Issue 23, 2011
From the journal:

Chemical Communications

Novel protection–deprotection strategies in diazeniumdiolate chemistry: synthesis of V-IPA/NO†

Rahul S. Nandurdikar,*a   Larry K. Keefera  and  Joseph E. Saavedrab  

* Corresponding authors

a Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, MD, USA
E-mail: nandurdikarr@mail.nih.gov
Fax: +1 301-846-5946
Tel: +1 301-846-7145

b Basic Science Program, SAIC-Frederick Inc., National Cancer Institute at Frederick, Frederick, USA
Fax: +1 301-846-5946
Tel: +1 301-846-1602

Abstract

Synthesis of previously inaccessible, potentially liver selective HNO donor V-IPA/NO ([iPrHN3–N1(O1)[double bond, length as m-dash]N2–O2–R], where R = vinyl) is reported here. A novel fluoride-labile TOM group at O-2 in conjunction with MOM protection at N-3 in IPA/NO is employed. The strategy developed is also extended to synthesis of other NO-releasing prodrugs and has applications in diversity-oriented synthesis of HNO- and NO-prodrugs.

Graphical abstract: Novel protection–deprotection strategies in diazeniumdiolate chemistry: synthesis of V-IPA/NO

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Article information

DOI
https://doi.org/10.1039/C1CC12130H
Article type
Communication
Submitted
13 Apr 2011
Accepted
26 Apr 2011
First published
10 May 2011

Chem. Commun., 2011,47, 6710-6712

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Novel protection–deprotection strategies in diazeniumdiolate chemistry: synthesis of V-IPA/NO

R. S. Nandurdikar, L. K. Keefer and J. E. Saavedra, Chem. Commun., 2011, 47, 6710 DOI: 10.1039/C1CC12130H

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