Synthesis, Antifungal Activity and Structure-Activity Relationships of Vanillin Oxime-N-O-Alkanoates

Abstract

Vanillin oxime-NO -alkanoates were synthesized following reaction of vanillin with hydroxylamine hydrochloride, followed by reaction of the resultant oxime with acyl chlorides. The structures of the compounds were confirmed by IR, 1 H, 13 C NMR and mass spectral data. The test compounds were evaluated for their in vitro antifungal activity against three phytopathogenic fungi Macrophomina phaseolina, Rhizoctonia solani and Sclerotium rolfsii by the poisoned food technique. The moderate antifungal activity of vanillin was slightly increased following its conversion to vanillin oxime, but significantly increased after conversion of the oxime to oxime-NO -alkanoates. While vanillin oxime-NO -dodecanoate with an EC 50 value 73.1 μg/mL was most active against M. phaseolina, vanillin oxime-NO -nonanoate with EC 50 of value 66.7 μg/mL was most active against R. solani. The activity increased with increases in the acyl chain length and was maximal with an acyl chain length of nine carbons.

Oxidation of Eugenol Derivatives with KMnO4 and CrO3

“…Vanillin oxime ( 9 ) is a compound that has been shown different activities like anti-inflammatory, 18 antifungal, 19 antimicrobial and antioxidant. 20 Vanillin oxime was synthesized from compound 4 , which was transformed to vanillin ( 8 ) by the deprotection of the ester function to alcohol in one and simple step in good yield.…”

One-pot Multicomponent Synthesis of Novel Polyfunctionalized Pyridines

“…Vanillin is considered one of the most important safe natural products for many uses. Not only that we can‫׳‬t do without it in our daily lives as a flavoring for taste and aroma [1], but also it has many biological properties as antitumor [2], antioxidant [3], antimicrobial [4], antibacterial [5], antiinflammatory [6], antimutagenic [7], antialzheimer's [8], antiproliferative activities [9], antidiabetic [10] and antidepressant [11]. Furthermore, vanillin is low toxicity, easy decomposition possesses general bio-safety, environmental friendliness, and specificity to target species [12].…”

Facile Synthesis of Novel Vanillin Derivatives Incorporating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents

“…Third, vanillin has desirable biological activities, such as antitumor, − antioxidant, , antimicrobial, , antifungal, − antiinflammatory, antimutagenic, and antiproliferative activities. In addition, vanillin derivatives possess desirable antifungal and antibacterial activities. However, studies on the application of vanillin derivatives in antiviral pesticides have not been reported.…”