O-(Aminosulfonylation) of phenols and an example of slow hydrolytic release.

Authors :: Yang, Baocheng
Sun, Zhexun
Liu, Changzhi
Cui, Yan
Guo, Zhilei
Ren, Yuwei
Lu, Zhijian
Knapp, Spencer
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Dec2014, Vol. 55 Issue 49, p6658-6661. 4p.
Publication Year :: 2014
Abstract: Sequential replacement of imidazole from sulfonyldiimidazole by phenols and then amines leads to O -arylsulfamate esters. Application of this coupling method to 19 phenols and 6 amines generates a library of 114 sulfamate esters, Ar-OSO 2 -NR 2 . A sulfamate based conjugate of ethinyl estradiol was prepared by using the steroid 3-hydroxyl as the phenol component, and an amino amide derived from linoleic acid as the amine. Hydrolysis of this conjugate was studied in aqueous buffer at pH values 2, 5, and 7.4, and (essentially identical) respective half-lives of 6.8, 6.6, and 6.7 days were observed. [ABSTRACT FROM AUTHOR]

Subjects :: *PHENOLS
*CONTROLLED release drugs
*SULFAMATES
*AMINO acid analysis
*LINOLEIC acid

Language :: English
ISSN :: 00404039
Volume :: 55
Issue :: 49
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 99402856
Full Text :: https://doi.org/10.1016/j.tetlet.2014.10.065