Molbank
2008, M570
molbank
ISSN 1422-8599
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Short Note
7-Hydroxy-8-acetylcoumarin
N-Phenylsulfonylhydrazone
Antigoni
Kotali 1,*, Ioannis S. Lafazanis 1 and Philip A. Harris
2
1 Laboratory of Organic Chemistry,
Department of Chemical Engineering, College of Engineering, University of Thessaloniki,
Thessaloniki 54124, Greece E-mail: [email protected]
2 GlaxoSmithKline, 1250 South Collegeville Road, P.O.Box
5089, Collegeville, PA 19426-0989, USA E-mail: [email protected]
*
Author to whom correspondence should be addressed.
Received:
24 April 2007; in revised form: 8 August 2008 /
Accepted: 18 August 2008 / Published: 24
August 2008
Keywords: 7-hydroxy-8-acetylcoumarin, sulfonylhydrazones.
As part of a research programme
targeting novel molecules derived from o-hydroxyaryl ketone
hydrazones[1] we synthesised 7-hydroxy-8-acetylcoumarin
phenylsulfonylhydrazone. It is well known than coumarins exhibit a variety of
pharmacological properties. Among these properties, their cytotoxic effects have
been most extensively investigated [2]. Sulfonyl hydrazone derivatives have
been also found to possess anticancer properties [3]. Thus, the combination of
coumarin and sulfonyl hydrazone moieties in one molecule could lead to an
interesting anticancer agent.
7-Hydroxy-8-acetylcoumarin
was prepared according to the literature method [4] whereas, commercially
available phenylsulfonyl hydrazide was supplied by Aldrich. Phenylsulfonyl
hydrazide (0.42 g, 2.45 mmol) was added to a solution of 7-hydroxy-8-acetylcoumarin (0.5 g, 2.45 mmol) in 1-propanol
(15 mL). The reaction mixture was
magnetically stirred at r.t. for 24 hours. The precipitate, which was formed,
was initially filtered, then washed with 5mL diethyl ether and finally dried
overnight to afford the desired 7-hydroxy-8-acetylcoumarin
phenylsulfonylhydrazone
as white crystals (1.38 g, 70 %). The product was identified by its 1H NMR, 13C NMR and MS without
further purification.
M.p. 196-197 °C.
1H NMR (400 MHz, DMSO-d6):
2.02 (s, 3H), 6.20-6.23 (d, 1H, J=9.6
Hz), 6.86-6.88 (d, J=8.4 Hz, 1H),
7.54-7.64 (m, 4H), 7.66-7.84(m, 2H), 7.93-7.95 (d, J=9.6 Hz, 1H), 10.22 (s, 1H), 10.81 (s, 1H).
13C NMR (100 MHz, DMSO-d6):
23.6, 109.6, 111.7, 111.8, 112.6, 127.1, 129.0, 129.8, 132.6, 139.8, 143.4,
147.6, 152.1, 157.4, 160.0.
MS m/z
(ESI+) : Calcd. for C17H14N2O5S
739.11391 [2M+Na]+, 381.05156 [M+Na]+. Found: 739.11366
[2M+Na]+, 381.05132 [M + Na]+
References
1. Kotali, A.; Harris, P. A. Org. Prep. Proc. Int. 1994,
26(2), 155.
2. Kostova, I. Curr. Med. Chem.-Anti Cancer Agents, 2005, 5, 29.
3. Cerecetto, H.; Porcal, W. Mini-Rev. in Med. Cmem., 2005, 5, 57.
4. Abramov, M. A.; Dehaen, W. Synthesis, 2000, 11, 1529.
© 2008 by the authors; licensee Molecular
Diversity Preservation International, Basel, Switzerland. This article is an
open-access article distributed under the terms and conditions of the Creative
Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).