Synlett 2004(6): 1007-1010  
DOI: 10.1055/s-2004-822897
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Carborane-hybrids Based on a Triazine Scaffold for Boron Neutron Capture Therapy

Silvia Ronchia, Davide Prosperib, Federica Compostellac, Luigi Panza*a
a DISCAFF, Università del Piemonte Orientale, viale Ferrucci 33, 28100 Novara, Italy
b Istituto di Scienze e Tecnologie Molecolari - CNR, via Golgi 19, 20133 Milano, Italy
c Dipartimento dii Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, via Saldini, 50, 20133 Milano, Italy
Fax: +39(0321)375821; e-Mail: panza@pharm.unipmn.it;
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Publikationsverlauf

Received 12 December 2003
Publikationsdatum:
25. März 2004 (online)

Abstract

Cyanuric chloride has been used as a scaffold for the synthesis of potential agents for BNCT containing a carborane cluster, a sugar moiety as hydrophilic arm and an amino acid for the con­jugation with bioactive molecules; this approach is, in principle, particularly suitable for a combinatorial approach.

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Reaction conditions: Z-α-N-l-lysine, 2 equiv DIPEA, MeCN, 15 min, r.t.; then, 7a or 7b, 48 h, 80 °C.

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Selected data for final compounds. MALDI-MS: 8a calcd for C27H47B10N5O12S: 773.9; found: 796.0 [M + Na]+, 812.8 [M + K]+; 8b calcd for C39H63B10N5O20S: 1062.1; found: 1085.2 [M + Na]+, 1101.2 [M + K]+; 9a calcd for C32H56B10N6O14S: 889.0; found: 928.44 [M + K]+; 12b calcd for C44H72B10N6O22S: 1177.2; found: 1216.3 [M + K]+. 11B NMR (CD3OD): 8a -3.62 (2 B), -10.54 (4 B), -12.36 (4 B); 8b -3.59 (2 B), -10.47 (4 B), -12.22 (4 B); 9a -3.55 (2 B), -10.50 (4 B), -12.25 (4 B); 9b -3.64 (2 B), -10.45 (4 B), -12.18 (4 B).