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Research Article

Melatonin analogue new indole hydrazide/hydrazone derivatives with antioxidant behavior: Synthesis and structure–activity relationships

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Pages 506-515 | Received 08 Jan 2008, Accepted 15 May 2008, Published online: 01 Apr 2009

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Waleed A. Bayoumi & Magda A. Elsayed. (2011) Synthesis of new phenylcarbamoylbenzoic acid derivatives and evaluation of their in vitro antioxidant activity. Medicinal Chemistry Research 21:8, pages 1633-1640.
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