• Basicities of some 9-substituted acridine-4-carboxamides: A density functional theory (DFT) calculation

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      https://www.ias.ac.in/article/fulltext/jcsc/116/04/0235-0241

    • Keywords

       

      Carboxamide; DFT method; anticancer drugs; DNA binding

    • Abstract

       

      Acid-base properties of drugs are important in understanding the behaviour of these compounds under physiological condition. In order to understand such behaviour the proton affinities of acri-dine 4-carboxamides with substitution (R) at the 9-position are theoretically studied, and considered for the basic sites of both the heterocyclic ring as well as side chain nitrogens. In 9-amino acridine 4-carbox-amide, the -NH2 group is observed to be an additional basic site. The heterocyclic nitrogen of substituted carboxamides (R =-NH2, -O-methyl, -O-ethyl, and -O-phenyl) is more basic than the side chain nitrogen, however, side chain nitrogen corresponds to more basic site for some carboxamides (R = -OH and-Cl) and the -NH2 group represents the least basic site of 9-amino acridine 4-carboxamide. In addition to presenting the basicities of these drugs an indication of another hydrogen-bond between heterocyclic ring N and carboxamide chain O is observed. The difference of basicities with substituents at 9-position are very narrow and carboxamides with substituents at 9-position are found to be suitable for studying intramolecular H-bonds between the heterocyclic N and carboxamide O. The resultant stabilization of a configuration due to such H-bonding is determined

    • Author Affiliations

       

      Raghab Parajuli1 C Medhi1

      1. Department of Chemistry, Gauhati University, Gauhati - 781 014, India
    • Dates

       
  • Journal of Chemical Sciences | News

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