Molbank 2008, M570

Text Box: OPEN ACCESS

ISSN 1422-8599

www.mdpi.org/molbank

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/).