New and Efficient Rout for One Pot Synthesis of acenaphtho[1,2-b] quinoxalines
محورهای موضوعی : Journal of Chemical Reactivity and Synthesis
Zahra Haghighi ju
1
(Department of Medicinal Chemistry , Mazandaran University of Medical Sciences , Sary, Iran)
کلید واژه: Synthesis, Acenaphthene-1, 2-dione, pyrimidine , quinoxalines,
چکیده مقاله :
Acenaphtho derivatives have been reported as antitumor agents. So, the reaction of acenaphthylene-1,2-dione with 3,4-diaminobenzenethiol, and then with the alkyl chloride derivatives for the synthesis of acenaphtho [1,2-b] quinoxalines are reviewed. Excellent yields of the products, short reaction times and simple work-up are attractive features of this suitable protocol.
1. Weber L, Illgen K, Almstetter M: Discovery of new multi component reactions with combinatorial methods. Synlett 1999, 3:366–374.
2. Tietze LF, Modi A: Multicomponent domino reactions for the synthesis of biologically active natural products and drugs. Med Res Rev 2000, 20:304–322.
3. Ganem B: Strategies for innovation in multicomponent reaction design. Acc Chem Res .2009, 42:463–472.
4. Marcaurelle LA, Johannes CW: Application of natural product-inspired diversity oriented synthesis to drug discovery. Prog Drug Res 2008, 66:187–216.
5. Brown, D. J.; Evans, R. F.; Cowden, W. B.. In The Pyrimidines; Taylor, E. C., Weissberger, A., Eds.; John Wiley: New York, 1994; Vol. 52,.
6. Johar, M.; Manning, T.; Kunimoto, D. Y.; Kumar, R. Bioorg. Med. Chem. 2005, 13, 6663.
7. Azas, N.; Rathelot, P.; Djekou, S.; Delmas, F.; Gellis, A.; Di Giorgio, C.; Vanelle, P.; Timon-David, P. Il Farmaco 2003, 58, 1263.
8. Ulaczyk-Lesanko A, Hall DG: Wanted: New multicomponent reactions for generating libraries of polycyclic natural products. Curr Opin Chem Biol 2005, 9:266–276.
9. Ahmed A, Daneshtalab M: Polycyclic quinolones (part 1)-thieno[2,3-b]benzo[h]- quinoline derivatives: design, synthesis, preliminary in vitro and in silico studies.
Heterocycles 2012, 85:103–122.
10. Kock I, Heber D, Weide M, Wolschendorf U, Clement B: Synthesis and biological evaluation of 11-substituted 6-aminobenzo [c] phenanthridine derivatives, a new class of
antitumor agents. J Med Chem 2005, 48:2772–2777.
11. Khan IA, Kulkarni MV, Gopal M, Shahabuddin MS, Sun CM: Synthesis and biological evaluation of novel angularly fused polycyclic coumarins. Bioorg Med Chem Lett 2005,
15:3584–3587.
12. 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.
13. Rescifina A, Zagni C, Romeo G, Sortino S: Synthesis and biological activity of novel bifunctional isoxazolidinyl polycyclic aromatic hydrocarbons. Bioorg Med Chem 2012,
20:4978–4984.
14. Banik BK, Becker FF: Polycyclic aromatic compounds as anticancer agents: structure-activity relationships of chrysene and pyrene derivatives. Bioorg Med Chem2001, 9:593–605.
15. Madakar Sobhani A, Rasoul Amini S, Tyndall JDA, Azizi E, Daneshtalab M, Khalaj A: A theory of mode of action of azolylalkylquinolines as DNA binding agents using
automated flexible ligand docking. J Mol Graph Model 2006, 25:459–469.
16. Lee CH, Jiang M, Cowart M, Gfesser G, Perner R, Kim KH, Gu YG, Williams M, Jarvis
MF, Kowaluk EA: Discovery of 4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3- yl) pyrido [2, 3-d] pyrimidine, an orally active, non-nucleoside adenosine kinase
inhibitor. J Med Chem 2001, 44:2133–2138.
17 .Javad Azizian , Mohammad K. Mohammadi , Omidreza Firuzi , Behrooz Mirza and Ramin Miri . Chem Biol Drug Des 2010; 75: 375–380
18. Mohammad K Mohammadi Omidreza , Firuzi , Mehdi khoshneviszadeh , Nima Razzaghi-Asl , Saghi Sepehri , Ramin Miri . DARU Journal of Pharmaceutical Sciences 2014, 22:2 .
