cas 53330-94-2, 5-Acetylindole | Articles data

Articles about 53330-94-2Total 18 be found

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Diaryl-substituted 1, 1-ethylene compounds and preparation method and application thereof
The invention discloses diaryl-substituted 1, 1-ethylene compounds shown as general formulas I, II, III and IV, and a preparation method and application thereof, and the compounds can be used for preparing medicines related to tumor treatment, tubulin activity inhibition and HDAC activity inhibition.
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Paragraph 0049-0051

(2021/02/24)

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen
The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.
Wei, Lanfeng,Wei, Yu,Xu, Liang,Zhang, Jinli
supporting information
p. 4446 - 4450
(2021/06/30)

Design, synthesis and anticancer properties of isocombretapyridines as potent colchicine binding site inhibitors
A series of novel isocombretapyridines were designed and synthesized based on a lead compound isocombretastatin A-4 (isoCA-4) by replacing 3,4,5-trimethoxylphenyl with substituent pyridine nucleus. The MTT assay results showed that compound 20a possessed the most potent activities against all tested cell lines with IC50 values at nanomolar concentration ranges. Moreover, 20a inhibited tubulin polymerization at a micromolar level and also displayed potent anti-vascular activity in vitro. Further mechanistic studies were conducted to demonstrate that compound 20a could bind to the colchicine site of tubulin,and disrupte the cell microtubule networks, induce G2/M phase arrest, promote apoptosis and depolarize mitochondria of K562 cells in a dose-dependent manner. Notably, 20a exhibited more potent tumor growth inhibition activity with 68.7% tumor growth inhibition than that of isoCA-4 in H22 allograft mouse model without apparent toxicity. The present results suggested that compound 20a may serve as a promising potent microtubule-destabilizing agent candidate for the development of therapeutics to treat cancer.
Shuai, Wen,Li, Xinnan,Li, Wenlong,Xu, Feijie,Lu, Lixue,Yao, Hong,Yang, Limei,Zhu, Huajian,Xu, Shengtao,Zhu, Zheying,Xu, Jinyi
(2020/04/24)

Acceptorless dehydrogenation of amines and alcohols using simple ruthenium chloride
A highly efficient, economic and environmental friendly catalyst system has been developed for the dehydrogenation of alcohols and amines using simple RuCl3·nH2O and N-benzylhexamethylenetetramine. The in situ catalyst system efficiently oxidized the primary and secondary amines and secondary alcohols into nitrile, imine and ketone products, respectively in moderate to excellent yields. The developed catalyst system was also found to be efficient for the dehydrogenation of N-heterocyles. A detailed mechanism study revealed the first example of N-benzylhexamethylenetetramine (HMTA-Bz) being simultaneously acting as base, reducing agent and hydride source to generate the [Ru(II)(H)2] species as the active catalyst. The mechanism studies also revealed both the alcohol and amine oxidation involves dehydrogenative pathway with the evolution of hydrogen as the only by-product. The developed catalyst system also provides possible platform for the release of hydrogen from liquid organic hydrogen carriers (LOHCs).
Barteja, Parul,Devi, Preeti,Kannan, Muthukumar,Muthaiah, Senthilkumar
p. 1 - 11
(2020/04/17)

Design, synthesis and biological evaluation of quinoline-indole derivatives as anti-tubulin agents targeting the colchicine binding site
A series of novel isocombretastatin A-4 (isoCA-4) analogs were designed and synthesized by replacing 3,4,5-trimethoylphenyl and isovanillin of isoCA-4 with quinoline and indole moieties, respectively. The structure activity relationships (SARs) of these synthesized quinoline-indole derivatives have been intensively investigated. Two compounds 27c and 34b exhibited the most potent activities against five cancer cell lines with IC50 values ranging from 2 to 11 nM, which were comparable to those of Combretastatin A-4 (CA-4, 1). Further mechanism investigations revealed that 34b effectively inhibited the microtubule polymerization by binding to the colchicine site of tubulin. Further cellular mechanism studies elucidated that 34b disrupted cell microtubule networks, arrested the cell cycle at G2/M phase, induced apoptosis and depolarized mitochondria of K562 cells. Moreover, 34b displayed potent anti-vascular activity in both wound healing and tube formation assays. Importantly, 27c and 34b significantly inhibited tumor growth in H22 xenograft models without apparent toxicity, suggesting that 27c and 34b deserve further research as potent antitumor agents for cancer therapy.
Li, Wenlong,Shuai, Wen,Sun, Honghao,Xu, Feijie,Bi, Yi,Xu, Jinyi,Ma, Cong,Yao, Hequan,Zhu, Zheying,Xu, Shengtao
p. 428 - 442
(2018/12/13)

Quinoline substituted indole compound, and preparation method and application thereof
The invention discloses a quinoline substituted indole compound, a pharmaceutical composition containing the quinoline substituted indole compound, and a preparation method for the quinoline substituted indole compound. The invention also discloses the quinoline substituted indole compound, a pharmaceutical application for the pharmaceutical composition containing the quinoline substituted indolecompound, specifically an application of the pharmaceutical composition containing the quinoline substituted indole compound in preparation of drugs used for treatment of tumors, and an application ofthe quinoline substituted indole compound in preparation of drugs used for treatment of diseases or symptoms by inhibition of tubulin activity.
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Paragraph 0076; 0077; 0078; 0079

(2019/04/26)

Synthesis of 3,5-Disubstituted isoxazoles containing privileged substructures with a diverse display of polar surface area
We designed and synthesized the molecular framework of 3,5-disubstituted isoxazoles containing privileged substructures with various substituents which uniquely display polar surface area in a diverse manner. A library of 3,5-disubstituted isoxazoles were systematically prepared via 1,3-dipolar cycloaddition of alkynes with nitrile oxides prepared by two complementary synthetic routes; method A utilized a halogenating agent with a base and method B utilized a hypervalent iodine reagent. Through the biological evaluation of corresponding isoxazoles via three independent phenotypic assays, the different pattern of biological activities was shown according to the type of privileged substructure and substituent. These results demonstrated the significance of molecular design via introducing privileged substructures and various substituents to make a diverse arrangement of polar surface area within a similar 3-dimensional molecular framework.
Kim, Mingi,Hwang, Yoon Soo,Cho, Wansang,Park, Seung Bum
p. 407 - 413
(2017/06/19)

COMPOUNDS FOR TREATING SPINAL MUSCULAR ATROPHY
Provided herein are compounds, compositions thereof and uses therewith for treating spinal muscular atrophy.
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(2013/08/28)

Effect of Oxime Ether Incorporation in Acyl Indole Derivatives on PPAR Subtype Selectivity
Compounds that simultaneously activate peroxisome proliferator-activated receptor (PPAR) subtypes α and γ have the potential to effectively treat dyslipidemia and type2 diabetes (T2D) in a single pharmaceutically active molecule. The frequently observed side effects of selective PPARγ agonists, such as edema and weight gain, were expected to be overcome by using additive PPARα activity, leading to dual PPARα/γ agonists with balanced activity for both subtypes. Herein we report the discovery, synthesis, and optimization of a new series of α-ethoxyphenylpropionic acid bearing 5- or 6-substituted indoles. The incorporation of oxime ethers on the carbonyl portion of the benzoyl group can bring the PPARα/γ potency ratio equal to or slightly greater than one, as is the case for compounds 20c and 21a. Compound 20c shows high efficacy in an ob/ob mouse model of T2D and dyslipidemia, similar to that of rosiglitazone and tesaglitazar, but with a significant increase in body weight gain. In contrast, compound 21a, less potent as a dual PPARα/γ activator than 20c, showed an interesting pharmacological profile, as it elicits a decrease in body weight relative to reference compounds.
LeNaour, Morgan,Leclerc, Veronique,Farce, Amaury,Caignard, Daniel-Henri,Hennuyer, Nathalie,Staels, Bart,Audinot-Bouchez, Valérie,Boutin, Jean-Albert,Lonchampt, Michel,Dacquet, Catherine,Ktorza, Alain,Berthelot, Pascal,Lebegue, Nicolas
p. 2179 - 2193
(2013/03/28)

10A-AZALIDE COMPOUND HAVING 4-MEMBERED RING STRUCTURE
A 10a-azalide compound having a 4-membered ring structure crosslinked at the 10a- and 12-positions, which is represented by the formula (I), and is effective on even Haemophilus influenzae, or erythromycin resistant bacteria (e.g., resistant pneumococci and streptococci).
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Page/Page column 40-41

(2011/04/14)

Acetylation of N-heteroaryl bromides via PdCl2/(o-tolyl) 3P catalyzed heck reactions
A new user-friendly and convenient method for the acetylation of N-heteroaryl bromides is described. This process is based on the palladium-catalyzed olefination of an N-heteroaryl bromide with butyl vinyl ether, followed by acid hydrolysis of the intermediate heteroaryl vinyl ether in situ. Isopropanol at 85°C, in the presence of K3PO 4·3H2O (2 equiv), PdCl2 (2 mol%) and (o-tolyl)3P (4 mol%), provided the best conditions, giving yields of N-heteroaryl bromides up to 75%. Georg Thieme Verlag Stuttgart.
He, Tianxiong,Tao, Xiaochun,Wu, Xinyan,Cai, Lisheng,Pike, Victor W.
p. 887 - 890
(2008/09/21)

Rhodium-catalyzed cycloisomerization: Formation of indoles, benzofurans, and enol lactones
(Chemical Equation Presented) Internal affairs: Indoles, benzofurans, and enol lactones are formed chemoselectively from the rhodium-catalyzed cyclo-isomerization reaction of easily prepared alkynyl aniline substrates (see scheme, cod = cycloocta-1,5-diene, DMF = N,N-dimethylformamide). The reaction may proceed by nucleophilic capture of a vinylidene intermediate. Indoles are formed under mild conditions using low catalyst loadings.
Trost, Barry M.,McClory, Andrew
p. 2074 - 2077
(2008/02/14)

THIENOPYRAZOLES
Thienopyrazoles, their preparation, pharmaceutical compositions comprising these compounds, and their pharmaceutical uses in the treatment of disease states capable of being modulated by the inhibition of the protein kinases, in particular interleukin-2 inducible tyrosine kinase (ITK).
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Page/Page column 73

(2008/06/13)

Synthesis of 5-acylindoles via regioselective acylation of 3-trifluoroacetylindole
5-Acylindoles were synthesized by regioselective acylation of 3-trifluoroacetylindole with acyl chloride under the catalysis of Lewis acids, followed by hydrolysis of trifluoroacetyl and decarboxylation. Polar solvents were beneficial to the acylation and most of the Lewis acids tested showed good catalytic activities.
Li, Jun,Li, Bogang,Chen, Xiaozhen,Zhang, Guolin
p. 1447 - 1450
(2007/10/03)

Electrophilic substitution of indole on the benzene moiety: A synthesis of 5-acyl- and 5-aroylindoles
The Vilsmeier-Haack intermediate of indole is acylated, in the presence of a certain excess of AlCl3, exclusively at the benzene ring and especially at position-5. The formed acylindolecarboxaldehydes are readily decarbonylated on heating with Pd/C in mesitylene. Thus, 5-acylindoles and 5- aroylindoles are synthesized in a two step sequence from indole with overall yield of 30-46%.
Demopoulos, Vassilis J.,Nicolaou, Ioannis
p. 1519 - 1522
(2007/10/03)

SYNTHESIS OF SOME 5-SUBSTITUTED INDOLES
A halogen-metal exchange strategy was employed to prepare several 5-substituted indoles from 5-bromoindole.Additional derivatives were elaborated from the formyl, acetyl, thiomethyl, boronic acid and trimethylstannyl analogues thus prepared.
Yang, Youhua,Martin, Arnold R.,Nelson, David L.,Regan, John
p. 1169 - 1175
(2007/10/02)

THE SYNTHESIS OF 5- and 7-ACETYLINDOLE DERIVATIVES. I. THE PHOTOCHEMICAL REARRANGEMENT OF 1-ACETYLINDOLINE
5- and 7-Acetyl substituted indole derivatives have been prepared via intramolecular photo rearrangement of acyl radical and intramolecular electrophilic acylation of 1-acetylindoline.
Akagi, Masao,Ozaki, Kazuko
p. 61 - 64
(2007/10/02)

Synthese d'(indolyl-3)-4 dihydro-2,5 furanonnes-2 hydrosolubles
Une cyclisation du type Dieckmann suivie d'une decarboxylation permet d'acceder directement aux (indolyl-3)-4 dihydro-2,5 furanonnes-2 acetylees ou non sur l'homocycle a partir des ethoxycarbonylacetoxyacetyl-3 indoles correspondants sans protection prealable de la position 1 du cycle indolique et du substituant acyle de l'homocycle.
Baron, Michel,Cointet, Paul de,Bauduin, Gerard,Pietrasanta, Yves,Pucci, Bernard
p. 249 - 256
(2007/10/02)