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Updated: Aug 17, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
[2-Amino-2-thiazoline derivatives--a novel chemotype possessing muscarinomimetic effect]
Iu Ia Ivanov1, S E Tkachenko, A N Proshin
1Institute of Physiologically, Active Compounds Russ. Acad. Sci., Russia, 142432, Chernogolovka, Moscow Region.
Abstract:
Derivatives of 2-amino-2-thiazoline exhibit muscarinomimetic properties in model experiments with isolated rat ileum. The activity of compounds strongly depends on the nature of substituents in 5-position of thiazoline ring. The most active spasmogenic compound is 5-iodomethyl-2-amino-2-thiazoline hydroiodide (EC50 = 13 +/- 2 microM). Its effect is very similar to activity of cholinergic agent pilocarpine (EC50 = 14 +/- 4 microM), but "intrinsic activity" parameter a (alpha = 0.87 +/- 0.12) of 5-iodomethyl-2-amino-2-thiazoline was more significant. Ileum contractions induced by this compounds were inhibited by atropine. Derivatives of 2-amino-2-thiazoline (like pilocarpine) were not demonstrated nicotinomimetic properties. These compounds demonstrate very weak anti-AChE activity. For 5-iodomethyl-2-amino-2-thiazoline hydroiodide the IC50 value is 0.39 +/- 0.09 mM.
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