- 2-(2,2-DIARYLETHYL)-CYCLIC AMINE DERIVATIVE OR SALT, SYNTHESIS THEREOF, AND APPLICATION AND COMPOSITION THEREOF
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The disclosure relates to a 2-(2,2-diarylethyl)-cyclic amine derivative or salt, a synthesis method, an application and a composition thereof. Biological activity test shows that this kind of 2-(2,2-diarylethyl)-cyclic amine derivative has good M-receptor antagonistic activity; and can be used as an active component of drugs for the treatment of the diseases mediated or regulated by muscarinic receptors, such as asthma, chronic obstructive pulmonary disease (COPD), overactive bladder (OAB), bronchospasm with chronic obstructive pulmonary disease, visceral spasm, irritable bowel syndrome, Parkinson's disease, depression or anxiety, schizophrenia and related mental diseases.
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Paragraph 0332-0333
(2021/05/28)
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- Half-wave potentials and in vitro cytotoxic evaluation of 3-acylated 2,5-bis(phenylamino)-1,4-benzoquinones on cancer cells
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A broad range of 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones were synthesized and their voltammetric values, as well as in vitro cancer cell cytotoxicities, were assessed. The members of this series were prepared from acylbenzoquinones and phenylamines, in moderate to good yields (47-74%), through a procedure involving a sequence of two in situ regioselective oxidative amination reactions. The cyclic voltammograms of the aminoquinones exhibit two one-electron reduction waves to the corresponding radical-anion and dianion, and two quasi-reversible oxidation peaks. The first and second half-wave potential values (E1/2) of the members of the series were sensitive to the push-pull electronic effects of the substituents around the benzoquinone nucleus. The in vitro cytotoxic activities of the 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones against human cancer cells (bladder and prostate) and non-tumor human embryonic kidney cells were measured using the MTT colorimetric method. The substitution of both aniline groups, by either methoxy (electron donating effect) or fluorine (electron withdrawal effect), decreased the cytotoxicity in the aminoquinones. Among the members of the unsubstituted phenylamino series, two of the 18 compounds showed interesting anti-cancer activities. A preliminary assay, looking for changes in the expression of selected genes, was performed. In this context, the two compounds increased TNF gene expression, suggesting an association with an inflammatory-like response.
- Benites, Julio,Valderrama, Jaime A.,Ramos, Maryan,Valenzuela, Maudy,Guerrero-Castilla, Angélica,Muccioli, Giulio G.,Calderon, Pedro Buc
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- Efficient microwave-assisted direct C-benzoylation of phenols and naphthols with benzoic acid catalyzed by bismuth triflate under solvent-free or ionic liquid conditions
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An efficient and simple route for the synthesis of ortho-hydroxyaryl ketones has been developed. The microwave-assisted direct C-benzoylation of phenols and naphthols in the presence of metal triflates afforded the corresponding ortho-hydroxyaryl ketones in moderate to excellent yields. Bismuth triflate showed the best catalytic performance compared to other metal triflates. The protocol has advantages including short reaction times, high chemoselectivity towards C-acylation, and simple work-up. Additionally, bismuth triflate can be easily recovered and reused several times without significant loss of catalytic performance.
- Tran, Phuong Hoang,Phung, Huy Quang,Duong, Minh Nhat,Pham-Tran, Nguyen-Nguyen
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supporting information
p. 1558 - 1563
(2017/04/03)
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- Chemoselective C-benzoylation of phenols by using ALCl3under solvent-free conditions
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Substituted phenols were chemo-selectively reacted with benzoylchloride in presence of aluminum chloride under solvent-free condition to afford the corresponding 2′-hydroxy aryl benzophenones in excellent yields (72-96%). Naphthol benzoylation resulted in lower yields as compared to phenols. Both reactions completed in 5-10 min with quantitative yields providing excellent control over regioselectivity of products.
- Gaikwad, Sunil V.,Nawghare, Beena R.,Lokhande, Pradeep D.
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p. 319 - 325
(2015/07/27)
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- Eco-friendly synthesis and antiproliferative evaluation of some oxygen substituted diaryl ketones
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A broad variety of oxygen-substituted diaryl ketones has been synthesized by solar energy-induced Friedel Crafts acylations of 1,4-benzo- and 1,4-naphthoquinones with benzaldehydes. The in vitro antiproliferative properties of the photoproducts were asses
- Arenas, Paola,Pena, Andres,Rios, David,Benites, Julio,Muccioli, Giulio G.,Calderon, Pedro Buc,Valderrama, Jaime A.
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p. 9818 - 9832
(2013/09/23)
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- Studies on quinones. Part 47. Synthesis of novel phenylaminophenanthridinequinones as potential antitumor agents
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In our search for potential anticancer agents, a series of 8- and 9-phenylamino-3,4-tetrahydro-phenanthridine-1,7,10(2H)-triones with substituent variations at 6-, 8- and 9-positions were prepared using a highly efficient sequence involving: a) solar photoacylation reactions of benzoquinone with arylaldehydes, b) one-pot procedure for the synthesis of 3,4- dihydrophenanthridine-1,7,10(2H)-trione intermediates from acylhydroquinones and c) highly regiocontrolled acid-induced amination reaction of phenanthridinequinones with phenylamines. The members of this series were in vitro evaluated using the MTT colorimetric method against one normal cell line and three human cancer cell lines. The SAR analysis indicates that the location of nitrogen substituents on the quinone nucleus, the presence of methyl, phenyl, furyl and thienyl groups at the 6-position and the aromatization of the angular cycloaliphatic ring of the phenylamino-3,4-tetrahydrophenanthridine-1,7,10(2H)- trione pharmacophore play key roles in the antitumor activity.
- Valderrama, Jaime A.,Ibacache, Andrea,Rodriguez, Jaime A.,Theoduloz, Cristina,Benites, Julio
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experimental part
p. 3398 - 3409
(2011/08/03)
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- Facile synthesis of regio-isomeric naphthofurans and benzodifurans
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Naphtho[1,2-b]furans 1a-f, naphtho[2,1-b]furans 2a-f, benzo[1,2-b:5,4- b′]difurans 3a-b, benzo[1,2-b:4,5-b′]difurans 4a-b, and benzo[1,2-b:4,3-b′]difurans 5a-b were synthesized by base-catalyzed cyclization reaction of the corresponding o-alkoxybenzoylarene derivatives. The o-alkoxybenzoylarenes were obtained from the etherification reaction of the o-hydroxybenzoylarenes, which were prepared either by the reaction of methoxyarenes with benzoyl chloride in the presence of aluminum chloride or by photo-Fries rearrangement of aryl benzoates. Graphical Abstract.
- Park, Kwanghee Koh,Jeong, Jinsuk
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p. 545 - 553
(2007/10/03)
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- Zinc Mediated Friedel-Crafts Acylation in Solvent-Free Conditions under Microwave Irradiation
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Zn powder is found to catalyze the Friedel-Crafts acylation of aromatic compounds with acyl halides efficiently under microwave irradiation in solvent-free conditions. Activated substrates undergo acylation predominantly at the para-position. The Zn powder can be re-used up to six times after simple washing with diethyl ether and dilute HCl.
- Paul, Satya,Nanda, Puja,Gupta, Rajive,Loupy, Andre
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p. 2877 - 2881
(2007/10/03)
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- An improved method for the preparation of 4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates from 2-acyl-1,4-benzoquinones and mercaptoacetates
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4,7-Dioxo-4,7-dihydrobenzo[b]thiophene-2-carboxylates (4) have been synthesized in a one-pot procedure from 2-acyl-1,4-benzoquinones (1) and mercaptoacetates (2) by using 1-trimethylsilylimidazole as a protective reagent as well as a base. Thus, reaction of 1 with 2 in THF at room temperature was followed by treatment with excess of 1-trimethylsilylimidazole at 80°C. Then the cooled mixture was hydrolyzed with hydrochloric acid and oxidized with cerium(IV) ammonium nitrate (CAN) to give the expected thiophenequinone derivatives (4). 4,9-Dioxo-4,9-dihydronaphtho[2,3-b]thiophene-2-carboxylates (7) were similarly prepared from 2-acyl-1,4-naphthoquinones (5) and mercaptoacetates, in general, by omitting the CAN oxidation procedure.
- Kobayashi, Kazuhiro,Yoneda, Keiichi,Uchida, Masaharu,Matsuoka, Hideki,Morikawa, Osamu,Konishi, Hisatoshi
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p. 2423 - 2430
(2007/10/03)
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- Photochemistry in supercritical carbon dioxide. The benzophenone-mediated addition of aldehydes to α,β-unsaturated carbonyl compounds
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The photo-induced addition of aldehydes to α,β-unsaturated carbonyl compounds is an effective, 'environmentally benign' method for the synthesis of 2-acyl-1,4-hydroquinones (from quinones) and 1,4-diketones (from enones). This process has been improved by eliminating benzene as a solvent and replacing it with supercritical carbon dioxide. Highest yields were obtained at higher CO2 pressures, or with the addition of 5% t-butyl alcohol as co-solvent.
- Pacut, Ryszard,Grimm, Michelle L.,Kraus, George A.,Tanko, James M
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p. 1415 - 1418
(2007/10/03)
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- Thermal cross fries acyl and benzoyl migrations from aromatic diesters to phenols
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A study of boron trifluoride etherate catalyzed thermal cross Fries reaction is reported in this paper. Acyl and benzoyl migrations from various aromatic diesters to phenols in dry benzene as solvent takes place selectively and in this, way offers an alternative route to the preparation of different hydroxy acetophenones and benzophenones.
- Thapliyal,Aggarwal
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p. 706 - 708
(2007/10/03)
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- Alumina in Methanesulfonic Acid (AMA) as a New Efficient Reagent for Direct Acylation of Phenol Derivatives and Fries Rearrangement. A Convenient Synthesis of o-Hydroxyarylketones
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Alumina in methanesulfonic acid (AMA) is used to prepare o-hydroxyaryl ketones by acylation of phenol and naphthol derivatives with carboxylic acids and the Fries rearrangement of phenolic esters. Mechanistic studies show that the acylation reaction in AMA occurred through an esterification followed by a Fries rearrangement of the phenolic ester by an intermolecular mechanism.
- Sharghi, Hashem,Kaboudin, Babak
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p. 2678 - 2695
(2007/10/03)
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- A direct route to acylhydroquinones from α-keto acids and α- carboxamido acids
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The reaction of quinones with in situ generated acyl- or carboxamido radicals provides a direct rome to the synthesis of acylhydroquinones not accessible by the photochemical reaction of quinones with aldehydes.
- Kraus, George A.,Melekhov, Alex
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p. 3957 - 3960
(2007/10/03)
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- STUDIES ON QUINONES XVII. THE REACTION OF ACYLBENZOQUINONES WITH HYDRAZOIC ACID: A ROUTE TO THE PREPARATION OF 2,1-BENZISOXAZOL-4,7-QUINONES
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A straightforward route to 2,1-benzisoxazol-4,7-quinones by oxidation of acylazido hydroquinones, obtained through reaction of acylbenzoquinones with hydrazoic acid, is described.
- Cassis, Raul,Fernandez, Monica,Tapia, Ricardo,Valderrama, Jaime A.
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p. 1077 - 1088
(2007/10/02)
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