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Molecules 2014, 19(6), 7770-7784; doi:10.3390/molecules19067770

Selective Substitution of 31/42–OH in Rapamycin Guided by an in Situ IR Technique

1
Key Laboratory of Structure-Based Drug Design and Discovery, Shenyang Pharmaceutical University, Ministry of Education, Shenyang 110016, China
2
Laboratory of Computer-Aided Drug Design & Discovery, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China
*
Authors to whom correspondence should be addressed.
Received: 25 April 2014 / Revised: 26 May 2014 / Accepted: 27 May 2014 / Published: 10 June 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

An in situ IR technique was applied in the selective synthesis of the key intermediate for rapamycin derivatives, which made the reaction endpoint easily defined. This technology solved a bothersome problem in the preparation of rapamycin derivatives, and based on this technique, the 31-OH and 42-OH of rapamycin were chemically modified by a series of quaternary ammonium salts to generate 11 compounds. The solubility of all these compounds was remarkably improved (25,000 times higher than that of rapamycin) and their structures were confirmed by MS, IR, 1D and 2D NMR techniques. View Full-Text
Keywords: rapamycin derivatives; in situ IR; selective substitution; aqueous solubility rapamycin derivatives; in situ IR; selective substitution; aqueous solubility
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MDPI and ACS Style

Cao, S.; Zhou, X.; Yang, Y.; Zhong, W.; Sun, T. Selective Substitution of 31/42–OH in Rapamycin Guided by an in Situ IR Technique. Molecules 2014, 19, 7770-7784.

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