- Effect of Tellurium Position on the Myocardial Uptake of Radioiodinated 18-Iodotellura-17-octadecenoic Acid Analogues
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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.
- Knapp, F.F.,Srivastava, P.C.,Callahan, A.P.,Cunningham, E.B.,Kabalka, G.W.,Sastry, K.A.R.
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- Synthesis of pyrinodemins A and B. Assignment of the double bond position of pyrinodemin A
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Condensation of aldehyde 3a with hydroxylamine 4b afforded nitrone 2, which underwent an intramolecular cycloaddition to give 1b, the proposed structure of pyrinodemin A. A similar condensation of aldehyde 3a and hydroxylamine 4a provided pyrinodemin A (1a), which has the double bond one carbon further away from the isoxazolidine. An analogous sequence gave pyrinodemin B (21).
- Snider, Barry B.,Shi, Bo
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- Streamlined One-Pot Synthesis of Nitro Fatty Acids
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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.
- 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.
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- Straightforward synthesis of a double-lasso macrocycle from a nonsymmetrical [c2]daisy chain
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The straightforward synthesis of a double-lasso macrocycle from a nonsymmetrical [c2]daisy chain, using the copper(I)-catalyzed Huisgen alkyne-azide 1,3-dipolar cycloaddition, is described. The preparation of the nonsymmetrical alkyne azide [c2]daisy chain precursor was realized in situ via the exchange of the monomers contained in both symmetrical alkyne and azide [c2]daisy chains and was followed by mass spectrometry.
- Romuald, Camille,Cazals, Guillaume,Enjalbal, Christine,Coutrot, Frédéric
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- The Effect of Two-dimensional Ordering on Photoreactions of Long-chain Unsaturated Carboxylic Acids
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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.
- Guo, Bo Zhang,Tripathi, Sadhana,Taylor, D. Martin,Stirling, Charles J. M.
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- LIPOSOME FORMULATION
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The present invention describes liposome formulations comprising a phospholipid, cholesterol and a fatty acid compound or fatty acid containing compound. Also, various medical uses of the liposome formulation are described.
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- Synergistic Gold and Copper Dual Catalysis for Intramolecular Glaser–Hay Coupling: Rapid Total Synthesis of Ivorenolide B
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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.
- Rangaraju, Sudheer K.,Gonela, Uma Maheshwar,Kavita, Aala,Yadav, Jhillu S.,Mohapatra, Debendra K.
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supporting information
p. 4376 - 4380
(2018/09/11)
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- Total Synthesis and Structural Elucidation of Two Unusual Non-Methylene-Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma
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In our previous study, unusual odd-numbered dienoic acids with a terminal olefin were found as minor components in ovaries of the Japanese limpet Cellana toreuma, and the synthetic interests have been focused onto their structural confirmation and the inspection into their potential biological activity. Here, we describe an efficient and stereoselective total synthesis of two new unusual dienoic acids, 19:2?7,18 and 21:2?7,20, through a common pathway involving the strategic combination of alkyne-zipper reaction and Lindlar hydrogenation for the construction of their unique carbon chains. In our synthetic study, 2-propyn-1-ol was at first subjected to alkylation and alkyne-zipper reaction to form the two fragments, and the subsequent carbon chain elongation was achieved by the usual coupling reaction to obtain the C-19 and C-21 products bearing an internal acetylenic group. Then, the internal acetylenic group of these products was subjected to Lindlar hydrogenation to form a Z-alkenyl moiety, and the subsequent deprotection of the products was carried out under an acidic condition without isomerization of the internal Z-alkenyl group. Total synthesis of target fatty acids, 19:2?7,18 and 21:2?7,20, was finally accomplished by two-step oxidation of the resulting alcohols into carboxylic acids in a highly chemoselective manner, and the structures of these unusual natural fatty acids were finally elucidated by identifying the GC–MS spectra of the methyl esters of authentic and synthetic fatty acids.
- Shimada, Kazuaki,Sugawara, Ayako,Korenaga, Toshinobu,Kawashima, Hideki
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p. 1019 - 1032
(2017/10/07)
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- α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation
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Readily available α-amino aldehydes, incorporating a methylthiomethyl (MTM) protecting group on nitrogen, are shown to be efficient substrates in Rh-catalyzed alkyne hydroacylation reactions. The reactions are performed under mild conditions, employing a small-bite-angle bis-phosphine ligand, allowing for good functional group tolerance with high stereospecificity. Amino aldehydes derived from glycine, alanine, valine, leucine, phenylalanine, isoleucine, serine, tryptophan, methionine, and cysteine were successfully employed, as was an enantiomerically enriched α-OMTM-aldehyde derived from phenyllactic acid. The synthetic utility of the α-amino enone products is demonstrated in a short enantioselective synthesis of the natural product sphingosine.
- Hooper, Joel F.,Seo, Sangwon,Truscott, Fiona R.,Neuhaus, James D.,Willis, Michael C.
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supporting information
p. 1630 - 1634
(2016/02/20)
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- A Sequential Homologation of Alkynes and Aldehydes for Chain Elongation with Optional 13C-Labeling
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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.
- Brunner, Andreas,Hintermann, Lukas
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p. 2787 - 2792
(2016/02/27)
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- Enantioselective Rhodium-Catalyzed Atom-Economical Macrolactonization
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A highly attractive route toward macrolactones, which form the cyclic scaffold of a multitude of diverse natural compounds, is described. Although many chemical approaches to this structural motif have been explored, an asymmetric variant of the cyclization is unprecedented. Herein we present an enantioselective macrolactonization through an intramolecular atom-economical rhodium-catalyzed coupling of ω-allenyl-substituted carboxylic acids. The use of a modified diop ligand, chiral DTBM-diop, led to high enantioselectivity (up to 93 % ee). The reaction tolerated a large variety of functionalities, including α,β-unsaturated carboxylic acids and depsipeptides, and provided the desired macrocycles with very high enantio- and diastereoselectivity.
- Ganss, Stephanie,Breit, Bernhard
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p. 9738 - 9742
(2016/08/10)
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- In situ proteome profiling of C75, a covalent bioactive compound with potential anticancer activities
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A library of cell-permeable, minimally tagged C75 analogues was synthesized and used to uncover biological targets in human liver cancer cells. Known targets of C75, namely FASN and CPT1A, together with other unknown targets, including PDIA3, TFRC, and GAPDH, were thus identified.
- Cheng, Xiamin,Li, Lin,Uttamchandani, Mahesh,Yao, Shao Q.
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p. 1414 - 1417
(2014/04/03)
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- Maltoside and Phosphocholine Derivatives, Uses thereof and Methods of Preparing Artificial Lipid Structures Thereof
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Disclosed are saccharide and phosphocholine derivatives. The derivatives include azide and alkyne derivatives which form one end of a variable length carbon chain. The opposite end of the variable length carbon chain is covalently linked to the saccharide or phosphocholine. The saccharide may be, for instance, a maltoside. The alkyne and azide derivatives of the saccharides and phosphocholine may be reacted together to form amphiphilic molecules useful in cellular membrane studies and applications. By adjusting the length of the carbon chain, the biochemical and biophysical properties of the resultant 1,4-disubstituted 1,2,3-triazole compounds may be custom tailored for the intended application. Resultant molecules may form micelles, bicelle, lipid bilayers and other like structures useful in the isolation and purification of membrane bound or membrane associated proteins and biochemical components. The saccharides and phosphocholine molecules may be alternatively substituted as desired to provide additional flexibility in designing the desired end product.
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Paragraph 0056
(2013/04/24)
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- HETEROCYCLIC DERIVATIVES THAT ARE USED IN THE TREATMENT OF NEURODEGENERATIVE DISEASES
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The present invention relates to compounds of Formula (I) below, to their pharmaceutically acceptable salts and to their isomers or mixtures of isomers: HetAr—X—CHR1R2 (I) in which: -HetAr represents a group chosen from: —X represents a linear, saturated or unsaturated, hydrocarbon-based chain comprising from 8 to 22 carbon atoms, optionally interrupted by an —NH— or —NH—CO— group, —R1 represents a hydrogen atom or an —OH, —O(C1-C6)alkyl, —OCO((C1-C6)alkyl), —OSO2((C1-C6)alkyl) or —OSO3H group, and —R2 represents a hydrogen atom or a (C2-C6)alkynyl, (C2-C6)alkenyl or (C3-C6)cycloalkyl group. The present invention also relates to a process for preparing the compounds of Formula (I), and also to the use thereof, especially in the treatment of neurodegenerative diseases.
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Page/Page column 14
(2011/06/10)
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- An efficient synthesis of liquid crystalline gigantocycles combining banana-shaped and rod-like mesogenic units
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The synthesis of monodisperse gigantocycles with 63, 87, and 147 ring atoms on the gram scale is described. These molecules were assembled from terphenylene derivatives and long, flexible chains which were mainly aliphatic, with terminal alkyne groups. The latter allowed for ring formation through oxidative alkyne dimerization in high yield (80-87%). The combination of a rod-like and a banana-shaped mesogen connected by flexible chains within the backbone of a ring gives rise to nematic and smectic mesophases.
- Godt, Adelheid,Duda, Stefan,Uensal, Oemer,Thiel, Juergen,Haerter, Alice,Roos, Mark,Tschierske, Carsten,Diele, Siegmar
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p. 5094 - 5106
(2007/10/03)
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- Catalytic asymmetric synthesis of macrocyclic (E)-allylic alcohols from ω-alkynals via intramolecular 1-alkenylzinc/aldehyde additions
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The ω-alkynals yielded macrocyclic (S)-allylic alcohols in a one-pot reaction sequence involving alkyne monohydroboration, boron to zinc transmetalation, and ((+)-DAIB)-catalyzed enantioselective intramolecular ring closure to the aldehyde function. A general study of this macrocyclization methodology is presented with respect to ligand type, size, and nature of the formed rings.
- Oppolzer,Radinov,El-Sayed
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p. 4766 - 4770
(2007/10/03)
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- Towards the synthesis of epothilone A: Enantioselective preparation of the thiazole side-chain and macrocyclic ring closure
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A synthetic approach to a new class of microtubule-stabilizing natural products is described which employs a macrocyclic olefination strategy to cyclize the 16-membered lactone ring. The C13-C19 thiazole subunit of epothilone A and B is prepared in high enantioselectivity using a catalytic asymmetric allylation reaction.
- Taylor, Richard E.,Haley, Jeffrey D.
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p. 2061 - 2064
(2007/10/03)
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- Synthesis of -Catenanes from -Rotaxanes
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Starting from the rotaxane 18a a mixture of catenane 21 and rotaxane 23 is obtained by attaching a polymethylene bridge between the methylene groups in α-position of the sulfonyl groups.The isocyclic catenane 28 containing a 28- and a 46-membered ring is
- Schill, Gottfried,Schweickert, Norbert,Fritz, Hans,Vetter, Walter
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p. 961 - 970
(2007/10/02)
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- THIA-ACYLIMINIUM CYCLISATIONS. SYNTHESIS OF FIVE-MEMBERED RINGS AND MACROCYCLES
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Cyclisations of carbinollactams 1b-3b afford macrocycles 4-6 in good yield by the intermediacy of N-acyliminium species.A similar process applied to lactams 21b-25b affords the pyrrolizidine type compounds 26-35 through consecutive azonium-Cope rearrangem
- Hamersma, J. A. M.,Nossin, P. M. M.,Speckamp, W. N.
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p. 1999 - 2006
(2007/10/02)
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- (Z)- and (E)-12-Tetradecenyl Acetates: Sex Pheromone Components of Oriental Corn Borer (Lepidoptera: Pyralidae)
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The female sex pheromone of the oriental corn borer, Ostrinia furnacalis Guenee, was presumed to be composed of (Z)-12-tetradecenyl acetate and its geometrical isomer using electroantennogram technique.From the extracts of female moths, the presence of these compounds in a ratio of ca. 3:2 was confirmed by gas-liquid chromatography and gas-liquid chromatography combined with mass spectrometry in selected ion monitoring mode.Since the male moths were not attracted to mixtures of the two synthetic compounds, the presence of minor component(s) was suggested.
- Ando, Tetsu,Saito, Osamu,Arai, Koshi,Takahashi, Nobutaka
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p. 2643 - 2650
(2007/10/02)
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