- Synthesis and biological evaluation of novel 4-(6-substituted quinolin-4-yl)-N-aryl thiazol-2-amine derivatives as potential antimicrobial agents
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Cyclocondensation reaction of 4-(2-bromoacetyl)quinolin-1-ium bromide (4a–d) with substituted arylthiourea, (5a–g) afforded 4-(6-substituted quinolin-4-yl)-N-aryl/pyridyl thiazol-2-amine (6a-ab). These newly synthesized derivatives were evaluated for in vitro antibacterial activity against Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388) (Gram-negative strains), Bacillus subtilis (NCIM 2063), Staphylococcus albus (NCIM 2178) (Gram-positive strains) and in vitro antifungal activity against Aspergillus niger (ATCC 504) and Candida albicans (NCIM 3100). Compounds 6a, 6b, 6d, 6f, 6k, and 6l showed moderate to good antibacterial activity against S. albus. Ten derivatives 6c, 6q, 6r, 6s, 6t, 6v, 6w, 6x, 6y, and 6aa, showed moderate to good activity against A. niger. N-[4-(Quinolin-4-yl)-1,3-thiazol-2-yl]pyridin-2-amine presented comparable activity against A. niger with respect to standard drug Rouconazole.
- Thakare, Prashant,Shinde, Abhijit,Dakhane, Sagar,Chavan, Abhijit,Bobade, Vivek D.,Mhaske, Pravin C.
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p. 1867 - 1877
(2021/06/21)
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- Isoindoline compound, and preparation method, pharmaceutical composition and application thereof
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The invention relates to a polysubstituted isoindoline compound represented by a general formula (I), and a preparation method, a pharmaceutical composition and an application thereof. Specifically, as a CRL4CRBNE3 ubiquitin ligase regulator with a novel structure, the polysubstituted isoindoline compound provided by the invention has stronger anti-tumor activity and an anti-tumor spectrum, and can be used for preparing medicines for treating diseases related to CRL4CRBNE3 ubiquitin ligase.
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Paragraph 0475; 1159-1161
(2020/04/17)
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- Facile and efficient synthesis of quinoline-4-carboxylic acids under microwave irradiation
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A facile and efficient method for the preparation of 2-non-substituted quinoline-4-carboxylic acids is described via the Pfitzinger reaction of isatins with sodium pyruvate following consequent decarboxylation under microwave irradiation.
- Zhu, Hui,Yang, Ri Fang,Yun, Liu Hong,Li, Jin
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experimental part
p. 35 - 38
(2010/11/04)
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- Preparation of 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid catalyzed by iron(III)porphyrins with (diacetoxyiodo)benzene
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Using iron(III)porphyrins in combination with (diacetoxyiodo)benzene allows for the conversion of 2,9-bis(bromomethyl)-4,7-diphenyl-1,10-phenanthroline into 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid. This method provides a cost-effective and environmentally-friendly oxidation procedure using less toxic PhI(OAc)2 and biologically relevant iron(III)porphyrins. The catalytic activity of five kinds of iron-metallated functional porphyrins were investigated using different oxidants, including air, H2O 2, PhI(OAc)2, PhIO and NaClO. Our results showed that the use of T(p-NO2)PPFeCl with PhI(OAc)2 as the oxidant in the presence of water displays remarkable activity for the desired oxidation reaction. The generality of this method was examined by synthesizing the carboxylic acids of pyridines and quinolines.
- Zhong, Qi-Di,Xue, Yun-Zhou,Yan, Hong,Song, Xiu-Qing,Zhong, Ru-Gang
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body text
p. 5532 - 5535
(2010/12/20)
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- Facile, one-step production of niacin (vitamin B3) and other nitrogen-containing pharmaceutical chemicals with a single-site heterogeneous catalyst
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Niacin (3-picolinic acid), which is extensively used as vitamin B 3 in foodstuffs and as a cholesterol-lowering agent, along with other oxygenated products of the picolines, 4-methylquinoline, and a variety of pyrimidines and pyridazines, may be produced in a single-step, environmentally benign fashion by combining single-site, open-structure, heterogeneous catalysts witha solid source of active oxygen, namely acetyl peroxyborate (APB), in the absence of an organic solvent. The high activities, selectivities, and the relatively mild conditions employed with this single-site heterogeneous catalyst, coupled with ease of transport, storage, and stability of the solid oxidant, augurs well for the future use of APB in conjunction with other open-structure, single-site catalysts for fine-chemical, pharmaceutical, and agrochemical applications.
- Raja, Robert,Thomas, John Meurig,Greenhill-Hooper, Michael,Ley, Steven V.,Almeida Paz, Filipe A.
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experimental part
p. 2340 - 2348
(2009/04/11)
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- Alkaloids from Nitraria komarovii. Structures of nitraridine, dihydronitraridine, and tetrahydronitraridine
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Three new alkaloids nitraridine (1), dihydronitraridine (2), and tetrahydronitraridine (3) were isolated from the aerial part of Nitraria komarovii. Their structures were established based on chemical transformations and spectral data. The compounds were synthesized. Spectral properties of the komarovine subgroup of alkaloids were discussed.
- Tulyaganov
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p. 459 - 461
(2008/02/09)
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- Synthesis and reactivity of lithium tri(quinolinyl)magnesates
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2-, 3- and 4-Bromoquinolines were converted to the corresponding lithium tri(quinolinyl)magnesates at -10°C when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines.
- Dumouchel, Sylvain,Mongin, Florence,Trécourt, Fran?ois,Quéguiner, Guy
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p. 8629 - 8640
(2007/10/03)
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- Remarkable effect of nitrogen dioxide for N-hydroxyphthalimide-catalyzed aerobic oxidation of methylquinolines
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Aerobic oxidation of methylquinolines was successfully achieved by the use of N-hydroxyphthalimide/Co(OAc)2/Mn(OAc)2 as catalyst in the presence of a small amount of nitrogen dioxide as an initiator.
- Sakaguchi, Satoshi,Shibamoto, Akihiro,Ishii, Yasutaka
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p. 180 - 181
(2007/10/03)
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- A new approach to the oxidation of methylquinolines with selenium dioxide
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A study of some parameters which influence the oxidation of 2- and 4-methylquinolines with selenium dioxide (or selenious acid) in dioxane has allowed to correct some erroneous opinions of this method and to elaborate a general, simple, fast, and cheap procedure of oxidation of methylquinolines having a methyl group in the position 2 or 4.
- Achremowicz, Lucjan
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p. 1681 - 1684
(2007/10/03)
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- The oxidation of aromatic aldehydes to carboxylic acids using hydrogen peroxide in formic acid
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Aromatic aldehydes and particularly heteroaromatic aldehydes 1 are efficiently and conveniently oxidized to their corresponding carboxylic acids 2 by hydrogen peroxide in formic acid at 4°C.
- Dodd,Le Hyaric
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p. 295 - 297
(2007/10/02)
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- Synthesis and aldose reductase inhibitory activity of N-(quinolinyl thiocarbonyl) glycine derivatives
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The onset of diabetic complications may be prevented by the inhibition of aldose reductase.Derivatives of N-(quinolinyl thiocarbonyl) glycine were prepared and their in vitro and ex vivo aldose reductase inhibitory activities were tested on rat lens.The cincophen derivatives were the most potent in vitro with an enzyme inhibition value of 29percent at 10-8 M and 91percent at 10-7 for the N--N-methylglycine compound 10a.This activity was shown to be dependent on the nature of the substituents and seems to be optimal for the acids; esterswerefound to be inactive.No compound have shown ex vivo inhibitory activity.It is concluded that the lack of ex vivo activity is likely due to a poor bioavailability or a bad penetration of the compounds in target tissue (lens). aldose reductase inhibitors / diabetic complications / N-(quinolinyl thiocarbonyl) glycine
- Nicolaie, E,Guengoer, T,Goyard, J,Cure, G,Fouquet, A,et al.
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p. 977 - 984
(2007/10/02)
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- SYNTHESIS OF QUINOLINE-4-CARBOXYLIC ACID AND ITS DERIVATIVES
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2-Methylquinoline-4-carboxylic acid was obtained by the reaction of isatin with acetone in the presence of alkali.This acid was converted through a step involving (E)-2-styrylquinoline-4-carboxylic acid to quinoline-2,4-dicarboxylic acid, from which quinoline-4-carboxylic acid was obtained by refluxing in nitrobenzene.The structures of the synthesized compounds were confirmed by 1H NMR spectroscopy using two-dimensional (2DJ) spectra.
- Brasyunas, V.B.,Andreyanova, T.A.,Safonova, T.S.,Solov'eva, N.P.,Turchin, K.F.,Sheinker, Yu.N.
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p. 670 - 673
(2007/10/02)
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- Photochemical Reaction of Ethoxycarbonyl-Substituted Quinolines
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The photochemical reactions of the quinoline derivatives substituted by an ethoxycarbonyl group at the 2-, 3-, and 4-positions of a quinoline nucleus have been investigated in several alcohols and cyclohexane.Irradiation of ethyl 4-quinolinecarboxylate (1) yielded ethyl 2-hydroxyalkyl-4-quinolinecarboxylates (4a-c) in alcohols and ethyl 2-cyclohexyl-4-quinolinecarboxylate (4d) in cyclohexane in a good yield, respectively.The photochemical reactions of ethyl 3-quinolinecarboxylate (2) showed remarkable solvent dependency.Irradiation in methanol and cyclohexane afforded a solvent-additive product, ethyl 4-hydroxymethyl-1,4-dihydro-3-quinolinecarboxylate (5a) and ethyl 4-cyclohexyl-1,4-dihydro-3-quinolinecarboxylate (5b), while such photoaddition of the solvent did not proceed in ethanol and 2-propanol but instead ethyl 1,4-dihydro-3-quinolinecarboxylate (6) and dimeric compounds were formed, both of which were unstable and finally reverted to 2 at room temperature in air.In the case of ethyl 2-quinolinecarboxylate two types of the products, ethyl 4-hydroxyalkyl-1,4-dihydro-2-quinolinecarboxylate (7) and ethyl 1,4-dihydro-2-quinolinecarboxylate (8) were obtained in ethanol and 2-propanol but the yields of those products were poor.On the basis of triplet quenching experiments, the photochemical reactions of those ethyl quinolinecarboxylates are suggested to occur through hydrogen abstraction from the solvents by the ring nitrogen in the S1 state.
- Ono, Isao,Hata, Norisuke
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p. 2891 - 2898
(2007/10/02)
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