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Songbai Liu Wu-Hong Wang Ya-Li DangYuanqing Fu Ruocheng Sang 《Tetrahedron letters》2012,53(32):4235-4239
A fluorescent-labeled jasmonate was rationally designed based on examination of the model of interaction between the jasmonate and its receptor. An efficient synthetic route has been developed for this molecule. The biological activity of this fluorescent probe was retained which was similar to that of the methyl jasmonate as examined by root growth inhibition bioassay. This fluorescent probe will greatly facilitate biological studies of jasmonates through fluorescent imaging. 相似文献
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We report the synthesis of the novel fluorescence-labeled jasmonate glycoside 2 based on β-d-glucopyranosyl 12-hydroxyjasmonate 1, which is a leaf-closing substance of Albizzia julibrissin Durazz. The fluorescence study using 2 revealed that the target cell for 1 is a motor cell. Probe 2 bound to the motor cells of two plants belonging to genus Albizzia. This result suggested that a receptor for 2, which is common among genus Albizzia would be involved in the nyctinastic leaf movement. 相似文献
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Christian Chapuis Robert Brauchli Jean‐Yves de Saint Laumer 《Helvetica chimica acta》2013,96(2):246-258
Dehydrohedione (DHH) 1 may be obtained in 20% overall yield by a Reformatsky reaction with enone methyl ether 3b , followed by acidic workup of the crude reaction mixture. Alternatively, epoxidation (3‐chloroperbenzoic acid, CH2Cl2, 84% yield) of the tertiary allyl alcohol derivative 4 affords a 1 : 2 mixture of 8a and 8b . The latter epoxy ester 8b may also be obtained stereoselectively either from 4 (tBuO2H, [Mo(CO)6], 1,2‐dichloroethane, 70°, 62% yield; or tBuO2H, [VO(acac)2], decane, 20°, 92% yield), or from 5 (AcOMe, LiN(SiMe3)2, THF, ?78°, 84–87%). BF3?Et2O‐Catalyzed cascade rearrangement and OH elimination of 8a afford selectively DHH 1 in 88% yield. The cis disposition of the side chains of the weakly odoriferous hedione‐like analogues 2b and 2c was maintained by means of either an epoxy or a cyclopropane moiety. 相似文献
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Weiping Zhu Zhenjiang Zhao Yufang Xu 《Monatshefte für Chemie / Chemical Monthly》2008,139(9):1067-1071
Salicylic acid (SA) and methyl jasmonate (MJ) are important plant signal molecules to cause systemic acquired resistance (SAR), while it’s reported that they also have wide spectrum antitumor activities. Benzothiadiazole-7-carboxylates are plant activators
which can cause SAR just like SA and MJ. To investigate whether the benzothiadiazole-7-carboxylate family is endowed with anticancer activities, several benzothiadiazole-7-carboxylate
derivatives are synthesized and their inhibition to P388 murine leukemia cell and A549 human lung cancer cell compared with
MJ are evaluated. The data indicated that benzo-1,2,3-thiadiazole-7-carboxylic acid 2-benzoyloxyethyl ester has a higher inhibition
ability to the cancer cell P388 and A549, compared with MJ.
Correspondence: Yufang Xu, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China. 相似文献
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Christian Chapuis Carole Cantatore Jean‐Yves deSaintLaumer 《Helvetica chimica acta》2006,89(6):1258-1264
We present an efficient three‐step, two‐pot synthesis of methyl jasmonate (trans‐ 1 ) based on Diels–Alder cycloaddition of cyclopent‐2‐enone ( 2 ) and chloroprene (= 2‐chlorobuta‐1,3‐diene; 3d ) in either CHCl3 or CH2Cl2, catalyzed by SnCl4 (0.2 mol‐equiv.) at 20° (75% yield). Subsequent ozonolysis of a cis/trans 55 : 45 mixture of the cycloadduct 4d in either CH2Cl2 or AcOEt at ? 78°, followed by addition of Me2S and MeOH in the presence of NaHCO3, afforded, in 64% yield, a cis/trans 40 : 60 mixture of the known aldehyde 5c . The latter was reacted at ? 50° under salt‐free conditions with the propyl Wittig reactant to furnish 1 as a cis/trans 20 : 80 mixture ((E/Z) 3 : 97). Alternatively, a cis/trans 7 : 93 mixture ((E/Z) 4 : 96) was obtained in 88% yield from epimerized 5c (AcOH, H2O, 40°; 99%) under usual Wittig conditions at ? 20°. 相似文献
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