115186-37-3Relevant articles and documents
A convenient synthesis of N-methoxy-N-methylamides from carboxylic acids
Sibi,Stessman,Schultz,Christensen,Lu,Marvin
, p. 1255 - 1264 (1995)
Carboxylic acids can be converted to their corresponding N-methoxy-N-methylamides in high yields using 2-chloro-1-methylpyridinium iodide as the coupling agent. The reaction proceeds without racemization when chiral carboxylic acids are used as the starting material.
Practical one-pot double functionalizations of proline
Huy, Peter,Schmalz, Hans-Guenther
, p. 954 - 960 (2011)
Solubilization of proline as the triethylammonium salt allows N-protection (as the Boc, Cbz or Moc derivative) and subsequent esterification or amidation of the carboxy terminus to be performed in an efficient one-pot fashion. Based on this concept, highly practical protocols were developed to prepare a series of proline derivatives (including Pro-Ser dipetides, Weinreb amides and N-protected proline esters), which are important intermediates, for instance, for the synthesis of proline-derived peptides, chiral reagents and catalysts for asymmetric synthesis. Georg Thieme Verlag Stuttgart - New York.
β-fluorinated proline derivatives: Potential transition state inhibitors for proline selective serine dipeptidases
Van Der Veken, Pieter,Senten, Kristel,Kertèsz, István,Haemers, Achiel,Augustyns, Koen
, p. 969 - 972 (2003)
Three new types of β-fluorinated proline derivatives were synthesized as potential transition state inhibitors for proline selective serine dipeptidases. The fluorophosponate derived from protected proline was tested as a Wadsworth-Horner-Emmons reagent for the synthesis of fluoro-olefin-containing pseudodipeptides.
1,2,3-Triazole Stabilized Neurotensin-Based Radiopeptidomimetics for Improved Tumor Targeting
Mascarin, Alba,Valverde, Ibai E.,Vomstein, Sandra,Mindt, Thomas L.
, p. 2143 - 2152 (2015)
Neurotensin (NT) is a regulatory peptide with nanomolar affinity toward NT receptors, which are overexpressed by different clinically relevant tumors. Its binding sequence, NT(8-13), represents a promising vector for the development of peptidic radiotracers for tumor imaging and therapy. The main drawback of the peptide is its short biological half-life due to rapid proteolysis in vivo. Herein, we present an innovative strategy for the stabilization of peptides using nonhydrolizable 1,4-disubstituted, 1,2,3-triazoles as amide bond surrogates. A triazole scan?of the peptide sequence yielded novel NT(8-13) analogues with enhanced stability, retained receptor affinity, and improved tumor targeting properties in vivo. The synthesis of libraries of triazole-based peptidomimetics was achieved efficiently on solid support by a combination of Fmoc-peptide chemistry, diazo transfer reactions, and the Cu(I)-catalyzed alkyne azide cycloaddition (CuAAC) employing methods that are fully compatible with standard solid phase peptide synthesis (SPPS) chemistry. Thus, the amide-to-triazole substitution strategy may represent a general methodology for the metabolic stabilization of biologically active peptides.
An expedient conversion of α-amino acids into Weinreb amides using COMU As a coupling agent
Tyrrell, Elizabeth,Brawn, Peter,Carew, Mark,Greenwood, Iain
, p. 369 - 372 (2011)
The use of COMU, as a non-hazardous partner, in the coupling of N-protected α-amino acids to N-methoxy-N-methylamine to afford the corresponding Weinreb amides is discussed. From a practical point of view the reaction can be monitored visually by virtue of the colour change associated with the conversion of substrates (yellow) into the products (orange). As the by-products of the reaction are conveniently water-soluble the products are isolated relatively pure and with minimal racemisation. These factors coupled with the short reaction time make this a very useful procedure.
In search of constrained FTY720 and phytosphingosine analogs as dual acting anticancer agents targeting metabolic and epigenetic pathways
Garsi, Jean-Baptiste,Sernissi, Lorenzo,Vece, Vito,Hanessian, Stephen,McCracken, Alison N.,Simitian, Grigor,Edinger, Aimee L.
, p. 217 - 242 (2018)
A series of compounds containing pyrrolidine and pyrrolizidine cores with appended hydrophobic substituents were prepared as constrained analogs of FTY720 and phytosphingosine. The effect of these compounds on the viability of cancer cells, on downregulation of the nutrient transport systems, and on their ability to cause vacuolation was studied. An attempt to inhibit HDACs with some phosphate esters of our analogs was thwarted by our failure to reproduce the reported inhibitory action of FTY720-phosphate.
Efficient Analysis of 2-Acetyl-1-pyrroline in Foods Using a Novel Derivatization Strategy and LC-MS/MS
Jost, Tobias,Heymann, Thomas,Glomb, Marcus A.
, p. 3046 - 3054 (2019)
2-Acetyl-1-pyrroline (2-AP) is a key odorant in many foods, such as aromatic rice and wheat bread, with a very low odor threshold of 0.05 μg/L in water. The small molecule with a popcornlike, roasty odor is generated biologically or by Strecker degradation within the Maillard-reaction cascades during thermal food processing with methylglyoxal and 1-pyrroline as the main direct precursors. Numerous gas-chromatographic methods for the analysis of 2-AP have been published, but the reactivity of the compound leads to discrimination or degradation during sample workup. We developed a novel derivatization method for 2-AP with o-phenylenediamine followed by HPLC-MS/MS analysis of the resulting stable quinoxaline. The precision (7%), repeatability (14%), recovery (92%), linearity (0.79-500 μg/kg), limit of detection (LOD, 0.26 μg/kg), and limit of quantitation (LOQ, 0.79 μg/kg) were validated for rice matrix and were excellent as compared with those of methods published before. With the novel method, 2-AP levels in typical foods like aromatic rice (131 μg/kg), wheat bread (18 μg/kg), brown bread (18 μg/kg), rye bread (18 μg/kg), and popcorn (38 μg/kg) were determined.
A convenient method for the conversion of hindered carboxylic acids to N-methoxy-N-methyl (Weinreb) amides
Woo, Jacqueline C. S.,Fenster, Erik,Dake, Gregory R.
, p. 8984 - 8986 (2004)
The conversion of sterically hindered carboxylic acids to N-methoxy-N-methyl amides can be efficiently carried out with 1.1 equiv of methanesulfonyl chloride, 3 equiv of triethylamine, and 1.1 equiv of N-methoxy-N-methylamine. Yields for this process rang
An intramolecular Tsuji-Trost reaction based approach to the synthesis of 6-methylene indolizidines
Martin, Romy E.,Polomska, Marta E.,Byrne, Lindsay T.,Stewart, Scott G.
, p. 4878 - 4881 (2011)
Herein we describe the efficient stereoselective preparation of C8 substituted indolizidines bearing a 6-methylene group, from the chiral pool starting material l-proline. This synthesis, employing a Tsuji-Trost reaction as the key step, represents a potentially, efficient route to pumiliotoxin natural product epimers. Crown Copyright
Synthesis and activity of 3-pyridylamine ligands at central nicotinic receptors
Balboni, Gianfranco,Marastoni, Mauro,Merighi, Stefania,Borea, Pier Andrea,Tomatis, Roberto
, p. 979 - 988 (2000)
A series of thirty 2-(3-pyridylaminomethyl)azetidine, pyrrolidine and piperidine analogues as nicotinic acetylcholine receptor (nAChR) ligands was explored. In general, pyrrolidinyl and many azetidinyl compounds were found to bind with enhanced affinity relative to the piperidines. In the three series, the parallel structural changes (stereochemistry, N-methylation and/or chloro substitution) do not consistently lead to parallel shifts in affinity. The more active compounds (K(i) affinity values ranging from 8.9 to 90 nM) were about as analgesic as nicotine in a tail-flick assay in mice after subcutaneous injections. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
