68892-27-3Relevant academic research and scientific papers
Natural trienoic acids as anticancer agents: First stereoselective synthesis, cell cycle analysis, induction of apoptosis, cell signaling and mitochondrial targeting studies
D’yakonov, Vladimir A.,Makarov, Alexey A.,Dzhemileva, Lilya U.,Ramazanov, Ilfir R.,Makarova, Elina Kh.,Dzhemilev, Usein M.
, (2021/04/13)
The first Z-stereoselective method was developed for the synthesis of unsaturated acids containing a 1Z,5Z,9Z-triene moiety in 61–64% yields using the new Ti-catalyzed cross-coupling of oxygen-containing and aliphatic 1,2-dienes as the key synthetic step. It was shown for the first time that trienoic acids with non-methylene-interrupted Z-double bonds show moderate cytotoxic activities against tumor cell lines (Jurkat, K562, U937, HL60, HeLa), human embryonic kidney cells (Hek293), normal fibroblasts and human topoisomerase I (hTop1) inhibitory activity in vitro. The synthesized acids efficiently initiate apoptosis of Jurkat tumor cells, with the cell death mechanism being activated by the mitochondrial pathway. A probable mechanism of topoisomerase I inhibition was also hypothesized on the basis of in silico studies resorting to docking. The activation and inhibition of the most versatile intracellular signaling pathways (CREB, JNK, NFkB, p38, ERK1/2, Akt, p70S6K, STAT3 and STAT5 tyrosine kinases) responsible for cell proliferation and for initiation of apoptosis were studied by multiplex assay technology (Luminex xMAP).
Method for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate
-
, (2019/08/01)
The invention discloses a method for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate. The method comprises the following steps: (1) preparing 3-tetradecyne alcohol-1; (2) preparing cis-3-tetradecenol-1; (3) preparing trans-3-tetradecenol-1; and (4) preparing the cis-3-tetradecanoacetate and trans-3-tetradecanoacetate. The method is used for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate which are main components of gyplure of holcocerus insularis Staudinger; the raw materials for reaction are easily obtained; the cost is low; technical processes are short; reaction conditions are mild; the operation is simple, convenient and free from risk; the product is easily separated; the yield is high; and massive production can be carried out.
Synthesis of long-chain fatty acid derivatives as a novel anti-Alzheimer's agent
Zhang, Hong-Yan,Yamakawa, Yu-Ichiro,Matsuya, Yuji,Toyooka, Naoki,Tohda, Chihiro,Awale, Suresh,Li, Feng,Kadota, Shigetoshi,Tezuka, Yasuhiro
, p. 604 - 608 (2014/01/23)
In order to develop new drugs for Alzheimer's disease, we prepared 17 fatty acid derivatives with different chain lengths and different numbers and positions of double bonds by using Wittig reaction and stereospecific hydrogenation of triple bonds as key reactions. Among them, (4Z,15Z)- octadecadienoic acid (10) and (23Z,34Z)-heptatriacontadienoic acid (16) showed the most potent neurite outgrowth activities on Aβ(25-35)-treated rat cortical neurons, which activities were comparable to that of a positive control, NGF. Both fatty acids 10 and 16 possess two (Z)-double bonds at the n-3 and n-14 positions, which might be important for the neurite outgrowth activity.
Synthesis of ω-Tritiated and ω-Fluorinated Analogues of the Trail Pheromone of Subterranean Termites
Carvalho, Joan F.,Prestwich, Glenn D.
, p. 1251 - 1258 (2007/10/02)
A series of unsaturated ω-fluoro alcohols have been prepared stereoselectively.These simple compounds are structural analogues of the trail pheromone of termites in the genus Reticulitermes.The toxicity of these ω-fluoro alcohols to R. flavipes is maximal for the C12 alcohols, and the attractiveness of these C12 analogues increases in the order saturated alkanol -12-fluoro alcohols and a -nonfluorinated analogue were prepared to examine the catabolism of the pheromone analogues.
