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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

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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

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