Coumarins: A Unique Scaffold With Versatile Biological Behavior

Abstract

Benzopyrones are the club of compounds that can be coumarins or flavonoids. The hydroxyl derivatives of coumarins such as 4-hydroxycoumarins and 7-hydroxycoumarins have extensive biological activities which have employed for the synthesis of miscellaneous coumarin derivatives. These derivatives have exhibited impressive pharmacological and physiological activities such as anticoagulant, antibacterial, antiviral, antitumor, bactericidal, fungicidal, anti-inflammatory agents, and anti-HIV activity. This review comprised pharmacokinetic studies, including absorption, distribution, and metabolism of coumarin analogs along with toxicological studies. The studies of coumarins and their derivatives exhibiting immense pharmacological activity are also summarized in the current study.

Mannich bases of hydroxycoumarins: synthesis, DFT/QTAIM computational study and assessment of biological activity

“…NMR experiments were carried out in solution using methanold 4 and DMSO-d 6 as solvents. 1 H and 13 C NMR experiments were recorded in an Agilent Technologies DD2 500 MHz spectrometer. Chemical shis are reported in ppm, multiplicity by means of coupling constants is measured in hertz (Hz).…”

“…The crude was puried by column chromatography using hexane-ethyl acetate mixture as eluent (8 : 2) to give 3.1 g (85% yield) of a yellow solid which is easily oxidized, thus it was stored at 5 C and used immediately. 1 H-NMR (500 MHz, CD 3 OD-d 4 ) d, ppm: 6.57 (d, 1H, J ¼ 8.5 Hz), 6.30 (d, 1H, J ¼ 2.8 Hz), 6.12 (dd, 1H, J ¼ 8.5, 2.8 Hz). 13 General procedure for the synthesis of 4-methylhydroxycoumarins (4).…”

“…7-Hydroxy-4-methyl-2H-chromen-2-one (4a). Yellow solid, 85% yield, mp 185-187 C. 1 General procedure for the synthesis of 8-substituted coumarin Mannich bases (5a-5f). In a round bottom ask equipped with a magnetic bar and condenser, the appropriate amine (0.03 mol) and aqueous formaldehyde (37%) (0.03 mol) were mixed in 20 mL absolute methanol at 50 C for 30 minutes.…”

“…Yellow solid 54% mp 60-62 C 1. H NMR (500 MHz, DMSO-d 6 ) d 7.50 (d, 1H, J ¼ 8.7 Hz), 6.69 (d, 1H, J ¼ 8.7 Hz), 4.01 (s, 2H), 2.66 (q, 4H, J ¼ 7.1 Hz), 2.34 (d, 4H, J ¼ 0.9 Hz), 1.06 (t, 6H, J ¼ 7.2 Hz) 13.…”

Coumarin-Based Triapine Derivatives and Their Copper(II) Complexes: Synthesis, Cytotoxicity and mR2 RNR Inhibition Activity

“…For example, the insertion of a biologically active morpholine fragment into TSC backbones improved their aqueous solubility and anticancer activity in various cancer cell lines [23,26]. Herein, a biologically active coumarin (or 2H-chromen-2-one) fragment (Chart 1, right) was selected to be incorporated, due to its well-documented wide spectrum of activities, including antibacterial, antifungal, neuroprotective, antiamoebic, anti-inflammatory, and cytotoxic properties [27][28][29][30][31][32][33][34][35][36][37][38]. In addition, another biologically active piperazine fragment was included, since heteroaromatic ring systems are considered highly impactful design elements for the optimisation of key pharmacological parameters [23,39].…”