74064-26-9Relevant academic research and scientific papers
L-DOPA Dioxygenase Activity on 6-Substituted Dopamine Analogues
Goldberg, Alexander M.,Robinson, Miranda K.,Starr, Erykah S.,Marasco, Ryan N.,Alana, Alexa C.,Cochrane, C. Skyler,Klugh, Kameron L.,Strzeminski, David J.,Du, Muxue,Colabroy, Keri L.,Peterson, Larryn W.
, p. 2492 - 2507 (2021/08/18)
Dioxygenase enzymes are essential protein catalysts for the breakdown of catecholic rings, structural components of plant woody tissue. This powerful chemistry is used in nature to make antibiotics and other bioactive materials or degrade plant material, but we have a limited understanding of the breadth and depth of substrate space for these potent catalysts. Here we report steady-state and pre-steady-state kinetic analysis of dopamine derivatives substituted at the 6-position as substrates of L-DOPA dioxygenase, and an analysis of that activity as a function of the electron-withdrawing nature of the substituent. Steady-state and pre-steady-state kinetic data demonstrate the dopamines are impaired in binding and catalysis with respect to the cosubstrate molecular oxygen, which likely afforded spectroscopic observation of an early reaction intermediate, the semiquinone of dopamine. The reaction pathway of dopamine in the pre-steady state is consistent with a nonproductive mode of binding of oxygen at the active site. Despite these limitations, L-DOPA dioxygenase is capable of binding all of the dopamine derivatives and catalyzing multiple turnovers of ring cleavage for dopamine, 6-bromodopamine, 6-carboxydopamine, and 6-cyanodopamine. 6-Nitrodopamine was a single-turnover substrate. The variety of substrates accepted by the enzyme is consistent with an interplay of factors, including the capacity of the active site to bind large, negatively charged groups at the 6-position and the overall oxidizability of each catecholamine, and is indicative of the utility of extradiol cleavage in semisynthetic and bioremediation applications.
Preparation method of compound 5,6-dihydroxy indoline and halogen acid salts thereof
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Paragraph 0055-0058, (2018/04/01)
The invention relates to a preparation method of a compound 5,6-dihydroxy indoline and halogen acid salts thereof. Phenylethylamine SM-0 sold in the market is used as a raw material and firstly reactswith acyl chloride to obtain amide SM-1; amide SM-1 rea
Phosphane-free Pd0-catalyzed cycloamination and carbonylation with Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3: Preparation of benzocyclic amines and benzolactams
Harada, Rika,Nishida, Naoto,Uchiito, Shiho,Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Masao, Tokuda,Ohkuma, Takeshi,Orito, Kazuhiko
experimental part, p. 366 - 379 (2012/02/04)
Phosphane-free Pd0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronauclefine] in good yields. Copyright
Regioselective, photochemical bromination of aromatic compounds using N-bromosuccinimide
Chhattise, Prakash K.,Ramaswamy,Waghmode, Suresh B.
, p. 189 - 194 (2008/03/30)
Regioselective nuclear bromination of aromatic compounds is investigated with N-bromosuccinimide as the brominating agent under UV irradiation to afford the corresponding brominated compounds. The reaction proceeds at ambient temperature (30 ± 2 °C) without any catalyst. In most of the reactions, regioselectively mono-brominated products are obtained in good to high yields. The conversion and selectivity for bromination depend on the nature of the substituent on the aromatic ring.
Photochemically induced cyclization of N-[2-(o-styryl)phenylethyl]acetamides and 5-styryl-1-methyl-1,2,3,4-tetrahydroisoquinolines: New total syntheses of 1-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines
Martínez, Elena,Estévez, Juan C,Estévez, Ramón J,Castedo, Luis
, p. 1981 - 1986 (2007/10/03)
Two new total syntheses of 1-methyl-1,2,3,4-dihydronaphtho[1,2-f]isoquinolines are based on photochemically induced cyclization of N-{2-[(E)-2-phenyl-1-etheynyl]phenylethyl]}acetamides or 1-methyl-5-[(E)-2-phenyl-1-ethenyl]-1,2,3,4-tetrahydroisoquinolines.
Synthesis of 2-acyltetrahydroisoquinolines and 2-acyl-1,2,3,4- tetrahydro-1,2-benzothiazine-1,1-diones by electrophilic substitution reactions of N-acyl-2-phenylethylamines
Lukanov, Ludmil K.,Venkov, Atanas P.
, p. 2137 - 2147 (2007/10/03)
l-Substituted- 5, 1,5-substituted 7,8-dioxygenated-2- acyltetrahydroisoquinolines 10 and 2-acyl-1,2,3,4-tetrahydro-1,2- benzothiazine-l,l-diones 12 has been obtained by the reaction of N-acyl-2- phenylethylamines with aldehydes or chlorosulfonic acid as a
Application of the ortho-Lithiation-Cyclization Strategy to N-Benzyl- and N-Phenethylamine Derivatives
Lete, Esther,Collado, M. Isabel,Sotomayor, Nuria,Vicente, Teresa,Villa, Maria-Jesus
, p. 1751 - 1758 (2007/10/03)
The ortho-lithiation-cyclization of iodinated N,N-diacylphenethylamines provides a convenient method for the preparation of 2-(2-acetoamidoethyl)acetophenones and 2-(2-benzamidoethyl)benzophenones, which could be easily transformed into dihydroisoquinolines.By contrast, the N-ethylamino, N-acetylamino, and N-trimethylsilylamino moieties studied as ortho-directing groups provide poor assistance to the metalation of N-benzyl- and N-phenyethylamines and the corresponding isoindolone or isoquinolone derivatives are obtained in low yields.
Studies on the Syntheses of Heterocyclic Compounds. Part 865. A Novel Synthesis of Indole Derivatives by Intramolecular Nucleophilic Aromatic Substitution
Kametani, Tetsuji,Ohsawa, Tatsushi,Ihara, Masataka
, p. 290 - 294 (2007/10/02)
Cyclisation of N-(2-bromo-4,5-dimethoxyphenethyl)acetamide (6) afforded 1-acetyl-2,3-dihydro-5,6-dimethoxy-1H-indole (13) by intramolecular nucleophilic aromatic substitution using sodium hydride and cuprous halide in dimethylformamide.The dihydroindoles (14), (15), and (16) were also synthesised from the corresponding amides (8) and (10) and the carbamate (12) in a similar manner.The dihydroindoles (13), (14), and (16) were converted into the indoles (20) and (21) in excellent yield by oxidation and subsequent alkaline hydrolysis.The 2-oxindoles (26) and (27) were also prepared under similar reaction condition from the phenylacetamide (24) and (25).
