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Synthesis 2002(15): 2165-2167
DOI: 10.1055/s-2002-34858
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Enantiopure N-(3,5-Dichlorophenyl)-2-hydroxysuccinimides (NDHS) and N-(3,5-Dichlorophenyl)-2-hydroxysuccinimide-O-sulfates (NSC)

Gary O. Rankin*a, Hang Suna, Bryson McCaina, John L. Hubbardb, Minghui Chaib
a Department of Pharmacology, Marshall University School of Medicine, Huntington, WV 25704, USA
b Department of Chemistry, Marshall University, Huntington, WV 25755, USA
Fax: +1(304)6967391; e-Mail: rankin@marshall.edu;
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Publication History

Received 14 June 2002
Publication Date:
21 October 2002 (online)

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Abstract

Enantiomerically pure N-(3,5-dichlorophenyl)-2-hydroxysuccinimides (NDHS) and N-(3,5-dichlorophenyl)-2-hy­droxysuccinimide-O-sulfates (NSC) have been synthesized in our laboratory in order to address their selectively related nephrotoxic mechanism. The key step for NDHS synthesis is the intramolecular nucleophilic cyclization via the amide N-atom with retention of configuration of the original stereogenic center. The corresponding sulfate conjugates (R)-NSC and (S)-NSC were prepared by reaction of enantiomeric NDHS with chlorosulfonic acid at -78 °C.

Key words

NDHS - NSC - enantiopure - nephrotoxicity - sulfate conjugates