We present the preparation of a series of novel natural product-like homobarrelenones, norcaranes, and dihydrofluorenones through a diversity-oriented synthetic (DOS) strategy that combines Diels-Alder reactions and phototransformations, as well as their biological evaluation against MCF-7, HT-29, and NCI-H460 human tumor cells. Six of these demonstrated activities in the micromolar range against the three cell lines, and none were predicted as cytotoxic against human nontumor cells according to in silico studies. In addition, within the set of active derivatives, three exhibited low unspecific cytotoxicity in a sperm motility assay.
View Article and Find Full Text PDFThe subfamily Cerambycinae, one of the most diverse in longhorn beetles, is well known for its remarkable chemical parsimony in male-emitted pheromones. Conserved shared structural motifs have been reported in numerous species, sometimes working in combination with plant volatile kairomones. Among other compounds, the most ubiquitous male pheromone in cerambycine species is 3-hydroxyhexan-2-one.
View Article and Find Full Text PDFThe citrus borer, Diploschema rotundicolle, is a Neotropical longhorn beetle that has become a serious citrus pest in southern South America. Management strategies for this insect rely on trimming off damaged shoots, which is expensive and inefficient. We studied the chemical communication system in D.
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