Обзор посвящен рассмотрению зависимости биологической активности 1,3-дифенил-2-пропен-1-онов (халконов) от строения молекул. Выявлены фармакофорные группы, обуславливающие проявление антимикробной, противогрибковой, противоопухолевой, антиоксидантной, цитотоксической, антипролиферативной, противовоспалительной, гипергликемической, гепатопротекторной и других видов активности. Наличие хлорхинолинового фрагмента обеспечивает проявление антималярийной и антиамебной активности. Халконы с электронодонорными заместителями (метокси-, гидрокси- и др. группами), а также содержащие один – два атома хлора или фтора показывают наибольшую противомикробную и противогрибковую активность. Основания Шиффа, полученные на основе халконов с гетероциклическим фрагментом, а также борсодержащие халконы характеризуются высокой цитотоксичностью в отношении раковых клеток человека линий РС-3, MCF-7, KB, KB-VIN. 1,3-Дифенил-2-пропен-1-оны с оксатиолоновым циклом помимо цитотоксичности проявляют активность в отношении Micobacterium tuberculosis H37Rv. Халконы, содержащие в бензольном кольце ацетамидную группу в положении 4, проявляют значительную антиноцицептивную активность. Дигидроксопроизводные халконов с орто- и пара-расположением ОН групп проявляют высокую антиоксидантную активность. Положение двух гидроксильных групп в бензольном кольце В халкона является важным структурным фактором их антирадикальной активности. Вицинально диоксигенированные халконы, а также халконы с цепью пропаноламина в пара-положении показывают высокую антигипергликемическую активность, хлорсодержащие халконы – антипротозойную активность, а халконы с триазольным, пиррольным и бензотриазольным кольцами – антипаразитарную активность. Присутствие 1,4-диоксанового цикла в структуре приводит к появлению антигепатотоксической активности, которая усиливается наличием в положении 2 диоксанового цикла 2-гидроксиметильной группы.
This review is devoted to the analysis of 1,3-diphenyl-2-propene-1-ones (chalcones) biological activity dependence on their molecular structure. Pharmacophores which determine antimicrobial, antifungal, antibacterial, anticancer, antioxidant, cytotoxic, antiproliferative, anti-inflammatory, hyperglycemic, hepatoprotective and other activities were found out. The presence of chloroquinolinic fragment provides antimalarial and antiamebic activities. Chalcones which have electron donating substituents (methoxy-, hydroxy- and others) or 1–2 chlorine or fluorine atoms show maximum antimicrobial and antifungal activity. Schiff’s bases obtained from chalcones with heterocyclic fragment as well as boron-containing chalcones are characterized with high cytotoxic activity against human cancer cell lines РС-3, MCF-7, KB, KB-VIN. 1,3-Diphenyl-2-propene-1-ones with oxothiolone cycle besides cytotoxicity show activity against Micobacterium tuberculosis H37Rv. Chalcones containing acetamide group in the position 4 of the benzene ring possess high antinociceptive activity. Dihydroxoderivatives of chalcones where OH groups are in the ortho- and para-position exhibit high antioxidant activity. The presence of two hydroxyl groups in the benzene ring B is an important factor of their antiradical activity. Both vicinal deoxygenated chalcones and chalcones with a propanolamine chain in the para-position show high antihyperglycemic activity, chlorine-containing chalcones possess antiprotosoic activity, and chalcones with triazole, pirrole and benzotriazole rings have antiparasitic activity. The presence of 1,4-dioxane cycle in the structure leads to appearance of antihepatotoxic activity that can be increased by 2-hydroxymethyl group in the position 2 of dioxane cycle.
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