Synthesis of 3-aryl-4-(N-aryl)aminocoumarins via photoredox arylation and the evaluation of their biological activity

• Published in: Bioorganic chemistry Vol. 114; p. 105141
• Main Authors: Carneiro, Leonardo S.A., Almeida-Souza, Fernando, Lopes, Yanne S.C., Novas, Rachel C.V., Santos, Kaique B.A., Ligiero, Carolina B.P., Calabrese, Kátia da S., Buarque, Camilla D.
• Format: Journal Article
• Language: English
• Published: SAN DIEGO Elsevier Inc 01.09.2021; Elsevier
• Subjects: ADMET; Aminocoumarin; Aminocoumarins - chemical synthesis; Aminocoumarins - chemistry; Aminocoumarins - pharmacology; Animals; Antiprotozoal Agents - chemical synthesis; Antiprotozoal Agents - chemistry; Antiprotozoal Agents - pharmacology; Arylation; Arylcoumarin; Biochemistry & Molecular Biology; Cell Proliferation - drug effects; Chemistry; Chemistry, Organic; Cytotoxicity; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Female; Humans; In silico; Leishmania - drug effects; Leishmaniasis; Life Sciences & Biomedicine; Mice; Mice, Inbred BALB C; Molecular Structure; Oxidation-Reduction; Parasitic Sensitivity Tests; Photochemical Processes; Photoredox catalysis; Physical Sciences; Science & Technology; Structure-Activity Relationship; Tumor Cells, Cultured; X-ray diffraction; Photoredox catalysis; Arylation; Aminocoumarin; X-ray diffraction; Cytotoxicity; In silico; Arylcoumarin; Leishmaniasis; ADMET; DESIGN; ANALOGS; CANCER; BREAST; IN-VITRO; POTENT; AMASTIGOTES; 4-SUBSTITUTED COUMARINS; DERIVATIVES; ACCESS

[Display omitted] •The synthesis of 18 new 3-aryl-4-(N-aryl)aminocoumarins was achieved in two steps.•The key step of the proposed route is a photoredox arylation.•Compound 17x was more selective to L. amazonensis than miltefosine.•In silico analysis suggested that 17x is a candidate for anti-leishm...