Synthesis of novel benzofurocoumarin analogues and their anti-proliferative effect on human cancer cell lines

Abstract

The synthesis of five new tetracyclic benzofurocoumarin (benzopsoralen) analogues is described. Their inhibitory effects on the growth of three human tumor cell lines (MDA MB 231 (breast adenocarcinoma), HeLa (cervix adenocarcinoma) and TCC-SUP (bladder transitional cell carcinoma) were evaluated, and discussed in terms of structure-activity relationship.

Evaluation of the Antioxidant Capacity of Synthesized Coumarins

“…Several recent studies have shown the ability of coumarins to reduce ROS production and consequently the damage to lipids, protein and DNA found in various biological processes, for instance in cancer [13,14] and inflammatory conditions [4,15]. In light of these studies, there is clearly a current interest in developing molecules with high antioxidant activity as potential drug candidates to be adopted against these pathologies, and coumarins stand out as promising antioxidants with pharmacological interest [16,17].…”

“…Some of them are physiologically active and have recently been extensively studied for their antioxidant properties. In fact, several studies have shown that coumarins elicit antitumoral [1,2], anti-inflammatory [3,4] and neuroprotective effects [5,6], and that the inhibition of oxidative stress is a contributing factor in each of these biological effects. Indeed, coumarins have been reported to affect the formation and scavenging of reactive oxygen species (ROS) and influence free radical-mediated oxidative damage, thus the development of new synthesized coumarin molecules is promising, especially regarding their antioxidant activities.…”

Novel benzopsoralen analogues: Synthesis, biological activity and molecular docking studies

“…Additionally, Psoralen and 8-methoxypsoralen (8-MOP, named Xanthotoxin) are used for the treatment of Psoriasis in combination with UVA irradiation (PUVA therapy) [3]. It is important to notice that these compounds have also been reported to have an anti-cancer effect independently of its photoactivation [4,5]. It has been reported that Bergapten (5-methoxypsoralen) enhances p53 gene expression and induces apoptosis in human breast cancer cells [6].…”

Oxidant‐Controlled Catalytic Transformations of Phenols with Unexpected Cleavage of Aromatic Rings

“…As shown in Scheme 4, the tert-butyl and methyl groupso f4a were easily removed by AlCl 3 in refluxing toluene, affording dibenzofuran-2-ol 7 in 91 %y ield. Compound 7 is an important intermediate for the synthesis of many bioactive substances, such as HeLa (cervix adenocarcinoma) and TCC-SUP (bladder transitional cell carcinoma) cells inhibitor 8, [20] HeLa and MDA MB231 (breasta denocarcinoma) cells inhibitor 9, [21] and H37Rv (mycobacterium tuberculosis) growth inhibitor 10. [22] In summary,an ovel coppercatalyzed tandemo xidative homocoupling/skeletal rearrangement of phenolst hat involves the cleavage of ab enzene ring under mild reaction conditions has been realized by using air or Ag 2 CO 3 as the oxidant.…”