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Academic literature on the topic 'Amide derivatives of N-benzyl-3-aminotropane'
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Journal articles on the topic "Amide derivatives of N-benzyl-3-aminotropane"
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Jílek, Jiří, Miroslav Rajšner, Vladimír Valenta, Miloš Borovička, Jiří Holubek, Miroslav Ryska, Emil Svátek, Jan Metyš, and Miroslav Protiva. "Synthesis of piperidine derivatives as potential analgetic agents." Collection of Czechoslovak Chemical Communications 55, no. 7 (1990): 1828–53. http://dx.doi.org/10.1135/cccc19901828.
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Reaction of N-(1-(2-phenylethyl)-4-piperidinyl)propionanilide (I) with phosphorus pentasulfide gave the thioamide VI. Acylation of N-(1-(2-phenylethyl)-4-piperidinyl)aniline with 2-(methoxy)acetic and 2-(methylthio)acetic anhydrides afforded the amides II and III. Treatment of 4-anilino-1-benzylpiperidine-4-methanol with thionyl chloride gave the spirocyclic sulfurous acid ester amide XIV. Reduction of the hydrochloride of ethyl 3-(1-ethoxycarbonyl-4-phenylimino-3-piperidinyl)propionate (XXII) with sodium cyanoborohydride gave the perhydro-1,6-naphthyridine derivative XIX, a model compound in the synthesis of the cyclic analogue of fentanyl (I). Ethyl 4-anilino-1-(2-phenylethyl)-1,2,3,6-tetrahydropyridine-3-carboxylate (XXIX) hydrochloride, obtained by reaction of ethyl 4-oxo-1-(2-phenylethyl)piperidine-3-carboxylate hydrochloride with aniline, was reduced with lithium aluminium hydride to 4-anilino-1-(2-phenylethyl)piperidine-3-methanol (XXXI). 1-Methyl- and 1-benzyl-4-piperidone were reacted with 4-cyclopropylphenylmagnesium bromide and the tertiary alcohols XXXVII and XXXVIII obtained were acylated with propionyl chloride to give the esters XXXIX and XL. The piperidine derivatives XLI, XLVI and XLVIII were prepared as potential neurotropic agents. Alkylation of 8-hydroxy-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine (XLIX) with 2-(2-chloroethyl)-1,3-dioxane and -1,3-dioxolane resulted in the 6,7-benzomorphan derivatives L and LI. Out of the compounds prepared, only the closest fentanyl analogues II, III, and VI showed very strong analgetic activity.
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Valenta, Vladimír, Zdeněk Vejdělek, Karel Šindelář, and Miroslav Protiva. "Potential anticonvulsants: Some derivatives and analogues of 2-propylpentanoic acid." Collection of Czechoslovak Chemical Communications 55, no. 4 (1990): 1067–76. http://dx.doi.org/10.1135/cccc19901067.
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Reaction of 2-(ethoxycarbonylamino)ethanol with 2-propylpentanoyl chloride gave the ester III. N-(4-Piperidinyl)-2-propylpentanamide (V) was prepared via the 1-benzyl-4-piperidinyl derivative IV and was acylated with ethanesulfonyl chloride and 2-propylpentanoyl chloride to give the amides VI and VII. Malonic ester syntheses afforded diethyl 2-ethyl- and 2-propyl-2-(2-(methylthio)ethyl)malonate VIII and XIII which were hydrolyzed and decarboxylated to the acids X and XV which, in turn, were transformed to the amides XII and XVII. 3-Thiapentanenitrile was alkylated with propyl bromide to the nitrile XIX which was hydrolyzed to the acid XX and the amide XXI. The acids X, XV, and XX, and the amides XII, XVII, and XXI are analogues of the anticonvulsant agents valproic acid (I) and valpromide (II). Compounds XX (V⁄FB-14 721) and XXI (V⁄FB-14 722) potentiate, in doses in which they ìper seî are ineffective as anticonvulsants in mice, significantly the anticonvulsant effect of diazepam.
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Ravikumar, Krishnan, Balasubramanian Sridhar, Jagadeesh Babu Nanubolu, Tamilselvan Rajasekaran, and Basi Venkata Subba Reddy. "Four oxoindole-linked α-alkoxy-β-amino acid derivatives." Acta Crystallographica Section C Structural Chemistry 71, no. 4 (March 21, 2015): 322–29. http://dx.doi.org/10.1107/s2053229615005604.
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Four structures of oxoindolyl α-hydroxy-β-amino acid derivatives, namely, methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-methoxy-2-phenylacetate, C24H28N2O6, (I), methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-ethoxy-2-phenylacetate, C25H30N2O6, (II), methyl 2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-[(4-methoxybenzyl)oxy]-2-phenylacetate, C31H34N2O7, (III), and methyl 2-[(anthracen-9-yl)methoxy]-2-{3-[(tert-butoxycarbonyl)amino]-1-methyl-2-oxoindolin-3-yl}-2-phenylacetate, C38H36N2O6, (IV), have been determined. The diastereoselectivity of the chemical reaction involving α-diazoesters and isatin imines in the presence of benzyl alcohol is confirmed through the relative configuration of the two stereogenic centres. In esters (I) and (III), the amide group adopts ananticonformation, whereas the conformation issynin esters (II) and (IV). Nevertheless, the amide group forms intramolecular N—H...O hydrogen bonds with the ester and ether O atoms in all four structures. The ether-linked substituents are in the extended conformation in all four structures. Ester (II) is dominated by intermolecular N—H...O hydrogen-bond interactions. In contrast, the remaining three structures are sustained by C—H...O hydrogen-bond interactions.
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Gomes, Ligia R., John Nicolson Low, Catarina Oliveira, Fernando Cagide, and Fernanda Borges. "Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives." Acta Crystallographica Section E Crystallographic Communications 72, no. 5 (April 15, 2016): 675–82. http://dx.doi.org/10.1107/s2056989016005958.
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The crystal structures of three benzamide derivatives,viz. N-(6-hydroxyhexyl)-3,4,5-trimethoxybenzamide, C16H25NO5, (1),N-(6-anilinohexyl)-3,4,5-trimethoxybenzamide, C22H30N2O4, (2), andN-(6,6-diethoxyhexyl)-3,4,5-trimethoxybenzamide, C20H33NO6, (3), are described. These compounds differ only in the substituent at the end of the hexyl chain and the nature of these substituents determines the differences in hydrogen bonding between the molecules. In each molecule, them-methoxy substituents are virtually coplanar with the benzyl ring, while thep-methoxy substituent is almost perpendicular. The carbonyl O atom of the amide rotamer istransrelated with the amidic H atom. In each structure, the benzamide N—H donor group and O acceptor atoms link the molecules intoC(4) chains. In1, a terminal –OH group links the molecules into aC(3) chain and the combined effect of theC(4) andC(3) chains is a ribbon made up of screw relatedR22(17) rings in which the ...O—H... chain lies in the centre of the ribbon and the trimethoxybenzyl groups forms the edges. In2, the combination of the benzamideC(4) chain and the hydrogen bond formed by the terminal N—H group to an O atom of the 4-methoxy group link the molecules into a chain ofR22(17) rings. In3, the molecules are linked only byC(4) chains.
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Romanenko, M. I., D. G. Ivanchenko, T. A. Sharapova, I. M. Bilay, and K. V. Aleksandrova. "Synthesis and hypoglycemic activity of 7-n-butyl-3-methyl-8-thioxanthine derivatives." Farmatsevtychnyi zhurnal, no. 6 (August 14, 2018): 95–104. http://dx.doi.org/10.32352/0367-3057.6.16.07.
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According to the International Diabetes Federation in 2015 were registered 59.8 million patients with diabetes in Europe. Synthetic drugs are widely applied in addition to a variety of insulins to normalize blood glucose level. It should be noted that the oral anti-diabetic drugs are the common therapeutic agents for the treatment of diabetes mellitus type II, and therefore the search for new non-toxic hypoglycemic agents is one of the most urgent problems of modern pharmaceutical science. It is known that 7,8-disubstituted xanthine derivatives exhibit hypoglycemic activity.
The aim of this work lies in developing unique method to synthesize undocumented in other scientific papers 7-n-butyl-3-methyl-8-thioxanthine derivatives and also studying of their hypoglycemic activity.
Acute toxicity of synthesized compounds has been studied with the application of Prozorovsky’s method. The glucose homeostasis characteristic has been performed on carbohydrate tolerance that has been determined by the glucose load test on the control group and on the intact rats.
The reactions of 7-n-butyl-3-methyl-8-thioxanthine with benzylchlorides, bromoketones, esters and an amide of chloroacetic acid have been studied. Reactions of mentioned syntons proceed smoothly in aqueous propanol-2 environment and lead to the formation of the corresponding 8-benzyl-, benzoylmethylthioxanthines and xanthinyl-8-thioacetic acid derivatives.
Accessible laboratory method has been elaborated to synthesize unspecified in scientific papers earlier 8-thiosubstituted 7-n-butyl-3-methylxanthine by reacting 7-n-butyl-3-methyl-8-thioxanthine with benzylchlorides, bromoketones, esters and an amide of chloroacetic acid, their structure having been proved by NMR-spectroscopy data. The acute toxicity of synthesized compounds has been studied. It has been established that LD50 is in the range 820–2477 mg/kg, i. e. obtained substances are low-toxic and practically non-toxic according to Sidorov’s classification. Also the study of hypoglycemic activity of synthesized compounds has been carried out. A significant perspective for further research to find the original antidiabetic agents has been shown by bioassay results. It has been found that 7-n-butyl-3-methylxanthinyl-8-thioacetamide is more active than reference substances.
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Prabu, D. Sam Daniel, Sivalingam Lakshmanan, K. Thirumurugan, N. Ramalakshmi, and S. Arul Antony. "Synthesis, Molecular Docking, DFT Study of Novel N-Benzyl-2-(3-cyano-4-isobutoxyphenyl)- 4-methylthiazole-5-carboxamide Derivatives and their Antibacterial Activity." Asian Journal of Chemistry 32, no. 3 (January 31, 2020): 619–26. http://dx.doi.org/10.14233/ajchem.2020.22390.
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A series of febuxostat based new chemical entities was synthesized using microwave method and characterized by NMR, mass and FT-IR spectral studies. Molecular docking of febuxostat amide nucleus substitution compounds 8c (-7.91kcal/mol), 8g (-7.94 kcal/mol) exhibiting high binding energy against ALK receptors. Theoretical investigation of MEPs, HOMO, LUMO and energy gap of HOMO-LUMO were calculated by B3LYP/6-31G method. Among the tested compounds, methoxy substituted compound 8g showed highest antibacterial activity against S. aereus and B. subtilis.
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Jones, R., A. G. M. Rattray, S. J. Rettig, J. R. Scheffer, and J. Trotter. "Structures and photochemistry of dibenzobarrelene monoamides." Acta Crystallographica Section B Structural Science 52, no. 6 (December 1, 1996): 1007–13. http://dx.doi.org/10.1107/s0108768196009056.
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The photochemistry of 9,10-ethenoanthracene-11-monoamides has been studied and correlated with the crystal structures determined for two derivatives; photoproduct structures have been established from a crystal structure analysis of one of the products and from NMR correlations. Crystal data are: (1)-Et, N, N-diethyl-9,10-dihydro-9,10-ethenoanthracene-11-carboxamide, C21H21NO, Pbca; (1)-Pr, 9,10-dihydro-N,N-di(isopropyl)-9,10-ethenoanthracene-11-carboxamide, C23H25NO, P21/c; (2 L)-Bz, 9,10-dihydro-9,10-ethenoanthracene-11-spiro-3′-(1-benzyl-4-phenylazetidine)-2′-one, C31H25NO (+ solvent), P21/a (Z = 8). The two dibenzobarrelene molecules have geometries and dimensions similar to those of related materials; the amide group in each molecule is only partially conjugated with the C 11=C 12 double bond. Mechanisms are derived for the formation of three types of photoproduct: (i) the well known di-π-methane reaction [(2M)-type photoproduct]; (ii) a hydrogen abstraction process (2H); (iii) β-lactam formation (2 L).
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Culletta, Giulia, Maria Zappalà, Roberta Ettari, Anna Maria Almerico, and Marco Tutone. "Immunoproteasome and Non-Covalent Inhibition: Exploration by Advanced Molecular Dynamics and Docking Methods." Molecules 26, no. 13 (July 2, 2021): 4046. http://dx.doi.org/10.3390/molecules26134046.
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The selective inhibition of immunoproteasome is a valuable strategy to treat autoimmune, inflammatory diseases, and hematologic malignancies. Recently, a new series of amide derivatives as non-covalent inhibitors of the β1i subunit with Ki values in the low/submicromolar ranges have been identified. Here, we investigated the binding mechanism of the most potent and selective inhibitor, N-benzyl-2-(2-oxopyridin-1(2H)-yl)propanamide (1), to elucidate the steps from the ligand entrance into the binding pocket to the ligand-induced conformational changes. We carried out a total of 400 ns of MD-binding analyses, followed by 200 ns of plain MD. The trajectories clustering allowed identifying three representative poses evidencing new key interactions with Phe31 and Lys33 together in a flipped orientation of a representative pose. Further, Binding Pose MetaDynamics (BPMD) studies were performed to evaluate the binding stability, comparing 1 with four other inhibitors of the β1i subunit: N-benzyl-2-(2-oxopyridin-1(2H)-yl)acetamide (2), N-cyclohexyl-3-(2-oxopyridin-1(2H)-yl)propenamide (3), N-butyl-3-(2-oxopyridin-1(2H)-yl)propanamide (4), and (S)-2-(2-oxopyridin-1(2H)-yl)-N,4-diphenylbutanamide (5). The obtained results in terms of free binding energy were consistent with the experimental values of inhibition, confirming 1 as a lead compound of this series. The adopted methods provided a full dynamic description of the binding events, and the information obtained could be exploited for the rational design of new and more active inhibitors.
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El Kayal, Wassim, Hanna Severina, Vadim Tsyvunin, Sergiy Zalevskyi, Sergiy Shtrygol’, Sergiy Vlasov, Olga Golovchenko, Sergiy Kovalenko, and Victoriya Georgiyants. "Synthesis and anticonvulsant activity evaluation of n-[(2,4-dichlorophenyl)methyl]-2-(2,4-dioxo-1h-quinazolin-3-yl)acetamide novel 1-benzylsubstituted derivatives." ScienceRise: Pharmaceutical Science, no. 1(35) (February 28, 2022): 58–69. http://dx.doi.org/10.15587/2519-4852.2022.253554.
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The aim. Synthesis of 1-benzylsubstituted derivatives of N-[(2,4-dichlorophenyl)methyl]-2-(2,4-dioxo-1h-quinazolin-3-yl)acetamide, and determination of affinity to GABAergic biotargets with the following anticonvulsant activity estimation using PTZ-induced seizures model in mice.
Materials and methods. Standard organic synthesis methods were used; the structure of the synthesized compounds was proved by elemental analysis, 1H and 13C NMR spectroscopy, and LC/MS method; composition of the synthesized compounds – by elemental analysis, their individuality – by TLC and LC/MS methods. AutoDockTools-1.5.6, as well as AutoDock Vina software, was used to perform molecular docking. Anticonvulsant activity was studied using pentylenetetrazole-induced seizures in mice.
Results. A targeted N-[(2,4-dichlorophenyl)methyl]-2-(1-(R-benzyl)-2,4-dioxo-quinazolin-3-yl)acetamides were obtained by alkylation of N-[(2,4-dichlorophenyl)methyl]-2-(2,4-dioxo-1H-quinazolin-3-yl)acetamide by corresponding 1-chloromethylbenzene in dimethylformamide environment with excess of potassium carbonate at a temperature 70-80 ˚С. Prediction of activity of 1-benzyl derivatives in the pentylenetetrazole-induced seizures in an in vivo experiment was carried out according to the obtained results of docking studies – affinity calculation for GABA receptor and GABA enzyme active sites, as well as analysis of conformational placement in them. In relation to the binding energy, the studied ligands were inferior to the reference drugs: GABA receptor positive allosteric modulators – benzamidine and diazepam, and GABA inhibitor – vigabatrin. The synthesized substances did not show anticonvulsant activity: only 2 compounds have shown a tendency to their activity manifestation according to the criterion of integral protective indicator – reduction of mortality by 17 % compared to control, as well as prolonging the time death of the animals. Comparison with the preliminary obtained results of the activity of the promising anticonvulsant N-[(2,4-dichlorophenyl)methyl] -2-(2,4-dioxo-1H-quinazolin-3-yl) acetamide N-[(2,4-dichlorophenyl)methyl]-2-(2,4-dioxo-1H-quinazolin-3-yl)acetamide made possible to prove the pharmacophore role of the cyclic amide fragment in anticonvulsant activity manifestation.
Conclusion. The synthesis of N-[(2,4-dichlorophenyl)methyl]-2-(1-(R-benzyl)-2,4-dioxo-quinazolin-3-yl)acetamides, which have not still described in the literature, was carried out, as well as the structure of the mentioned compounds was proved. Unfortunately, the substances did not show anticonvulsant activity on the model of pentylenetetrazole-induced seizures. However, the obtained results allowed establishing the key role of the NHCO cyclic fragment on anticonvulsant activity. A positive correlation between the results of in vivo studies and in silico calculations was found – the model of pentylenetetrazole-induced seizures and docking into the active sites of PAMs GABAА receptor and enzyme inhibitor GABAАТ, which allows to recommend the given docking methodology as a tool to streamline and optimize the screening on the mentioned model
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Li, Wen, Shu-Yi Chen, Wei-Nan Hu, Mei Zhu, Jia-Min Liu, Yi-Hong Fu, Zhen-Chao Wang, and Gui-Ping OuYang. "Design, synthesis, and biological evaluation of quinazoline derivatives containing piperazine moieties as antitumor agents." Journal of Chemical Research 44, no. 9-10 (March 17, 2020): 536–42. http://dx.doi.org/10.1177/1747519820910384.
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A series of novel quinazoline derivatives containing piperazine analogs are synthesized via substitution reactions with 6,7-disubstituted 4-chloroquinazoline and benzyl piperazine (amido piperazine). Potent antiproliferative activities are observed against A549, HepG2, K562, and PC-3 with N-(3-chlorophenyl)-2-(4-(7-methoxy-6-(3-morpholino-propoxy)quinazoline-4-yl)piperazine-1-yl)acetamidename C9 showing excellent activity. This active derivative was screened for cell migration ability, proliferation effects, and apoptosis against A549 and PC-3 cells, with the result showing biological activity almost equal to that of the control gefitinib.
Book chapters on the topic "Amide derivatives of N-benzyl-3-aminotropane"
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Lambert, Tristan H. "Functional Group Protection." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0014.
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Alfonso Iadonisi at the University of Naples Federico II developed (Eur. J. Org. Chem. 2013, 3137) a procedure for the selective acetolysis of the perbenzylated sugar 1 to furnish 3 using isopropenyl acetate (2) instead of the more typical and high-boiling acetic anhydride. The (3,4-dimethoxylphenyl)benzyl (DMPBn) protecting group, which is removed (cf. 4 → 5) under acidic conditions in the presence of the cation scavenger 5, was developed (J. Org. Chem. 2013, 78, 5264) by David S. Larsen at the University of Otago as an alternative to the p-methoxybenzyl (PMB) group. Another new hydroxyl-protecting group, the AzDMB group, which can be installed by simple acylation of (7 + 8 → 9) and removed under reductive conditions, was developed by Gijsbert A. van der Marel and Jeroen D.C. Codée of Leiden University. Stefan Grimme at the University of Bonn and Armido Studer at Westfälische-Wilhelms-Universität Münster found (Chem. Sci. 2013, 4, 2177) that NHC precatalyst 11 in the presence of NaH, benzaldehyde, and the oxidant 12 allows for the selective O-acylation of aminoalcohol 10 to 13. The reductive deprotection of benzyl carbamate 14 using the strong organic reductant 15 under photolytic conditions was achieved (Angew. Chem. Int. Ed. 2013, 52, 2239) by John A. Murphy at the University of Strathclyde. Liang-Qiu Lu and Wen-Jing Xiao at Central China Normal University found (Chem. Asian J. 2013, 8, 1090) that mixed imide 17 could be detosylated under visible light photoredox catalysis in the presence of Hantzsch ester 18. Frank Glorius at Westfälische-Wilhelms-Universität Münster developed (Org. Lett. 2013, 15, 1776) a ruthenium-catalyzed procedure for the N-formylation of amine 20 using methanol as the source of the formyl group. Protection of the thymine derivative 22 with a 2-(methoxycarbonyl)ethenyl (MocVinyl) group to produce 23 was developed (J. Org. Chem. 2013, 78, 5832) by Jaume Vilarrasa at the University of Barcelona. Deprotection of the MocVinyl group is readily achieved by treatment with a nucleophilic reagent such as pyrrolidine. Robert H. Grubbs at Caltech demonstrated (Chem. Sci. 2013, 4, 1640) that ether 24 could be demethylated with triethylsilane and potassium t-butoxide at high temperatures.