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Straightforward synthesis and crystal structures of the 3-piperazine-bisbenzoxaboroles and their boronic acid analogs
Affiliation:1. Department of Microbioanalytics, Faculty of Chemistry, Warsaw University of Technology, Warsaw, Poland;2. Department of Physical Chemistry, Faculty of Chemistry, Warsaw University of Technology, Warsaw, Poland;1. Anacor Pharmaceuticals, Inc., 1020 E. Meadow Circle, Palo Alto, CA 94303, USA;2. Global Alliance for Livestock and Veterinary Medicine, Doherty Building, Pentlands Science Park, Penicuik, Edinburgh EH26 0PZ, UK;3. Swiss Tropical and Public Health Institute, Socinstrasse 57, 4051 Basel, Switzerland;4. University of Basel, Petersplatz 1, 4003 Basel, Switzerland;5. Avista Pharma Solutions, 350 Tricenter Boulevard, Suite C, Durham, NC 27713, USA;6. Wuxi AppTec (Tianjin) Co. Ltd., No. 168 NanHai Road, 10th Avenue, TEDA, Tianjin 300457, PR China;1. Arnold and Marie Schwartz College of Pharmacy and Health Sciences, Long Island University, Brooklyn, NY, USA;2. Department of Medicine and Pharmacological Sciences, Icahn School of Medicine at Mount Sinai, New York, NY 10029, USA;3. Nathan S. Kline Institute for Psychiatric Research, Orangeburg, NY 10962, USA;4. Department of Medicine, Division of Infectious Diseases and Department of Pathology Division of Parasitology and Tropical Medicine, Albert Einstein College of Medicine, Bronx NY-10461, USA
Abstract:The straightforward synthesis of a highly biologically active 3-piperazine-bisbenzoxaborole and its fluorine analog has been described. The obtained bisbenzoxaboroles have been used in the synthesis of their phenylboronic acids analogs. One diboronic acid has been also isolated as hydrochloride salt as well as its methyl monoester. All the described compounds display unique molecular architectures, which have been determined by X-ray measurements.
Keywords:Benzoxaborole  Diboronic  Bisboronic  Monoester  Piperazine  Boronic acid  ACZYAABNXWTSRG-UHFFFAOYSA-N  DXZQBHJXVXKYJB-UHFFFAOYSA-N  FOZMGUROFYGZJW-UHFFFAOYSA-N  DGUWACLYDSWXRZ-UHFFFAOYSA-N  DQWGFPZHRPGZEZ-UHFFFAOYSA-N  MEXNIAOZYQCBAF-UHFFFAOYSA-N  GLUUGHFHXGJENI-UHFFFAOYSA-N  DQSCWDAMLHGZGL-UHFFFAOYSA-N  QWUBOCQWTPCPNE-UHFFFAOYSA-N
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