- The use of chloroacetic acid in the Mitsunobu reaction
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Reaction of chloroacetic acid with TPP-DEAD was found to be very effective for the inversion of sterically congested alcohols, including carbohydrates and nucleosides.
- Saiah,Bessodes,Antonakis
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- Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process
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In this study, we screened a large library of (+)-camphor and (?)-borneol derivatives to assess their filovirus entry inhibition activities using pseudotype systems. Structure-activity relationship studies revealed several compounds exhibiting submicromolar IC50 values. These compounds were evaluated for their effect against natural Ebola virus (EBOV) and Marburg virus. Compound 3b (As-358) exhibited the good antiviral potency (IC50 = 3.7 μM, SI = 118) against Marburg virus, while the hydrochloride salt of this compound 3b·HCl had a strong inhibitory effect against Ebola virus (IC50 = 9.1 μM, SI = 31) and good in vivo safety (LD50 > 1000 mg/kg). The results of molecular docking and in vitro mutagenesis analyses suggest that the synthesized compounds bind to the active binding site of EBOV glycoprotein similar to the known inhibitor toremifene.
- Baev, Dmitriy S.,Maksyutov, Rinat A.,Mordvinova, Ekaterina D.,Pyankov, Oleg V.,Salakhutdinov, Nariman F.,Shcherbakov, Dmitriy N.,Shcherbakova, Nadezhda S.,Sokolova, Anastasiya S.,Tolstikova, Tatyana G.,Yarovaya, Olga I.,Zaykovskaya, Anna V.,Zybkina, Anastasiya V.
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- Synthesis and in vitro study of novel borneol derivatives as potent inhibitors of the influenza A virus
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Herein, we present the design and synthesis of a series of novel heterocyclic derivatives of (-)-borneol and (-)-isoborneol as potent inhibitors of the influenza A virus. All compounds were tested for their toxicity against MDCK cells and for virus-inhibiting activity against the influenza virus A/Puerto Rico/8/34 (H1N1). Compounds 7, 16 and 26 containing a morpholine fragment exhibited the highest efficiency as agents inhibiting the replication of the influenza virus A(H1N1) with selectivity indices of 82, 45 and 65, correspondingly. Derivatives 9 (SI = 23) and 18 (SI = 25) containing a 1-methylpiperazine motif showed moderate antiviral activity. Structure-activity analysis of this new series of borneol derivatives revealed that a 1,7,7-trimethylbicyclo[2.2.1]heptan scaffold is required for the antiviral activity.
- Sokolova,Yarovaya,Semenova,Shtro,Orshanskaya,Zarubaev,Salakhutdinov
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supporting information
p. 960 - 963
(2017/07/12)
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- Cinchona-alkaloid-based catalysts, and asymmetric alcoholysis of cyclic anhydrides using them
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One aspect of the present invention relates to cinchona-alkaloid-based catalysts. A second aspect of the invention relates to a method of preparing a derivatized cinchona alkaloid catalyst by reacting a cinchona-alkaloid with base and a compound that has a suitable leaving group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral cyclic anhydride or a meso cyclic anhydride, comprising the step of: reacting a prochiral cyclic anhydride or a meso cyclic anhydride with a nucleophile in the presence of a catalyst; wherein said prochiral cyclic anhydride or meso cyclic anhydride comprises an internal plane of symmetry or point of symmetry or both; thereby producing a chiral, non-racemic compound; wherein said catalyst is a derivatized cinchona-alkaloid. Yet another aspect of the present invention relates to a method of kinetic resolution, comprising the step of: reacting a racemic cyclic anhydride with an alcohol in the presence of a derivatized cinchona-alkaloid catalyst.
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Page/Page column 20
(2008/06/13)
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- SYNTHESES OF CHIRAL C=N DIENOPHILES : SULFONYLOXYIMINOMALONONITRILE AND ALKYL SULFONYLOXYIMINOCYANOACETATES
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High yield syntheses of one chiral sulfonyloxyiminomalononitrile and four alkyl sulfonyloxyimonocyanoacetate derivatives (3a-e), to be used in asymmetric hetero-Diels-Alder additions, are described.
- Blanco, Jose M.,Caamano, Olga,Eirin, Ana,Fernadez, Franco,Medina, Lucia
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p. 923 - 930
(2007/10/02)
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