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Molbank 2008, 2008(2), M570; https://doi.org/10.3390/M570

Short Note
7-Hydroxy-8-acetylcoumarin N-Phenylsulfonylhydrazone
1
Laboratory of Organic Chemistry, Department of Chemical Engineering, College of Engineering, University of Thessaloniki, Thessaloniki 54124, Greece
2
GlaxoSmithKline, 1250 South Collegeville Road, P.O.Box 5089, Collegeville, PA 19426-0989, USA
*
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.
Molbank 2008 m570 i001
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]+

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

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.
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