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Argentini M, Dos Santos DF, Weinreich R, et al. Synthesis of an o-Carboranyl Derivative of 4-[5-(4-Methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazol-2'-yl]phenol. Inorg Chem. 1998;37(23):6018-6022doi: 10.1021/ic980505e.
Argentini, M., Dos Santos, D. F., Weinreich, R., & Hansen, H. J. (1998). Synthesis of an o-Carboranyl Derivative of 4-[5-(4-Methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazol-2'-yl]phenol. Inorganic chemistry, 37(23), 6018-6022. https://doi.org/10.1021/ic980505e
Argentini, Mario, et al. "Synthesis of an o-Carboranyl Derivative of 4-[5-(4-Methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazol-2'-yl]phenol." Inorganic chemistry vol. 37,23 (1998): 6018-6022. doi: https://doi.org/10.1021/ic980505e
Argentini M, Dos Santos DF, Weinreich R, Hansen HJ. Synthesis of an o-Carboranyl Derivative of 4-[5-(4-Methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazol-2'-yl]phenol. Inorg Chem. 1998 Nov 16;37(23):6018-6022. doi: 10.1021/ic980505e. PMID: 11670736.
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Inorg Chem. 1998 Nov 16;37(23):6018-6022. doi: 10.1021/ic980505e.

Synthesis of an o-Carboranyl Derivative of 4-[5-(4-Methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazol-2'-yl]phenol.

Inorganic chemistry

Mario Argentini, Deborah F. Dos Santos, Regin Weinreich, Hans-Jürgen Hansen

Affiliations

  1. Institut für Medizinische Radiobiologie der Universität Zürich und des Paul Scherrer Instituts, CH-5232 Villigen-PSI, Switzerland, and Organisch-Chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.

PMID: 11670736 DOI: 10.1021/ic980505e

Abstract

Synthesis of an o-carboranyl derivative of 4-[5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazol-2'-yl]phenol (1), a candidate for application in boron neutron capture therapy for cancer treatment, is described. Decaborane was introduced into 3-(p-cyanophenoxy)-1-propyne (11) to form 1-(4-cyanophenoxymethyl)-1,2-dicarba-closo-dodecaborane(12) (12), which was transformed into the corresponding imidate 10 in order to be coupled with 4-cyano-o-phenylenediamine (13) to give 1-[4-(5'-cyano-1H-benzimidazol-2'-yl)phenoxymethyl]-1,2-dicarba-closo-dodecaborane(12) (14). The latter was reacted to the related imidate salt 15 and condensed with 5-(4-methyl-1-piperazinyl)-o-phenylenediamine (6) to the title compound 1-{4-[5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazol-2'-yl]phenoxymethyl}-1,2-dicarba-closo-dodecaborane(12) (2).

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