Synthesis, Biological Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of Novel 4-Methyl-1,2,4-triazole-thioethers Containing gem-Dimethylcyclopropane Ring

Abstract

A series of novel 4-methyl-1,2,4-triazole-thioethers containing gem-dimethylcyclopropane ring were designed and synthesized by multi-step reactions in search of potent novel bioactive molecules. Structures of all the target compounds were characterized by means of UV-Vis, FTIR, NMR, ESI-MS, and elemental analysis. The antifungal and herbicidal activities of the target compounds were preliminarily evaluated. As indicated in bioassay results, 2 compounds exhibited excellent antifungal activity against Physalospora piricola, which are much better than that of the commercial fungicide of chlorothalonil used as positive control. Also, at 100 µg/mL, 4 compounds displayed prominent herbicidal activity against the root-growth of rape (Brassica campestris), which are much better than that of the commercial herbicide of flumioxazin used as positive control. In the interest of developing more effective antifungal compounds against P. piricola, the preliminary analysis of three-dimensional quantitative structure-activity relationship (3D-QSAR) was carried out using the molecular field analysis (CoMFA) method, and a reasonable and effective 3D-QSAR model (r 2 ＝0.985, q 2 ＝0.509) has been established.

Synthesis, Antifungal Activity, and 3D-QSAR Study of Novel Nopol-Derived 1,3,4-Thiadiazole-Thiourea Compounds

“…In continuation of our long-term focus on natural product-based bioactive compounds [ 28 , 29 , 30 , 31 , 32 ], a series of novel nopol-derived 1,3,4-thiadiazole-thiourea compounds were synthesized by integrating bioactive 1,3,4-thiadiazole and thiourea moieties into the molecular skeleton of nopol. Structural characterization, antifungal evaluation, and structure–activity relationships of the title compounds were determined as well.…”

Synthesis, Antifungal Activity and 3D‐QSAR Study of Novel (E)‐Longifolene‐Derived Tetralone Oxime Ethers

“…In view of the clues above and as a continuation of our interest in search of bioactive compounds from abundant and renewable biomass resources, [31][32][33][34][35][36] a series of (E)-longifolenederived tetralone oxime ether compounds were designed, synthesized and characterized by integrating bioactive oxime ether group into the skeleton of longifolene-derived tetralin. All of the target compounds were preliminarily evaluated for in vitro antifungal activity and in vitro cytotoxicity.…”

Synthesis and Biological Activities of Novel (Z)‐/(E)‐Anisaldehyde‐Based Oxime Ester Compounds

“…In continuation of our focus on natural productbased bioactive compounds, [23][24][25][26][27][28] ten pairs of (Z)-/(E)anisaldehyde-based oxime ester compounds, which maintained the phenylpropanoid C6-C3 active structural unit of anethole, were synthesized by combining the bioactive oxime ester unit with the skeleton of anisaldehyde. The synthesized compounds were preliminarily screened for their herbicidal and antifungal activities as well.…”