Synthetic Utility and Single Crystal X-ray Diffraction Studies of Biologically Active Carbazoles and Indoloacridines.
Posted: 7 Feb 2020
Date Written: January 22, 2020
Abstract
Carbazole alkaloids and their derivatives have gained greater importance due to their high level of biological as well as pharmacological activities. Much interest centers on these carbazoles and their derivatives because these can be utilized as synthons to prepare various substituted analogs such as pyrido-, pyrimido-, imidazo- and pyridazino- carbazoles which possess properties such as anti-cancer, anti-fungal, anti-HIV and DNA-intercalating agents. Based on the structural, biological and pharmacological importance of the carbazole derivatives, the present investigation was aimed to devise a viable synthetic route to prepare these classes of compound using different synthetic methodologies. For our synthetic strategy 2,3,4,9-tetrahydro-1H-carbazol-1-ones, prepared in our laboratory were used as potential precursors, which have opened new avenues for the synthesis of highly functionalized carbazole derivatives such as 1-hydroxyimino-2,3,4,9-tetrahydro-1H-carbazoles, 1-hydroxycarbazoles, 1-hydroxy-2-formylcarbazoles, 1-hydroxy-2-acetylcarbazoles, 1-hydroxy-2-cinnomoylcarbazoles. These functionalized carbazoles thus prepared lead to mukonine isomers, oxazolocarbazoles, girinimbine isomers, pyranocarbazoles, and pyrazolo-, isoxazolo-, furo-, oxazino-, pyrido-, pyrazino- indolo-, carbazoles in excellent yields. Single crystal X-ray diffraction studies for some of the compounds synthesized will be discussed. For optimal drug design knowledge the exact geometry and shape of the molecules are essential, and thus we decided to subject the compounds synthesized to X-ray diffraction studies. Since we used 2,3,4,9-tetrahydrocarbazol-1-ones as precursors for syntheses of all the compounds and it was felt worthwhile to study the exact crystallographic behavior of these compounds with different substituents. The interesting crystallographic behavior was observed for some of the synthesized compounds and has been resolved using advanced crystallographic software programs.
Keywords: Carbazoles, Indoloacridines, Single Crystal X-ray Diffraction
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