6 - Iranian Journal of Organic Chemistry Vol. 2, No. 1...

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Iranian Journal of Organic Chemistry Vol. 2, No. 1 (2010) 304-308 M. Esnaashari Isfahani, et al. 304 Synthesis of N -(3, 4, 4a, 10a-tetrahydro-2H, 5H-pyrano [2,3-b]chromen-5- yl)amines derivatives as antitumor compounds Manzarbanoo Esnaashari Isfahani, a* Narges Shojafard a and Ali Reza Foroumadi b a Department of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran b Pharmaceutical Sciences Research Center, Medical Science University of Tehran, Tehran, Iran Abstract: A Considering the importance of aromatic amines derivatives due to their biological activities, a new synthesis of 1- aminoanthraquinone and 4-nitroaniline through a one-pot three-component reaction with salicylaldehyde and 3,4-dihydro-2 H - pyran under mild conditions is reported. Keywords: Anthraquinone; Salicylaldehyd; Aniline; Antitumor; Multicomponent reaction. Introduction Secondary and Tertiary amino group is often engraved as a structural motif in various biologically active compounds [1-3] and also, are important and crucial intermediates in the synthesis of pharmaceutically active substances, dyes, and fine chemicals [4]. Aminoanthraquinones have drawn considerable attention from both synthetic and medicinal chemists due to their biological activities covering a wide range of applications. In recent years, the problem of multidrug resistance (MDR) towards multitudinous antitumor compounds has also become important and seminal and much effort has been directed towards incorporation of a five- or six-membered heterocyclic ring in the anthracenedione moiety [5]. Numerous aminoanthraquinone derivatives were identified as DNA intercalating agents [6] and the antitumor antibiotics, daunomycin and adriamycin [7] are examples of derivatives. Anthraquinone derivatives have been utilized for the activation of human telomerase reverse transcriptase expression [8, 9]. Annulated arene heterocycles and carbocycles such as chromanones, chromans, quinolines and tetrahydroquinolines [10, 14] are present as important and vital core structures in many biologically active natural products and pharmaceuticals. 2 H -1-Benzopyrans (chromenes) and 3, 4-dihydro-2 H -1-benzopyrans (chromens) are important and paramount classes of oxygenated heterocycles that have attracted much synthetic interest because of the biological activity of naturally betiding representatives [15-17]. Numerous 4- aminobenzopyrans and their derivatives have attracted considerable attention in the last decade as the modulators of potassium channels influencing cardiac activity of the heart and blood pressure [18]. The appropriate choice of aldehyde and amine in these reactions provides a facile entry to bis-heterocyclic systems, which is an essential moiety in many active pharmaceuticals. A number of Lewis acids such as lanthanide triflates,
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6 - Iranian Journal of Organic Chemistry Vol. 2, No. 1...

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