THE SYNTHESIS AND STUDY OF CARBONIC ANHYDRASE ACTIVITY OF SULFONAMIDE-CONTAINING DIBENZO[1,4]THIAZEPINES

Authors

  • Daria S. Smirnova Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Ave., Petergof, Saint Petersburg 198504
  • Vladimir V. Sharoiko Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Ave., Petergof, Saint Petersburg 198504
  • Stanislav A. Kalinin Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Ave., Petergof, Saint Petersburg 198504
  • Alexander V. Sapegin Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Ave., Petergof, Saint Petersburg 198504

Keywords:

dibenzo[1,4]thiazepine, sulfonamide, carbonic anhydrase, denitrocyclization reaction, Smiles rearrangement

Abstract

A one-pot synthesis approach to access sulfonamide-containing derivatives of dibenzo[1,4]thiazepine using primary amines and 2-[(2-nitro-4-sulfamoylphenyl)sulfanyl]benzoic acid as precursors was developed. The approach is based on a sequence of amidation steps and the subsequent tandem of the Smiles rearrangement and denitrocyclization reaction. The resulting tricyclic systems showed pronounced activity as inhibitors of bovine carbonic anhydrase isoform II.

Author Biographies

Daria S. Smirnova, Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Ave., Petergof, Saint Petersburg 198504

инженер-исследователь, Кафедра медицинской химии,Лаборатория синтеза биоактивных малых молекул

Vladimir V. Sharoiko, Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Ave., Petergof, Saint Petersburg 198504

д.б.н., Ведущий научный сотрудник

Stanislav A. Kalinin, Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Ave., Petergof, Saint Petersburg 198504

к.х.н., ассистент, Кафедра медицинской химии, Лаборатория синтеза биоактивных малых молекул

Alexander V. Sapegin, Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Ave., Petergof, Saint Petersburg 198504

к.х.н., доцент, Кафедра медицинской химии,Лаборатория синтеза биоактивных малых молекул

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Published

2024-01-10

Issue

Vol. 59 No. 11/12 (2023)

Section

Original Papers