González-Jiménez, M. , Arenas-Valgañón, J., Calle, E. and Casado, J. (2011) Aromatic C-nitrosation of a bioactive molecule. Nitrosation of minoxidil. Organic and Biomolecular Chemistry, 9(22), pp. 7680-7684. (doi: 10.1039/C1OB05686G) (PMID:21779549)
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Abstract
Minoxidil (2,4-diamino-6-(piperidin-1′-yl)pyrimidine N(3)-oxide; CASRN 38304-91-5) is a bioactive molecule with several nitrosatable groups widely used as an antihypertensive and antialopecia agent. Here the nitrosation of minoxidil was investigated. The conclusions drawn are as follows: (i) In the pH = 2.3–5.0 range, the minoxidil molecule undergoes aromatic C-nitrosation by nitrite. The dominant reaction was C-5 nitrosation through a mechanism that appears to consist of an electrophilic attack on the nitrosatable substrate by H2NO2+/NO+, followed by a slow proton transfer; (ii) the reactivity of minoxidil as a C-nitrosatable substrate proved to be 7-fold greater than that of phenol, this being attributed to the preferred para- and ortho-orientations of the two -NH2groups at positions 2 and 4 of the minoxidil molecule, which activate electrophilic substitution in the C-5 position through their mesomeric effect. The N-nitrosominoxidil resulting from the nitrosation could be potentially harmful to the minoxidil users.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Gonzalez Jimenez, Dr Mario |
| Authors: | González-Jiménez, M., Arenas-Valgañón, J., Calle, E., and Casado, J. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Organic and Biomolecular Chemistry |
| Publisher: | Royal Society of Chemistry |
| ISSN: | 1477-0520 |
| ISSN (Online): | 1477-0539 |
| Published Online: | 26 May 2011 |
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