193073-85-7Relevant academic research and scientific papers
Stereoselective synthesis of (?)-cytoxazone and its unnatural congener (+)-5-epi-cytoxazone
Miranda, Izabel Luzia,dos Santos, Pedro Henrique Costa,Kohlhoff, Markus,Purgato, Gislaine Aparecida,Diaz, Marisa Alves Nogueira,Diaz-Mu?oz, Gaspar
, p. 479 - 489 (2021)
An interesting protocol for stereoselective synthesis of (?)-cytoxazone and its unnatural stereoisomer (+)-5-epi-cytoxazone from d-4-hydroxyphenylglycine in overall yields of 10% and 16%, respectively, is described. The stereoselective addition of cyanide
Preparation method of (-) - Cytoxazone and (+) -4 - epi-Cytoxazone
-
, (2021/11/14)
The preparation method of (-) - Cytoxazone and (+) -4 - epi-Cytoxazone takes D - p-hydroxyphenylglycine as a raw material, the intermediate 2 is obtained through methyl esterification reaction under catalysis of thionyl chloride, and then the amino is protected with Boc anhydride to obtain the intermediate 3. The compound 4 is obtained by using potassium carbonate as a base and reacting with methyl iodide under reflux conditions. The methyl ester was reduced with sodium borohydride/lithium chloride to give the primary alcohol compound 5. An intermediate IBX is then obtained with 6 primary alcohol, then reacted with acetone cyanohydrin SN2 to give intermediate 7, and the intermediate 8 is obtained by reacting with the methanol solution of hydrogen chloride to obtain two five-membered ring compound compounds 9 and 10, respectively, with sodium borohydride to obtain (-) - Cytoxazone and its isomers (+) -4 - epi-Cytoxtoxtoxtoxol, respectively.
PENICILLIN-BINDING PROTEIN INHIBITORS
-
Paragraph 00169, (2018/12/13)
Described herein are certain boron-containing compounds, compositions, preparations and their use as modulators of the transpeptidase function of bacterial penicillin-binding proteins and as antibacterial agents. In some embodiments, the compounds described herein inhibit penicillin-binding proteins. In certain embodiments, the compounds described herein are useful in the treatment of bacterial infections.
Synthesis of bicyclic tripeptides inspired by the ABC-ring system of vancomycin through ruthenium-based cyclization chemistries
Yang, Xin,Beroske, Lucas P.,Kemmink, Johan,Rijkers, Dirk T.S.,Liskamp, Rob M.J.
supporting information, p. 4542 - 4546 (2017/10/31)
The synthesis of a bicyclic tripeptide that mimics the ABC ring system of vancomycin is described by using a ring closing metathesis (RCM) – peptide coupling – ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) strategy.
Construction of the biaryl-part of vancomycin aglycon via atropo-diastereoselective Suzuki-Miyaura coupling
Leermann, Timo,Broutin, Pierre-Emmanuel,Leroux, Frederic R.,Colobert, Franoise
scheme or table, p. 4095 - 4102 (2012/06/15)
An atropo-diastereoselective synthesis with dr up to 98/2 towards the biaryl subunit of vancomycin based on the use of enantiopure β-hydroxysulfoxide derivatives as novel chiral auxiliary is reported.
Asymmetric Ni-H insertion reaction cooperatively catalyzed by rhodium and chiral spiro phosphoric acids
Xu, Bin,Zhu, Shou-Fei,Xie, Xiu-Lan,Shen, Jun-Jie,Zhou, Qi-Lin
supporting information; experimental part, p. 11483 - 11486 (2012/01/11)
So near so SPA: Achiral dirhodium(II) carboxylates and chiral spiro phosphoric acids (SPA) cooperatively catalyzed asymmetric Ni-H insertion reactions with high enantioselectivity, high yields, and fast reaction rates at low catalyst loading (see scheme;
Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies
Bello, Claudia,Cea, Michele,Bello, Giovanna Dal,Garuti, Anna,Rocco, Ilaria,Cirmena, Gabriella,Moran, Eva,Nahimana, Aimable,Duchosal, Michel A.,Fruscione, Floriana,Pronzato, Paolo,Grossi, Francesco,Patrone, Franco,Ballestrero, Alberto,Dupuis, Marc,Sordat, Bernard,Nencioni, Alessio,Vogel, Pierre
experimental part, p. 3320 - 3334 (2010/07/05)
Novel α-mannosidase inhibitors of the type (2R,3R,4S)-2-({[(1R)-2-hydroxy-1-arylethyl]amino}methyl)pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibits the proliferation of primary cells and cell lines of different origins, irrespective of Bcl-2 expression levels, inducing a G2/Mcell cycle arrest and by modification of genes involved in cell cycle progression and survival.
Asymmetric synthesis of amlnocyclopropanes and N-cyclopropylamino alcohols through direct amidocyclopropanation of alkenes using chiral organozinc carbenoids
Begis, Guillaume,Cladingboel, David E.,Jerome, Laure,Motherwell, William B.,Sheppard, Tom D.
experimental part, p. 1532 - 1548 (2009/09/08)
Chiral N-(diethoxymethyl)oxazolidinones, prepared from the corresponding oxazolidinones by heating in trielhyl orthoformate, can be used as organozinc carbenoid precursors for the direct enantioselective amidocyclopropanation of alkenes. The reaction is successful with a wide range of oxazolidinones and alkenes and proceeds with moderate to excellent yield and stereoselectivity. In most cases the trans/exo amidocyclopropane product, is favoured, although certain cyclic alkenes such as indene favour the formation of the endo cyclopropane. The products can be readily elaborated to produce cyclopropylamino alcohols and amino acids. Wiley-VCH Verlag GmbH & Co. KGaA.
Derivatives of Dihydroxypyrrolidine as Anti-Cancer Compounds
-
Page/Page column 12, (2009/06/27)
The present invention relates to derivatives of dihydroxypyrrolidine useful in the treatment of cancer. The invention further relates to a process for making the compounds. The compounds are inhibitors of α mannosidase, and possibly, also inhibit nicotina
Stereoselective synthesis of (-)-cytoxazone and (+)-5-epi-cytoxazone
Ravi Kumar,Bhaskar,Madhan,Venkateswara Rao
, p. 2907 - 2916 (2007/10/03)
A novel, stereo selective synthesis of (-)-cytoxazone 1a and stereoselective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.
