7737-17-9Relevant academic research and scientific papers
Aerobic co-oxidation of hemoglobin and aminoacetone, a putative source of methylglyoxal
Ramos, Luiz D.,Mantovani, Mariana C.,Sartori, Adriano,Dutra, Fernando,Stevani, Cassius V.,Bechara, Etelvino J.H.
, p. 178 - 186 (2021)
Aminoacetone (1-aminopropan-2-one), a putative minor biological source of methylglyoxal, reacts like other α-aminoketones such as 6-aminolevulinic acid (first heme precursor) and 1,4-diaminobutanone (a microbicide) yielding electrophilic α-oxoaldehydes, ammonium ion and reactive oxygen species by metal- and hemeprotein-catalyzed aerobic oxidation. A plethora of recent reports implicates triose phosphate-generated methylglyoxal in protein crosslinking and DNA addition, leading to age-related disorders, including diabetes. Importantly, methylglyoxal-treated hemoglobin adds four water-exposed arginine residues, which may compromise its physiological role and potentially serve as biomarkers for diabetes. This paper reports on the co-oxidation of aminoacetone and oxyhemoglobin in normally aerated phosphate buffer, leading to structural changes in hemoglobin, which can be attributed to the addition of aminoacetone-produced methylglyoxal to the protein. Hydroxyl radical-promoted chemical damage to hemoglobin may also occur in parallel, which is suggested by EPR-spin trapping studies with 5,5-dimethyl-1-pyrroline-N-oxide and ethanol. Concomitantly, oxyhemoglobin is oxidized to methemoglobin, as indicated by characteristic CD spectral changes in the Soret and visible regions. Overall, these findings may contribute to elucidate the molecular mechanisms underlying human diseases associated with hemoglobin dysfunctions and with aminoacetone in metabolic alterations related to excess glycine and threonine.
The Wacker-type oxidation of allylamine
Kaufmann, Werner,Venanzi, Luigi M.
, p. 205 - 209 (1991)
Wacker-type oxidation of allylamine in acid solution can be used to produce 1-aminopropan-2-one hydrochloride, 1, in yields ranging from 26 to 42percent depending on reaction conditions.However, the difficulty of its separation from the hyproducts limits the scope of this reaction.
Synthesis method for medicine raw material aminoacetone hydrochloride
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Paragraph 0009; 0015; 0016, (2018/04/21)
The invention relates to a practical synthesis method for preparing an important medicine raw material aminoacetone hydrochloride. The method comprises the following steps: glycine used as a raw material reacts with acetic anhydride and pyridine in a refluxing state to obtain acetyl protected aminoacetone; and the acetyl protected aminoacetone is hydrolyzed to obtain the aminoacetone hydrochloride.
High-Throughput Screening and Hit Validation of Extracellular-Related Kinase 5 (ERK5) Inhibitors
Myers, Stephanie M.,Bawn, Ruth H.,Bisset, Louise C.,Blackburn, Timothy J.,Cottyn, Betty,Molyneux, Lauren,Wong, Ai-Ching,Cano, Celine,Clegg, William,Harrington, Ross. W.,Leung, Hing,Rigoreau, Laurent,Vidot, Sandrine,Golding, Bernard T.,Griffin, Roger J.,Hammonds, Tim,Newell, David R.,Hardcastle, Ian R.
supporting information, p. 444 - 455 (2016/08/16)
The extracellular-related kinase 5 (ERK5) is a promising target for cancer therapy. A high-throughput screen was developed for ERK5, based on the IMAP FP progressive binding system, and used to identify hits from a library of 57-617 compounds. Four distinct chemical series were evident within the screening hits. Resynthesis and reassay of the hits demonstrated that one series did not return active compounds, whereas three series returned active hits. Structure-activity studies demonstrated that the 4-benzoylpyrrole-2-carboxamide pharmacophore had excellent potential for further development. The minimum kinase binding pharmacophore was identified, and key examples demonstrated good selectivity for ERK5 over p38α kinase.
NOVEL HIGH AFFINITY QUINOLINE-BASED KINASE LIGANDS
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Paragraph 0220, (2014/01/09)
Quinoline-based inhibitors of cyclin dependent kinase 2, compositions including the inhibitors, and methods of using the inhibitors and inhibitor compositions are described. The inhibitors and compositions including them are useful for treating disease or disease symptoms. The invention also provides for methods of making CDK-2 inhibitor compounds, methods of inhibiting CDK-2, and methods for treating disease or disease symptoms.
Rearrangement of N-tert-butanesulfinyl α-halo imines with alkoxides to N-tert-butanesulfinyl 2-amino acetals as precursors of N-protected and N-unprotected α-amino carbonyl compounds
Colpaert, Filip,Mangelinckx, Sven,Denolf, Bram,De Kimpe, Norbert
experimental part, p. 6023 - 6032 (2012/10/08)
Reaction of N-tert-butanesulfinyl α-halo imines with alkoxides afforded new N-tert-butanesulfinyl 2-amino acetals in good to excellent yield. These N-tert-butanesulfinyl 2-amino acetals are convenient precursors for the TMSOTf-promoted synthesis of the co
A small molecule that mimics the metabolic activity of copper-containing amine oxidases (CuAOs) toward physiological mono- and polyamines
Largeron, Martine,Fleury, Maurice-Bernard,Strolin Benedetti, Margherita
scheme or table, p. 3796 - 3800 (2010/09/06)
Primary aliphatic biogenic amines have been successfully oxidized using a quinonoid species that mimics the metabolic activity of copper-containing amine oxidase (CuAO) enzymes. Especially, high catalytic performances were observed with aminoacetone, a threonine catabolite, and methylamine, a metabolite of adrenaline, and with the primary amino groups of putrescine and spermidine which are both decarboxylation products of ornithine and S-adenosyl-methionine. Furthermore, contrary to flavine adenine dinucleotide (FAD)-dependent amine oxidase enzymes, no activity was found toward secondary and tertiary amines.
Novel high affinity quinoline-based kinase ligands
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Page/Page column 92, (2008/06/13)
Quinoline-based inhibitors of cyclin dependent kinase 2, compositions including the inhibitors, and methods of using the inhibitors and inhibitor compositions are described. The inhibitors and compositions including them are useful for treating disease or disease symptoms. The invention also provides for methods of making CDK-2 inhibitor compounds, methods of inhibiting CDK-2, and methods for treating disease or disease symptoms.
2-ARYLTHIAZOLE DERIVATIVES AS CXCR3 RECEPTOR MODULATORS
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Page/Page column 69, (2010/11/28)
The invention encompasses compounds of Formula I or pharmaceutically acceptable salts thereof, which are modulators of the CXCR3 chemokine receptor function useful for the treatment or prevention of pathogenic inflammatory processes, autoimmune diseases or graft rejection processes. Methods of use and pharmaceutical compositions are also encompassed.
Synthesis and biological evaluation of lisofylline (LSF) analogs as a potential treatment for Type 1 diabetes
Cui, Peng,Macdonald, Timothy L.,Chen, Meng,Nadler, Jerry L.
, p. 3401 - 3405 (2007/10/03)
Lisofylline (LSF, 1-(5-R-hydroxyhexyl)-3,7-dimethylxanthine) is an anti-inflammatory agent that protects β-cells from Th1 cytokine-induced dysfunction and reduces the onset of Type 1 diabetes in non-obese diabetic (NOD) mice. Due to its low potency, poor oral bioavailability, and short half-life, the widespread clinical utility of LSF may be limited. Our goal has been to develop new agents based on the LSF structural motif that resolve the potency and pharmacokinetic liabilities of LSF. In this study, we have generated a focused library of LSF analogs that maintain the side chain (5-R-hydroxyhexyl) constant, while substituting a variety of nitrogen-containing heterocyclic substructures for the xanthine moiety of LSF. This library includes the xanthine-like (5-aza-7-deazaxanthine), as well as non-xanthine-like skeletons. The LSF analogs were evaluated in a pancreatic β-cell line for the effects on apoptosis protection and insulin release. The metabolic stability of selected compounds was also tested.
