Chromene scaffold

The antiproliferative and antitubulin activities of libraries of pyranopyridones and pyranoquinolones 147 (Scheme 28) derived from aldehydes, malononitrile and pyridones 146 have been examined [65]. The compounds were evaluated for their ability to reduce cell viability by 50% after 48 h of treatment relative to control. The HeLa and MCE-7 cell fines were used as models for human cervical and breast adenocarcinoma, respectively. Numerous compounds exhibited submicromolar antiproliferative activities with the quinolones being more potent than their pyridine counterparts (Eig. 20). Because of the structural similarity of pyranopyridones with chromene scaffolds known to inhibit tubulin polymerization, compounds 149 and 150 were further evaluated in Jurkat cells for their apoptotic... 

M. R. Naimi-Jamal, S. Mashkouri, A. Sharifi, Mol. Divers. 2010, 14, A13-A11. An efficient, multicomponent approach for solvent-free synthesis of 2-amino-47/-chromene scaffold. 

Brahmachari, G., and Laskar, S. (2014). Nano-MgO-catalyzed one-pot synthesis of phosphonate ester functionalized 2-amino-3-cyano-4//-chromene scaffolds at room temperature. Phosphorus, Sulfur, and Silicon and the Related Elements, 189, 873-888. 

M.N. EUnson, A.S. Dorofeev, F.M. Miloserdov, A.l. Ilovaisky, S.K. Feducovich, P.A. Belyakov, G.l. Nikishina, Catalysis of salicylaldehydes and two different C-H acids with electricity first example of an efficient multicomponent approach to the design of functionalized medicinally privileged 2-amino-4H-chromene scaffold, Adv. Synth. Catal. 350 (2008) 591-601. 

In 2011, Wu and co-workers developed a palladium-catalyzed reaction of 2-allq nylhalobenzenes with 2-alkynylphenols in the presence of PCys for the synthesis of indeno[l,2-c]chromenes (Scheme 3.39)/ This reaction works efficiently, leading to the corresponding products in good to excellent yields. Additionally, the group reported later that the scaffold of indeno[l,2-c]-chromene could he constructed via a palladium-catalyzed reaction of 2-allgmylhromohenzene with water, in which four bonds are formed with high efficiency. 

Dihydropyrano[3,2-c]chromenes have recently attracted much attention as an important class of heterocycles having useful biological and pharmacological properties such pyran-annulated scaffolds are obtained from the reaction of 4-hydroxycoumarin (13) with aldehydes and C-H activated acids (e.g., malononitrile, ethyl 2-cyanoacetate, etc.). Recently, Khoobi et al. [95] developed an efficient protocol for the synthesis of dihydropyrano[3,2-c]chromenes 14 in aqueous medium in the presence of nanocatalyst, (2-aminomethyl)phenol, supported on HAp-encapsulated-Y-Fe203 ([Y-Fe203 Hap-Si(CH2)3-AMP]) under reflux condition (Scheme 7). "Qn-water" syntheses of such scaffolds were also reported earlier by Khurana et al. [81] and Shaabani et al. [86] (Scheme 7). 

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