A series of C‐alkylated chalcones on ring ‘B’ of C6‐C3‐C6 system of the basic flavonoid skeleton were synthesized by taking different alkyl substituted aldehydes by conventional approaches. The compounds (5 a‐l) were obtained by condensing di‐O‐methylated phloroacetophenone with various alkylated (methyl, di‐methyl, ethyl and n‐propyl) substituted aromatic aldehydes (4 a‐l) and characterized by different spectroscopic methods (IR, NMR, LC–MS and elemental analysis) and further studied their inhibitory action on 5‐lipoxygenase (5‐LOX) enzyme. The compounds (E)‐3‐(4‐ethoxy‐5‐methoxy‐2‐methylphenyl)‐1‐(2‐hydroxy‐4,6‐dimethoxyphenyl) prop‐2‐en‐1‐one (5 k), (E)‐3‐(2,4‐dimethoxy‐5‐methylphenyl)‐1‐(2‐hydroxy‐4,6‐dimethoxy phenyl)prop‐2‐en‐1‐one (5 i), (E)‐3‐(4,5‐dimethoxy‐2‐methylphenyl)‐1‐(2‐hydroxy‐4,6‐dimethoxyphenyl)prop‐2‐en‐1‐one (5 j), and (E)‐1‐(2‐hydroxy‐4,6‐dimethoxyphenyl)‐3‐(2‐methoxy‐4,5‐dimethylphenyl)prop‐2‐en‐1‐one (5 l) showed a significant 5‐LOX enzyme inhibitory action with IC50 ranging between 49.1 and 52.3 μM, whereas positive control curcumin exhibited IC50 of 22 μM. The molecular docking simulation study revealed that the compounds were well accommodated in the allosteric site of the enzyme, 5‐LOX.
Ad iverses cope of 2-aryl-1,3-dicarbonyl substrates was investigated in an efficient and facile enolate-directed CÀHa lkenylation process using readily availablee lectron-deficient alkenes. The developed domino strategy works under rhodium catalysis, providing ar ange of benzopyran heterocycles by the formationo ft wo distinct CÀCa nd CÀOb onds and one new six-membered ring. The salient features of the protocoli nclude the broad range of previously unexplored 1,3-dicarbonyl substrates for CÀHa lkenylations, good functional group tolerance and rapid assembly of new benzopyrans in generally good to excellent isolated yields. Figure 1. Selected examples of bioactive benzopyrans.[a] Dr.
Sonogashira coupling between diversely substituted 2‐benzyloxy‐5‐bromopyrimidines and various aryl and aliphatic alkynes in the presence of catalytic amount of PdCl2(PPh3)2 with diethylamine and CuI as a co catalyst in THF at 60 °C afforded 17 new 2‐benzyloxy‐5‐alkyne substituted pyrimidines in good yields (85–94 %). The cytotoxic activity of resulted compounds were evaluated against A549 (Human lung adenocarcinoma cell line), HepG2 (Human liver cancer cell line) and HCT116 (Human colon cancer cell line) cancer cell lines. Some of the 2‐benzyloxy‐5‐alkyne pyrimidines synthesized were found to be shown moderate in vitro cytotoxic activity against A549 cell line.
A series of seventeen C-dimethyl chalcones on ring ‘A’ were synthesized by using a known condensation method. The chalcones include the utilization of heterocyclic aldehydes such as N,N-dimethyl benzaldehyde, furfural-2-aldehyde, and N-methyl indole aldehyde. All the compounds were found to possess moderate to potent anticancer activity on human lung adenocarcinoma cell line “A549” in the MTT cell proliferation method. The dimethyl chalcone 9f with furfural ring was found to possess potent anti-cancer activity followed by 9m with o-chloro substitution on ring ‘B’ with IC50values of 1.0 and 1.2 μg/mL respectively. Similarly compounds 9n, 9j, 9g, 9k, 9p, 9d, 9b,and 9ealso showed good anti-cancer activity (IC50values from 6.5 to 9.8μg/mL). Further, the compounds were also compared with the known anti-TB activities in order to ascertain their properties towards dual acting agents against tuberculosis and cancer for more beneficiaries.
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