Abstract
Six new series of pyrazolo[4,3-f]quinoline derivatives with potential bioactivities were synthesized by the three-component reactions of aromatic aldehydes, 5-aminoindazole, and various cyclic 1,3-dicarbonyl compounds under microwave irradiation. This protocol has the valuable features of structural diversity of products, broader substrate scope, operational simplicity, high yields, and short reaction time. Moreover, the structure of compound 88a was confirmed by an X-ray crystallographic analysis and attested to the chemoselectivity of reaction where 1-methyl barbituric acid participated.
Similar content being viewed by others
References
Bekhit AA, El-Sayed OA, Aboul-Enein HY, Siddiqui YM, Al-Ahdal MN (2004) Synthesis of aldehydo-sugar derivatives of pyrazoloquinoline as inhibitors of herpes simplex virus type 1 replication. J Enzym Inhib Med Chem 19: 33–38. doi:10.3109/14756360409162406
Fujita M, Egawa H, Miyamoto T, Nakano J, Matsumoto J (1996) Pyridione carboxylic acids as antibacterial agents. Part 18. Pyrroloquinolines and pyrazoloquinolones as potential antibacterial agents. Synthesis and antibacterial activity. Eur J Med Chem 31: 981–988. doi:10.1016/S0223-5234(97)86177-6
Wathen MW, Wathen LK (2004) Method using quinolinecarboxamides and other heterocyclic compounds for preventing or treating atherosclerosis or restenosis. WO 2004019932; Chem Abstr 140:247064
Ajami AM (2008) Preparation of (fused) imidazoacridines for treating FLT3-mediated disorders. WO 2008016665; Chem Abstr 148:239202
Ajami AM (2008) Compounds for treating inflammatory disorders, demyelinating disorders and cancers. US 2008108641; Chem. Abstr. 2008, 148:529475
Kasiotis KM, Fokialakis N, Haroutounian SA (2006) Synthesis of novel conformationally constrained pyrazolo[4,3-c]quinoline derivatives as potential ligands for the estrogen receptor. Synthesis 1791–1802. doi:10.1055/s-2006-926466
Plaskon AS, Ryabukhin SV, Volochnyuk DM, Gavrilenko KS, Shivanyuk AN, Tolmachev AA (2008) Synthesis of quinolines from 3-formylchromone. J Org Chem 73: 6010–6013. doi:10.1021/jo800950y
Carotti A, Altomare C, Savini L, Chiasserini L, Pellerano C, Mascia MP, Maciocco E, Busonero F, Mameli M, Biggio G, Sanna E (2003) High affinity central benzodiazepine receptor ligands. Part 3: insights into the pharmacophore and pattern recognition study of intrinsic activities of pyrazolo[4,3-c]quinolin-3-ones. Bioorg Med Chem 11: 5259–5272. doi:10.1016/S0968-0896(03)00527-3
Sunderhaus JD, Martin SF (2009) Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds. Chem Eur J 15: 1300–1308. doi:10.1002/chem.200802140
Kappe CO, Dallinger D (2009) Controlled microwave heating in modern organic synthesis: highlights from the 2004–2008 literature. Mol Divers 13: 71–193. doi:10.1007/s11030-009-9138-8
Dai WM, Shi JY (2007) Diversity-oriented synthesis and solid-phase organic synthesis under controlled microwave heating. Comb Chem High Throughput Screen 10: 837–856. doi:10.2174/138620707783220338
Jiang B, Tu S, Kaur P, Wever W, Li G (2009) Four-component domino reaction leading to multifunctionalized quinazolines. J Am Chem Soc 131: 11660–11661. doi:10.1021/ja904011s
Han Z, Zhang G, Jiang B, Ma N, Shi F, Tu S (2009) Diversity synthesis of pyrimido[4,5-b][1,6]naphthyridine and its derivatives under microwave irradiation. J Comb Chem 11: 809–812. doi:10.1021/cc800196u
Jiang B, Hao W, Wang X, Shi F, Tu S (2009) Diversity-oriented synthesis of Krohnke pyridines. J Comb Chem 11: 846–850. doi:10.1021/cc900052b
Shi F, Li C, Xia M, Miao K, Zhao Y, Tu S, Zheng W, Zhang G, Ma N (2009) Green chemoselective synthesis of thiazolo[3,2-a]pyridine derivatives and evaluation of their antioxidant and cytotoxic activities. Bioorg Med Chem Lett 19: 5565–5568. doi:10.1016/j.bmcl.2009.08.046
Deady LW, Desneves J, Kaye AJ, Finlay GJ, Baguley BC, Denny WA (2000) Synthesis and antitumor activity of some indeno[1,2-b]quinoline-based bis carboxamides. Bioorg Med Chem 8: 977–984. doi:10.1016/S0968-0896(00)00039-0
Horino H, Mimura T, Kagechika K, Ohta M, Kubo H, Kitagawa M (1998) Synthesis and antihypertensive activity of 4-(diazabicyclo [4.1.0] heptenyloxy) benzopyran derivatives and their analogs. Chem Pharm Bull 46: 602–609. doi:10.1002/chin.199845163
Hajela K, Kapil RS (1997) Synthesis and post-coital contraceptive activity of a new series of substituted 2,3-diaryl-2H-1-benzopyrans. Eur J Med Chem 32: 135–142. doi:10.1016/S0223-5234(97)87540-X
Deady LW, Kaye AJ, Finlay GJ, Baguley BC, Denny WA (1997) Synthesis and antitumor properties of N-[2-(dimethylamino) ethyl] carboxamide derivatives of fused tetracyclic quinolines and quinoxalines: a new class of putative topoisomerase inhibitors. J Med Chem 40: 2040–2046. doi:10.1021/jm970044r
Deady LW, Desneves J, Kaye AJ, Thompson M, Finlay GJ, Baguley BC, Denny WA (1999) Ring-substituted 11-oxo-11H-indeno [12-b]quinoline-6-carboxamides with similar patterns of cytotoxicity to the dual topo I/II inhibitor DACA. Bioorg Med Chem 7: 2801–2809. doi:10.1016/S0968-0896(99)00231-X
Kossakowski J, Zawadowski T, Slawomir S (1998) Synthesis of aminopropanol derivatives of 7-ethoxy-8-hydroxy- and 6,7-diethoxy-8-hydroxy-2H-1-benzopyran-2-one with an expected β-adrenolytic activity. Acta Pol Pharm 55: 77–79
El-Shaaer HM, Foltinova P, Lacova M, Chovancova J, Stankovicova H (1988) Synthesis, antimicrobial activity and bleaching effect of some reaction products of 4-oxo-4H-benzopyran-3-carboxaldehydes with aminobenzothiazoles and hydrazides. II Farmaco 53: 224–232. doi:10.1016/S0014-827X(98)00015-9
Johnson AT, Wang L, Standeven AM, Escobar M, Chandraratna RAS (1999) Synthesis and biological activity of high-affinity retinoic acid receptor antagonists. Bioorg Med Chem 7: 1321–1338. doi:10.1016/S0968-0896(99)00055-3
Hitotsuyanagi Y, Kobayashi M, Fukuyo M, Takeya K, Itokawa H (1997) A facile synthesis of the 4-aza-analogs of 1-arylnaphthalene lignans chinensin, justicidin B, and taiwanin C. Tetrahedron Lett 38: 8295–8296. doi:10.1016/S0040-4039(97)10204-0
Khurana JM, Maikap GC, Mehta S (1990) Reductive coupling of geminal dichlorides by iron(II) oxalate dihydrate. Synthesis 731–732. doi:10.1055/s-1990-26998
Atwal KS, Swanson BN, Unger SE, Floyd DM, Moreland S, Hedberg A, O’Reilly BC (1991) Dihydropyrimidine calcium channel blockers. 3. 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. J Med Chem 34: 806–811. doi:10.1021/jm00106a048
Giri A, Narasu ML (2000) Production of podophyllotoxin from podophyllum hexandrum: a potential natural product for clinically useful anticancer drugs. Cytotechnology 34: 17–26. doi:10.1023/A:1008138230896
Rampa A, Bisi A, Belluti F, Gobbi S, Valenti P, Andrisano V, Cavrini V, Cavalli A, Recanatini M (2000) Acetylcholinesterase inhibitors for potential use in Alzheimer’s disease: molecular modeling, synthesis and kinetic evaluation of 11H-indeno-[1,2-b]-quinolin-10-ylamine derivatives. Bioorg Med Chem 8: 497–506. doi:10.1016/S0968-0896(99)00306-5
Moyer MP, Weber FH, Gross JL (1992) Structure-activity relationships of imidazo[4,5-f]quinoline partial structures and analogs. Discovery of pyrazolo[4,3-f]quinoline derivatives as potent immunostimulants. J Med Chem 35: 4595–4601. doi:10.1021/jm00102a013
Tu SJ, Jiang B, Jia RH, Zhang JY, Zhang Y, Yao CS, Shi F (2006) An efficient one-pot, three-component synthesis of indeno[1,2-b]quinoline-9,11(6H,10H)-dione, acridine-1,8 (2H,5H)-dione and quinoline-3-carbonitrile derivatives from enaminones. Org Biomol Chem 4: 3664–3668. doi:10.1039/b607575d
Author information
Authors and Affiliations
Corresponding authors
Additional information
Feng Shi and Shu Zhang contributed equally to the work.
Rights and permissions
About this article
Cite this article
Shi, F., Zhang, S., Wu, SS. et al. A diversity-oriented synthesis of pyrazolo[4,3-f]quinoline derivatives with potential bioactivities via microwave-assisted multi-component reactions. Mol Divers 15, 497–505 (2011). https://doi.org/10.1007/s11030-010-9272-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11030-010-9272-3