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Volume 2012
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N1-((1H-Indazol-5-yl)methylene)-N2-(2-((2-((2-(((1H-indazol-6-yl)methylene)amino)ethyl)amino)ethyl)amino)ethyl)ethane-1,2-diamine

by
Cristina Núñez
1,*,
Javier Fernández-Lodeiro
2,
Adrián Fernández-Lodeiro
2,
Emília Bértolo
3,
José Luis Capelo
1,2 and
Carlos Lodeiro
1,2,*
1
REQUIMTE, Chemistry Department, Faculty of Science and Technology, University Nova of Lisbon, 2829-516, Monte de Caparica, Portugal
2
BIOSCOPE Group, Faculty of Science, Physical-Chemistry Department, Ourense Campus, University of Vigo, 32004, Ourense, Spain
3
Ecology Research Group, Department of Geographical and Life Sciences, Canterbury Christ Church University. Canterbury, Kent. CT1 1QU, UK
*
Authors to whom correspondence should be addressed.
Molbank 2012, 2012(3), M770; https://doi.org/10.3390/M770
Submission received: 18 June 2012 / Accepted: 31 July 2012 / Published: 9 August 2012
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Abstract

:
One novel molecular emissive probe L has been synthesized by classical Schiff-base reaction between 1H-indazole-6-carboxaldehyde and tetraethylenepentamine. The structure of compound L was confirmed by melting point, elemental analysis, ESI-MS spectrometry and by IR and 13C-NMR and 1H-NMR spectroscopy.

Graphical Abstract

Indazole ring systems have an interesting chemistry, which has been used in biology, catalysis, and medicinal chemistry [1]. Although rare in nature [2], indazoles exhibit a variety of biological activities such as HIV protease inhibition [3,4,5], antiarrhythmic and analgesic activities [6], antitumor activity [7,8], and antihypertensive properties [9]. Furthermore, antimicrobial and antineoplastic activities have also been shown to be associated with certain indazole derivatives [10].
As a part of our ongoing research into the design and synthesis of novel organic molecular probes, luminescent materials and MALDI-TOF-MS matrices [11,12,13,14], here we report the synthesis and characterization of a new Schiff-base compound L containing two indazole units linked by a flexible polyethylene bridged (See scheme 1).

Experimental

A solution of 1H-indazole-6-carboxaldehyde (0.254 g, 1.718 mmol) in absolute ethanol (10 mL) was added dropwise to a refluxing solution of tetraethylenepentamine (0.162 g, 0.859 mmol) in the same solvent (30 mL) (See scheme 1). The resulting solution was gently refluxed with magnetic stirring for ca. 4 h. The colour changed from yellow to brown. After that time, the mixture was allowed to cool to room temperature and a brown powder precipitate was formed; this was then filtered off, washed with cold absolute ethanol and cold diethyl ether and dried under vacuum. The resulting compound was characterized as L follow purification by column chromatography.
Melting point: 163–165 °C.
Yield: 382 mg (L) (93%).
ESI-MS: m/z (rel. int%): 446.27 (100) ([L+H]+.
1H-NMR (CDCl3) (L): δ = 12.1 (s, 2H, N–H); 8.4 (s, 2H, N=C–H); 8.2–7.0 (m, 6H, C-Har); 3.9–2.1 (m, 16H, CH2); 1.5 (s, 3H, NH) ppm.
13C-NMR (CDCl3) (L): δ = 160.5; 150.3; 147.2; 133.6; 131.2; 127.9; 126.1; 125.0; 124.2; 119.7; 112.3; 110.4; 56.2; 50.6; 49.8.
IR (cm−1) (L): 3051 (C–H, Ar), 1638 (C=N, Imine), 1618, 1593, 1562 and 1509 (C=C, Ar).
Elemental analysis: Calcd for C24H37N9O3: C, 57.70; H, 7.45; N, 25.25. Found (L): C, 58.00; H, 7.15; N, 25.00.
Uv-vis (CHCl3), [L] = 1.00 × 10−5 M, λmax 275 and 324 nm.
Fluorescence Emission (CHCl3); [L] = 1.00 × 10−5): λmax 427 nm.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

We are grateful to Xunta de Galicia (Spain) for projects 09CSA043383PR and 10CSA383009PR (Biomedicine) and to the Scientific Association ProteoMass for financial support. C.N. thanks the Fundação para a Ciência e a Tecnologia/FEDER (Portugal/EU) programme postdoctoral contract SFRH/BPD/65367/2009. J.F.L. thanks Xunta de Galicia (Spain) for a research contract by project 09CSA043383PR in Biomedicine. J.L.C. and C.L. thank Xunta de Galicia for the Isidro Parga Pondal Research program.

References and Notes

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Molbank 2012 m770 sch001 550
Scheme 1. Schematic representation of compound L.
Scheme 1. Schematic representation of compound L.
Molbank 2012 m770 sch001

Share and Cite

MDPI and ACS Style

Núñez, C.; Fernández-Lodeiro, J.; Fernández-Lodeiro, A.; Bértolo, E.; Capelo, J.L.; Lodeiro, C. N1-((1H-Indazol-5-yl)methylene)-N2-(2-((2-((2-(((1H-indazol-6-yl)methylene)amino)ethyl)amino)ethyl)amino)ethyl)ethane-1,2-diamine. Molbank 2012, 2012, M770. https://doi.org/10.3390/M770

AMA Style

Núñez C, Fernández-Lodeiro J, Fernández-Lodeiro A, Bértolo E, Capelo JL, Lodeiro C. N1-((1H-Indazol-5-yl)methylene)-N2-(2-((2-((2-(((1H-indazol-6-yl)methylene)amino)ethyl)amino)ethyl)amino)ethyl)ethane-1,2-diamine. Molbank. 2012; 2012(3):M770. https://doi.org/10.3390/M770

Chicago/Turabian Style

Núñez, Cristina, Javier Fernández-Lodeiro, Adrián Fernández-Lodeiro, Emília Bértolo, José Luis Capelo, and Carlos Lodeiro. 2012. "N1-((1H-Indazol-5-yl)methylene)-N2-(2-((2-((2-(((1H-indazol-6-yl)methylene)amino)ethyl)amino)ethyl)amino)ethyl)ethane-1,2-diamine" Molbank 2012, no. 3: M770. https://doi.org/10.3390/M770

APA Style

Núñez, C., Fernández-Lodeiro, J., Fernández-Lodeiro, A., Bértolo, E., Capelo, J. L., & Lodeiro, C. (2012). N1-((1H-Indazol-5-yl)methylene)-N2-(2-((2-((2-(((1H-indazol-6-yl)methylene)amino)ethyl)amino)ethyl)amino)ethyl)ethane-1,2-diamine. Molbank, 2012(3), M770. https://doi.org/10.3390/M770

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