Michael/Michael Addition Cascade of 2‐Benzylidene‐1‐indanones with Chalcones: Synthesis and Biological Evaluations of Novel Polycyclic Compounds

Abstract

A series of novel racemic 2-aryloyl-1,3-diaryl-2,3,3a,8a-tetrahydrocyclopenta[a]inden-8(1H)-one derivatives were synthesized from KOtBu mediated Michael/Michael addition reaction of 2benzylidene-1-indanones with chalcones in high yields. This method provides an efficient route for the synthesis of a new class of polycyclic compounds have five stereo centers. The obtained polycyclic compounds were evaluated for the antimicrobial and anticancer activities against fifteen microorganism and three cell lines. The compound 3 r have the best activity value against the cells (MCF-7 IC 50 = 18.01 � 0.39 μg/ mL) (MDA-MB-231 IC 50 = 18.78 � 1.75 μg/mL) (MCF-10 A IC 50 = 31.31 � 0.05 μg/mL).

Synthesis and Caracterizations of New Thiosemicarbazone and Thiazole Derivatives From Polycyclic Chiral 1,5‐Diketones

“…In our previous work, we performed diastereoselective synthesis and structure determination of polycyclic chiral 1,5diketone derivatives. [28] Here, the structure determination of new thiosemicarbazone and thiazole derivatives is discussed. When the 1 H-NMR spectrum of the compound 3 a is examined, it is seen that the À NH proton on the thiosemicarbazone unit gives a singlet at 8.30 ppm, one of the À NH 2 protons in the structure gives a singlet at 8.00 ppm, and the other one gives multiplets between 7.69-7.62 ppm by overlapping with aromatic protons in the ortho position with respect to the ketone group in the 4-chlorophenylethanone unit in the structure.…”

“…In our previous work, we performed diastereoselective synthesis and structure determination of polycyclic chiral 1,5‐diketone derivatives [28] . Here, the structure determination of new thiosemicarbazone and thiazole derivatives is discussed.…”

“…(Scheme 1). Considering the three‐dimensional structure of polycyclic chiral compounds ( 1 a – n ), it is understood that the indanone unit in the structure folds inward and sterically blocks the related ketone unit [28] …”

“…In this respect, in this study, aimed to synthesis and characterization of new thiosemicarbazone (3 a-n) (Table 1) and thiazole derivatives (5 a-n) (Table 2) from polycyclic 1,5-diketone derivatives with five stereocenters, which we synthesized in our previous study (1 a-n). [28]…”

“…In the light of this information, it is seen that the synthesis of new thiosemicarbazone derivatives allow the synthesis of new bioactive and polyfunctional compounds and plays a key role. In this respect, in this study, aimed to synthesis and characterization of new thiosemicarbazone ( 3 a – n ) (Table 1) and thiazole derivatives ( 5 a – n ) (Table 2) from polycyclic 1,5‐diketone derivatives with five stereocenters, which we synthesized in our previous study ( 1 a – n ) [28] …”