Hexaazatrinaphthylenes: synthesis, self-assembly properties and biological activities

Daniel Garca Velzquez,a Alejandro Gonzlez Orive,b Alberto Hernndez Creus,b Flix Machn,c Atteneri
Lpez Arencibia,d Jacob Lorenzo Morales,d Carmen Martn Navarro,d Jos Piero Barrosod and ngel
Gutirrez Raveloa.
a

Instituto Universitario de Bio-Orgnica "Antonio Gonzlez", Universidad de La Laguna e Instituto Canario de Investigacin del Cncer, C/
Astrofsico Francisco Snchez, 2, 38206 La Laguna, Tenerife, Espaa.
b
Departamento de Qumica Fsica, Facultad de Qumica, ULL, Campus de Anchieta s/n. 38206 La Laguna.
c
Unidad de Investigacin Hospital Universitario Ntra. Sra. Candelaria. Ctra. del Rosario, 145. S/C Tenerife.
d
Instituto Universitario de Enfermedades Tropicales y Salud Pblica de Canarias. Laboratorio de Quimioterapia de Protozoos. ULL, C/ Astrofsico
Francisco Snchez s.n. 38206, La Laguna, Tenerife.

dgvelazq@ull.es
We have synthesized a novel family of water soluble -conjugated hexaazatrinaphthylenes (HATNAs)
dendritic architectures G1, G2, G3, derivates 3a-e and other analogues compounds using commercial
available building blocks (1 and 2) by a short and efficient microwave assisted reaction 1 as depicted in the
Figure 1. The G1 properties and other compounds as nanomaterials have been studied by TEM, SEM, DSC,
STM, XRPD and cyclic voltammetry. We will show physical characterization, as well as the study of some
properties of these compounds, such as organogelating,2 metal coordination3 and potential biological activity.4

Figure 1. Synthesis of compound G1 and amide-derivates (left). Representation of families of analogues-compounds with HATNA
core (right).

Furthermore, preliminary studies in several compounds showed potential leishmanicidal activity and DNA
intercalation.5
Acknowledgements: Financial support by MEC (SAF2006-06720 and CTQ2008-06017/BQU). DGV acknowledges Gobierno de
Canarias for pre-doctoral fellowship.
References:
1. Velzquez D. G., Orive A. G., Arrieta, A. A., Sacau, E. P., Creus A. H., Ravelo A. G., Chem. Comm. 2009, (submitted).
2. Velzquez D. G., Orive A. G., Creus A. H., Ravelo A. G., (sent)
3. Velzquez D. G., Orive A. G., Creus A. H., Ravelo A. G., (manuscripts in preparation)
4. Preliminary results show endonuclease inhibitory activity.
5. Results not published.