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

Baocheng Yang, Zhexun Sun, Changzhi Liu, Yan Cui, Zhilei Guo, Yuwei Ren, Zhijian Lu, Spencer Knapp

Research output: Contribution to journalArticlepeer-review

3 Scopus citations


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-OSO2-NR2. 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.

Original languageEnglish (US)
Pages (from-to)6658-6661
Number of pages4
JournalTetrahedron Letters
Issue number49
StatePublished - Dec 3 2014

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


  • Sulfonyldiimidazole Drug conjugate Sulfamate ester N-methylation Sulfatase


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