optimization of pyrazolo[3,4-d]pyrimidines as Abl inhibitors and antiproliferative agents toward human leukemia cell lines. J Med Chem 51:1252-1259
33. Meegalla SK, Doller D, Sha DY, Soll R, Wisnewski N, Silverb GM, Dhanoaa D (2004) Synthesis and GABA receptor potency of 3-thiomethyl-4-(hetero)aryl-5- amino-1-phenylpyrazoles. Bioorg Med Chem Lett 14:4949-4953
34. Mercep M, Mesic M, Pesic D (2004) PCT Int Appl WO 03 99, 822. Chem Abstr 140:16724j
35. Michon V, Hervé du Penhoat C, Tombret F, Gillardin JM, Lepage F, Berthon L (1995) Preparation, structural analysis and anticonvulsant activity of 3- and 5-aminopyrazole N-benzoyl derivatives. Eur J Med Chem 30:147-155
36. Okunji CO, Okeke CN, Gugnani HC, Iwu MM (1990) An antifungal Spirostanol Saponin from Fruit Pulp of Dracaena mannii. Int J Crude Drug Res 28:193-199
37. Perez C, Pauli M, Bezerque P (1990) An antibiotic assay by the agar-well diffusion method. J Aotabiol 15:113-115
38. Rios JL, Recio MC, Vilar (1988) A. Screening methods for natural products with antimicrobial activity: a review of the literature. J Ethnopharmacol 23:127-149
39. Sellery S, Gratteri P, Costagli C, Bonaccini C, Coztanzo A, Melani F, Guerrini G, Ciciani G, Costa B, Spinetti F, Martini C, Bruni F (2005) Insight into 2-phenylpyrazolo[1,5-a]pyrimidin-3-yl acetamides as peripheral benzodiazepine receptor ligands: synthesis, biological evaluation and 3D-QSAR investigation. Bioorg Med Chem 13:4821-4834
40. Sherif AFR (2006) Synthesis and in vitro antitumor evaluation of some indeno[1,2-c]pyrazol(in)es substituted with sulfonamide, sulfonylurea(-thiourea) pharmacophores, and some derived thiazole ring systems. Bioorg Med Chem 14:6475-6485
41. Shetty NS, Lamani RS, Khazi IM (2009) Synthesis and antimicrobial activity of some novel thienopyrimidines and triazolothinopyrimidines. J Chem Sci 121:301-307
42. Soliman R, Darwish SAS (1983) Antidiabetic activity of some 1-substituted 3,5-dimethylpyrazoles. J Med Chem 26:1659-1663
43. 3 of cytotoxicity to HL-60 cells produced by cytarabine and hydroxyurea. J Natl Cancer Inst 76(4):641-648
44. Wei F, Zhao B, Huang B, Zhang L, Sun C, Dong W, Shin D, Miao J (2006) Design, synthesis, and preliminary biological evaluation of novel ethyl 1-(2′-hydroxy-3′-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate. Bioorg Med Chem Lett 16:6342-6347
45. Zhao W, Zhang T, Qu B, Wu X, Zhu X, Meng F, Gu Y, Shu Y, Shen Y, Sun Y, Xu Q (2011) Sorafenib induces apoptosis in HL60 cells by inhibiting Src kinase-mediated STAT3 phosphorylation. Anticancer Drugs 22(1):79-88
46. Zoltewicz JA, Uray G (1994) Thiamin: a critical evaluation of recent chemistry of the pyrimidine ring. Bioorg Chem 22:1-28