18202-11-4Relevant articles and documents
Effect of Tellurium Position on the Myocardial Uptake of Radioiodinated 18-Iodotellura-17-octadecenoic Acid Analogues
Knapp, F.F.,Srivastava, P.C.,Callahan, A.P.,Cunningham, E.B.,Kabalka, G.W.,Sastry, K.A.R.
, p. 57 - 63 (1984)
The effect of tellurium (Te) position on myocardial specifity and retention of fatty acids in which radioiodide is stabilized as a trans-(E)-vinyl iodode has been evaluated in rats.Five analogues of 18-iodo-17-octadecenoic acid (ICH=CH-R-Te-R'-COOH) with Te at positions 5,7,9,11, and 13 were prepared by coupling of a trans-diiodoalkene (ICH=CH-R-I) with the requisite sodium telluride substrate (NaTe-R'-COOR''; R''=Me or Et), followed by basic hydrolysis.By varying R and R', a series of analogues with a chain length of 18 carbon atoms was prepared.T he telluride substrates were generated in situ by NaBH4 reduction of the corresponding ditellurides, and the diiodoalkenes were prepared by sodium iodide-chloramine-T treatment of the corresponding vinylboronic acids .The vinylboronic acids were prepared by treatment of the terminal acetylenes (HCC-R-I), synthesized from commercially available materials, with catecholborane.All new compounds were analyzed by TLC, NMR, MS, and elemental analyses.The 125I analogues were prepared in the same manner and evaluated in rats (four per group).Heart uptake and retention were dependent upon the Te position.The analogue with Te at position 5 showed the most pronounced (5-min values) heart uptake (3.7-4.1 dose/g), myocardial retention, and heart/blood ratios (37:1) and is a candidate for radiolabeling with 123I and further evaluation as a myocardial imaging agent.
Streamlined One-Pot Synthesis of Nitro Fatty Acids
El Rady, Eman A.,Hassan, Mohamed,Krieg, Sara-Cathrin,Maier, Thorsten J.,Manolikakes, Georg,Ndefo Nde, Cedric,Raslan, Mohamed A.,Roos, Jessica,Sadek, Kamal U.
, p. 2239 - 2252 (2021)
A novel method for the synthesis of nitro fatty acids (NFAs), an intriguing class of endogenously occurring lipid mediators, is reported. This one-pot procedure enables the controlled and stereoselective construction of nitro fatty acids from a simple set of common building blocks in a highly facile manner. Thereby, this methodology offers a streamlined, highly modular access to naturally occurring nitro fatty acids as well as non-natural NFA derivatives.
The Effect of Two-dimensional Ordering on Photoreactions of Long-chain Unsaturated Carboxylic Acids
Guo, Bo Zhang,Tripathi, Sadhana,Taylor, D. Martin,Stirling, Charles J. M.
, p. 479 - 481 (1991)
Long chain alkanoic acids with terminal alkenyl and alkynyl groups are subjected to UV irradiation in ordered (Langmuir-Blodgett) and disordered films; polymerisation occurs in the LB films but only dissociation and desorption in the disordered films.
Synergistic Gold and Copper Dual Catalysis for Intramolecular Glaser–Hay Coupling: Rapid Total Synthesis of Ivorenolide B
Rangaraju, Sudheer K.,Gonela, Uma Maheshwar,Kavita, Aala,Yadav, Jhillu S.,Mohapatra, Debendra K.
supporting information, p. 4376 - 4380 (2018/09/11)
A synergistic dual catalysis approach involving gold and copper catalysts for the synthesis of macrolactones bearing 1,3-butadiynes through an intramolecular Glaser–Hay coupling reaction in good yield is described. This dual catalytic system exhibited good selectivity, reactivity and functional group tolerance. This unique process offers a paradigm shift: the potential as well as the versatility of this novel method is not only exemplified for the synthesis of macrolactones of different ring size but also for the rapid total synthesis of ivorenolide B, a new class of macrolides endowed with conjugated 1,3-diyne motif, having impressive immunosuppressive activities.
A Sequential Homologation of Alkynes and Aldehydes for Chain Elongation with Optional 13C-Labeling
Brunner, Andreas,Hintermann, Lukas
, p. 2787 - 2792 (2016/02/27)
Terminal alkynes (RCCH) are homologated by a sequence of ruthenium-catalyzed anti-Markovnikov hydration of alkyne to aldehyde (RCH2CHO), followed by Bestmann-Ohira alkynylation of aldehyde to chain-elongated alkyne (RCH2CCH). Inverting the sequence by starting from aldehyde brings about the reciprocal homologation of aldehydes instead. The use of 13C-labeled Bestmann-Ohira reagent (dimethyl ((1-13C)-1-diazo-2-oxopropyl)phosphonate) for alkynylation provides straightforward access to singly or, through additional homologation, multiply 13C-labeled alkynes. The labeled alkynes serve as synthetic platform for accessing a multitude of specifically 13C-labeled products. Terminal alkynes with one or two 13C-labels in the alkyne unit have been submitted to alkyne-azide click reactions; the copper-catalyzed version (CuAAC) was found to display a regioselectivity of >50 000:1 for the 1,4- over the 1,5-triazine isomer, as shown analytically by 13C NMR spectroscopy.
