Synthesis and Photooxygenation of Furo[3,2‐c]coumarin Derivatives as Antibacterial and DNA Intercalating Agent

Abstract

Syntheses of 2,3‐dimethyl‐4H‐furo[3,2‐c]coumarin and 3‐phenyl‐4H‐furo[3,2‐c]coumarin as angular furocoumarins were carried out through Williamson reaction of 4‐hydroxycoumarin with α‐haloketones followed by cyclization. Photooxygenation of the synthesized furocoumarin derivatives was performed and the photoproducts were isolated and characterized. The affinity of 2,3‐dimethyl‐4H‐furo[3,2‐c]coumarin towards DNA and the antibacterial activity were evaluated and compared with 8‐methoxypsoralen (8‐MOP).

Radioiodination of 2,3-dimethyl-4H-furo[3,2-c]coumarin and biological evaluation in solid tumor bearing mice

“…Synthesis of 2,3-dimethyl-4 H -furo[3,2- c ]coumarin and 3-phenyl-4 H -furo[3,2- c ] coumarin. The synthetic route for the preparation of the furocoumarin derivative is displayed as phenol was converted in 50% yield to the 4-hydroxycoumarin by the reaction with malonic acid in the presence of phosphorous oxychloride as described in the literature by Al-Sehemi and El-Gogary (2012) . Synthetic compound was evaluated by IR, NMR and mass spectroscopy.…”

Synthesis, Photooxygenation and DNA Studies of Novel Fused Furo, Dioxolo, and Dioxino Derivatives of Coumarin

“…Accoding to equation 1, the stability constant (K S ) was calculated through the decrease of peak currents with increasing concentration of DNA. The stability constant (K S ), which is usually used to characterize the intercalation phenomena of DNA systems, was 204 and 1770 M À 1 for 8-MOP [34] and furocoumarin 3 respectively as calculated from the y-intercept, Figures 2 and 3. The calculated value of K S of the synthesized furocoumarin (3) demonstrates an enhancement of complex formation with DNA by a factor of 8.7 compared to 8-MOP.…”

The crystal structure of 2-oxo-2H-chromen-4-yl acetate, C11H8O4

“…These compounds have been observed to have multiple biological and pharmaceutical activities [8][9][10]. Coumarins have been prepared by several methods which include von Pechmann, Perkin, Reformatsky, Knoevenagel and Wittig reactions [11]. In addition, coumarins serve as building blocks in the synthesis of novel biological active compounds.…”