1,661
Views
19
CrossRef citations to date
0
Altmetric
Research Article

A convenient synthesis and molecular modeling study of novel pyrazolo[3,4-d]pyrimidine and pyrazole derivatives as anti-tumor agents

, &
Pages 396-405 | Received 22 May 2014, Accepted 23 Jun 2014, Published online: 28 Jul 2014

References

  • Wise LD, Butler DE, Dewald HA, et al. 1,3-Dialkyl-4-(iminoarylmethyl)-1H-pyrazol-5-ols. A series of novel potential antipsychotic agents. J Med Chem 1987;30:1807–12
  • Gursoy SA, Demirayak S, Capan G, Vural K. Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents. Eur J Med Chem 2000;35:359–64
  • Tsuji K, Nakamurana K, Konishi N, et al. Studies on anti-inflammatory agents. IV. Synthesis and pharmacological properties of 1,5-diarylpyrazoles and related derivatives. Chem Pharm Bull 1997;45:987–95
  • Badawey AM, El-Ashmawey IM. Non-steroidal anti-inflammatory agents – Part 1: Anti-inflammatory, analgesic and antipyretic activity of some new 1-(pyrimidin-2-yl)-3-pyrazolin-5-ones and 2-(pyrimidin-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-ones. Eur J Med Chem 1998;33:349–61
  • Daidone G, Maggio B, Plescia S, et al. Antimicrobial and antineoplastic activities of new 4-diazopyrazole derivatives. Eur J Med Chem 1998;33:375–82
  • (a) Hilgard P, Thornes RD. Anticoagulants in the treatment of cancer. Eur J Cancer 1976;12:755–62. (b) Taylor C, Patel H, Kumar H. Synthesis of pyrazolo 3,4-dpyrimidine analogues of the potent agent N-4-2-2-amino-4 3H-oxo-7H-pyrrolo 2,3-dpyrimidin-5-ylethylbenzoyl-l-glutamic acid (LY231514). Tetrahedron 1992;48:8089–100
  • Thumar NJ, Patel MP. Synthesis, characterization, and antimicrobial evaluation of carbostyril derivatives of 1H-pyrazole. Saudi Pharm J 2011;19:75–83
  • Nauduri D, Reddy GP. Antibacterials and antimycotics. Chem Pharm Bull 1998;46:1254–60
  • Foks H, Pancechowska-Ksepko D, Kedzia A, et al. Synthesis and antibacterial activity of 1H-pyrazolo[3,4-b]pyrazine and pyridine derivatives. Farmaco 2005;60:513–17
  • Dardari Z, Lemrani M, Sebban A, et al. Antileishmanial and antibacterial activity of a new pyrazole derivative designated 4-[2-(1-(ethylamino)-2-methyl-propyl)- phenyl]-3-(4-methyphenyl)-1-phenylpyrazole. Arch Pharm Chem Life Sci 2006;339:291–8
  • Gilbert AM, Failli A, Shumsky J, et al. Pyrazolidine-3,5-diones and 5-hydroxy-1H-pyrazol-3(2H)-ones, inhibitors of UDP-N-acetylenolpyruvyl glucosamine reductasen. J Med Chem 2006;49:6027–36
  • Jiang JB, Hesson DP, Dusak BA, et al. Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization. J Med Chem 1990;33:1721–8
  • Parlok JJ. Synthesis of pyrazolecarbonylaminopyridinecarboxamides as herbicides. J Heterocycl Chem 1998;35:1493–9
  • Saad HA, Osman NA, Moustafa AH. Synthesis and analgesic activity of some new pyrazoles and triazoles bearing a 6,8-dibromo-2-methylquinazoline moiety. Molecules 2011;16:10187–201
  • Han X, Xu-hong H, Xiao-mao Z, et al. Synthesis and herbicidal activity of 5-heterocycloxy-3-substituted-1-(3-trifluoromethyl)phenyl-1H-pyrazole. Chem Res Chinese Universities 2012;28:824–7
  • Schallner O, Heinz KH, Karl K. Ger. Offen DE19615259, 1997. Chem Abstr 1997;127:346387
  • Eicher T, Hauptmann S. The Chemistry of heterocycles: structure, reactivity, syntheses and applications. New York: Thieme-Verlag; 1995
  • (a) Jolly C, Morimoto RI. Role of the heat shock response and molecular chaperones in oncogenesis and cell death. J Natl Cancer Inst 2000;92:1564–1572. (b) Maloney A, Workman P. HSP90 as a new therapeutic target for cancer therapy. Expert Opin Biol Ther 2002;2:3–24. (c) Workman P. Overview: translating Hsp90 biology into Hsp90 drugs. Curr Cancer Drug Targets 2003;3:297–300. (d) Drysdale MJ, Dymock BW, Barril-Alonso X, et al. Preparation of 3,4-diarylpyrazoles as inhibitors of heat shock protein 90 (HSP90) and their use in the therapy of cancer. PCT Int. Appl. WO 2003/055860; 2003
  • Rathelot P, Azas N, El-Kashef H, et al. 1,3-Diphenylpyrazoles: synthesis and antiparasitic activities of azomethine derivatives. Eur J Med Chem 2002;37:671–9
  • Bernardino AMR, Gomes AO, Charret KS, et al. Synthesis and leishmanicidal activities of 1-(4-X-phenyl)-N′-[(4-Y-phenyl)methylene]-1H-pyrazole-4-carbohydrazides. Eur J Med Chem 2006;41:80–7
  • Katiyar SB, Srivastava K, Purib SK, Chauhana PMS. Synthesis of 2-[3,5-substituted pyrazol-1-yl]-4,6-trisubstituted triazine derivatives as antimalarial agents. Bioorg Med Chem Lett 2005;15:4957–60
  • Moukha-Chafiq O, Taha ML, Lazrek HB, et al. Synthesis and biological activity of some 4-substituted 1-[1-(2,3-dihydroxy-1-propoxy)methyl-1,2,3-triazol-(4&5)-yl methyl]-1H-pyrazolo[3,4-d]pyrimidines. Farmaco 2002;57:27–32
  • Allen SH, Johns BA, Gudmundsson KS, et al. Synthesis of C-6 substituted pyrazolo[1,5-a]pyridines with potent activity against herpesviruses. Bioorg Med Chem 2006;14:944–54
  • Baraldi PG, Beria I, Cozzi P, et al. Cinnamoyl nitrogen mustard derivatives of pyrazole analogues of tallimustine modified at the amidino moiety: design, synthesis, molecular modeling and antitumor activity studies. Bioorg Med Chem 2004;12:3911–21
  • Daidone G, Raffa D, Maggio B, et al. Synthesis and antiproliferative activity of triazenoindazoles and triazenopyrazoles: a comparative study. Eur J Med Chem 2004;39:219–24
  • Gopalsamy A, Yang H, Ellingboe JW, et al. 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 2005;15:1591–4
  • Cocco MT, Congiu C, Lilliu V, Onnis V. Amidrazones as precursors of biologically active compounds-Synthesis of Diaminopyrazoles for Evaluation of Anticancer Activity. Arch Pharm Chem Life Sci 2006;339:7–13
  • Tanitame A, Oyamada Y, Ofugi K, et al. Synthesis and antibacterial activity of a novel series of potent DNA gyrase inhibitors. Pyrazole Derivatives. J Med Chem 2004;47:3693–96
  • Tsurumi K, Abe A, Fujimura H, et al. General pharmacological actions of l-(m-chlorophenyl)-3-N,N-dimethylcarbamoyl-5-methoxypyrazole (PZ-177). Folia Pharmacol Jpn 1976;72:41–52
  • Bakavoli M, Bagherzadeh G, Vaseghifar M, et al. Molecular iodine promoted synthesis of new pyrazolo[3,4-d]pyrimidine derivatives as potential antibacterial agents. Eur J Med Chem 2010;45:647–50
  • Capdeville R, Buchdunger E, Zimmermann J, Matter A. Glivec (STI571, imatinib), a rationally developed, targeted anticancer drug. Nat Rev Drug Disc 2002;1:493–502
  • Taylor EC, Patel H, Kumar H. Synthesis of pyrazolo 3,4-dpyrimidine analogues of the potent agent N-4-2-2-amino-4 3 H-oxo-7 H-pyrrolo 2,3-dpyrimidin-5-yl ethylbenzoyl-l-glutamic acid (LY231514). Tetrahedron 1992;48:8089–100
  • Al-Saadi MS, Rostom SAF, Faidallah HM. 4-{2-[(E)-Cyclo-pentyl-idene]hydrazin-1-yl}benzene-sulfonamide. Arch Pharm Chem Life Sci 2008;341:181–90
  • Ghorab MM, Ismail ZH, Abdel-Gawad SM, Abdel Aziem A. Antimicrobial activity of amino acid, imidazole, and sulfonamide derivatives of pyrazolo[3,4-d]pyrimidine. Heteroatom Chem 2004;15:57–62
  • Anderson JD, Cottam HB, Larson SB, et al. Synthesis of certain pyrazolo[3,4-d]pyrimidin-3-one nucleosides. J Heterocycl Chem 1990;27:439–53
  • Rashad AE, Hegab MI, Abdel-Megeid R, et al. Synthesis and antiviral evaluation of some new pyrazole and fused pyrazolopyrimidine derivatives. Bioorg Med Chem 2008;16:7102–6
  • Holla BS, Mahalinga M, Karthikeyan MS, et al. Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents. Bioorg Med Chem 2006;14:2040–7
  • Nassar IF, Assaly SA-E. Synthesis, reactivity and antitumor activity of some new pyrazolo[3,4-d] pyrimidine and their triazole derivatives. Der Pharma Chemica 2011;3:229–38
  • Ribeiro DA, Marques ME, Salvadori BDM. In vitro cytotoxic and non-genotoxic effects of gutta-percha solvents on mouse lymphoma cells by single cell gel (comet) assay. Braz Dent J 2006;17:228–32
  • Elgazwy A-SSH, Nassar IF, Jones PG. Ethyl 5-amino-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carboxylate. Acta Cryst 2013;E69:o1376
  • An information portal to biological macromolecular structures. Available from: http://www.rcsb.org/pdb
  • Laskowaski RA, MacArthur MW, Moss DS, Thornton JM. PROCHECK: a program to check the stereochemical quality of protein structures. J Appl Cryst 1993;26:283–91
  • Ramachandran GN, Ramakrishnan C, Sasisekharan V. Stereochemistry of polypeptide chain configurations. J Mol Biol 1963;7:95–9
  • Schrodinger LLC. New York, NY: Schrodinger Suite; 2010
  • Taverna DM, Goldstein RA. Why are proteins marginally stable? Proteins 2002;46:105–9
  • Hamilton-Miller JMT. Antimicrobial properties of tea (Camellia sinensis L). Antimicrobial Agents Chemother 1995;39:2375–7
  • Halgren TA, Murphy RB, Friesner RA, et al. Glide: a new approach for rapid, accurate docking and scoring 2. Enrichment factors in database screening. J Med Chem 2004;47:1750–9

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.