Ultrasound-promoted synthesis, biological evaluation and molecular docking of novel 7-(2-chloroquinolin-4-yloxy)-4-methyl-2H-chromen-2-one derivatives

Synthesis and Biological Properties of Coumarin Derivatives. A Review

“…EtOH, using piperidine as base-catalyst, Scheme 44. [71] 7-(2-Chloroquinolin-4-yloxy)-4-methyl-2H-chromen-2-ones, Scheme 45, were synthesized by Balaji et al [72] from substituted 1,3-dichloroquinoline and 7-hydroxy-4-methylcoumarin using conventional or under ultrasonic irradiation conditions. Kavetsou et al [73] described the synthesis of new 3-aryl-5substituted-coumarin derivatives in three steps starting from phenylacetic acid and dihydroxyacetophenone, Scheme 46.…”

“…3‐Cinnamoyl‐2 H ‐chromen‐2‐one was synthesized in two‐steps allying Knoevenagel condensation using salicylaldehyde, ethyl acetoacetate and piperidine in catalytic amount at room temperature and a Claisen‐Schmidt condensation in. EtOH, using piperidine as base‐catalyst, Scheme 44 [71] …”

Recent advances and perspectives in the synthesis of bioactive coumarins

“…All compounds showed moderate to good activity against all the tested organisms. With an eye to the relevance of both quinoline (antimalarial, anti-inflammatory, antiasthmatic, antibacterial, antihypertensive and anticancer activity) and coumarin as pharmacophoric units, Balaji et al (2013), 63 While the observed reactivity of the halogen atoms in the various quinolines varied widely, kinetic studies underlined the fact that the chlorine atom on the C-4 of 2,4-dichloroquinolines showed doubled reactivity towards nucleophilic reactions (making this a highly regioselective procedure), which predominantly take place via a σ X complex in an additionelimination mechanism. All synthesized compounds were screened for antibacterial (E. coli, P. aeruginosa, S. aureus, and B. subtilis) and antioxidant activities.…”

“…With an eye to the relevance of both quinoline (antimalarial, anti-inammatory, antiasthmatic, antibacterial, antihypertensive and anticancer activity) and coumarin as pharmacophoric units, Balaji et al (2013), 63 have reported the synthesis of 7-(2chloroquinolin-4-yloxy)-4-methyl-2H-chromen-2-one derivatives and their in vitro antibacterial, antioxidant and molecular docking studies. Quinoline-based coumarin derivatives were synthesized via the one-pot alkylation of 2,4-dichloroquinolines with 7-hydroxy-4-methyl-2H-chromen-2-one in the presence of catalytic amounts of K 2 CO 3 under ultrasonic irradiation (60 C, 20 min) (Scheme 22).…”

Microwave-assisted clean synthesis of xanthenes and chromenes in [bmim][PF6] and their antioxidant studies

“…With all of this in mind, and as part of our ongoing research devoted to the development of novel synthetic methods in heterocyclic chemistry [26][27][28][29][30], here we describe the microwave-assisted synthesis of xanthene and chromene derivatives by the reactions of arylaldehydes, 2-naphthol or 4-hydroxycoumarin and 1,3-cyclodiones in 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF 6 ]).…”