56530-39-3Relevant articles and documents
Monodentate Transient Directing Group Assisted Ruthenium(II)-Catalyzed Direct ortho-C-H Imidation of Benzaldehydes for Diverse Synthesis of Quinazoline and Fused Isoindolinone
Wu, Yongdi,Liu, Na,Qi, Meifang,Qiao, Huihao,Lu, Xuelian,Ma, Li,Zhou, Yirong,Zhang, Fang-Lin
supporting information, p. 3923 - 3927 (2021/05/29)
2-Fluoro-5-(trifluoromethyl)aniline was found to be a suitable monodentate transient directing group (MonoTDG) to enable Ru(II)-catalyzed intermolecular direct ortho-C(sp2)-H imidation of benzaldehydes. N-Tosyloxyphthalimide was used as an alternative azide-free amidation reagent to achieve high efficiency and good functional group tolerance. Moreover, the reaction could be enlarged to gram scale, and the amidated product could be readily converted into useful quinazoline and fused isoindolinone scaffolds by one-step derivatization.
Structure-activity relationship and molecular modelling studies of quinazolinedione derivatives MMV665916 as potential antimalarial agent
Albrecht, Sébastien,Florent, Isabelle,Mouray, Elisabeth,Mourot, Laura,Schmitt, Marjorie,Spichty, Martin
supporting information, (2021/11/22)
A series of new quinazolinedione derivatives have been readily synthesized and evaluated for their in vitro antiplasmodial growth inhibition activity. Most of the compounds inhibited P. falciparum FcB1 strain in the low to medium micromolar concentration. The 2-ethoxy 8ag’, 2-trifluoromethoxy 8ai’ and 4-fluoro-2-methoxy 8ak’ showed the best inhibitory activity with EC50 values around 5 μM and were non-toxic to the primary human fibroblast cell line AB943. However, these compounds were less potent than the original hit MMV665916, which showed remarkable growth inhibition with EC50 value of 0.4 μM and presented the highest selectivity index (SI > 250). In addition, a novel approach for determining the docking poses of these quinazolinedione derivatives with their potential protein target, the P. falciparum farnesyltransferase PfFT, was investigated.
Electrochemically induced oxidative S-O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazoles
Terent'ev, Alexander O.,Mulina, Olga M.,Parshin, Vadim D.,Kokorekin, Vladimir A.,Nikishin, Gennady I.
supporting information, p. 3482 - 3488 (2019/04/14)
The process of oxidative S-O coupling under the action of electric current was developed. Aryl, hetaryl and alkyl sulfonyl hydrazides and N-hydroxy compounds (N-hydroxyimides and N-hydroxybenzotriazoles) are applied as starting reagents for the preparation of sulfonates. The reaction is carried out under constant current conditions in an experimentally convenient undivided electrochemical cell equipped with a graphite anode and a stainless steel cathode under a high current density (60 mA cm?2). NH4Br in this process acts as a supporting electrolyte and participates in the oxidation of the starting compounds to form a coupling product. The developed strategy represents a quite atom-efficient approach: one partner loses two nitrogen and three hydrogen atoms, while another one loses only one hydrogen atom. Cyclic voltammetry and the control experiment allowed us to propose possible reaction pathways: generated through anodic oxidation molecular bromine or its higher oxidation state derivatives oxidize the starting compounds to form reactive species, which couple to form the S-O bond.
Ruthenium-catalyzed ortho -C-H mono- and di-imidation of arenes with n -tosyloxyphthalimide
Yadav, M. Ramu,Shankar, Majji,Ramesh,Ghosh, Koushik,Sahoo, Akhila K.
supporting information, p. 1886 - 1889 (2015/04/27)
The Ru(II)-catalyzed imidation of the o-C-H bond in arenes with N-tosyloxyphthalimide is realized with the assistance of a methyl phenylsulfoximine (MPS) directing group. This method is applicable to access the hitherto difficult o-C-H di-imidation produc
One-pot efficient synthesis of N α-urethane-protected β- And γ-amino acids
Cal, Marta,Jaremko, Mariusz,Jaremko, Lukasz,Stefanowicz, Piotr
, p. 1085 - 1091 (2013/07/05)
1-[(4-Methylphenyl)oxy]pyrrolidine-2,5-dione and 1-[(4-methylphenyl)oxy] piperidine-2,6-dione react in a Lossen-type reaction with primary alcohols in the presence of triethylamine to furnish corresponding N α- urethane-protected β-alanine and γ-aminopropionic acid (GABA), respectively, with excellent yields and purities, in an essentially "one-pot" procedure.
Studies on the Lossen-type rearrangement of N-(3-phenylpropionyloxy) phthalimide and N-tosyloxy derivatives with several nucleophiles
Chanmiya Sheikh,Takagi, Shunsuke,Ogasawara, Asako,Ohira, Masayuki,Miyatake, Ryuta,Abe, Hitoshi,Yoshimura, Toshiaki,Morita, Hiroyuki
supporting information; experimental part, p. 2132 - 2140 (2010/04/26)
The reaction of N-(3-phenylpropionyloxy)phthalimide (1a) and N-tosyloxy (5a,b) derivatives with nucleophiles was examined and found to give the products via Lossen-type rearrangement. In order to obtain the scope of this reaction mechanism, further studies the reaction of several N-sulfonyloxyimide derivatives with various nucleophiles under similar conditions were carried out and found to afford the corresponding same types of products in high yields.
Crystal-state studies on p-toluenesulfonates of N-oxyimides - A possible structural basis of serine proteases inhibition
Stefanowicz, Piotr,Jaremko, Lukasz,Jaremko, Mariusz,Lis, Tadeusz
, p. 258 - 265 (2007/10/03)
A series of p-toluenesulfonates of N-oxyimides has been synthesized and their X-ray structures show a flattened pyramidal geometry of the hydroxyimide ring nitrogen. This structural feature is considered to be responsible for a specific chemical reactivit
Photocleavage of o-nitrobenzyl ether derivatives for rapid biomedical release applications
Kim, Moon Suk,Diamond, Scott L.
, p. 4007 - 4010 (2007/10/03)
The externally controlled cleavage of covalently linked prodrugs, proteins, or solid-phase formulation vehicles offers potential advantages for controlled drug or gene delivery. A series of o-nitrobenzyl ester compounds (1-8) were synthesized to allow a systematic study of photolability. The o-nitrobenzyl ester was strictly required for photolability, while imido esters were not photolabile. The degradation kinetics of 1-o-phenylethyl ester was an order of magnitude faster than that of o-nitrobenzyl ester. Tosylate, phosphate, and benzoate derivatives of 1-o-nitrophenylethyl displayed similar photolability (>80% decomposition within 10 min at 3.5 mW/cm2 at 365 nm). O-o-Nitrobenzyl O′,O″-diethyl phosphate displayed the fastest decomposition at photoirradiation condition (3.5 mW/cm2, 365 nm) suitable for biological systems. We report the synthesis and photo-decomposition of 1-o-nitrophenylethyl derivatives amenable for the creation of photolabile prodrugs or formulation particles for drug depots, DNA condensation, or tissue engineering applications.
Acid generator, sulfonic acid, sulfonic acid derivatives and radiation-sensitive resin composition
-
, (2008/06/13)
A novel photoacid generator containing a structure of the following formula (I), wherein R is a monovalent organic group with a fluorine content of 50 wt % or less, a nitro group, a cyano group, or a hydrogen atom, and Z1 and Z2 are individually a fluorine atom or a linear or branched perfluoroalkyl group having 1-10 carbon atoms, is provided. When used in a chemically amplified radiation-sensitive resin composition, the photoacid generator exhibits high transparency, comparatively high combustibility, and no bioaccumulation, and produces an acid exhibiting high acidity, high boiling point, moderately short diffusion length in the resist coating, and low dependency to mask pattern density.
