Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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


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.