Abstract
The reaction of 2-hydroxyheptadecanoyl chloride (2) and anthranilic acid gave 2-(1-hydroxyheptadecyl)-4H-3,1-benzoxazin-4-one (3) which was used as starting material to synthesize some condensed and non-condensed heterocyclic compounds by a reaction with nitrogen nucleophiles (e.g., hydrazine hydrate, and formamide). The subsequent reaction of the synthetic products with different amounts of propylene oxide gave a novel group of nonionic compounds having a double function as antibacterial and surface active agents which may serve in the manufacturing of drugs, cosmetics, pesticides or as antibacterial and/or antifungal products. The surface active properties such as surface and interfacial tensions, cloud point, foaming height, wetting time, and emulsification power were determined. Antimicrobial and biodegradability were also screened.
Highlights
Varied biological activities have been attributed to 2-substituted-3,1-benzoxazin-4-ones (Madkour, 2005) as well as the corresponding quinazoline derivatives including antipyretic (El-Sayed et al, 2005; Amin, 1998), antiinflammatory agents (Amin et al, 1998), antimitotic, anticancer agents (Aly, 2003) and they have good storage stability in detergents (Mohamed et al, 2003). This led us to synthesize a new series of 4H-3,1-benzoxazin-4-one and corresponding quinazoline derivatives which have high expectations for pharmaceutical and industrial applications
This encouraged us to synthesize a novel group of nonionic surface active agents containing the nucleus from α-hydroxy fatty acid
The synthesized compounds which have an active hydrogen atom were subjected to react with propylene oxide with different moles (n = 5, 10, 15) to produce a novel group of nonionic compounds having a double function as antimicrobial and surface active agents which can be useful in the manufacturing of drugs, cosmetics, pesticides or can be use as antibacterial and/or antifungal additives
Summary
T2-Hydroxyheptadecanoic acid chloride (2) reacted with anthranilic acid to produce 2-substituted-3,1-benzoxazin-4-one (3) which was used as starting material to synthesize some condensed and non-condensed heterocyclic compounds by reaction with nitrogen nucleophiles e.g., hydrazine hydrate, and formamide. The products were subjected to reaction with different moles of propylene oxide (n = 5, 10, 15) to produce a novel group of nonionic compounds having a double function as antibacterial and surface active agents which can be used in the manufacturing of drugs, cosmetics, pesticides or can be used as antibacterial and/or antifungal additives. The surface active properties as surface and interfacial tension, cloud point, foaming height, wetting time, and emulsification power were determined, the antimicrobial and biodegradability were screened. KEY-WORDS: Antimicrobial properties - Heterocyclic derivatives - Physical properties - Surface active agents
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