50632-82-1Relevant articles and documents
Pictet-Spengler condensations using 4-(2-aminoethyl)coumarins
Sviripa, Vitaliy M.,Fiandalo, Michael V.,Begley, Kristin L.,Wyrebek, Przemyslaw,Kril, Liliia M.,Balia, Andrii G.,Parkin, Sean R.,Subramanian, Vivekanandan,Chen, Xi,Williams, Alexander H.,Zhan, Chang-Guo,Liu, Chunming,Mohler, James L.,Watt, David S.
, p. 13415 - 13429 (2020/08/28)
Androgen-deprivation therapy (ADT) is only a palliative measure, and prostate cancer invariably recurs in a lethal, castration-resistant form (CRPC). Prostate cancer resists ADT by metabolizing weak, adrenal androgens to growth-promoting 5α-dihydrotestosterone (DHT), the preferred ligand for the androgen receptor (AR). Developing small-molecule inhibitors for the final steps in androgen metabolic pathways that utilize 17-oxidoreductases required probes that possess fluorescent groups at C-3 and intact, naturally occurring functionality at C-17. Application of the Pictet-Spengler condensation to substituted 4-(2-aminoethyl)coumarins and 5α-androstane-3-ones furnished spirocyclic, fluorescent androgens at the desired C-3 position. Condensations required the presence of activating C-7 amino or N,N-dialkylamino groups in the 4-(2-aminoethyl)coumarin component of these condensation reactions. Successful Pictet-Spengler condensation, for example, of DHT with 9-(2-aminoethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one led to a spirocyclic androgen, (3R,5S,10S,13S,17S)-17-hydroxy-10,13-dimethyl-1,2,2′,3′,4,5,6,7,8,8′,9,9′,10,11,12,12′,13,13′,14,15,16,17-docosahydro-7′H,11′H-spiro-[cyclopenta[a]phenanthrene-3,4′-pyrido[3,2,1-ij]pyrido[4′,3′:4,5]pyrano[2,3-f]quinolin]-5′(1′H)-one. Computational modeling supported the surrogacy of the C-3 fluorescent DHT analog as a tool to study 17-oxidoreductases for intracrine, androgen metabolism. This journal is
Direct C-H alkylation of naphthoquinones with amino acids through a revisited Kochi-Anderson radical decarboxylation: Trends in reactivity and applications
Naturale, Guillaume,Lamblin, Marc,Commandeur, Claude,Dessolin, Jean,Felpin, Francois-Xavier
supporting information, p. 5774 - 5788,15 (2020/09/15)
In our ongoing research program into the discovery of new anticancer drugs, we were interested in the preparation of naphthoquinone scaffolds bearing aminoalkyl side-chains. Following this aim, we revisited the Kochi-Anderson radical decarboxylation of amino acids in order to set up a versatile route to the direct functionalization of naphthoquinones. The best reaction conditions were applied to a selected series of compounds in a systematic methodological study which allowed us to establish important trends in reactivity. We found that α-substituted β-amino acids were the most suitable substrates for the radical addition. In contrast, α-amino acids gave modest results. The influence of the amine protecting groups on the reaction outcome has also been studied. This practical procedure allows the introduction of various unsymmetrical moieties, including orthogonally protected linear aminoalkyl chains or chiral dipeptidic chains, and opens the door to a wide scope of easily accessible chemical diversity.
PROTECTED AMINE LABELS AND USE IN DETECTING ANALYTES
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Page/Page column 56, (2011/05/05)
The invention is directed towards novel amino acid based compounds, which may be isotopically enriched, and methods of use of such compounds for characterising one or more molecules of a sample by mass spectrometry, the method comprising: (a) reacting the
Construction of highly reactive probes for abasic site detection by introduction of an aromatic and a guanidine residue into an aminooxy group
Kojima, Naoshi,Takebayashi, Toshie,Mikami, Akiko,Ohtsuka, Eiko,Komatsu, Yasuo
supporting information; experimental part, p. 13208 - 13209 (2010/01/30)
(Chemical Equation Presented) Abasic sites (AP sites) arise from hydrolysis of glycosidic bonds of DNA that is damaged by various external and internal processes; unrepaired AP sites give rise to genetic mutations. We have constructed highly reactive AP-s
N-trifluoroacetyl-β-alanine in the synthesis of carnosine
Cherevin,Zubreichuk,Popova,Gulevich,Knizhnikov
, p. 1576 - 1579 (2008/03/13)
Conditions have been developed for the synthesis of N-trifluoroacetyl- β-alanine, N-tifluoroacetyl-β-alanyl chloride, and N-trifluoroacetyl-β-alanine 4-nitrophenyl ester. These compounds reacted with histidine methyl ester or sodium salt to give N-trifluoroacetyl-β- alanyl-l-histidine methyl ester CF3CONHCH2CH 2?CONHCH(CH2C3H3N 2)COOCH3 and N-trifluoroacetyl-β-alanyl-l-histidine CF3CONHCH2CH2CONHCH?(CH2C 3H3N2)COOH. Their hydrolysis with a solution of sodium hydroxide in aqueous ethanol, followed by acidification with trifluoroacetic acid, led to the formation of β-alanyl-l-histidine (l-carnosine).
Regioselective functionalization of chiral nickelacycles derived from N-protected aspartic and glutamic anhydrides
Castano,Echavarren
, p. 4783 - 4786 (2007/10/02)
The electrophilic cleavage of the nickelacycles resulting from oxidative addition of Ni(o) complexes to N-protected aspartic and glutamic anhydrides, followed by decarbonylation, gives rise regioselectively to derivatives of α- and β-alanine or α- and γ-aminobutyric acid, respectively.
Stereochemistry of Catabolism of the RNA Base Uracil
Gani, David,Young, Douglas W.
, p. 1355 - 1362 (2007/10/02)
A mammalian enzyme system has been used to study the stereochemistry of the catabolism of the pyrimidine uracil (1) to the amino acid β-alanine (4).Use of - and - uracils and of (2)H2O in the incubations yielded sterospecifically deuteriated samples of β-alanine.Assays, involving total synthesis of samples of β-alanine unambigously labelled with deuterium in each of the four C-H bonds have shown that, in the first step in the catabolic process, uracil is reduced by dihydrouracil dehydrogenase with overall anti addition of hydrogen, at the si face at C-6 and the si face at C-5.
