87462-66-6Relevant academic research and scientific papers
Lewis Acid-Catalyzed Intramolecular [3+2] Cross-Cycloaddition of Aziridine 2,2-Diesters with Conjugated Dienes for Construction of Aza-[n.2.1] Skeletons
Zhan, Yizhou,Liu, Tao,Ren, Jun,Wang, Zhongwen
supporting information, p. 17862 - 17866 (2017/11/27)
A novel Lewis acid-catalyzed [3+2] intramolecular cross-cycloaddition (IMCC) between aziridine 2,2-diesters and conjugated dienes has been developed. This is the first regiospecific IMCC of intramolecular 1,3-dipolar cycloadditions of azomethine ylides with carbon=carbon double bonds, and supplies a general and efficient strategy for construction of structurally complex and diverse aza-[n.2.1] skeletons. The [3+2]IMCC could be carried out under mild conditions and in gram scale. More importantly, 3-alkyl-substituted aziridines were also successful. The excellent structural diversity, the facile operation and the versatile post-modifications will support the applications of the [3+2]IMCC in natural products synthesis and drugs discovery.
Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding
Opie, Christopher R.,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information, p. 3349 - 3353 (2017/03/17)
A linear molecular architecture equipped with complementary three-fold hydrogen-bonding units embedded with a photoswitchable trans-tetrafluoroazobenzene moiety was synthesized. The transto cis photoisomerism of the azobenzene unit induced drastic changes
Copper(I)-Catalyzed Interrupted Click Reaction: Synthesis of Diverse 5-Hetero-Functionalized Triazoles
Wang, Weiguo,Peng, Xianglong,Wei, Fang,Tung, Chen-Ho,Xu, Zhenghu
supporting information, p. 649 - 653 (2016/02/27)
The 5-heterofunctionalized triazoles are important scaffolds in bioactive compounds, but current click reactions (CuAAC) cannot produce these core structures. A copper(I)-catalyzed interrupted click reaction to access diverse 5-functionalized triazoles is reported. Various 5-amino-, thio-, and selenotriazoles were readily assembled in one step in high yields. The reaction proceeds under mild conditions with complete regioselectivity. It also features a broad substrate scope and good functional group compatibility.
In situ selection of lead compounds by click chemistry: Target-guided optimization of acetylcholinesterase inhibitors
Krasinski, Antoni,Radic, Zoran,Manetsch, Roman,Raushel, Jessica,Taylor, Palmer,Sharpless, K. Barry,Kolb, Hartmuth C.
, p. 6686 - 6692 (2007/10/03)
The target-guided, in situ click chemistry approach to lead discovery has been successfully employed for discovering acetylcholinesterase (AChE) inhibitors by incubating a selected enzyme/tacrine azide combination with a variety of acetylene reagents that were not previously known to interact with the enzyme's peripheral binding site. The triazole products, formed by the enzyme, were identified by HPLC-mass spectrometry analysis of the crude reaction mixtures. The target-guided lead discovery search was also successful when performed with reagent mixtures containing up to 10 components. From 23 acetylene reagents, the enzyme selected two phenyltetrahydroisoquinoline (PIQ) building blocks that combined with the tacrine azide within the active center gorge to form multivalent inhibitors that simultaneously associate with the active and peripheral binding sites. These new inhibitors are up to 3 times as potent as our previous phenylphenanthridinium-derived compounds, and with dissociation constants as low as 33 femtomolar, they are the most potent noncovalent AChE inhibitors known. In addition, the new compounds lack a permanent positive charge and aniline groups and possess fewer fused aromatic rings. Remarkably, despite the high binding affinity, the enzyme displayed a surprisingly low preference for one PIQ enantiomer over the other.
NEW RADIOHALOGENATED ALKENYL TELLURIUM FATTY ACIDS
Srivastava, Prem C.,Knapp, Furn F.,Kabalka, George W.
, p. 49 - 58 (2007/10/02)
Radiolabeled long-chain fatty acids have diagnostic value as radiopharmaceutical tools in myocardial imaging.Some applications of these fatty acids are limited due to their natural metabolic degradation in vivo with subsequent washout of the radioactivity
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 (2007/10/02)
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.
