Publication: Structure-activity relationships of some indolo[3,2-c]quinolines with antimalarial activity
Issued Date
1998-01-01
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ISSN
09280987
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2-s2.0-0031983679
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Mahidol University
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SCOPUS
Bibliographic Citation
European Journal of Pharmaceutical Sciences. Vol.6, No.1 (1998), 19-26
Suggested Citation
Mei Lin Go, Tong Lan Ngiam, Agnes Lay Choo Tan, Kunnika Kuaha, Prapon Wilairat Structure-activity relationships of some indolo[3,2-c]quinolines with antimalarial activity. European Journal of Pharmaceutical Sciences. Vol.6, No.1 (1998), 19-26. doi:10.1016/S0928-0987(97)00064-X Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/18638
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Title
Structure-activity relationships of some indolo[3,2-c]quinolines with antimalarial activity
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Abstract
The synthesis, physicochemical characterization and in vitro antimalarial activity of a series of indolo[3,2-c]quinolines (9a-f) are described. There is only a poor correlation between the activity and hydrophobicity. In contrast, 33% of the observed variation in antimalarial activity can be attributed to the size of the side chain attached to position 9 of the indoloquinoline ring. An increase in the size of this dibasic side chain generally results in a reduction in activity, suggesting that it is accommodated in a site/cavity of limited size on the receptor. More significantly, the charge on the distal nitrogen (N3) on the side chain, located 10-11 Å from the quinoline N, could account for 75% of the observed variation. Since a large charge on N3 is associated with improved antimalarial activity, it is suggested that N3 is protonated and functions as a H bond donor in the drug-receptor interaction.