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Paper | Regular issue | Vol 29, No. 12, 1989, pp.2353-2359
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5132
■ Some Physicochemical Parameters of 11H-Indole[3,2-c]quinoline

Go Mei Lin and Ngiam Tong Lan*

*Department of Pharmacy, National University of Singapore, Lower Kent Ridge Road, 119260, Singapore

Abstract

The hydrophobicity (log P), pKa and limiting solubility of 3-chloro-8-methoxy-11H-indolo[3,2-c]quinoline (I), a representative 11H-indolo[3,2-c]quinoline, were determined. A significant difference was observed between the basicity of I and its non-cyclized analogue, 7-chloro-4-N-(p-methoxyphenyl)aminoquinolie (II). I was found to be a weaker base (pKa 3.99) than II (pKa 7.59), which suggested that the indolo N, unlike the 4-amino group of II, did not affect the basicity oi the quinolyl N. I was also much less hydrophobic and more water soluble than II, which could only be attributed partly to a reduction of surface area on ring formation. Based on the present determinations, the unique hydrophobicity of the 11H-indolo[3,2-c]quinoline ring system was calculated to have a log P value of 2.22.