Synthesis of Polyalkoxy-3-(4-Methoxyphenyl)Coumarins with Antimitotic Activity from Plant Allylpolyalkoxybenzenes

Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents

“…4,7-Dimethoxy-1,3-benzodioxol-5-ol ( 12) was synthesized according to a published procedure. 38 Synthesis of Isoapiol (10). A suspension of apiol ( 7) (666.6 g, 3 mol) and finely powdered KOH (118 g, 2.1 mol) was heated for 2.5 h at 85−95 °C in a rotary-film evaporator.…”

“…Synthesis of 5-Allyloxy-4,7-dimethoxy-1,3-benzodioxol (13). A solution of 4,7-dimethoxy-1,3-benzodioxol-5-ol ( 12) 38 (279 mg, 1.41 mmol) and powdered NaOH (60 mg, 1.5 mmol) in dimethylformamide (DMF) (2 mL) was stirred for 20 min at room temperature, and then allyl bromide (188 mg, 1.55 mmol) was added. The mixture was stirred for 1 h, diluted with water (10 mL), neutralized with HCl, and extracted with CH 2 Cl 2 (2 × 5 mL).…”

“…14 A combination of the specialized ozonolysis equipment and optimized protocols described earlier 37 allowed for preparation of the targeted aldehyde 11 in yields up to 80% on a 100 g scale (Scheme 1). Oxidation of apiol aldehyde (11) under Bayer−Villiger rearrangement conditions at room temperature afforded phenol 12, 38 which was further alkylated by allyl bromide to ether 13. Aromatic Claisen rearrangement of 13 to hydroxyapiol (14) followed by alkylation with dimethyl sulfate afforded the target nothoapiol (9).…”

3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade

“…Compound 46 proved to be an interesting candidate against A549, a pancreatic cancer cell line (Panc-28), and human colorectal carcinoma cells (HCT-116), with GI 50 values of 7.39, 25 and 19.17 µM, respectively [3]. Novel polyalkoxy-3-(4 -methoxyphenyl)coumarin analogues, i.e., compound 47 and natural antimitotic compounds, have been synthesized from plant allylpolyalkoxybenzenes and tested in vivo in the phenotypic sea urchin embryo assay for antiproliferative antitubulin activity [126]. The described 4 -amino-derivative 48 induces Hes 1 downregulation and displays antitumor effects against HCT-116 cells [127].…”

Natural source, bioactivity and synthesis of 3-Arylcoumarin derivatives

“…They are widely distributed in fruits, flowers, seeds, vegetables and in both legumes and non-legume plants 3 . In the past decade, they have attracted increasing attention, and medicinal chemists have constructed a series of 3-arylcoumarin structures with diverse biological effects and studied their pharmacological activities such as antiviral 4 , 5 , antibacterial 6–8 , antimicrobial 9 , anti-inflammatories 10–13 , antiplatelet 14 , antioxidant activity 15–20 , antimitotic activity 21 , 22 , antidepressant 23 , and anti-Alzheimer’s disease 24 , 25 .…”