A diversity-oriented synthesis of pyrazolo[4,3-f]quinoline derivatives with potential bioactivities via microwave-assisted multi-component reactions

Molecular Diversity

Volumn 15, Issue 2, 2011, Pages 497-505

  Shi, Feng ^a   Zhang, Shu ^b   Wu, Shan Shan ^a   Gao, Yuan ^c   Tu, Shu Jiang ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b THE FIRST AFFILIATED HOSPITAL OF NANJING MEDICAL UNIVERSITY   (China)

^c SHENZHEN UNIVERSITY   (China)

Author keywords

Diversity oriented synthesis; DOS; MCR; Microwave irradiation; Multi component reactions; MW; Pyrazolo 4,3 f quinoline derivatives

Indexed keywords

1 METHYL BARBITURIC ACID; 1,3 DICARBONYL COMPOUND; 5 AMINOINDAZOLE; ALDEHYDE DERIVATIVE; BARBITURIC ACID DERIVATIVE; INDAZOLE DERIVATIVE; KETONE; PYRAZOLO[4,3 F]QUINOLINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; 1,3 INDANDIONE; 1,3-INDANDIONE; 5-AMINOINDAZOLE; ALDEHYDE; INDAN DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DIVERSITY ORIENTED SYNTHESIS; DRUG ACTIVITY; DRUG SYNTHESIS; MICROWAVE RADIATION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY; CATALYSIS; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG DESIGN; RADIATION EXPOSURE;

ALDEHYDES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; INDANS; INDAZOLES; MICROWAVES; QUINOLINES;

EID: 80051562895     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-010-9272-3     Document Type: Article

References (30)

1. 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 (Pubitemid 38239928)
2. 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 (Pubitemid 26418442)
3. 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
4. Ajami AM (2008) Preparation of (fused) imidazoacridines for treating FLT3-mediated disorders. WO 2008016665; Chem Abstr 148:239202
5. Ajami AM (2008) Compounds for treating inflammatory disorders, demyelinating disorders and cancers. US 2008108641; Chem. Abstr. 2008, 148:529475
6. 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 (Pubitemid 43893394)
7. 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
8. 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 (Pubitemid 37353013)
9. 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
10. 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
11. Dai WM, Shi JY (2007) Diversity-oriented synthesis and solidphase organic synthesis under controlled microwave heating. Comb Chem High Throughput Screen 10:837-856. doi:10.2174/138620707783220338 (Pubitemid 351409254)
12. 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
13. 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
14. 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
15. 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
16. 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 (Pubitemid 30336393)
17. 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 (Pubitemid 28216934)
18. 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 (Pubitemid 27085480)
19. 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 (Pubitemid 27265980)
20. 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 (Pubitemid 30105852)
21. 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 (Pubitemid 28120385)
22. 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
23. 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 (Pubitemid 29292373)
24. 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 (Pubitemid 27509107)
25. 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
26. 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
27. 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
28. 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 (Pubitemid 30122355)
29. 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 (Pubitemid 23006678)
30. 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 (Pubitemid 44439887)