Synthesis of Some N, N′‐Diacylhydrazine Derivatives with Radical‐Scavenging and Antifungal Activity

Abstract

These authors contributed equally to this work.A series of N,N¢-diacylhydrazines were prepared and their structures were confirmed by 1 H NMR, MS and FTICR-MS. They were tested radical-scavenging activity in vitro. The preliminary bioassays of title compounds showed that two compounds had excellent radical-scavenging activity comparable with vitamin C, while the activity is highly relative to the substituents. Surprisingly, several compounds also exhibit favorable fungicidal activities. To further explore the comprehensive structureactivity relationships about the fungicidal activity, a three-dimensional quantitative structure-activity relationship analysis using the method of comparative molecular field analysis was performed.

Synthesis, biological activities and SAR studies of novel 1‐Ethyl‐7‐methyl‐4‐oxo‐1,4‐dihydro‐[1,8]naphthyridine‐3‐carboxylic acid based diacyl and sulfonyl acyl hydrazines

“…But very few have been studied for the evaluation of other biological activities like fungicidal, bactericidal, etc. apart from IGR activity …”

“…apart from IGR activity. 12,13 In addition, many compounds containing 1,8-naphthyridine moiety have been found biologically active as IGRs, fungicides, bactericides, herbicides, insecticides, and nematicides. 14 -19 Nalidixic acid, 1,8-napthyridine derivative, is the first quinolone based antibacterial drug that showed great importance in both pharmaceutical and agrochemical fields.…”

Design, Synthesis, Biological Activities, and 3D‐QSAR of New N,N′‐Diacylhydrazines Containing 2‐(2,4‐dichlorophenoxy)propane Moiety

“…More recently, diacylhydrazine derivatives have become one of the focuses in the development of agrochemicals because of their high biological activities (1–6), especially herbicidal activities as well as fungicidal activities. Some examples of diacylhydrazines are presented in Scheme 1.…”

Design, Synthesis, Antifungal Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moiety

“…In our laboratory, we synthesized some diacylhydrazine derivatives successfully. They displayed good herbicidal activities [8], antifungal activities [6], radical scavenging activity [6], and plant growth regulatatory activity [8]. In order to find novel structural and non-resistance antifungals, the title compounds were designed by introducing 2-(2,4-dichlorophenoxy) acetic acid pharmacophore into the diacylhydrazine scaffold.…”

“…Also diacylhydrazines are a class of insect growth regulators that have been found to act as nonsteroidal ecdysone agonists [4]. On the other hand, many synthetic diacylhydrazine compounds also exhibit a broad spectrum of biological activities, such as anti-HIV [5], fungicidal [6], ketol-acid reductoisomerase inhibitor (KARI) [6], plant growth regulatory activity [7], etc. 2,4-Dichlorophenoxyacetic acid (2,4-D) and their derivatives also exhibit many biological activities, such as antifungal activities [8], herbicidal activities [9], plant growth regulation activities [10] and so on.…”