- Synthesis of 2-aminothiophenes on ionic liquid phase support using the Gewald reaction
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The first report of the use of task-specific ionic liquid as soluble support for the Gewald synthesis of 2-aminothiophenes is reported in this article. This synthetic method is simple and efficient, and the products are obtained in good to excellent yields with high purities, without the need for chromatographic purification. Copyright Taylor & Francis Group, LLC.
- Hu, Yi,Wei, Ping,Huang, He,Han, Shi-Qing,Ouyang, Ping-Kai
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- Preparation method and application of tetrahydrobenzothiophene compound and pharmaceutical composition
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The invention belongs to the field of medicines, and particularly relates to a tetrahydrobenzothiophene compound as well as a pharmaceutical composition and a preparation method and application thereof. The tetrahydrobenzothiophene compound is a compound I as shown I. In-flight R1 And R2 The C1 -4 is a saturated/unsaturated hydrocarbon group. - OCH3 , OCH2 CH3 Phenyl, substituted phenyl, NO2 One - COR of - OH - F, Cl - Br. I - H R1 AND R2 Or different. R3 It is-F. - Cl, Br, I, OH, Amino, C1 -4 saturated/unsaturated hydrocarbon group, OCH3 , OCH2 CH3 , H, Wherein one of them is, n ≥ 5, n Being an integer. The compound effectively inhibits salmonella by inhibiting the synthesis of ATP-dependent transporter in the lipopolysaccharide synthesis pathway. Aeruginosa, escherichia coli and staphylococcus aureus.
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Paragraph 0043-0045; 0052-0054; 0061-0063; 0070-0072; ...
(2021/10/16)
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- Synthesis, Characterization, and Antibacterial and Anti-Inflammatory Activities of New Pyrimidine and Thiophene Derivatives
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Substituted[4,5]thieno[2,3-d]thiazolo[3,2-a]pyrimidin-5-one (3a-b) and pyrimidin-5(6H)-imine (3c-e) were synthesized via reaction of the starting compounds, ethyl 2-amino-substituted[b]thiophene-3-carboxylate (2a-c) and 2-amino-substituted [b]thiophene-3-carbonitrile (2d-f), respectively, with 2-bromothiazole. Synthesis of (bromo-substituted[b]thiophen-2-yl)alkanamide derivatives (4a-e) and thieno[2,3-d][1,3]oxazin-4-imine derivative (5) was accomplished via reaction of the starting compounds with bromoalkyl chloride through nucleophilic substitution; however, for the synthesis of compound 5, nucleophilic substitution was followed by nucleophilic addition to a nitrile group to form the oxazinimine ring. 1-(3-cyano-substituted[b]thiophen-2-yl)-3-(4-(trifluoromethyl)phenyl)thiourea derivatives (6a-c) were obtained via reaction of the starting compounds (2d-f) and 4-(trifluoromethyl phenyl)isothiocyanate. The lead compounds (2d-f) rapidly reacted with 4-(trifluoromethyl)benzaldehyde or 4-(2-pyridyl)benzaldehyde in acidic medium to yield compounds (7a-f) in large quantities. X-ray crystallography of compounds 4c and 7e confirmed their structures. Antimicrobial studies revealed that compound 6a was equally potent to ampicillin against Bacillus strains. Moreover, compounds 3e, 4d, and 6a possessed greater anti-inflammatory potency than that of the standard drug.
- Lahsasni, Siham,Al-Hemyari, Dunya A. M.,Ghabbour, Hazem A.,Mabkhoot, Yahia Nasser,Aleanizy, Fadilah S.,Alothman, Asma A.,Almarhoon, Zainab M.
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- Tetrahydro benzothiophene derivative and application thereof to preparation of glycogen synthase kinase 3 beta inhibitor
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The invention discloses a tetrahydro benzothiophene derivative and the application thereof to the preparation of a glycogen synthase kinase 3 beta inhibitor. The tetrahydro benzothiophene derivative, pharmaceutically acceptable salt, optical active body or racemate thereof has a chemical structure as shown in a formula I. Experiments show that the compound has good GSK-3 beta inhibitory activity. In addition, the invention further provides a method for preparing a tetrahydro benzothiophene compound. The method is short in synthesis route, simple in preparation process and easy to operate, and can meet the requirements of large-scale industrial production.
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Paragraph 0071; 0072; 0073
(2017/10/25)
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- Aqueous DABCO, an efficient medium for rapid organocatalyzed Knoevenagel condensation and the Gewald reaction
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In the presence of water and 1,4-diazabicyclo[2.2.2]octane, several aldehydes and cyclic ketones underwent efficient Knoevenagel condensation with malononitrile and ethyl cyanoacetate to produce the respective α.β-unsaturated systems within fairly short time periods. As a result, high yields of conjugated products were easily obtained. Products could be engaged in a Gewald reaction, either stepwise or in situ, to produce efficiently their respective 2-aminothiophenes within 4-7 h. TUeBITAK.
- Abaee, Mohammad Saeed,Cheraghi, Somayeh
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p. 650 - 660
(2014/07/07)
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- A simple synthesis of alkyl 2-aminobenzo[ b ]thiophene-3-carboxylates via an unexpected dehydrogenation of alkyl 2-amino-4,5,6,7-tetrahydrobenzo[ b ]thiophene-3-carboxylates
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A simple method for the preparation of alkyl 2-aminobenzo[b]thiophene-3-carboxylates is described. Alkyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates, generated from the Gewald three-component reaction between cyclohexanones, alkyl cyanoacetates and sulfur, undergo dehydrogenation in benzonitrile under an air atmosphere to afford alkyl 2-aminobenzo[b]thiophene-3-carboxylates in good to excellent yields.
- Adib, Mehdi,Bayanati, Maryam,Soheilizad, Mehdi,Ghazvini, Helia Janatian,Tajbakhsh, Mahmood,Amanlou, Massoud
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p. 2918 - 2922
(2015/01/09)
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- FLT3 INHIBITORS AND USES THEREOF
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The present invention provides methods of using compounds of formula I: or compositions thereof for the inhibition of FLT3, and the treatment of FLT3-mediated disorders.
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Paragraph 00271-00272; 00340-00341; 00620
(2014/12/12)
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- Synthesis and anxiolytic activity of some novel 5-oxo-1, 4-oxazepine derivatives
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A novel synthetic procedure for a series of 4-Aryl-3-phenyl-6,7,8,9- tetrahydro-benzothieno[3,2- f][l,4]oxazepin-5(4H)-one 8a-s derivatives had been described. Six compounds 8a,b,h,j,m,s were selected and submitted to pharmacological evaluation for anxiolytic activity in the open field test. All the test compounds except 8b significantly reduced the exploratory activity and the emotionality of the rats in the open-field. These inhibitory results are in agreement with the effect of reference standard chlorpromazine as a tranquillizer and anxiolytic in the same conditions.
- AbdelFattah, Bothiana A.,Khalifa, Maha M.A.,El-Sehrawi, Hend,Fayed, Eman,Bayoumi, Ashraf,Said, Makarem
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scheme or table
p. 330 - 338
(2012/05/05)
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- An efficient one-pot synthesis of substituted 2-aminothiophenes via three-component gewald reaction catalyzed by l -proline
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An efficient one-pot procedure for the direct catalytic synthesis of substituted 2-aminothiophenes catalyzed by l-proline under mild reaction conditions has been developed. A variety of functionalized 2-aminothiophene scaffolds were assembled in high yields by this catalytic protocol. Low catalyst loading, simple procedure, and high yields are the important attributes of this methodology.
- Wang, Tao,Huang, Xian-Gui,Liu, Jia,Li, Bo,Wu, Jin-Jin,Chen, Kai-Xian,Zhu, Wei-Liang,Xu, Xiao-Yong,Zeng, Bu-Bing
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scheme or table
p. 1351 - 1354
(2010/08/20)
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- Microwave-assisted gewald synthesis of 2-amimothio-phenes using functional ionic liquid as soluble support
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A microwave-assisted liquid-phase Gewald synthesis of 2-aminothiophenes was developed using task-specific ionic liquid - [2-hydemim][BF4] as soluble support. This new synthetic method is simple and efficient, and the products are obtained in good to excellent yields with high purities, without the need for chromatographic purification.
- Hu, Yi,Wei, Ping,Huang, He,Han, Shi-Qing,Ouyang, Ping-Kai
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p. 375 - 380
(2007/10/03)
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- Novel compounds and their use in therapy
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Thiophenepyrimidinone compounds and their use in therapy, especially for use in the treatment and/or prevention of a steroid hormone dependent diseases or disorders, such as steroid hormone dependent diseases or disorders requiring inhibition of 17β-hydroxysteroid dehydrogenase enzymes.
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- FUNGICIDES
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A method of combating phytopathogenic diseases on plants and harvested food crops which comprises applying to a plant, to the seed of a plant, to the locus of the plant or seed or to a harvested crop a fungicidally effective amount of 2-aminothiophene derivatives of formula (1). The invention further relates to fungicidal compositions containing these compounds, processes for preparing these compounds and to some of the compounds themselves.
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Page/Page column 90
(2010/02/11)
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- Synthesis and local anaesthetic activity of some 2-aminoacetylamino-3-carbetoxy/anilido-4,5,6,7-tetrahydro-benzothiophenes
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Twenty new 2-substituted aminoacetylamino-3-carbetoxy/anilido-4,5,6,7-tetrahydrobenzothiophenes (4a-4t) have been synthesised with a view to studying the effect of structural modification of carticaine (B) on the local anaesthetic activity and evaluated by Sollman's method as well as Bulbring and Wajda method using lignocaine hydrochloride as a standard.All the tested compounds show moderate to good activity and 4a has been found to be the most active drug comparable to the standard.
- Gadad, A K,Kumar, Hemant,Shishoo, C J,Khazi, I M,Mahajanshetti, C S
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p. 298 - 301
(2007/10/02)
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- Mechanistic Observations in the Gewald Syntheses of 2-Aminothiophenes
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The Gewald syntheses were employed to prepare a series of 2-amino-3-carboethoxythiophenes, and the syntheses of two of these, namely, the 3,4-trimethylene (1f) and 3,4-tetramethylene (1g) derivatives, were examined in detail.In two preparations of 1f, octahydro-6a-(4-morpholinyl)-2-thioxocyclopentapyrrole-3-carboxylic acid (7) was a co-product.The structure of 7 was ascertained from its 300 MHz 1H nmr and 13C nmr spectra, and by its conversion to 1,4,5,6-tetrahydro-2-mercaptocyclopentapyrrole-3-carboxylic acid ethyl ester (8).Isolation of 7 and other observations led to postulated mechanisms for three of the Gewald thiophene syntheses.
- Peet, Norton P.,Sunder, Shyam,Barbuch, Robert J.,Vinogradoff, Anna P.
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p. 129 - 134
(2007/10/02)
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- Use of polycyclic thiophene compounds as ripeners for sugarcane
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Sucrose yield of sugarcane is increased by treating the cane crop a few weeks prior to harvest with a certain type of polycyclic thiophene compound of the formula SPC1 Wherein X is cyano, carboalkoxy or carbamido and Y is an amino or substituted amino group, or with mixtures comprising one or more such compounds.
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