Synthesis of novel tetrahydroisoquinolines and study of their anti-fungal and contraceptive activities
- Author:
Jia-Guo LÜ
1
Author Information
1. Department of Medicinal Chemistry
- Publication Type:Journal Article
- Keywords:
Antifungal agents;
Contraceptives;
Tetrahydroisoquinolines
- From:
Academic Journal of Second Military Medical University
2010;27(12):1304-1309
- CountryChina
- Language:Chinese
-
Abstract:
Objective: To synthesize novel tetrahydroisoquinolines with both anti-fungal and contraceptive activities, so as to provide precursor structures for contraceptives with anit-fungal activities. Methods: 3,4-dimethoxyphenylethylamine was taken as the template and the title compounds were synthesized through Pictet-Spengler reaction, neutralization reaction, substitution, hydrolysis, and acylation. The anti-fungal activity and sperm-killing activity of the target compounds were tested in vitro. Results: Fourteen title compounds were obtained and they were: 2-octyl-6, 7-dimethyl-1, 2, 3, 4-tetrahydro-isoquinoline hydrochloride(1), 2-nonyl-6, 7-dimethyl-1,2, 3,4-tetrahydro-isoquinoline hydrochloride(2), 2-decyl-6, 7-dimethy-1, 2, 3, 4-tetrahydro-isoquinoline hydrochloride(3), 2-dodecyl-6, 7-dimethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride(4), 2-dodecyl 6, 7-diacetoxy-1, 2,3,4-tetrahydro-isoquinoline hydrochloride(5), 2-pentyl-6,7-diacetoxy-1,2,3,4-tetrahydro-isoquinoline hydrobromide(6), 2-hexyl-6, 7-diacetoxy-1,2,3,4-tetrahydro-isoquinoline hydrobromide(7), 2-heptyl-6, 7-diacetoxy-1,2,3,4-tetrahydro isoquinoline hydrobromide (8), 2-octyl-6, 7-dimethyl-1, 2, 3, 4-tetrahydro-isoquinoline hydrobromide(9), 2-nonyl-6, 7-dimethyl-1, 2, 3, 4-tetrahydro-isoquinoline hydrobromide(10), 2-decyl-6, 7-dimethy-1, 2, 3, 4-tetrahydro-isoquinoline hydrobromide(11), 2-dodecyl-6, 7-dihydroxyl 1, 2, 3, 4-tetrahydro-isoquinoline hydrobromide(12), 2-tetradecyl-6, 7-dihydroxyl-1, 2, 3, 4-tetrahydro-isoquinoline hydrobromide(13), and 2-cetyl-6, 7-dihydroxyl-1,2,3,4-tetrahydro-isoquinoline hydrobromide(14). Compounds 5-14 were firstly reported. It was found that all the 14 compounds had anti-fungal activity and 6 compounds also showed sperm-killing activities, with compounds 11, 12 having the strongest activities. Conclusion: A group of novel compounds with both anti-fungal and contraceptive activities have been synthesized, which provide a precursor structure for developing new contraceptives with anti-fungal activities.
