Synthesis and antitumor activities of 4H-Pyrano[3,2-h]quinoline-3- carbonitrile, 7H-Pyrimido[4',5':6,5]pyrano[3,2-h]quinoline, and 14HPyrimido[4',5':6,5]pyrano[3,2-h][1,2,4]triazolo[1,5-c]quinoline derivatives

Letters in Drug Design and Discovery

Volumn 9, Issue 5, 2012, Pages 459-470

  Al Ghamdi, Abdullah Megbas ^a   Abd El Wahab, Ashraf Hassan Fekry ^b   Mohamed, Hany Mostafa ^b   El Agrody, Ahmed Mohamed ^a  

^a KING KHALID UNIVERSITY   (Saudi Arabia)

^b Assiut Branch   (Egypt)

Author keywords

(E) 2 (4 chlorostyryl) 8 hydroxyquinoline; 4H pyrano 3,2 h quinoline; 7H pyrimido 4',5':6,5 pyrano 3,2 h quinoline; Antitumor; SAR

Indexed keywords

14 (4 CHLOROPHENYL) 9 (4 CHLOROTYRYL) 2 CYANOMETHYL 14H PYRIMIDO[4',5':6,5]PYRANO[3,2 H][1,2,4]TRIAZOLO [1,5 C]QUINOLINE; 14 (4 CHLOROPHENYL) 9 (4 CHLOROTYRYL) 2 PHENYL 14H PYRIMIDO [4',5':6,5]PYRANO[3,2 H][1,2,4]TRIAZOLO[1,5 C]QUINOLINE; 2 AMINO 4 (4 CHLOROPHENYL) 9 (4 CHLOROSTYRYL) 4H PYRANO[3,2 H]QUINOLINE 3 CARBONITRILE; 2 AMINOMETHYLENEAMINO 4 (4 CHLOROPHENYL) 9 (4 CHLOROSTYRYL) 4H PYRANO[3,2 H]QUINOLINE 3 CARBONITRILE; 2 BENZYLIDENEAMINO 4 (4 CHLOROPHENYL) 9 (4 CHLOROSTYRYL)4H PYRANO[3,2 H]QUINOLINE 3 CARBONITRILE; 2 ETHOXYMETHYLENEAMINO 4 (4 CHLOROPHENYL) 9 (4 CHLOROSTYRYL)4H PYRANO[3,2 H]QUINOLINE 3 CARBONITRILE; 4 (4 CHLOROPHENYL) 9 (4 CHLOROSTYRYL) 2 DIMETHYLAMINOMETHYLENEAMINO 4H PYRANO[3,2 H]QUINOLINE 3 CARBONITRILE; 9 AMINO 7 (4 CHLOROPHENYL) 2 (4 CHLOROSTYRYL) 8 IMINO 8,9 DIHYDRO 7H PYRIMIDO[4',5':6,5]PYRANO[3,2 H]QUINOLINE; 9 BENZYLIDENEAMINO 7 (4 CHLOROPHENYL) 2 (4 CHLOROSTYRYL)8 IMINO 8,9 DIHYDRO 7H PYRIMIDO[4',5':6,5]PYRANO [3,2 H]QUINOLINE; 9 METHYL 7 (4 CHLOROPHENYL) 2 (4 CHLOROSTYRYL) 8 IMINO 8,9 DIHYDRO 7H PYRIMIDO [4',5':6,5]PYRANO[3,2 H]QUINOLINE; ANTINEOPLASTIC AGENT; ELECTROPHILE; ETHYL 14 (4 CHLOROPHENYL) 9 (4 CHLOROTYRYL) 14H PYRIMIDO[4',5':6,5]PYRANO[3,2 H][1,2,4]TRIAZOLO[1,5 C]QUINOLINE 2 CARBOXYLATE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; VINBLASTINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN HEPG2; CELL STRAIN MCF 7; CELL VIABILITY; COLORIMETRY; CONTROLLED STUDY; CYTOTOXICITY TEST; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IC 50; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NITROBLUE TETRAZOLIUM TEST; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 84860709647     PISSN: 15701808     EISSN: 1875628X     Source Type: Journal    
DOI: 10.2174/157018012800389331     Document Type: Article

References (45)

1. Ramesh, R. D.; Manian, R. S.; Raghunathan, R.; Sainath, S.; Raghunathan, M. Synthesis and antibacterial property of quinolines with potent DNA gyrase activity. Bioorg. Med. Chem., 2009, 17, 660-666
2. Larghi, E. L.; Bohn, M.L.; Kaufman, T. S. Aaptamine and related products. Their isolation, chemical syntheses, and biological activity. Tetrahedron, 2009, 65, 4257-4282
3. Liu, Xin-Hua; Zhu, Jing; Zhou, An-na; Song, Bao-An; Zhu, Hai- Liang; bai, Lin-Shan; Bhadury, Pinaki S.; Pan, Chun-Xiu. Synthesis, structure and antibacterial activity of new 2-(1-(2- (substituted-phenyl)-5-methyloxazol-4-yl) -3-(2-substitued-phenyl)- 4,5-dihydro-1H-pyrazol-5-yl)-7-substitued-1,2,3,4- tetrahydroisoquinoline derivatives. Bioorg. Med. Chem., 2009,17, 1207-1213
4. Ganesh, T.; Min, J.; Thepchatri, P.; Du, Y.; Li, L.; Lewis, I.; Wilson, L.; Chiosis, H. Fu, G.; Dingledine, R.; Liotta, D.; Snyder, J. P.; Sun, A. Discovery of aminoquinolines as a new class of potent inhibitors of heat shock protein 90 (Hsp90): Synthesis, biology, and molecular modeling. Bioorg. Med. Chem. 2008, 16, 6903-6910
5. Righi, G.; Ciambrone, S.; Bonini, C.; Campaner, P. Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir. Bioorg. Med. Chem,. 2008, 16, 902-908 (Pubitemid 351163051)
6. Bhuwan, B. M.; Rakesh K. S.; Srivastava, A.; Tripathi, V.J.; Vinod, K. T. Fighting Against Leishmaniasis: Search of Alkaloids as Future True Potential Anti-Leishmanial Agents. Mini-Reviews Med. Chem., 2009, 9, 107-123.
7. Sanjay, K. S.; Amrita, J.; Shiv, K. A., Rama, M.; Anand, C. B. Synthesis and Structure-Activity Relationships of Potent Antitumor Active Quinoline and Naphthyridine Derivatives. Anti-Cancer Agents Med. Chem., 2012, 12, 685-709.
8. Vladimir, V. K.; Fedor I. Z.; Uriel, M. C.; Leonid, G. V.; Leonor, Y. V. M.; Luis A.; Elena, E. S. An Efficient Synthesis of Hexahydro Oxaisoindolo[2,1-a]Quinoline Derivatives via the Diels-Alder Reactions. Lett. Org. Chem., 2004, 1, 37-39.
9. Thomas L., Roy, K. Exploring molecular shape analysis of styrylquinoline derivatives as HIV-1 integrase inhibitors. Eur. J. Med. Chem., 2008, 43, 81-92
10. Philippe, C. Patented HIV-1 Integrase Inhibitors (1998-2005). Recent Pat Anti-Infect Drug Discov 2006, 1, 1-15
11. Zouhiri, F.; Danet, M.; Bernard, C.; Normand-Bayle, M.; Mouscadet, J. F.; Leh, H.; Thomas, C. M.; Mbemba, G.; d'Angelo, J.; Desmaele, D. HIV-1 replication inhibitors of the styrylquinoline class: introduction of an additional carboxyl group at the C-5 position of the quinoline. Tetrahedron Lett. 2005, 46, 2201-2205 (Pubitemid 40332212)
12. Bernard Ch., Zouhiri F., Normand-Bayle M., Danet M., Desmaele D., Leh H., Mouscadet J. F., Mbemba G., Thomas C., Bonnenfant M., Le Bret M., d'Angelo J. Linker-modified quinoline derivatives targeting HIV-1 integrase: synthesis and biological activity. Bioorg. Med. Chem. Let., 2004, 14, 2473-2476. (Pubitemid 38515687)
13. Polanski J., Zouhiri F., Jeanson L., Desmaele D., d'Angelo J., Mouscadet J., Gieleciak R., Gasteiger J., Bret M. L. Use of the Kohonen Neural Network for Rapid Screening of Ex Vivo Anti- HIV Activity of Styrylquinolines. J. Med. Chem., 2002, 45, 4647-4654.
14. Ouali M., Laboulais C., Leh H., Gill D., Desmaele D., Mekouar K., Zouhiri F., Auclair C., d'Angelo J., Mouscadet J. F., Le Bret M. Modeling of the Inhibition of Retroviral Integrases by Styrylquinoline Derivatives. J. Med. Chem., 2000, 43, 1949-1957 (Pubitemid 30340934)
15. Mrozek-Wilczkiewicz, A.; Kalinowski, D. S.; Musiol, R.; Finster, J.; Szurko, A.; Serafin, K.; Knas, M.; Kamalapuram, S. K.; Kovacevic, Z.; Jampilek, J.; Ratuszna, A.; Rzeszowska-Wolny, J.; Richardson, D.R.; Polanski, J. Investigating the anti-proliferative activity of styrylazanaphthalenes and azanaphthalenediones. Bioorg. Med. Chem., 2010, 18, 2664-2671.
16. Polanski, J.; Niedbala, H.; Musiol, R.; Podeszwa, B.; Tabak, B.; Palka, A.; Mencel, A.; Finster, J.; Mouscadet, J.-F.; Bret, L. 5- Hydroxy-6-Quinaldic acid as a Novel Molecular Scaffold for HIV- 1 Integrase Inhibitors. Lett. Drug Des. Discov., 2006, 3, 175-178.
17. Pommier, Y.; Johnson, A. A.; Marchand, C. Integrase inhibitors to treat HIV/Aids Nat. Rev. Drug. Discov. 2005, 4, 236-248 (Pubitemid 40372557)
18. Chang F.-S., Chen W., Wangb C., Tzeng C.-C., Chen Y.-L. Synthesis and antiproliferative evaluations of certain 2- phenylvinylquinoline (2-styrylquinoline) and 2-furanylvinylquinoline derivatives. Bioorg. Med. Chem., 2010, 18, 124-132.
19. Podeszwa B., Niedbala H., Polanski J., Musiol R., Tabak D., Finster J., Serafin K., Milczarek M., Wietrzyk J., Boryczka S., Mol W., Jampilek J., Dohnal J., Kalinowski D. S., Richardson D. R. Investigating the antiproliferative activity of quinoline-5,8-diones and styrylquinolinecarboxylic acids on tumor cell lines. Bioorg. Med. Chem. Lett., 2007, 17, 6138-6141. (Pubitemid 47552839)
20. Behforouz, M.; Cai, W.; Mohammadi, F.; Stocksdale, M. G.; Gu, Z.; Ahmadian, M.; Baty, D. E.; Etling, M. R.; Al-Anzi, C. H.; Swiftney, T. M.; Tanzer, L. R.; Merriman, R. L.; Behforouz, N. C. Synthesis and evaluation of antitumor activity of novel Nacyllavendamycin analogues and quinoline-5,8- diones. Bioorg. Med. Chem. 2007, 15, 495-510 (Pubitemid 44738558)
21. Behforouz M., Cai W., Stocksdale M. G., Lucas J. S., Jung J. Y., Briere D., Wang A., Katen K. S., Behforouz N. C. Novel Lavendamycin Analogues as Potent HIV-Reverse Transcriptase Inhibitors: Synthesis and Evaluation of Anti-Reverse Transcriptase Activity of Amide and Ester Analogues of Lavendamycin. J. Med. Chem., 2003, 46, 5773-5779.
22. Fang Y., Linardic C. M., Richardson D. A., Cai W., Behforouz M., Abraham R. T. Characterization of the Cytotoxic Activities of Novel Analogues of the Antitumor Agent, Lavendamycin. Mol. Cancer Ther., 2003, 2, 517-526.
23. Behforouz M., Haddad J., Cai W., Arnold M. B., Mohammadi F., Sousa A. C., Horn M. A. Highly Efficient and Practical Syntheses of Lavendamycin Methyl Ester and Related Novel Quinolindiones. J. Org. Chem., 1996, 61, 6552-6555. (Pubitemid 26328640)
24. Andrew, T.; Marilena V.; Maria G.; Aphrodite E.; Constantine I.; Anna K.; Pandelis A. A.; Dimitri M.; Christos, R. Symmetrical Derivatives of C2-Substituted Pyrrolo[2,3-f]-quinolines: Synthesis, Cytotoxicity and Drug Delivery Studies. Lett. Drug Des. Discov., 2007, 4, 87-91.
25. Narender, P.; Srinivas, U.; Ravinder, M.; Ch. Ramesh, B.; K.; Gangadasu, B.; Murthy, U. S. N.; Jayathirtha Rao, V. Synthesis of multisubstituted quinolines from Baylis-Hillman adducts obtained from substituted 2-chloronicotinaldehydes and their antimicrobial activity. Bioorg. & Med. Chem. 2006, 14, 4600-4609 (Pubitemid 44255774)
26. Musiol, R.; Jampilek, J.; Buchta, V.; Silva, L.; Niedbala, H.; Podeszwa, B.; Palka, A.; Majerz-Maniecka, K.; Oleksyn, B.; Polanski, J. Antifungal properties of new series of quinoline derivatives. Bioorg. Med. Chem. 2006, 14, 3592-3598.
27. Ma X. H., Zhang X.Y., Tan J. J., Chen W. Z., Wang C. X. Exploring binding mode for styrylquinoline HIV-1 integrase inhibitors using comparative molecular field analysis and docking studies Acta Pharmacol. Sin., 2004, 25, 950-958.
28. El-Agrody A. M. Condensation Reactions of α -Cyanocinnamonitriles with Naphthols: Synthesis of Naphthopyranopyrimidines and a Naphthopyranone. J. Chem. Res. (S), 1994, 280-281.
29. El-Agrody A. M., Emam H. A., El-Hakim M. H., Abd El-Latif M. S., Fakery A. H. Activated Nitriles in Heterocyclic Synthesis: Synthesis of Pyrano[3,2-d]pyrimidine and pyrano[3,2- e][1,2,4]triazolo[1,5-c]pyrimidine Derivatives. J. Chem. Res. (S), 1997, 320-321. (Pubitemid 127516305)
30. El-Agrody A. M., Emam H. A., El-Hakim M. H., Abd El-Latif M. S., Fakery A. H. Activated Nitriles in Heterocyclic Synthesis: Synthesis of Pyrano[3,2-d]pyrimidine and pyrano[3,2- e][1,2,4]triazolo[1,5-c]pyrimidine Derivatives.J. Chem. Res. (M) 1997, 2039-2048.
31. Bedair A. H., El-Hady N. A., Abd El-Latif M. S., Fakery A. H., El- Agrody A. M. 4-Hydroxycoumarin in Heterocyclic Synthesis Part III: Synthesis of Some New Pyrano[2,3-d]-pyrimidine, 2- Substituted[1,2,4]triazolo[1,5-c]pyrimidine and Pyrimido[1,6- b][1,2,4]triazine Derivatives. IL Farmaco, 2000, 55, 708-714. (Pubitemid 32037102)
32. El-Agrody A. M., El-Hakim M. H., Abd El-Latif M. S., Fakery A. H., El-Sayed E. S. M., El-Ghareab K. A. Synthesis of Pyrano[2,3- d]pyrimidine and Pyrano[3,2-e][1,2,4]triazolo[2,3-c]pyrimidine Derivatives with Promising Antimicrobial Activities. Acta Pharm. 2000, 50, 111-120. (Pubitemid 30620126)
33. Sayed A. Z., El-Hady N. A., El-Agrody A. M. Condensation of α- Cyanocinnamonitriles with 6-Bromo-2-naphthols: Synthesis of Pyrano[2,3-d] pyrimidine and Pyrano[3,2-e]-[1,2,4]triazolo[2,3- c]pyrimidine Derivatives. J. Chem. Res. (S), 2000, 164-166.
34. El-Agrody A. M., Abd El-Latif M. S., El-Hady N. A., Fakery A. H., Bedair A. H. Heteroaromatization with 4-Hydroxycoumarin Part II: Synthesis of Some new Pyrano[2,3-d]pyrimidine ,[1,2,4]triazolo[1,5-c]pyrimidine and Pyrimido[1,6-b][1,2,4]triazine Derivatives. Molecules, 2000, 6, 519-527.
35. Bedair A. H., Emam H. A., El-Hady N. A., Ahmed K.A.R., El- Agrody A. M. Synthesis and Antimicrobial Activities of Novel Naphtho[2,1-b]pyran, Pyrano[3,2-d]pyrimidine and Pyrano[3,2- e][1,2,4]triazolo-[2,3-c]pyrimidine Derivatives. IL Farmaco, 2001, 56, 965-973. (Pubitemid 34017403)
36. El-Agrody A. M., Eid F. A., Emam H. A., Mohamed H. M., Bedair A. H. 9-Acetoxy-3-amino-1-(4-methoxyphenyl)-1H-benzo[f]chromene- 2-carbonitriles via 2-(iminopiperidin-1-yl-methyl)-3-(4-methoxyphenyl)acrylonitrile as intermediate. Z. Naturforsch. Teil B, 2002, 57, 579-585.
37. Khafagy M. M., Abd El-Wahab A. H. F., Eid F. A., El-Agrody A. M. Synthesis of Halogen Derivatives of Benzo[h]cheromene and Benzo[a]anthracene with Promising Antimicrobial Activities. IL Farmaco, 2002, 57, 715-722. (Pubitemid 35287005)
38. Eid F. A., Bedair A. H., Emam H. A., Mohamed H. M., El-Agrody A. M. Reaction of Activated Nitriles with Methanolic Piperidine and Synthesis of 1H-Benzo[f]chromene, Diazabenzo[j]anthracene and Diazabenzo[a][1,2,4]triazolo[j] anthracene Derivatives. Al- Azhar Bull. Sci., 2003, 14, 311-342.
39. Abd-El-Aziz A. S., El-Agrody A. M., Bedair A. H., Christopher Corkery T., Ata, A. Synthesis of Hydroxyquinoline Derivatives, Aminohydroxy-chromene, Aminocoumarin and Their Antimicrobial Activities. Heterocycles, 2004, 63, 1793-1812.
40. Abd-El-Aziz A. S., Mohamed H. M., Mohammed S., Zahid S., Ata A., Bedair A. H., El-Agrody A. M. Harvey P. D. Synthesis of Novel Coumarin and Benzocoumarin Derivatives and their Biological and Photophysical Studies. J. Heterocycl. chem., 2007, 44, 1287-1300.
41. Sabry N. M., Mohamed H. M., Khattab Essam Shawky, A. E. H., Motlaq S. S., El-Agrody A. M. Synthesis of 4H-chromene, coumarin, 12H-chromeno[2,3-d] pyrimidine derivatives and some of their antimicrobial and cytotoxicity activities. Eur. J. Med. Chem., 2011, 46, 765-772.
42. El-Agrody A. M., Sabry N. M., Motlaq S. S. Synthesis of some new 2-substituted 12H-chromeno[3,2-e][1,2,4]-triazolo[1,5-c] pyrimidine, 3-ethoxycarbonyl-12H-chromeno[3,2-e]-[1,2,4]triazolo [1,5-c]pyrimidine-2-one, ethyl 2-formylamino\acetylamino-4Hchromene- 3-carboxylate and some of their antimicrobial activities. J. Chem. Res., 2011, 35, 77-83.
43. El-Agrody, A. M., Al-Ghamdi A. M. Synthesis of certain novel 4H-pyrano[3,2-h]-quinoline derivatives. Arkivoc, 2011, xi, 134-146.
44. Rahman A.U., Choudhary M. I., Thomsen W. J., 2001, Bioassay Technique for Drug Development. Harwood Academic Publishers
45. Mossman T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.