5754-35-8Relevant academic research and scientific papers
Synthetic studies towards N-substituted 3-vinyl-4-piperidineacetic acid derivatives
Johnson, David A.,Gribble, Gordon W.
, p. 178 - 195 (2019/05/15)
The synthesis and full characterization of two new (E)-2-butenyl)-5-amino-2-pentenoates, (Z)-4-[N-(3-buten-1-yl)benzamido]-2-buten-1-ol, and (Z)-1-chloro-4-[N-(3-buten-l-yl)benzamido]-2-butene are reported. These were designed as substrates for a projected thermal ene cyclization leading to the N-substituted 3-vinyl-4-piperidineacetic acid scaffold. Although conditions for this ene-cyclization have not yet been uncovered, the ease of preparation of these ene-cyclization substrates gives promise for their future use.
CLEAVABLE NUCLEOTIDE ANALOGS AND USES THEREOF
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Page/Page column 4; 19; 22, (2018/06/22)
Cleavable nucleotide analogs are provided. The nucleotide analog includes a nucleotide molecule attached to a cleavable moiety wherein the cleavable moiety comprises a protective group and/or a linker attached to a fluorophore. The cleavable moiety is linked to the oxygen atom of the 3'-OH of the pentose of the nucleotide molecule. The nucleotide analogs can be used in making polynucleotide molecules using template independent polymerases. The nucleotide analogs can act as reversible terminators during DNA sequencing by synthesis. The cleavage of the cleavable moiety restores a free 3'-OH functional group allowing growth of the polynucleotide molecule. The general structures as well as proposed synthetic schemes for the nucleotide analogs are also provided.
In Situ Proteome Profiling and Bioimaging Applications of Small-Molecule Affinity-Based Probes Derived from DOT1L Inhibitors
Zhu, Biwei,Zhang, Hailong,Pan, Sijun,Wang, Chenyu,Ge, Jingyan,Lee, Jun-Seok,Yao, Shao Q.
supporting information, p. 7824 - 7836 (2016/06/09)
DOT1L is the sole protein methyltransferase that methylates histone H3 on lysine 79 (H3K79), and is a promising drug target against cancers. Small-molecule inhibitors of DOT1L such as FED1 are potential anti-cancer agents and useful tools to investigate the biological roles of DOT1L in human diseases. FED1 showed excellent in vitro inhibitory activity against DOT1L, but its cellular effect was relatively poor. In this study, we designed and synthesized photo-reactive and "clickable" affinity-based probes (AfBPs), P1 and P2, which were cell-permeable and structural mimics of FED1. The binding and inhibitory effects of these two probes against DOT1L protein were extensively investigated in vitro and in live mammalian cells (in situ). The cellular uptake and sub-cellular localization properties of the probes were subsequently studied in live-cell imaging experiments, and our results revealed that, whereas both P1 and P2 readily entered mammalian cells, most of them were not able to reach the cell nucleus where functional DOT1L resides. This offers a plausible explanation for the poor cellular activity of FED1. Finally with P1/P2, large-scale cell-based proteome profiling, followed by quantitative LC-MS/MS, was carried out to identify potential cellular off-targets of FED1. Amongst the more than 100 candidate off-targets identified, NOP2 (a putative ribosomal RNA methyltransferase) was further confirmed to be likely a genuine off-target of FED1 by preliminary validation experiments including pull-down/Western blotting (PD/WB) and cellular thermal shift assay (CETSA). Minimalist "clickable" probes: Small-molecule probes P1 and P2 based on FED1 (a known DOT1L inhibitor) were developed and successfully used in experiments including live-cell imaging, in situ proteome profiling, and off-target identification (see scheme).
BILE ACID CONJUGATES, DERIVATIVES THEREOF WITH METAL COMPLEXES AND RELATED USES
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, (2008/06/13)
Novel paramagnetic metal ion chelates and their use as contrast agents in the diagnostic technique known as "magnetic resonance imaging" (M.R.I.) of the gastrointestinal tract and particularly of the liver, are described. The novel compounds result from the conjugation of a bile acid with a chelating agent and are capable of chelating the ions of bivalent and trivalent metals. The compounds have formula A-L-B in which A is the residue of a bile acid and derivatives of a bile acid, B is the residue of a chelating agent of a bivalent or trivalent metal ion having an atomic number of 20 to 31, 39, 42, 43, 44, 49, 57 to 83, L is a ligand between A and B.
SELECTIVE HYDROGENATION OF ORGANIC AZIDES TO AMINES BY INTERLAMELLAR MONTMORILLONITEDIPHENYLPHOSPHINE PALLADIUM(II) CATALYST
Sharma, G. V. M.,Chandrasekhar, S.
, p. 3289 - 3294 (2007/10/02)
Organic azides are selectively and catalytically hydrogenated to amines by a heterogenized homogeneous catalyst for the first time.
A PRACTICAL SYNTHESIS OF (+/-)-ELAEOCARPIDINE
Gribble, Gordon W.,Switzer, Frank L.
, p. 377 - 384 (2007/10/02)
The Elaeocarpus densiflorus indole alkaloid (+/-)-elaeocarpidine (1) is synthesized in five steps and 31percent yield from the commercially available materials 2-(2-bromoethyl)-1,3-dioxolane, ethyl 4-bromobutyrate, and tryptamine hydrochloride (7).The key step is a diisobutylaluminum hydride reductive cyclization of amine lactam 8 to give 1 in 86percent yield.
α-Nitro Ketones and Esters from Acylimidazoles
Crumbie, Robyn L.,Nimitz, Jonathan S.,Mosher, Harry S.
, p. 4040 - 4045 (2007/10/02)
The anion of 2-(2-nitroethyl)-1,3-dioxolane (4), prepared from the corresponding 2-bromo compound (3), undergoes condensation with acylimidazoles to give the 3-nitro-4-oxobutanal acetals (9), which can serve as valuable polyfunctional intermediates.Condensation with 1-(methoxyoxalyl)imidazole gives the tetrafunctionalized methyl 4-(1,3-dioxolan-2-yl)-3-nitro-2-oxobutanoate (13), which, however, decomposed on attempted deprotection of the ester function.The syntheses in excellent yields of simple α-nitro ketones and α-nitro esters from acylimidazoles and nitroethane and 2-nitropropane are also described.
