Inspired by Nature: Isostere Concepts in Plant Hormone Chemistry

Abstract

Chemical concepts such as isosteres and scaffold hopping have proven to be powerful tools in agrochemical innovation processes. They offer opportunities to modify known molecular lead structures with the aim to improve a range of parameters, including biological efficacy and spectrum, physicochemical properties, stability, and toxicity. While recent biochemical insights into plant-specific receptors and signaling pathways trigger the discovery of the first lead structures, the disclosure of such a new chemical structure sparks a broad range of synthesis activities giving rise to diverse chemical innovation and often a considerable boost in biological activity. Herein, recent examples of isostere concepts in plant-hormone chemistry will be discussed, outlining how synthetic creativity can broaden the scope of natural product chemistry and giving rise to new opportunities in research fields such as abiotic stress tolerance and growth promotion.

Synthesis and Biological Activity Evaluation of Novel Chalcone Analogues Containing a Methylxanthine Moiety and Their N-Acyl Pyrazoline Derivatives

“…Melting points were determined with an X-4 binocular microscope apparatus (uncorrected). 1 H NMR (400 MHz) and 13 C NMR (101 MHz) spectra were recorded on a Bruker AV 400 spectrometer. High-resolution mass spectrometry (HRMS) was performed by using a Bruker solariX XR Fourier transform ion cyclotron resonance mass spectrometer.…”

“…In order to increase crop yields and overcome the defects of traditional pesticides such as environmental pollution and resistance problems, it is a permanent subject for researchers to discover and develop new agrochemicals with novel structures and excellent properties. , Structural modification and transformation of bioactive natural products is one of the practical ways for the design and discovery of new agrochemicals . In this way, there is often a high possibility of obtaining new pesticidal agents with high biological activity and favorable biocompatibility.…”

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

“…Thus, several bicyclic heteroaromatic motifs containing two nitrogen atoms serve as structural surrogates of cinmethylin ( 1 ), bearing a substituted 7-oxabicyclo[2.2.1]heptane scaffold [ 16 ]. Based on the findings outlined above and based on other plant-specific modes of action, it is plausible that FAT inhibitors encompass a broader range of structural motifs [ 16 – 17 ]. Herein, we present our approach to complement heteroaromatic lead structures 4 – 6 by introducing a nonaromatic motif via preparation of the novel 2,3-dihydro[1,3]thiazolo[4,5- b ]pyridines 7 .…”

Novel Insecticidal Butenolide‐Containing Methylxanthine Derivatives: Synthesis, Crystal Structure, Biological Activity Evaluation, DFT Calculation and Molecular Docking

“…[1] In this process, the design of novel agrochemicals based on the natural product structures that have pesticidal potentials is one of the most effective ways commonly used; by this means, it would lead to a high probability of obtaining new molecules with good activity and biocompatibility. [2,3] Methylxanthines are natural alkaloids originated from the purine base xanthine, and can be obtained from many different plants. Some of natural methylxanthines, such as caffeine, theophylline and theobromine (Figure 1), [4] have been given a popular recognition, as these non-toxic ingredients exist in coffee, tea, chocolate, cocoa, etc.…”