SYNTHESIS AND CHARACTERIZATION OF 4-NITROPHENYLHYDRAZONE-N-ACYLHYDRAZONES (HAH) USING A GREEN MECHANOCHEMICAL PROTOCOL
Autor(es): HUMBERTO AGUIAR DIAS NETO e orientado por JOSÉ MAURÍCIO DOS SANTOS FILHO
Chronic inflammatory diseases such as asthma and rheumatoid arthritis affect millions of people around the world and represent a burden to these populations. The treatment with corticoids and immunosuppressive therapy allows the diseases’ control, but not the cure, usually with severe side effects. The external regulation of some genetic factors, such as NF-kB, can lead to the control of these diseases. Since N-acylhydrazones have demonstrated anti-inflammatory activity, acting by different molecular mechanisms, the research group with the SintMed® has designed and synthesised a new class of hydrazone-N-acylhydrazones (HAH), in order to investigate their anti-inflammatory and immunomodulatory properties. Following a new green, stereoselective and highly efficient synthetic protocol developed by our group, the targeting compounds were prepared using the grindstone methodology, which has proved to be appropriate to our purposes. This new approach for the synthesis of N-acylhydrazones has overcome the difficulties faced when the traditional methodology is applied, mainly due to the nature of the Japp-Klingermann product used as one of the reactants, which bears an acid sensitive vinylogous keto group.
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