Pyridazines are of chemical and biological interest. They have been reported to be anticonvulsive agents [1], [2]. Furthermore, BELLASIO et al. have described the antihypertensive effects of hydrazinopyridazine compounds [3]. In continuation of this line of investigation, we have synthesized compound (I); it will be subjected to further pharmacological investigations, especially tests of its anticancer activity.
To ( 0.96 g, 3 mmol) of ethyl [4-(2-chlorobenzyl)-3-methyl-6-oxopyridazin-1(6H)-yl)] acetate (I), was added 10 ml of hydrazine hydrate. The mixture was placed in a pyrex tube which was then introduced into a Maxidigest MX 350 Prolabo microwave[4] monomode reactor and refluxed for 10 min on 60 w as irradiation power. After cooling, the product precipitates, and then is recristallised in absolute ethanol, yield : 80 % of (II) solid.
Melting point: 201-205°C
IR (KBr, cm-1): 3352(NH), 1682 , 1469 , 1622 (C = O)
1HNMR (300.14 MHz, CDCl3) δ (ppm): 2.49 (s, 3H, CH3), 3.97 (s, 2H, CH2), 4.21 (s, 2H, NH2), 4.52 (s, 2H, CH2), 6.03 (s, 1H, H4), 7.53 (m, 4H, H aromatic), 9.24 (s, 2H, NH2).
13CNMR (75 MHz, CDCl3) δ (ppm): 19.38 (CH3), 35.6 (CH2), 52.76 (CH2), 126.98 (CH aromatic), 128.85 (CH aromatic), 130.25 (CH aromatic), 130.68 (CH aromatic), 132.6 (CH aromatic), 134.54, 135.43, 144.93, 146.03, 160.31 (C=O), 167.16 (C=O).
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3References
- Wermuth, C.G.; Leclerc, G.; Melounov, P. Chim. Ther. 1971, 2, 109.
- Laborit, H.; Weber, B.; Wermuth, C.G.; Delbarre, B.; Chekler, C.; Baron, C.; Rosen Garten, H. AGRESSOLOGIE 1965, 6, 415. [PubMed]
- Bellasio, E.; Parravicini, F.; Testa, E. Il Farmaco Ed Sci. 1969, 11, 919.
- (a) Kappe, C.O.; Dallinger, D. Nature Reviews Drug Discovery 2006, 5, 51. (b) De la Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164.
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