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.
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.
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.
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.
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
Convenient Synthesis of Alternatively Bridged Tryptophan Ketopiperazines and Their Activities against Trypanosomatid Parasites
Cockram, Peter E.,Turner, Callum A.,Slawin, Alexandra M. Z.,Smith, Terry K.
, (2022/01/11)
There is an urgent need for the development of new treatments against trypanosomatid parasites; the causative agents of some of the most debilitating diseases in the developing world. This work targets an interesting 6-5-6-6 fused carboline scaffold, accessing a range of substituted derivatives through stereospecific intramolecular Pictet–Spengler condensation. Modification of the cyclisation conditions allowed retention of the carbamate protecting group and gave insight into the reaction mechanism. Compounds’ bioactivities were measured against T. brucei, T. cruzi, L. major and HeLa cells. We have identified promising pan-trypanocidal lead compounds based on the core scaffold, and highlight key SAR trends which will be useful for the future development of these compounds as potent trypanocidal agents.
Macrocyclic compound serving as ALK and ROS regulators
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Paragraph 0309-0312, (2021/05/19)
The invention belongs to the field of medicinal chemistry, and relates to a macrocyclic compound serving as an ALK and ROS regulators, in particular to a compound as shown in a formula I or pharmaceutically acceptable salt thereof, a preparation method, a
SYNTHETIC CYTOTOXIC MOLECULES, DRUGS, METHODS OF THEIR SYNTHESIS AND METHODS OF TREATMENT
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Paragraph 0052; 0170, (2020/01/08)
Small molecules compounds and methods of their synthesis are provided. Formulations and medicaments are also provided that are directed to the treatment of disease, such as, for example, neoplasms, cancers, and other diseases. Therapeutics are also provided containing a therapeutically effective dose of one or more small molecule compounds, present either as pharmaceutically effective salt or in pure form, including, but not limited to, formulations for oral, intravenous, or intramuscular administration.