In this work, efficient synthesis of isoindolin-1-one-3-phosphonates under catalyst-and solvent-free conditions was reported to afford the desired compounds in excellent yields with potent pharmacological properties. The synthesis method involves the preparation of isoindolin-1-one-3-phosphonates by a "one-pot" three-component reaction of 2-formylbenzoic acid with primary amines and dimethyl phosphite under solvent-and catalyst-free conditions.All new compounds were characterized by 1 H NMR, 13 C NMR, FT-IR and elemental analysis techniques. The compounds were investigated for their bioactivities against a group of microorganisms, Leishmania major, Toxoplasma gondii parasites, and the DA-MB-231 and MCF-7 cancer cell lines in vitro.Compound 4a was found to be the most active against L. M. luteus, L. monocytogenes and C. albicans microorganisms, with inhibition zones of 35, 22 and 38 mm, respectively. The compounds were also investigated for their antiparasitic activities, and compounds 4a and 4b were the most active against L. major amastigotes and promastigotes with EC 50 < 1 μM. All tested compounds had potent anticancer activity against the MDA-MB-231 and MCF-7 human cell lines with EC 50 < 1.5 μM. Compounds 4a and 4b are good drug candidates for antimicrobial, antileishmanial and anticancer drug discovery, and further in vivo studies are highly recommended prior to any clinical trials.
We reported in this study the hydroboration of enamides in methanol at room temperature catalyzed by copper complexes. Under such conditions, a Gram-scale reaction with a high yield was also completed. Hydroboration of 3-methylene, 2-(alkyl and phenylisoindolin-1-one 5 with bis(pinacolato)diboron yields the respective compounds 6 in good yields with high-to-moderate enantioselectivity (58% ee). Furthermore, the antimicrobial properties of the synthesized compounds were tested against four indicator microorganisms: the two Gram-positive bacteria L. monocytogenes ATCC 1911 and S. aureus ATCC 6538, the Gram-negative bacterium S. typhimurium ATCC 14028, and the fungus C. albicans (ATCC 90028). The MIC values of compounds 5-6 range from 0.312 to 2.5 (μg/mL) against L. monocytogenes, from 2.1 to 0.136 (μg/mL) against S. aureus, and from 0.126 to 0.923 (μg/mL) against S. typhimurium.
Multicomponent cyclocondensation of hydrazine derivatives, ethyl acetoacetate, aromatic aldehydes, and 4-hydroxycoumarin has been reported. The optimization details of the developed novel protocol are recorded. The novel procedure features short reaction time, moderate yields, and simple workup. In addition, BMIM[triflate] was chosen as a green solvent. The structures of the obtained benzylpyrazolyl coumarins were determined and confirmed by 1H NMR, 13C NMR, IR, and elemental analysis. The MIC values of benzylpyrazolyl coumarin derivatives were determined by the microbroth dilution method using 96-well plates. However, the derivatives 5a, 5b, 5d, and 5g possess the strongest activities. Compound 5b was the most active derivative against Candida albicans. Moreover, the antioxidant activity determination of these coumarins derivatives 5(a–g)–6(a–g) were studied with the DPPH and compared with gallic acid (GA)and butylated hydroxytoluene (BHT). Molecular modelling studies using DFT (density functional theory) calculations showed that there two tautomers A and B in which A is more stable than B. The benzylpyrazolyl coumarin derivatives 5e and 6f exhibited the most cytotoxic effect on the promising cytotoxic activity with IC50 values 4.45 μg/mL against MDA-MB-231 and 4.85 μg/mL against MCF7, respectively.
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