Identification of anthranilamide derivatives as potential factor Xa inhibitors: Drug design, synthesis and biological evaluation

Xing, Junpeng; Yang, Lingyun; Li, Hui; Li, Qing; Zhao, Leilei; Wang, Xinning; Zhang, Yuan; Zhou, Muxing; Zhou, Jinpei; Zhang, Huibin

doi:10.1016/j.ejmech.2015.03.052

Cited by 27 publications

(10 citation statements)

References 39 publications

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“…Современные тенденции в области разработки препаратов, связанных с фактором свертывания Ха, характеризуются двумя направлениями. С одной стороны, растет число случаев идентификации новых классов прямых ингибиторов фактора Ха, причем чаще всего с использованием методов молекулярного моделирования [52][53][54][55][56]. Примеры некоторых новых ингибиторов, разработанных с помощью компьютерного моделирования, приведены в таблице 2.…”

Section: прямые ингибиторы ключевых факторов свертыванияunclassified

Blood coagulation in the 21st century: existing knowledge, current strategies for treatment and perspective

Подоплелова

Сулимов

Tashchilova

et al. 2020

Voprosy gematologii/onkologii i immunopatologii v pediatrii

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Disorders in the blood coagulation system are the leading cause of death and disability in the modern world. So the search for new drugs that can prevent pathological thrombosis, while not affecting normal hemostasis, becomes more relevant than ever. Recent studies has been a revolution in the understanding of the principles of work and the regulation of blood coagulation. In addition, new, more effective approaches to drug development have now appeared. For example computer simulation methods that can significantly reduce the time and resources spent on the search for new candidate molecules. In the review, the blood clotting system, the molekular mechanisms of thrombosis, the role of blood coagulation factors Xa and XIa, and the urgency of developing new inhibitors of these targets are shown, and the most interesting inhibitors of factors Xa and XIa are presented.

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Section: прямые ингибиторы ключевых факторов свертыванияunclassified

Blood coagulation in the 21st century: existing knowledge, current strategies for treatment and perspective

Подоплелова

Сулимов

Tashchilova

et al. 2020

Voprosy gematologii/onkologii i immunopatologii v pediatrii

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“…The solvent removal gave a residual yellow solid (0.205 g, 56% yield) which was recrystallized from hexane to give 4-phenylmorpholin-3-one (0.135 g, 35% yield). 1 The second step was carried out following the experimental methodology reported by Xing et al [49]. To a solution of 4-phenylmorpholin-3-one (0.995 g, 5.62 mol) at 98%, H2SO4 (2.33 mL) cooled to −10 °C 65% HNO3 was carefully added dropwise (0.4 mL) over 45 min.…”

Section: Synthesis Of 4-(4-nitrophenyl)morpholin-3-onementioning

confidence: 99%

“…The samples were evaluated in triplicate by microwave-assisted digestion of 0.05 g of the catalyst in 10 mL of concentrated HNO3/HCl dissolution (1:3, v/v). Solid-state 13 C and 29 Si cross-polarization (CP)-magic angle The second step was carried out following the experimental methodology reported by Xing et al [49]. To a solution of 4-phenylmorpholin-3-one (0.995 g, 5.62 mol) at 98%, H 2 SO 4 (2.33 mL) cooled to −10 • C 65% HNO 3 was carefully added dropwise (0.4 mL) over 45 min.…”

Section: Characterizationmentioning

confidence: 99%

“…The catalysts were prepared in different nominal metal loadings: 0.25, 0.50 and 1.00 Au wt%. All the catalysts were evaluated in the catalytic hydrogenation of 4-(2-fluoro-4-nitrophenyl)-morpholine (NFMF) and 4-(4-nitrophenyl)-3-morpholinone (NFMO) used as intermediates in the synthesis of linezolid (antibiotic action) and rivaroxaban (anticoagulant action), respectively [48,49]. In both molecules, different operational conditions were evaluated to produce the respective aren-anilines.…”

Section: Introductionmentioning

confidence: 99%

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Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

et al. 2020

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In this work, Au nanoparticles, supported in Al2O3 nanowires (ANW) modified with (3-aminopropyl)trimethoxysilane were synthetized, for their use as catalysts in the hydrogenation reaction of 4-(2-fluoro-4-nitrophenyl)-morpholine and 4-(4-nitrophenyl)morpholin-3-one. ANW was obtained by hydrothermal techniques and the metal was incorporated by the reduction of the precursor with NaBH4 posterior to superficial modification. The catalysts were prepared at different metal loadings and were characterized by different techniques. The characterization revealed structured materials in the form of nanowires and a successful superficial modification. All catalysts show that Au is in a reduced state and the shape of the nanoparticles is spherical, with high metal dispersion and size distributions from 3.7 to 4.6 nm. The different systems supported in modified-ANW were active and selective in the hydrogenation reaction of both substrates, finding for all catalytic systems a selectivity of almost 100% to the aromatic amine. Catalytic data showed pseudo first-order kinetics with respect to the substrate for all experimental conditions used in this work. The solvent plays an important role in the activity and selectivity of the catalyst, where the highest efficiency and operational stability was achieved when ethanol was used as the solvent.

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“…Alternatively, compound 1 was also prepared by the condensation of 4-bromo nitrobenzene with 2-amino ethanol, followed by cyclization with methyl 2-chloro acetate. Both methods displayed low efficiency because of two reactive sites existing in both reactants, resulting in a complicated reaction system (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Facile Preparation of 4-(4-Nitrophenyl)morpholin-3-one via the Acid-Catalyzed Selective Oxidation of 4-(4-Nitrophenyl)morpholine by Sodium Chlorite as the Sole Oxidant

Liu¹,

Yu²,

Yang³

et al. 2020

Org. Process Res. Dev.

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4-(4-Nitrophenyl)morpholin-3-one and 4-(4-aminophenyl) morpholin-3-one are the key intermediates for rivaroxaban synthesis. A facile and economically efficient process has been developed for the preparation of these intermediates. Excellent yield of 4-(4-nitrophenyl)morpholine is obtained by condensing 4-chloro nitrobenzene and morpholine, and 4-(4-nitrophenyl)morpholine is oxidized using inexpensive sodium chlorite to achieve a good yield of the corresponding 4-(4-nitrophenyl)morpholin-3-one. Finally, the key intermediate of rivaroxaban, 4-(4-aminophenyl) morpholin-3-one, is achieved by the iron(III)-catalyzed reduction of the nitro group with aqueous hydrazine. No high-cost materials were used, and the process did not require column purification.

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Identification of anthranilamide derivatives as potential factor Xa inhibitors: Drug design, synthesis and biological evaluation

Cited by 27 publications

References 39 publications

Blood coagulation in the 21st century: existing knowledge, current strategies for treatment and perspective

Blood coagulation in the 21st century: existing knowledge, current strategies for treatment and perspective

Liquid Phase Hydrogenation of Pharmaceutical Interest Nitroarenes over Gold-Supported Alumina Nanowires Catalysts

Facile Preparation of 4-(4-Nitrophenyl)morpholin-3-one via the Acid-Catalyzed Selective Oxidation of 4-(4-Nitrophenyl)morpholine by Sodium Chlorite as the Sole Oxidant

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