2-Amino-4-(nitroalkyl)-4H-chromene-3-carbonitriles as new cytotoxic agents

Iranian Journal of Pharmaceutical Research

Volumn 12, Issue 4, 2013, Pages 679-685

  Zonouzi, Afsaneh ^a   Mirzazadeh, Roghieh ^a   Safavi, Maliheh ^b   Ardestani, Sussan Kabudanian ^a   Emami, Saeed ^c   Foroumadi, Alireza ^b,d  

^a UNIVERSITY OF TEHRAN   (Iran)

^b TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

4H chromenes; Benzopyran; Cytotoxic activity; DBU; One pot synthesis

Indexed keywords

2 AMINO 4 (1 NITROETHYL) 4H CHROMENE 3 CARBONITRILE; 2 AMINO 4 (NITROALKYL) 4H CHROMENE 3 CARBONITRILE DERIVATIVE; 2 AMINO 4 (NITROMETHYL) 4H CHROMENE 3 CARBONITRILE; 2 AMINO 6 BROMO 4 (1 NITROETHYL) 4H CHROMENE 3 CARBONITRILE; 2 AMINO 6 BROMO 4 (NITROMETHYL) 4H CHROMENE 3 CARBONITRILE; 2 AMINO 6 CHLORO 4 (1 NITROETHYL) 4H CHROMENE 3 CARBONITRILE; 2 AMINO 6 CHLORO 4 (NITROMETHYL) 4H CHROMENE 3 CARBONITRILE; CYTOTOXIC AGENT; ETOPOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CELL GROWTH; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC 50; INFRARED SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROPHOTOMETRY;

EID: 84888098807     PISSN: 17350328     EISSN: 17266890     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Witte EC, Neubert P and Roesch A. 7-(Piperazinylpropoxy)-2H-1-benzopyran-2-ones. Ger. Offen. DE3427985, 1986. Chem. Abstr. (1986) 104: 224915f.
2. CP Dell and Smith CW. Antiproliferative derivatives of 4H-naphtho[1,2-b]pyran and process for their preparation, Eur. Pat. 537,94,9 21 Apr, 1993. Chem. Abstr. (1993) 119: 139102d.
3. Doshi JM, Tian D and Xing C. Structure-activity relationship studies of ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (HA 14-1), an antagonist for antiapoptotic Bcl-2 proteins to overcome drug resistance in cancer. J. Med. Chem. (2006) 49: 7731-7739.
4. Kemnitzer W, Drewe J, Jiang S, Zhang H, Wang Y, Zhao J, Crogan-Grundy C, Xu L, Lamothe S, Gourdeau H, Denis R, Tseng B, Kasibhatla S and Cai SX. Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell-and caspase-based high-throughput screening assay. 3. structure-activity relationships of fused rings at the 7,8-positions. J. Med. Chem. (2007) 50: 2858-2864.
5. Kumar RR, Perumal S, Senthilkumar P, Yogeeswari P and Sriram D. An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles. Bioorg. Med. Chem. Lett. (2007) 17: 6459-6462.
6. Kidwai M, Saxena S, Khan MKR and Thukral SS. Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in-vitro study as antibacterial agents. Bioorg. Med. Chem. Lett. (2005) 15: 4295-4298.
7. Martínez-Grau A and Marco JL. Friedländer reaction on 2-amino-3-cyano-4H-pyrans: Synthesis of derivatives of 4H-pyran[2,3-b]quinoline, new tacrine analogues. Bioorg. Med. Chem. Lett. (1997) 7: 3165-3170.
8. Gao M, Miller KD, Hutchins GD and Zheng Q-H. Synthesis of carbon-11-labeled 4-aryl-4H-chromens as new PET agents. Appl. Radiat. Isot. (2010) 68: 110-116.
9. Thompson LA. Recent applications of polymer-supported reagents and scavengers in combinatorial, parallel, or multistep synthesis. Curr. Opin. Chem. Biol. (2000) 4: 324-337.
10. Nefzi A, Ostresh JM and Houghten RA. The current status of heterocyclic combinatorial libraries. Chem. Rev. (1997) 97: 449-472.
11. Akbarzadeh T, Rafinejad A, Malekian Mollaghasem J, Safavi M, Fallah-Tafti A, Kabudanian Ardestani S, Shafiee A and Foroumadi A. 2-Amino-3-cyano-4-(5-arylisoxazol-3-yl)-4H-chromenes: Synthesis and in vitro cytotoxic activity. Arch. Pharm. (2012) 345: 386-392.
12. Rafinejad A, Fallah-Tafti A, Tiwari R, Shirazi AN, Mandal D, Shafiee A, Parang K. Foroumadi A, Akbarzadeh T. 4-Aryl-4H-naphthopyrans derivatives: One-pot synthesis, evaluation of Src kinase inhibitory and anti-proliferative activities. DARU J. Pharm. Sci. (2012) 20:100.
13. Wiener C, Schroeder CH, West BD and Link KP. Studies on the 4-hydroxycoumarins. XVIII. 3-[α-(acetamidomethyl)benzyl]-4-hydroxycoumarin and related products. J. Org. Chem. (1962) 27: 3086-3088.
14. Kemnitzer W, Kasibhatla S, Jiang S, Zhang H, Zhao J, Jia S, Xu L, Crogan-Grundy C, Denis R, Barriault N, Vaillancourt L, Charron S, Dodd J, Attardo G, Labrecque D, Lamothe S, Gourdeau H, Tseng B, Drewe J and Cai SX. Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell-and caspase-based high-throughput screening assay. 2. Structure-activity relationships of the 7-and 5-, 6-, 8-positions. Bioorg. Med. Chem. Lett. (2005) 15: 4745-4751.
15. Wang J-L, Liu D, Zhang Z-J, Shan S, Han X, Srinivasula SM, Croce CM, Alnemri ES, and Huang Z. Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc. Natl. Acad. Sci. USA (2000) 97: 7124-7129.
16. Saeedi M, Mahdavi M, Foroumadi A, Shafiee A. Synthesis of novel fused 4,5-dihydro-1,2,3-triazolo[1,5-a][1,4]benzodiazepine derivatives via four-component Ugi-Smiles-type reaction. Tetrahedron (2013) 69: 3506-3510.
17. Hosseini-Zare MS, Mahdavi M, Saeedi M, Asadi M, Javanshir S, Shafiee A, Foroumadi A. Synthesis of 2,3-diaryl-5H-imidazo[2,1-a]isoindol-5-ones via the one-pot reaction of 1,2-diketones, 2-formylbenzoic acids, and ammonium acetate. Tetrahedron Lett. (2012) 53: 3448-3451.
18. Dömling A. Recent advances in isocyanide-based multicomponent chemistry. Curr. Opin. Chem. Biol. (2002) 6: 306-313.
19. Dömling A and Ugi I. Multicomponent reactions with isocyanides. Angew. Chem., Int. Ed. (2000) 39: 3168-3210.
20. Breslow R. Water as a solvent for chemical reactions. In: Green Chemistry, Anastas PT and Williamson TC (Eds.) Oxford Press, New York (1998) pp 225-232.
21. Grieco PA. Organic Synthesis in Water; Blacky academic & Professional: London, (1998) 82-141.
22. Li CJ. Organic reactions in aqueous media with a focus on C-C bond formations: A decade update. Chem. Rev. (2005) 105: 3095-3165.
23. Makarem S, Mohammadi AA and Fakhari AR. A multi-component electro-organic synthesis of 2-amino-4H-chromenes. Tetrahedron Lett. (2008) 49: 7194-7196.
24. Maggi R, Ballini R, Sartori G and Sartorio R. Basic alumina catalysed synthesis of substituted 2-amino-2-chromenes via three-component reaction. Tetrahedron Lett. (2004) 45: 2297-2299.
25. Ballini R, Bosica G, Conforti ML, Maggi R, Mazzacani A, Righi P and Sartori G. Three-component process for the synthesis of 2-amino-2-chromenes in aqueous media. Tetrahedron (2001) 57: 1395-1398.
26. Elinson MN, Ilovaisky AI, Valentina MM Pavel AB Belyakov PA and Alexander OC. Solvent-free cascade reaction: direct multicomponent assembling of 2-amino-4H-chromene scaffold from salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes. Tetrahedron (2010) 66: 4043-4048.
27. Miri R, Firuzi O, Peymani P, Nazarian Z, Shafiee A. Synthesis and Cytotoxicity Study of New Cyclopenta [b] quinoline-1,8-dione Derivatives. Iranian J. Pharm. Res. (2011) 10: 489-496.
28. Miri R, Javidnia K, Amirghofran Z, Salimi SH, Sabetghadam Z, Meilia S, Mehdipour AR. Cytotoxic Effect of Some 1, 4-Dihydropyridine Derivatives Containing Nitroimidazole Moiety. Iranian J. Pharm. Res. (2011) 10: 497-503.
29. Vosooghi M, Yahyavi H, Divsalar K, Shamsa H, Kheirollahi A, Safavi M, Ardestani SK, Sadeghi-Neshat S, Mohammadhosseini N, Edraki N, Khoshneviszadeh M, Shafiee A, Foroumadi A. Synthesis and In vitro cytotoxic activity evaluation of (E)-16-(substituted benzylidene) derivatives of dehydroepiandrosterone. DARU J. Pharm. Sci. (2013) 21:34.
30. Noushini S, Emami S, Safavi M, Ardestani SK, Gohari AR, Shafiee A, Foroumadi A. Synthesis and cytotoxic properties of novel (E)-3-benzylidene-7-methoxychroman-4-one derivatives. DARU J. Pharm. Sci. (2013) 21:31.
31. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods (1983) 65: 55-63.
32. Khurana JM, Nand B, Saluja P. DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium. Tetrahedron (2010) 66: 5637-5641.
33. Aggarwal VK, Mereu A. Superior amine catalysts for the Baylis-Hillman reaction: the use of DBU and its implications. Chem. Commun. (1999) 2311-2312.
34. Reed R, Réau R, Dahan F, Bertrand G. DBU and DBN are strong nucleophiles: X-ray crystal structures of onio-and dionio-substituted phosphanes Angew. Chem., Int. Ed. Engl. (1993) 32: 399-401.