An overview on synthetic methodologies and biological activities of pyrazoloquinolines

Mini-Reviews in Medicinal Chemistry

Volumn 10, Issue 2, 2010, Pages 1194-1210

  Gaurav, A ^a   Gautam, V ^a   Singh, R ^a  

^a SHOBHIT UNIVERSITY   (India)

Author keywords

Adenosine receptor; Benzodiazepine receptor; Chk1kinase; Phosphodiesterase; Pyrazoloquinoline; Ras; Sar; Topoisomerase ii

Indexed keywords

1 ARYL 3 METHYL 4 (4 METHYLPIPERAZINYL) 1H PYRAZOLO[4,5 C]QUINOLIN 4 ONE; 1 ARYL 3 METHYL 4,5 DIHYDRO 1H PYRAZOLO[4,3 C]QUINOLIN 4 ONE; 1 ARYL 3,5 DIMETHYL 4,5 DIHYDRO 1H PYRAZOLO[4,5 C]QUINOLIN 4 ONE; 1 ARYL 4,9 DIHYDRO 3 METHYL 1H PYRAZOLO[3,4 B]QUINOLINE 4 ONE; 1,3 DIARYL 4,5 DIHYDRO 1H PYRAZOLO[4,3 C]QUINOLIN 4 ONE; 2 (THIEN 2 YL) 2,5 DIHYDRO 3H PYRAZOLO[4,3 C]QUINOLIN 3 ONE; 2 (THIEN 3 YL) 2,5 DIHYDRO 3H PYRAZOLO[4,3 C]QUINOLIN 3 ONE; 2 ARYL PYRAZOLO[4,3 C]QUINOLIN 3 ONE; 2 ARYLPYRAZOLO[3,4 C]QUINOLIN 4 (HETERO)ARYLAMIDE; 2 ARYLPYRAZOLO[3,4 C]QUINOLIN 4 ONE; 2 ARYLPYRAZOLO[3,4 C]QUINOLINE; 2,5 DIHYDROPYRAZOLE[4,3 C]QUINOLIN 3 ONE; 6 BENZYLOXY 4 METHOXYMETHYL BETA CARBOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 7 CHLORO 3,5 DIHYDRO 2 (4 METHOXYPHENYL) LH PYRAZOLO[3 4 C]QUINOLINE 1,4 (2H) DIONE; ADENOSINE RECEPTOR; AMINE; BENZODIAZEPINE RECEPTOR; CHECKPOINT KINASE 1; DNA TOPOISOMERASE (ATP HYDROLYSING); PHOSPHODIESTERASE IV; PYRAZOLOQUINOLINE DERIVATIVE; PYRAZOLO[3,4 B]QUINOLINE; PYRAZOLO[3,4 B]QUINOLINE NUCLEOSIDE; PYRAZOLO[3,4 C]QUINOLINE; PYRAZOLO[4,3 B]QUINOLINE; PYRAZOLO[4,3 C]QUINOLIN 3 ONE; PYRAZOLO[4,3 C]QUINOLINE; PYRAZOLO[4,5 C]QUINOLINE; PYRAZOLO[5,4 C]QUINOLINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; PYRAZOLE; PYRAZOLE DERIVATIVE;

ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ANXIETY; ARTICLE; BIOLOGICAL ACTIVITY; DEPRESSION; DRUG PROTEIN BINDING; DRUG SYNTHESIS; EPILEPSY; HUMAN; IC 50; NONHUMAN; PHARMACOPHORE; ANIMAL; CHEMISTRY; CYCLIZATION; REVIEW; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; CYCLIZATION; HUMANS; PYRAZOLES; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84871114553     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/13895575110091194     Document Type: Article

References (79)

1. Squire, R. F.; Braestrup, C. Benzodiazepine receptors in rat brain. Nature (London), 1977, 266, 732.
2. Mohler, H.; Okada, T. Benzodiazepine receptor: demonstration in the central nervous system. Science, 1977, 198, 849.
3. Lippa, A. S.; Critchet, D.; Sano, M. C.; Klepner, C. A.; Greenblatt, E. N.; Couplet, J.; Beer, B. Benzodiazepine receptors: Cellular and behavioral characteristics. Pharmacol. Biochem. Behav., 1979, 10, 831.
4. Blanchard, J. C.; Boireau, A.; Garret, C.; Julau, L. In vitro and in vivo inhibition by zopiclone of benzodiazepine binding to rodent brain receptors Life Sci., 1978, 24, 2417.
5. Braestrup, C.; Nielsen, M.; Olsen, C. E. Urinary and brain betacarboline- 3-carboxylates as potent inhibitors of brain benzodiazepine receptors. Proc. Natl. Acad. Sci. U.S.A., 1980, 77, 2288.
6. Gueremy, C. G. A.; Uzan, A. Multiple benzodiazepine receptors: Evidence of a dissociation between anticonflict and anticonvulsant properties by PK 8165 and PK 9084 (two quinoline derivatives). Life Sci., 1981, 28, 1439.
7. Yokoyama, N.; Ritter, B.; Neubert, A.D. 2-Arylpyrazolo[4,3- c]quinolin-3-ones: Novel Agonist, Partial Agonist, and Antagonist of Benzodiazepines J. Med. Chem., 1982, 25, 337-339.
8. Yokohama, N. Pyrazoloquinolines. US Patent 4,312,870, January 26, 1982.
9. Cain, M.; Weber, R. W.; Guzman, F.; Cook, J. M.; Baker, S. A.; Rice, K. C.; Crawley, J. N.; Paul, S. M.; Skolnick, P. beta.- Carbolines: synthesis and neurochemical and pharmacological actions on brain benzodiazepine receptors. J. Med. Chem., 1982, 25, 1081.
10. Ceechi, L.; Melani, F.; Palazzino, G.; Martini, C.; Pennacchi, E.; Lncacchini, A. Synthesis and binding studies of 1-Aryl pyrazolo [4, 5-c] - and 2- aryl pyrazolo [4, 3-c] quinolins-4-ones. Il. Farmaco[sci], 1985, 40(7), 509-516.
11. Melani, F.; Cecchi, L.; Palazzino, G.; Filacchioni, G.; Martini, C.; Pennacchi, E.; Lucacchini, A. Pyrazolo[4, 5-c]quinolines. 3. Synthesis, receptor binding, and 13C NMR study J. Pharm. Sci., 1986, 75(12), 1175-1179.
12. Melani, F.; Cecchi, L.; Palazzino, G.; Filacchioni, G.; Martini, C.; Pennacchi, E.; Lucacchini A. Pyrazolo[4,5-c]quinolines. 2. Synthesis and Specific Inhibition of Benzodiazepine Receptor Binding. J. Med. Chem., 1986, 29, 291-295.
13. Gupta, S. P.; Saha, R.N.; Gupta, J. K.; Singh, P. Aquantitative structure activity relationship study as inhibitors of benzodiazepine receptor binding. Res. Commun. Chem. Pathol. Pharmacol., 1989, 65(1), 119-122.
14. Singh, P.; Ojha, T. N.; Sharma, R. C. Quantitative structure activity relationship study on some ligands acting as inhibitors of benzodiazepine-receptors binding. Res. Commun. Chem. Pathal. Pharmacol., 1990, 67(1), 151-154.
15. Wentland, M. P. Pyrazoloquinolones as anticancer agents. US Patent 5,33,495, August 2, 1994.
16. Wentland, M.P.; Aldous, S.C.; Gruett, M.D.; Perni, R.B.; Powles, R.G.; Danz, D.W.; Klingbeil, K.M.; Peverly, A.D.; Robinson, R.G.; Corbctt, T.H.; Rake, J.B.; Coughlin, S.A.; The antitumor activity of novel pyrazoloquinoline derivatives Bioorg. Med. Chem. Lett., 1995, 5(4), 405-410.
17. Brnardic, E. J.; Garbaccio, R. M.; Fraley, M. E.; Tarber, E. S.; Steen, J.T.; Arrington, K.L.; Vadin, Y.D.; Hartman, G.D.; Stardivant, S.M.; Drakas, B.A.; Rickert, K.; Wals, E.S.; Hamilton, K.; Buser, C. A.; Hardwick, J.; Tao, W.; Beck, S.C.; Mao, X.; Labele, R. B.; Sepp-Lorenzino, L.; Yan, Y.; Ikuta, M.; Munshi, S.K.; Kno, L. C.; Kereatsoulas, C. Optimisation of a pyrazoloquinolone class of chk1 kinase inhibitors. Bioorg. Med. Chem. Lett., 2007, 17, 5989-5994.
18. Crespo, M.I.; Gracia, J.; Puig, C.; Vega, A.; Bon, J.; Beleta, J.; Domenech, T.; Rydor, H.; Segarra, V.; Palacios, J. M. Synthesis and Biological Evaluation of 2,5-dihydropyrazolo (4,3-c) Quinolin- 3-ones a novel series of PDE4 inhibitors with low emetic potential and antiasthmatic properties. Bioorg. Med. Chem. Lett., 2000, 10, 2661-2664.
19. Baraldi, P.G.; Tabrizi, M. A.; Preti, D.; Borero, A.; Fruttarolo, F.; Romagnoli, R.; Zaid, N. A.; Moorman, A. R.; Varani, K.; Berea, P. A. New 2- Aryl pyrazolo [4, 3-c] quinoline derivativesas potent and selective human A3 Adenosine Receptor Antagonists. J. Med. Chem., 2005, 48, 5001-5008.
20. de Oliveira, M.R.; Alves, T.R.; Pinto, A.C.; Pereira Hde, S.; Leão- Ferreira, L.R.; Moussatché, N.; de Frugulhetti, I.C.; Ferreira, V.F.; de Souza, M.C. Synthesis and antiviral activities of new pyrazolo[4,3-c]quinolin-3-ones and their ribonucleoside derivatives. Nucleosides Nucleotides Nucleic Acids, 2004, 23(5),735-748.
21. Bekhit, A.A.; El-Sayed, O.A.; Aboul-Enein, H.Y.; Siddiqui, Y.M.; Al-Ahdal, M.N.; Synthesis of Aldehydo-sugar Derivatives of Pyrazoloquinoline as Inhibitors of Herpes Simplex Virus Type 1 Replication. J. Enzyme Inhib. Med. Chem., 2004, 19(1), 33-38.
22. Takada, S.; Shindo, H.; Sasatani, T.; Chomei, N.; Matsashita, A.; Masami, E.; Kawasaki, K.; Murata, S.; Takahara, Y.; Shintaku, H. Thienylpyrazoloquinolines: Potent Agonists and Inverse Agonists to Benzodiazepine Receptors. J. Med. Chem., 1988, 31, 1738.
23. Shindo, H.; Takada, S.; Murata, S.; Masami, E.; Matsushita, A. Thienylpyrazoloquinolines with High Affinity to Benzodiazepine Receptors: Continuous Shift from Inverse Agonist to Agonist Properties Depending on the Size of the Alkyl Substituent J. Med. Chem., 1989, 32, 1213.
24. Wang, C. G.; Langer, T.; Kamath, P. G.; Gu, Z.-Q.; Skolnick, P.; Ian Fryer, R. Computer-Aided Molecular Modeling, Synthesis, and Biological Evaluation of 8-(Benzyloxy)-2-phenylpyrazolo[4,3- c]quinoline as a Novel Benzodiazepine Receptor Agonist Ligand. J. Med. Chem., 1995, 38 (6), 950-957.
25. Hollinshead, S. P.; Trudell, M. L.; Skolnick, P.; Cook, J. M. Structural Requirements for Agonist Actions at the Benzodiazepine Receptor: Studies with Analogs of 6-(Benzyloxy)-4-(methoxymethyl)- β- carboline-3-carboxylic Acid Ethyl Ester. J. Med. Chem., 1990, 33, 1062-1069.
26. Carotti, A.; Altomarc, C.; Savini, L.; Chiassrrini, L.; Pellerano, C.; Mascia, M.P.; Maciocco, E.; Busonero, F.; Mameli, M.; Biggio, G.; Enrico, S. High affinity central benzodiazepine receptor ligands. Part 3- Insights Into the pharmacophore and pattern recognition study of intricsic activities of pyrazolo [4, 3-c] quinalin-3-ones. Bioorg. Med. Chem. Lett., 2003, 11, 5259-5272.
27. Ferlin, M G.; Chiarelotto, G.; Acqua, S.D.; Maciocco, E.; Mascia, M.P.; Pisu, M.G. Biggio, G. Novel anellated pyrazoloquinolin-3- ones: synthesis and in vitro benzodiazepine receptor activity Bioorg. Med. Chem., 2005, 13, 3531-3541.
28. Zhang, W.; Koehler, K. F.; Zhang, P.; Cook, J. M. Development of a comprehensive pharmacophore model for the benzodiazepine receptor. Drug Des. Dis., 1995, 12, 193-248.
29. Palazzino, G.; Cecchi, L.; Melani, F.; Colotta, C.; Filacchioni, G.; Martini, C.; Lucacchini, A.; 1,3-Diarylpyrazolo[4,5-c 1- and -[5,4-c ]quinolin-4-ones. 4. Synthesis and Specific Inhibition of Benzodiazepine Receptor Binding. J. Med. Chem., 1987, 30, 1737-1742.
30. Catarzi, D.; Calotta, V.; Varano, F.; Cecchi, L.; Filacehioni, G.; Galli, A.; Costagali, C. Tricyclic heteroaromatic systems. Pyrazolo (3, 4-c) quinolin-4-4ones and pyrazolo (3, 4-c) quinaline-1, 4- diones: Synthesis and benzodiazepine receptors activity. Arch. Pharm.(weinheim), 1997, 330(12), 383-386.
31. Allen, M.S.; Skolnick, P.; Cook, J. M.; Synthesis of novel 2- phenyl-2h-pyrazolo (4, 3-c) isoquinolin-3-ols: Topological comparisons with Analogues of 2-phenyl-2, 5-dihydropyrazolo (4, 3-c) quinalin-3(3H)-ones at Benzodiazepine receptors. J. Med. Chem., 1992, 35, 368-374.
32. Watkins, J. C.; Krogsgaard-Larsen, P.; Honore, T. Structureactivity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists. Trends Pharmacol. Sci., 1990, 11, 25-33.
33. Wong, E. H. F.; Kemp, J. A.; Priestley, T.; Knight, A. R.; Woodruff, G. N.; Iversen, L. L. The anticonvulsant MK-801 is a potent N-methyl-D-aspartate antagonist. Proc. Natl. Acad. Sci., U.S.A., 1986, 83, 7104-7108.
34. Kemp, J. A.; Leeson, P. D. The glycine site on the NMDA receptor - five years on. Trends Pharmacol. Sci., 1993, 14, 20-25.
35. Carter, C.; Rivy, J. P.; Scatton, B. Ifenprodil and SL 82.0715 are antagonists at the polyamine site of the N-methyl-Daspartate (NMDA) receptor. Eur. J. Pharmacol., 1989, 164, 611-612.
36. MacLeod, A. M.; Grimwood, S.; Barton, C.; Bristow, L.; Saywell, K. L.; Marshall, G. R.; Ball, R. G. Identification of 3,5-Dihydro-2- aryl-1H-pyrazolo[3,4-c]quinoline-1,4-(2H)-diones as Novel High- Affinity Glycine Site N-Methyl-D-aspartate Antagonists. J. Med. Chem., 1995, 38, 2239-2243.
37. Ali, H.; Choi, O.H.; Yamada, K.; Beaven, M.A.; Gonzaga, H.M.S. Sustained activation of phospholipase D via A3-adenosine receptor is associated with enhancement of antigen- and Ca2+-ionophore induced secretion in RBL-2H3 cells. J. Pharmacol. Exp. Ther., 1996, 276, 837-845.
38. Forsythe, P.; Ennis, M. Adenosine, mast cells and asthma. Adenosine, mast cells and asthma. Inflamm. Res., 1999, 48(6), 301-307.
39. Jacobson, K.A.; Tchilibon, S.J.; Bhalchandra, V.; Gao, Z.-G. A3 Adenosine Receptors. Ann. Rep. Med. Chem., 2003, 38, 121-130.
40. Nieber, K.; Lewerenz, A.; Hentschel, S.; Vissiennon, Z. Adenosine A1 and A3 receptors: Neuroprotective targets with perspectives. Bioforum, 2002, 25 (4), 237-240.
41. Catarzi, D.; Cecchi, L.; Colotta, V.; Melani, F.; Filacchioni, G.; Tacchi, P.; Tonelli, M.; Martini, C. Tricyclic heteroaromatic systems. Synthesis and adenosine receptor binding evaluation of pyrazolo-quinoline and benzopyrano-pyrazole derivatives. Int. J. Purine Pyrimidine Res., 1991, 2, 113-121.
42. Colotta, V.; Cecchi, L.; Catarzi, D.; Melani, F.; Filacchioni, G.; Martini, C.; Tacchi, P.; Lucacchini, A. 1-(3-Aminopheny1)-3- methyl[llbenzopyrano[2,3-c]pyrazol-4-one: a new selective A2 adenosine receptor antagonist. Pharm. Pharmacol. Lett., 1992, 2, 74-76.
43. Colotta, V.; Cecchi, L.; Catarzi, D.; Melani, F.; Filacchioni, G.; Martini, C.; Tacchi, P.; Lucacchini, A. Novel adenosine receptor ligands: 1,3-disubstituted[llbenzopyrano[2,3-clpyrazol-4-ones. Synthesis and structure-activity relationships. Recept. Channels, 1993, 1, 111-119.
44. Colotta, V.; Cecchi, L.: Catarzi, D.: Filacchioni, G.: Martini, C.: Tacchi, P.; Lucacchini A. Synthesis of some tricyciic heteroaromatic systems and their A1 and A2, adenosine binding activity. Eur. J. Med. Chem., 1995, 30, 133-139.
45. Catarzi, D.; Cecchi, L.; Colotta, V.; Filacchioni, G.; Martini, C.; Tacchi, P.; Lucacchini, A. Tricyclic heteroaromatic systems. Synthesis and A1 and A2a adenosine binding activities of some 1- aryl-1,4-dihydro-3-methyl[1]benzopyrano[2,3-c]pyrazol-4- ones, 1- aryl-4,9-dihydro 3-methyl-1H-pyrazolo[3,4-b]quinolin-4- ones, and 1-aryl-1H-imidazo[4,5-b]quinoxalines. J. Med. Chem., 1995, 38, 1330-1336.
46. Colotta, V.; Catarzi, D.; Varano, F.; Cecchi, L.; Filacchioni, G.; Martini, C.; Trincavelli, L.; Lucacchini, A. Synthesis and Structure- Activity relationships of a New Set of 2-Arylpyrazolo[3,4- c]quinoline Derivatives as Adenosine Receptor Antagonists. J. Med. Chem., 2000, 43, 3118-3124.
47. Colotta, V.; Catarzi, D.; Varano, F.; Capelli, F.; Lenzi, O.; Filacchioni, G.; Martini, C.; Trincavelli, L.; Ciampi, O.; Pugliese, A. M.; Pedata, F.; Schiesaro, A.; Morizzo, E.; Moro, S. New 2- Arylpyrazolo[3,4-c]quinoline Derivatives as Potent and Selective Human A3 Adenosine Receptor Antagonists. Synthesis, Pharmacological Evaluation, and Ligand-ReceptorModeling Studies. J. Med. Chem., 2007, 50, 4061.
48. Colotta, V.; Capelli, F.; Lenzi, O.; Catarzi, D.; Varano, F.; Poli, D.; Vincenzi, F.; Varani, K.; Borea, P.A.; Ben, D.D.; Volpini, R.; Cristalli, G.; Filacchioni, G. Novel potent and highly selective human A3 adenosine receptor antagonists belonging to the 4-amido- 2-arylpyrazolo[3,4-c]quinoline series: Molecular docking analysis and pharmacological studies Bioorg. Med. Chem., 2009, 17, 401-410.
49. Zhou B.B.; Elledge, S.J. The DNA damage response: putting checkpoints in perspective. Nature, 2000, 408, 433-39.
50. Bartek, J.; Lukas, J. Chk1 and Chk2 kinases in checkpoint control and cancer. Cancer Cell, 2003, 3, 421-429.
51. Vermeulen, K.; Van Bockstaele, D.R.; Berneman, Z.N. The cell cycle: a review of regulation, deregulation and therapeutic targets in cancer. Cell Prolif., 2003, 36, 131-149.
52. Cuddihy, A.R.; O'Connell, M.J. Cell-cycle responses to DNA damage. Int. Rev. Cytol., 2003, 222, 99-140.
53. Carrassa, L.; Broggini, M.; Erba, E.; Damia, G. Chk1, but not Chk2, is involved in the cellular response to DNA damaging agents. Differential activity in cells expressing or not p53. Cell Cycle, 2004, 3, 1177-81.
54. Chen, Y.; Sanchez, Y. Chk1 in the DNA damage response: conserved roles from yeasts to mammals. DNA Repair, 2004, 3, 1025-1032.
55. Delia, D.; Fontanella, E.; Ferrario, C.; Chessa, L.; Mizutani S. DNA damage-induced cell-cycle phase regulation of p53 and p21waf1 in normal and ATM-defective cells. Oncogene, 2003, 22, 7866-7869.
56. McGowan, C.H. Running into problems: how cells cope with replicating damaged DNA. Mutation Res., 2003, 532, 75-84.
57. Prudhomme, M. Novel Checkpoint 1 Inhibitors. Recent Pat. Anti- Cancer Drug Discov., 2006, 1, 55.
58. Barbacid, M. ras genes. Annu. Rev. Biochem., 1987, 56, 779.
59. Barbacid, M. ras oncogenes: their role in neoplasia. Eur. J. Clin. Invest., 1990, 20, 225.
60. Hall, A. The cellular functions of small GTP-binding proteins. Science., 1990, 249, 635.
61. Bourne, H. R.; Sanders, D. A.; McCormick, F. The GTPase superfamily: a conserved switch for diverse cell functions. Nature., 1990, 348, 125.
62. Wolin, R.; Wang, D.; Kelly, J.; Afonso, A.; James, L.; Kirschmeier P.; McPhail, A T. Synthesis and evaluation of pyrazolo[3,4- b]quinoline ribofuranosides and their derivatives as inhibitors of oncogenic ras. Bioorg. Med. Chem. Lett., 1996, 6(2), 195-200.
63. Giembycz, M.A. Phosphodiesterase 4 and tolerance to β2- adrenoceptor agonists in asthma. Trends Pharm. Sci.,1996, 17, 331-336.
64. Hanton, G.; Sobry, C.; Dague's, N.; Provost, J.-P.; Le Net, J.-L.; Comby, P.; Chevalier, S. Characterisation of the vascular and inflammatory lesions induced by the PDE4 inhibitor CI-1044 in the dog. Toxicol. Lett., 2008, 179, 15-22.
65. Dague's, N.; Pawlowski, V.; Sobry, C.; Hanton, G.; Borde, F.; Soler, S.; Freslon, J.-L.; Chevalier, S. Investigation of the molecular mechanisms preceding PDE4 inhibitor-induced vasculopathy in rats: tissue inhibitor of metalloproteinase 1, a potential predictive biomarker. Toxicol. Sci., 2007, 100, 238-247.
66. Stachlewitz, R. F. Bringing biomarkers to the masses: an elegant approach to discover potential biomarkers of vascular injury. Toxicol. Sci., 2007, 100, 5-6.
67. McCluskie, K.; Klein, U.; Linnevers, C.; Ji, Y.-h.; Yang, A.; Husfeld, C.; Thomas, G. R. Phosphodiesterase type 4 inhibitors cause proinflammatory effects in vivo. J. Pharmacol. Exp. Ther., 2006, 319, 468-476.
68. Masamune, H.; Cheng, J. B.; Cooper, K.; Eggler, J. F.; Marfat, A.; Marshall, S. C.; Shirley, J. T.; Tickner, J. E.; Umland, J. P.; Vazquez, E. Discovery of micromolar PDE IV inhibitors that exhibit much reduced affinity for the [3H]rolipram binding site: 3- norbornyloxy-4-methoxyphenylmethylene oxindoles. Bioorg. Med. Chem. Lett., 1995, 5, 1965-1968.
69. Cheng, J. B.; Cooper, K.; Duplantier, A. J.; Eggler, J. F.; Kraus, K. G.; Marshall, S. C.; Marfat, A.; Masamune, H.; Shirley, J. T.; Tickner, J. E.; Umland, J. E. Synthesis and in vitro profile of a novel series of catechol benzimidazoles. The discovery of potent, selective phosphodiesterase type IV inhibitors with greatly attenuated affinity for the [3H]rolipram binding site. Bioorg. Med. Chem. Lett., 1995, 5, 1969-1972.
70. Guerin, P. J.; Olliaro, P.; Sundar, S.; Boelaert, M.; Croft, S. L.; Desjeux, P.; Wasunna, M. K.; Bryceson, A. D. Lancet Infect. Dis., 2002, 2, 494-501.
71. Ahmed, A-.Q.; Yunus, M.S.; Adnan, A.B.; Ola, A. E-.S, Hassan, Y. A-.E.; Mohammed N.A-.A. Effect of Pyrazoloquinoline Derivatives on the Growth of Leishmania donovani Promastigotes. Arch. Pharm. Chem. Life Sci., 2005, 338, 484-487.
72. Oaks, S.C.; Mitchell, V.S.; Perason, G.W.; Carpenter C.C.J (eds): Malaria: Obstacle and Opportunities; National Academy Press: Washington, DC, 1991.
73. Dominguez, J.N.; Basante, W.; Charris, J.; Riggione, F. Synthesis and activity of some quinolone derivatives against Plasmodium falciparum in vitro. Farmaco, 1996, 51, 407.
74. Dominguez, J.N.; Charris, J.E.; Basante, W.; Mendez B. 13C NMR spectral characterization of some antimalarial tricyclic quinolone derivatives. Magn. Reson. Chem., 1998, 36, 454.
75. Sangwan, N.K.; Kelkar, K.; Prabhakar, M.; Rastogi, S.N.; Anand, N.; Antifertiliy agents: Part XLIII. Synthesis of 3-aryl4,5-dihydro- 2-substituted-5-tosyl-2H-pyrazolo[4,3-c]quinolines and 2,4- dihydro-3-phenyl[1]benzopyrano[4,3-c]pyrazoles and their derivatives. Indian J. Chem., 1985, 24B (6), 639-644.
76. De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. A Mild Procedure for the Preparation of 3-Aryl-4-formylpyrazoles. Synlett., 2004, 2299-2302
77. Phadtare, S.K; Kamat, S.K.; Panse, G.T. Synthesis of pyrazoloquinoline and quinazoline derivatives: part I reactions of o-aminobenzoic acid, methylester and its hydrazides with ethylacetoacetate and diethylmalonate. Indian J. Chem., 1983, 22, 496.
78. Puetter, R.; Wolfnun, G.; Hanke, H.G. German Patent 1,143515, 1963.
79. Charris, J. E; Dominguez, J.N.; Lobo, G.; Cordero, M.I.; Lopez, S.E.; Mendez, B.; Pekerar, S.; Riggione, F. 1H and 13C NMR spectral characterization of some antimalarial in vitro 3-amino-9- methyl-1H-pyrazolo[3,4-b]-4-quinolones. Magn. Reson. Chem., 2000, 38, 1039-1040.