53293-00-8Relevant articles and documents
A concise synthesis of xestospongic acid methyl ester with pancreatic lipase inhibitory activity
Gong, Jing-Xu,Wang, He-Yao,He, Wen-Fei,Wang, Zhen-Zhong,Xiao, Wei,Guo, Yue-Wei
, p. 916 - 919 (2013)
Xestospongic acid methyl ester, a naturally brominated fatty acid with potent pancreatic lipase inhibitory activity in vitro, was synthesized from 5-hexynol in 30% total yield.
A boron-based Ireland-Claisen approach to the synthesis of pordamacrine A
Seizert, Curtis A.,Ferreira, Eric M.
, p. 4186 - 4194 (2017)
A synthetic approach to pordamacrine A that features two key transformations is discussed. The first transformation applies an Ireland-Claisen rearrangement to establish sterically congested vicinal carbon centers. Although a hard enolization technique for accessing the silyl ketene acetal failed, a soft enolization, boron-based reaction was highly successful. The second step involves a proposed cascade palladium-catalyzed biscyclization to construct two carbocycles of the natural product. The overall strategy is presented, demonstrating the challenges of the cyclization events in this complex setting.
Palladium-catalysed direct synthesis of optically active dienols
Jeffery
, p. 1133 - 1136 (1993)
A direct and highly chemo, regio and stereocontrolled method for constructing optically active conjugated dienols is described and illustrated by a short, convenient and efficient synthesis of methyl (9R)-9-hydroxytetradeca-5Z,7E-dienoate(-)-1.
DIMERIC IMMUNO-MODULATORY COMPOUNDS AGAINST CEREBLON-BASED MECHANISMS
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Page/Page column 144-145, (2020/02/06)
Disclosed are small molecules against cereblon to enhance effector T cell function. Methods of making these molecules and methods of using them to treat various disease states are also disclosed.
Luminescence modulations of rhenium tricarbonyl complexes induced by structural variations
Bertrand, Helene C.,Clede, Sylvain,Guillot, Regis,Lambert, Francois,Policar, Clotilde
, p. 6204 - 6223 (2014/07/07)
Octahedral d6 low-spin Re(I) tricarbonyl complexes are of considerable interest as noninvasive imaging probes and have been deeply studied owing to their biological stability, low toxicity, large Stokes shifts, and long luminescence lifetimes. We reported recently the bimodal IR and luminescence imaging of a Re(I) tricarbonyl complex with a Pyta ligand (4-(2-pyridyl)-1,2,3-triazole) in cells and labeled such metal-carbonyl complexes SCoMPIs for single-core multimodal probes for imaging. Re(I) tricarbonyl complexes have unique photophysical properties allowing for their unequivocal detection in cells but also present some weaknesses such as a very low luminescence quantum yield in aqueous medium. Further optimizations would thus be desirable. We therefore developed new Re(I) tricarbonyl complexes prepared from different ancillary ligands. Complexes with benzothiadiazole- triazole ligands show interesting luminescent quantum yields in acetonitrile and may constitute valuable luminescent metal complexes in organic media. A series of complexes with bidentate 1-(2-quinolinyl)-1,2,3-triazole (Taquin) and 1-(2-pyridyl)-1,2,3-triazole (Tapy) ligands bearing various 4-substituted alkyl side chains has been designed and synthesized with efficient procedures. Their photophysical properties have been characterized in acetonitrile and in a H 2O/DMSO (98/2) mixture and compared with those of the parent Quinta- and Pyta-based complexes. Tapy complexes bearing long alkyl chains show impressive enhancement of their luminescent properties relative to the parent Pyta complex. Theoretical calculations have been performed to further characterize this new class of rhenium tricarbonyl complexes. Preliminary cellular imaging studies in MDA-MB231 breast cancer cells reveal a strong increase in the luminescence signal in cells incubated with the Tapy complex substituted with a C12 alkyl chain. This study points out the interesting potential of the Tapy ligand in coordination chemistry, which has been so far underexploited.
Synthesis and functional pharmacological effects on human bronchi of 20-hydroxyeicosatetraenoic acid
Proteau-Gagne,St-Jean,Morin,Gendron,Rousseau,Dory
experimental part, p. 841 - 847 (2011/04/25)
We have synthesized 20-hydroxyeicosatetraenoic acid (20-HETE) following a new route and delineated its functional effects in human bronchi. Isometric tension measurements were performed, and they demonstrated that synthetic 20-HETE induced a concentration-dependent relaxant effect in ASM on resting tone and on bronchi pre-contracted with methacholine.
Preparation of large ring acetylenic lactones by iodo lactonisation
Rousseau, Gérard,Strzalko, Tekla,Roux, Marie-Claude
, p. 4503 - 4505 (2007/10/03)
Reaction of ω-ene-7-yne carboxylic acids with (biscollidine)iodine(I) hexafluorophosphate led to large ring acetylenic lactones. In the case of 5- or 6-yne carboxylic acids, iodo enol lactones were preferentially obtained.
A new base mediated method for the cleavage of tert-butyl esters
Paul, Soumendu,Schmidt, Richard R.
, p. 1107 - 1108 (2007/10/03)
A new method for the cleavage of tert-butyl esters with NaH in DMF is described.
Synthesis of ω-and (ω - 1)-acetylenic acids from five-, six-, or seven-membered cycloalkanones
Starostin,Ignatenko,Lapitskaya,Pivnitsky,Nikishin
, p. 833 - 837 (2007/10/03)
A convenient method for the synthesis of ω-and (ω - 1)-acetylenic acids involves free-radical oxidative scission of cycloalkanones containing five-, six, or seven-membered cycles to give the corresponding ω-olefinic acids followed by bromination of the latter and subsequent dehydrobromination under the action of alkalis.
Practical synthesis of hex-5-ynoic acid from cyclohexanone
Starostin,Lapitskaya,Ignatenko,Pivnitsky,Nikishin
, p. 81 - 84 (2007/10/03)
Hex-5-ynoic acid, a multipurpose synthon, was synthesized in three steps starting from cyclohexanone by bromination-dehydrobromination of the intermediate hex-5-enoic acid.
