- Biosynthesis of berninamycin: Incorporation of 13C-labeled amino acids
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Two-dimensional NMR and FABMS/MS studies agree with the structure for berninamycin A proposed by Abe et al. (Tetrahedron Lett. 1988, 29, 1401-1404). Biosynthetic studies with 13C-enriched amino acids confirm our earlier results that the dehydro
- Lau, Raymond C. M.,Rinehart, Kenneth L.
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Read Online
- Radical 1,4-Aryl Migration Enabled Remote Cross-Electrophile Coupling of α-Amino-β-Bromo Acid Esters with Aryl Bromides
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We report an unprecedented, efficient nickel-catalysed radical relay for the remote cross-electrophile coupling of β-bromo-α-benzylamino acid esters with aryl bromides via 1,4-aryl migration/arylation cascades. β-Bromo-α-benzylamino acid esters are consid
- Chen, Shi-Lu,He, Jin,Hong, Yu,Li, Jin-Heng,Liu, Jian,Liu, Ting,Tang, Shi,Wang, Shuo-Wen,Xu, Zhen-Hua,Yu, Jian
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supporting information
p. 21360 - 21367
(2021/08/23)
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- Alpha-substituted-alpha-amino acid ester compound and preparation method thereof
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The invention discloses an alpha-substituted-alpha-amino acid ester compound and a preparation method thereof. Aromatic amine and alkenyl ether are added into a reactor and dissolved in a solvent, a reaction is carried out under the action of a palladium catalyst, a ligand and an oxidizing agent, separation and purification are carried out, the alpha-substituted-alpha-amino acid ester compound is obtained, and the reaction formula of the preparation method is shown in the formula (I). According to the method, alkenyl ether and aromatic amine which are simple and easy to obtain are used as reaction raw materials to synthesize a series of alpha-substituted-alpha-amino-acid ester compounds, and the method has the advantages that the raw materials are simple and easy to obtain, operation is convenient, conditions are mild, step atom economy is high, substrate applicability is wide, and functional group tolerance is good.
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Paragraph 0102-0110
(2021/06/09)
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- Manganese-catalysed transfer hydrogenation of esters
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Manganese catalysed ester reduction using ethanol as a hydrogen transfer agent in place of dihydrogen is reported. High yields can be achieved for a range of substrates using 1 mol% of a Mn(i) catalyst, with an alkoxide promoter. The catalyst is derived from a tridentate P,N,N ligand.
- Oates, Conor L.,Widegren, Magnus B.,Clarke, Matthew L.
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supporting information
p. 8635 - 8638
(2020/08/21)
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- Intermediate compound of medicine LB80380 and preparing method and application thereof
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The invention provides an LB80380 intermediate compound (as shown in formula I in the specification). In the LB80380 intermediate compound, R1, R2, R3 and R4 are chosen from linear chain or branched chain alkyl group, benzyl group which is replaced by one or five R5, or R5CO independently, wherein the R1, the R1, the R3 and the R4 are identical or different; R5 is chosen from hydrogen, C1-C4 alkoxy which is replaced or not replaced, C3-C7 alkenyl alkoxy, or benzyloxy- which is replaced or not replaced. The invention also provides a preparing method and an application of the compound in the formula I. When the compound in formula I is used for preparing a compound (specific chemical formula is in the specification), reaction route raw materials and intermediate materials are low in price and easy to get, cost is low, safety is good, and thus the LB80380 intermediate compound in formula I is applicable to industrial production.
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Paragraph 0190; 0191; 0192; 0193
(2017/05/12)
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- Disubstituted beta-lactones as inhibitors of N-acylethanolamine acid amidase (NAAA)
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The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.
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Page/Page column 126; 127
(2016/06/28)
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- Synthesis, structure-activity, and structure-stability relationships of 2-substituted-n-(4-oxo-3-oxetanyl) n-acylethanolamine acid amidase (NAAA) inhibitors
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N-Acylethanolamine acid amidase (NAAA) is a cysteine amidase that preferentially hydrolyzes saturated or monounsaturated fatty acid ethanolamides (FAEs), such as palmitoylethanolamide (PEA) and oleoylethanolamide (OEA), which are endogenous agonists of nu
- Vitale, Romina,Ottonello, Giuliana,Petracca, Rita,Bertozzi, Sine Mandrup,Ponzano, Stefano,Armirotti, Andrea,Berteotti, Anna,Dionisi, Mauro,Cavalli, Andrea,Piomelli, Daniele,Bandiera, Tiziano,Bertozzi, Fabio
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supporting information
p. 323 - 336
(2014/04/03)
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- DISUBSTITUTED BETA-LACTONES AS INHIBITORS OF N-ACYLETHANOLAMINE ACID AMIDASE (NAAA)
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The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.
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Paragraph 0366
(2013/06/06)
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- ETHYNYLBENZENE DERIVATIVES
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Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R1, R2, R3, R101, L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.
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Page/Page column 70
(2012/03/26)
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- Copper-catalyzed amination of ketene silyl acetals with hydroxylamines: Electrophilic amination approach to α-amino acids
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Role reversal: The title reaction has been developed to deliver α-amino acids under very mild reaction conditions (see scheme; dpppen=1,5-bis(diphenylphosphino)pentane). The catalysis provides a new C-N bond-forming approach for the synthesis of α-amino a
- Matsuda, Naoki,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information
p. 11827 - 11831
(2013/01/15)
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- Fluoroalkyl substituted (Z)-dehydro α-amino ester as a building block for the fluorine-containing cyclopropyl α-amino esters and dihydrooxazole
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Multi-functionalized β-trifluoromethyl and β-difluoromethyl substituted (Z)-α,β-dehydro α-amino esters have been successfully prepared from N-protected fluorinated threonine ester. Applications of this new fluorine-containing building block to the synthes
- Wan, Wen,Gao, Yinghong,Jiang, Haizhen,Hao, Jian
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scheme or table
p. 510 - 514
(2009/04/03)
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- SUBSTITUTED IMIDAZOQUINOLINES, IMIDAZOPYRIDINES, AND IMIDAZONAPHTHYRIDINES
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Imidazo-quinoline, -pyridine, and -naphthyridine ring systems (particularly quinolines, tetrahydroquinolines, pyridines, [1,5]naphthyridines, [1,5]tetrahydronaphthyridines) substituted at the 1-position with a cyclic substituent, pharmaceutical compositions containing the compounds, methods of making these compounds, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.
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Page/Page column 159
(2010/10/20)
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- A new method for generation of non-stabilized α-amino-substituted carbanions by the reaction of magnesium carbenoids with N-lithio arylamines: their reactivity and a new synthesis of α-amino acid derivatives
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Magnesium carbenoids were generated from aryl 1-chloroalkyl sulfoxides with i-PrMgCl in THF at low temperature in quantitative yields. The magnesium carbenoids were found to be reactive with N-lithio alkylamines to afford an olefin, which was derived from dimerization of the magnesium carbenoid, in moderate yield. On the other hand, reaction of the magnesium carbenoids with N-substituted N-lithio arylamines gave non-stabilized α-amino-substituted carbanions in good yields. Reactivity of the α-amino-substituted carbanions with some electrophiles was investigated and it was found that ethyl chloroformate reacted to give α-amino acid derivatives in good yields. As a whole, a new method for one-pot, three-component combined synthesis of α-amino acid derivatives from aryl 1-chloroalkyl sulfoxides was realized.
- Satoh, Tsuyoshi,Osawa, Atsushi,Ohbayashi, Tohru,Kondo, Atsushi
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p. 7892 - 7901
(2007/10/03)
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- Synthesis of serine analogues to be used as modified phospho acceptor sites in substrates of protein kinase C
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Serine and threonine analogues (compounds 2-6) are readily accessible by reaction of the anion of N,N-dibenzylglycine ethyl ester (1) with an appropriate carbonyl compound.These analogues will be incorporated into Protein Kinase C (PKC) substrates.The serine aldehyde derivative 7 was used for the preparation of the corresponding diethyl acetal 9.This compound was the starting material in the synthesis of the suicide precursor 8, featuring a reductive amination leading to 12 and a Lewis-acid-catalysed cyclization giving 8.
- Broxterman, H. J. G.,Liskamp, R. M. J.
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