Synthesis and immunological activity of 5,6,6a,8,9,11a-hexahydronaphth[1',2':4,5]imidazo[2,1-b]thiazoles and 5,6,6a,9,10,11a-hexahydroanaphth[2',1':4,5]imidazo[2,1-b]thiazoles.
Abstract |
A series of 5,6,6a,8,9,11a-hexahydroanaphth[1',2':4,5]imidazo[2,q-b] thiazoles (17 and 20) and 5,6,6a,9,10,11a-hexahydronaphth[2',1':4,5]imidazo[2,1-b] thiazoles has been synthesized with cis- and/or trans-1,2-diamino-1,2,3,4-tetrahydronaphthalenes as the key intermediates and subsequently evaluated for immunological activity (effects on antibody formation and delayed-type hypersensitivity reaction). Among the compounds tested trans-5,6,6a,8,9,11a-hexahydronaphth[1',2':4,5]imidazo[2,1-b] thiazole (trans-17a) and (+/-)-5,6,6a beta,8,9,11a alpha-hexahydro-8 beta-hydroxy-9 beta-methyl-8 alpha-phenylnaphth[1',2':4,5]imidazo[2,1-b] thiazole (20a) showed the largest immunological activity in mice with a magnitude comparable to that of levamisole and were found to be considerably less toxic than levamisole in acute toxicological study. The structures of 18a and 20a were determined by X-ray crystallography.
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Authors | M Saito, Y Kayama, T Watanabe, H Fukushima, T Hara, K Koyano, A Takenaka, Y Sasada |
Journal | Journal of medicinal chemistry
(J Med Chem)
Vol. 23
Issue 12
Pg. 1364-72
(Dec 1980)
ISSN: 0022-2623 [Print] United States |
PMID | 7005449
(Publication Type: Journal Article)
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Chemical References |
- Adjuvants, Immunologic
- Imidazoles
- Thiazoles
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Topics |
- Adjuvants, Immunologic
(chemical synthesis)
- Animals
- Chemical Phenomena
- Chemistry
- Hemolytic Plaque Technique
- Hypersensitivity, Delayed
(immunology)
- Imidazoles
(chemical synthesis, pharmacology)
- Lethal Dose 50
- Mice
- Sheep
(immunology)
- Thiazoles
(chemical synthesis, pharmacology)
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