17478-44-3Relevant academic research and scientific papers
A metal-free and mild approach to 1,3,4-oxadiazol-2(3: H)-ones via oxidative C-C bond cleavage using molecular oxygen
Lim, Bumhee,Park, Seunggun,Park, Jae Hyun,Gam, Jongsik,Kim, Sanghee,Yang, Jung Woon,Lee, Jeeyeon
supporting information, p. 2105 - 2113 (2018/03/26)
A mild metal-free approach to 1,3,4-oxadiazol-2(3H)-ones via 1,3,4-oxadiazin-5(6H)-ones is described. This novel transformation, promoted by the electron-withdrawing p-substituents on the phenyl group at the α-carbonyl position, features a tandem reaction consisting of oxidative hydroxylation and C-C bond cleavage using molecular oxygen. The method utilizes K2CO3 in CH3CN without any oxidants, transition metals, or additives, enabling the tunable synthesis of 1,3,4-oxadiazin-5(6H)-ones, 1,3,4-oxadiazol-2(3H)-ones, and α-ketoamides under mild aerobic conditions.
REAGENTS AND METHODS FOR ESTERIFICATION
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Paragraph 00160, (2016/10/31)
Methods and reagents for esterification of biological molecules including proteins, polypeptides and peptides. Diazo compounds of formula (I): where R is hydrogen, an alkyl, an alkenyl or an alkynyl, RA represents 1-5 substituents on the indicated phenyl ring and RM is an organic group, which includes a label, a cell penetrating group, a cell targeting group, or a reactive group or latent reactive group for reaction to bond to a label, a cell penetrating group, or a cell targeting group, among other organic groups are useful for esterification of biological molecules. Also provided are diazo compounds which are bifunctional and trifunctional coupling reagents as well as reagents for the synthesis of compounds of formula (I).
Optimized Diazo Scaffold for Protein Esterification
Mix, Kalie A.,Raines, Ronald T.
supporting information, p. 2358 - 2361 (2015/06/02)
The O-alkylation of carboxylic acids with diazo compounds provides a means to esterify carboxylic acids in aqueous solution. A Hammett analysis of the reactivity of diazo compounds derived from phenylglycinamide revealed that the (p-methylphenyl)-glycinamide scaffold has an especially high reaction rate and ester/alcohol product ratio and esterifies protein carboxyl groups more efficiently than any known reagent. (Chemical Equation Presented).
Anti-viral compounds
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, (2008/06/13)
The present invention relates to compounds of Formula (I) below, which inhibit the growth of picornaviruses, Hepatitus viruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus. wherein: A is phenyl, pyridyl, substituted phenyl, substituted pyridyl, or benzyl; R is hydrogen, COR4, or COCF3; X is N—OH, O, or CHR1; R1is hydrogen, halo, CN, C1-C4alkyl, —C≡CH, CO(C1-C4alkyl), CO2(C1-C4alkyl), or CONR2R3; R2and R3are independently hydrogen or C1-C4alkyl; A′ is hydrogen, halo, C1-C6alkyl, benzyl, naphthyl, thienyl, furyl, pyridyl, pyrollyl, COR4, S(O)nR4, or a group of the formula R4is C1-C6alkyl, phenyl, or substituted phenyl; n is 0, 1, or 2; R5is independently at each occurrence hydrogen or halo; m is 1, 2, 3, or 4; and R6is hydrogen, halo, CF3, OH, CO2H, NH2, NO2, CONHOCH3, C1-C4alkyl, or CO2(C1-C4alkyl), C1-C4alkoxy; or a pharmaceutically acceptable salt thereof.
Synthesis and Antineoplastic Activity of Bisoxy>methyl>-Substituted 3-Pyrrolines as Prodrugs of Tumor Inhibitory Pyrrole Bis(carbamates)
Anderson, Wayne K.,Milowsky, Arnold S.
, p. 2241 - 2249 (2007/10/02)
A series of bispyrrolines 2-4 were synthesized from either the appropriate α-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions.The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles.The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive.The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the correspondingphenylpyrroles all showed comparable activity.The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole.Electron-withdrawing substituents on the phenyl ring appear to retard this process.
