38453-71-3Relevant academic research and scientific papers
Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity
Fujii, Yoshiharu,Iwata, Takayuki,Kano, Arihiro,Kodama, Kozue,Makigawa, Saki,Matsumoto, Kenji,Morita, Miyo Terao,Shindo, Mitsuru,Sugiyama, Hiromi,Wasano, Naoya
, (2020/09/09)
Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition, and revealed the structure–activity relationship in this inhibitory activity. The conformation of ku-76 is flexible owing to the open-chain structure of pentan-2,4-dienoic acid with freely rotating single bonds, and the (2Z)-alkene moiety may be isomerized by external factors. To develop more potent inhibitors and obtain insight into the target biomolecules, various analogues of ku-76, fixed through conformation and/or configuration, were synthesized and evaluated. Stereochemical fixation was effective in improving the potency of gravitropic bending inhibition. Finally, we found highly potent conformational and/or configurational analogues (ku-257, ku-294 and ku-308), that did not inhibit root growth. The inhibition of root curvature by these analogues was comparable to that of naptalam.
Selenium-mediated synthesis of biaryls through rearrangement
Shahzad, Sohail A.,Vivant, Clotilde,Wirth, Thomas
supporting information; experimental part, p. 1364 - 1367 (2010/06/17)
"Chemical Equation Presented" A new cyclization of β-keto ester substituted stilbene derivatives using selenium electrophiles in the presence of Lewis acids is described. Substituted naphthols are obtained through cyclization and subsequent 1,2-rearrangement of aryl groups under very mild reaction conditions.
Diselenide- and disulfide-mediated synthesis of isocoumarins
Shahzad, Sohail A.,Venin, Claire,Wirth, Thomas
experimental part, p. 3465 - 3472 (2010/09/07)
Cyclizations of stilbenecarboxylic acids to the corresponding isocoumarin derivatives using diselenide or disulfide reagents have been developed. By employing bis(triflouroacetoxy)iodobenzene as oxidant for the 6-endo-trig cyclizations a variety of dihydroisocoumarins have been prepared in good yields. This method is capable of forming isocoumarins and dihydroisocoumarin derivatives by a cyclization-elimination route.
The Synthesis and Anti-geotropic Activity of o-Arylethenylbenzoic Acids
Teitei, Tsutomu
, p. 1669 - 1674 (2007/10/02)
Fourteen new and three known o-arylethenylbenzoic acids (10-18), required for testing as potential plant growth regulators, have been synthesized by the Wittig reaction.The cis- and trans-isomers were separated by fractional crystallization and identified by NMR spectroscopy.The preliminary assay results on cress seedlings are reported and show that both geometric isomers appear to have nearly identical anti-geotropic activity in this test system.
