Copper-Catalyzed Asymmetric Hydroboration Reaction of Novel Methylene Isoindolinone Compounds through Microwave Irradiation and Their Antileishmanial and Antitoxoplasma Activities

Abstract

The aim of this study was devoted into molecular docking calculations to discover the potential antileishmania and antitoxoplasma activities of newly synthesized compounds obtained by applying a practical and simple method under microwave irradiation. All these compounds were tested in vitro for their biological activity against Leishmania major promastigotes, amastigotes, and Toxoplasma gondii tachyzoites. Compounds 2a, 5a, and 5e were the most active against both L. major promastigotes and amastigotes, with IC 50 values of less than 0.4 μM mL −1 . Compounds 2c, 2e, 2h, and 5d had a strong antitoxoplasma activity of less than 2.1 μM mL −1 against T. gondii. We can conclude that aromatic methyleneisoindolinones are potently active against both L. major and T. gondii. Further studies for mode of action evaluation are recommended. Compounds 5c and 5b are the best drug candidates for antileishmania and antitoxoplasma due to their SI values being over 13. The docking studies of compounds 2a-h and 5a-e against pteridine reductase 1 and T. gondii enoyl acyl carrier protein reductase reveal that compound 5e may be an effective antileishmanial and antitoxoplasma drug discovery initiative.

Synthesis, DFT calculations, and investigation of catalytic and biological activities of back‐bond functionalized re‐NHC‐Cu complexes

“…[68][69][70][71] These findings support our previous claim that NHC complexes of potent antileishmanial and antitoxoplasmal activity. 70,71 T A B L E 4 Antioxidant activity of 3a-e complexes assessed by DPPH, ABTS antiradical scavenging power, and β-carotene bleaching test presented by their IC 50 in μM mL À1 of mean ± SD.…”

Microwave-Assisted Semisynthesis and Leishmanicidal Activity of Some Phenolic Constituents from Lichens

“…Additionally, this technique is regarded as an ecofriendly source of energy in chemical synthesis, with better yields and higher purities when compared with traditional processes [5]. This approach has been employed to obtain new antileishmanial compounds such as natural-product-inspired functionalized spiro[indoline-3,2 -pyrrolidin]-2-one/spiro[indoline-3,3 -pyrrolizin]-2-one derivatives [6], γ-butyrolactones derivatives [7], methylene isoindolinone compounds [8], and 5-substituted benzylidene amino-2-butyl benzofuran-3-yl-4-methoxyphenyl methanones [9]. Keeping this in mind, we focused our interest on the condensation of amines with ketones to form imines, a reaction that has proven to be feasible under microwave conditions with promising results [10].…”