89299-71-8Relevant articles and documents
The use of chloroacetic acid in the Mitsunobu reaction
Saiah,Bessodes,Antonakis
, p. 4317 - 4320 (1992)
Reaction of chloroacetic acid with TPP-DEAD was found to be very effective for the inversion of sterically congested alcohols, including carbohydrates and nucleosides.
Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process
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.
, (2020/09/09)
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.
Synthesis and in vitro study of novel borneol derivatives as potent inhibitors of the influenza A virus
Sokolova,Yarovaya,Semenova,Shtro,Orshanskaya,Zarubaev,Salakhutdinov
supporting information, p. 960 - 963 (2017/07/12)
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.
Cinchona-alkaloid-based catalysts, and asymmetric alcoholysis of cyclic anhydrides using them
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Page/Page column 20, (2008/06/13)
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.
SYNTHESES OF CHIRAL C=N DIENOPHILES : SULFONYLOXYIMINOMALONONITRILE AND ALKYL SULFONYLOXYIMINOCYANOACETATES
Blanco, Jose M.,Caamano, Olga,Eirin, Ana,Fernadez, Franco,Medina, Lucia
, p. 923 - 930 (2007/10/02)
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.
