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

doi:10.1016/j.tetlet.2014.10.065

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 journal › Article › peer-review

3 Scopus citations

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-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 language	English (US)
Pages (from-to)	6658-6661
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2014.10.065
State	Published - Dec 3 2014

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Sulfonyldiimidazole Drug conjugate Sulfamate ester N-methylation Sulfatase

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10.1016/j.tetlet.2014.10.065

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title = "O-(Aminosulfonylation) of phenols and an example of slow hydrolytic release",

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-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.",

keywords = "Sulfonyldiimidazole Drug conjugate Sulfamate ester N-methylation Sulfatase",

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

note = "Funding Information: We thank Huanghe Science & Technology College and Samos Pharmaceuticals for financial assistance, and Jian Guo, Yanchun Li, and Xibin Liao for organizing and supporting activities. Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd.",

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doi = "10.1016/j.tetlet.2014.10.065",

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T1 - O-(Aminosulfonylation) of phenols and an example of slow hydrolytic release

AU - Yang, Baocheng

AU - Sun, Zhexun

AU - Liu, Changzhi

AU - Cui, Yan

AU - Guo, Zhilei

AU - Ren, Yuwei

AU - Lu, Zhijian

AU - Knapp, Spencer

N1 - Funding Information: We thank Huanghe Science & Technology College and Samos Pharmaceuticals for financial assistance, and Jian Guo, Yanchun Li, and Xibin Liao for organizing and supporting activities. Publisher Copyright: © 2014 Elsevier Ltd.

PY - 2014/12/3

Y1 - 2014/12/3

N2 - 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.

AB - 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.

KW - Sulfonyldiimidazole Drug conjugate Sulfamate ester N-methylation Sulfatase

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U2 - 10.1016/j.tetlet.2014.10.065

DO - 10.1016/j.tetlet.2014.10.065

M3 - Article

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SN - 0040-4039

VL - 55

SP - 6658

EP - 6661

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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