Design, Synthesis, and Biological Evaluation of Angiogenesis Inhibitors: Aromatic Enone and Dienone Analogues of Curcumin.

Synthesis and biological analysis of new curcumin analogues bearing an enhanced potential for the medicinal treatment of cancer

“…GO-Y030 and GO-Y031 have a higher capacity for growth suppression in many cancer cell lines than has been reported in curcumin analogues to date. Some points of success of the modification were consistent with previous reports (26,27). It was also proposed that the unsaturated structures, such as a,h-unsaturated ketone moiety, are likely to act as Michael acceptors (26,27); however, the effects of these structural modifications on the cellular biological reactions have not been described thus far.…”

“…Some points of success of the modification were consistent with previous reports (26,27). It was also proposed that the unsaturated structures, such as a,h-unsaturated ketone moiety, are likely to act as Michael acceptors (26,27); however, the effects of these structural modifications on the cellular biological reactions have not been described thus far. This is the first time that an a,h-unsaturated ketone modification has been shown to be important in cell growth regulation.…”

“…As the results of the first screening, one direction of development, in which the 7-carbon tether of curcumin is converted to 5-carbon tether, was chosen. During the course of our work, we noted that Bowen et al and the Shoji-Snyder team published results on the high degree of anticancer activity of diarylpentanoids, including a molecule identical to GO-035 (26,27). However, our studies indicate that the second direction in which the location and dimensions of the substitutions on the aromatic rings are also important.…”

“…However, it has some short points, including its low bioavailability claimed in vivo. These characters of curcumin are encouraging investigators to modify it into more aggressive forms to induce tumor suppression (23,26,27). Our strategy is to develop the new curcumin analogues systemically.…”

An Expeditious and Safe Synthesis of Some Exocyclic α,β-Unsaturated Ketones by Microwave-Assisted Condensation of Cyclic Ketones with Aromatic Aldehydes over Anhydrous Potassium Carbonate

“…Some of the exocyclic α,β-unsaturated ketones, namely, aurones and E-3-benzylidenechromanones, are natural compounds [1,[5][6][7]. It may be mentioned here that several classes of compounds belonging to this category show interesting biological properties, for example, α,α -(E,E)-bis(arylidene)-cycloalkanones show antiangiogenic [8,9], quinine reductase inducer [10], arginine methyltransferase inhibitor [11], cytotoxic [12,13], cholesterol-lowering [14], and antitubercular [15] activities, and E-3-benzylidenechromanones and related homoisoflavonoids show antioxidant, antiinflammatory, antifungal, antiviral, antiallergic, antihistaminic, antirhinovirus, antimutagenic, angioproductive, hypocholesterolemic, and cytotoxic activities [7,16]. Moreover, α,α -(E,E)-bis(arylidene)-cycloalkanones find application as fluorescent materials [17] and in the preparation of nonlinear optical materials and liquid-crystalline polymers [18].…”