51-79-6Relevant articles and documents
Reactions of trimethylsilyl isocyanate with alcohols and phenols
Pudovik,Krepysheva,Kharitonov,Pudovik
, p. 325 - 326 (2001)
Mono-and diphenols add to trimethyl isocyanate on heating to give the corresponding aryl urethanes. Ethanol reacts with trimethylsilyl isocyanate to give ethyl urethane and ethyl allophanate in a ratio determined by reaction conditions.
CARBONYLATION OF 2 AND 2; A NEW SELECTIVE METHOD FOR PREPARATION OF
Monica, G. La,Monti, C.,Pizzotti, M.,Cenini, S.
, p. 241 - 244 (1983)
Carbonylation of 2 (COD=1,5-cyclooctadiene) in ethanol gave the rhodium cluster selectively in high yield; when non polar solvents were used, the known 2 and 2 were obtained.Reaction of carbon monoxide with the isocyanato-bridged derivative 2 in ethanol also gave .In both cases the carbonylation reaction also gave NH2COOEt.Carbonylation of the iridium dichloride dimer 2 in the presence of sodium citrate gave .
Preparation method of carbamate
-
Paragraph 0041; 0045-0047, (2020/09/23)
The invention belongs to the technical field of synthesis of amino and carboxyl compounds connected to the same carbon frame through urea alcoholysis, and particularly relates to a preparation methodof carbamate. The preparation method of the carbamate comprises the following steps of: sequentially introducing urea, alcohol and a catalyst into a reactor, sealing, and reacting at 90-120 DEG C for8-12 hours to obtain the carbamate, wherein the catalyst includes an alumina supported metal oxide. By adopting the method for preparation of the carbamate, the side reaction of urea decomposition canbe effectively avoided, impurities such as carbamate are not detected, and the yield of the carbamate is high.
Discovery of a dual tubulin polymerization and cell division cycle 20 homologue inhibitor via structural modification on apcin
Huang, Pan,Le, Xiangyang,Huang, Fei,Yang, Jie,Yang, Haofeng,Ma, Junlong,Hu, Gaoyun,Li, Qianbin,Chen, Zhuo
, p. 4685 - 4700 (2020/06/08)
Apcin is one of the few compounds that have been previously reported as a Cdc20 specific inhibitor, although Cdc20 is a very promising drug target. We reported here the design, synthesis, and biological evaluations of 2,2,2-trichloro-1-aryl carbamate derivatives as Cdc20 inhibitors. Among these derivatives, compound 9f was much more efficient than the positive compound apcin in inhibiting cancer cell growth, but it had approximately the same binding affinity with apcin in SPR assays. It is possible that another mechanism of action might exist. Further evidence demonstrated that compound 9f also inhibited tubulin polymerization, disorganized the microtubule network, and blocked the cell cycle at the M phase with changes in the expression of cyclins. Thus, it induced apoptosis through the activation of caspase-3 and PARP. In addition, compound 9f inhibited cell migration and invasion in a concentration-dependent manner. These results provide guidance for developing the current series as potential new anticancer therapeutics.
An Fe3O4@SiO2/Schiff base/Cu(ii) complex as an efficient recyclable magnetic nanocatalyst for selective mono: N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids
Sardarian, Ali Reza,Dindarloo Inaloo, Iman,Zangiabadi, Milad
, p. 8557 - 8565 (2019/06/14)
An efficient, convenient and novel method for the selective mono N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids in the presence of a recyclable magnetic Cu(ii) nanocatalyst is described. A variety of mono N-arylated O-alkyl thiocarbamates and O-alkyl carbamates were prepared in good to excellent yields with a broad range of aryl coupling partners. The magnetic nanocatalyst can be easily recovered with an external magnetic field and reused at least five times without noticeable leaching or loss of its catalytic activity. This cost-effective and eco-friendly methodology has some other advantages, such as easy preparation of the catalyst, simple workup procedure, and easy purification, which makes this protocol interesting for the users in various fields of pharmacology and biotechnology systems.
EXON SKIPPING OLIGOMER CONJUGATES FOR MUSCULAR DYSTROPHY
-
, (2019/12/24)
Antisense oligomer conjugates complementary to a selected target site in the human dystrophin gene to induce exon 52 skipping are described.
Preparation method of (5-toluenesulfonyl-5H-pyrrolo[2,3-b]pyrazine-2-yl)ethyl carbamate
-
Paragraph 0012-0014, (2019/10/01)
The invention discloses a preparation method of (5-toluenesulfonyl-5H-pyrrolo[2,3-b]pyrazine-2-yl)ethyl carbamate, and belongs to the field of the chemical industry. The preparation method comprises the following steps: (1) preparation of N-ethyl carbamate: adopting ethanol as a solvent, performing a reaction on isocyanate and ethyl bromide zinc acetate at a molar ratio of 1:(2-3) at 35-40 DEG C for 6-8 hours under the protection of nitrogen, performing quenching with a saturated ammonium chloride solution after completion of the reaction, extracting the organic phase by using diethyl ether, and performing separation through column chromatography so as to obtain the target product; and (2) preparation of a mixed acid: adding fuming sulphuric acid with a mass concentration of 20-40% to sulfonic acid with a mass concentration of 50-70% so as to prepare the mixed acid. Through the preparation method, the preparation steps are reduced, the production cost is reduced, the production time issaved, the preparation efficiency is improved, and the preparation method is suitable for popularization and application.
A Physical Organic Approach to Tuning Reagents for Selective and Stable Methionine Bioconjugation
Christian, Alec H.,Jia, Shang,Cao, Wendy,Zhang, Patricia,Meza, Arismel Tena,Sigman, Matthew S.,Chang, Christopher J.,Toste, F. Dean
supporting information, p. 12657 - 12662 (2019/09/04)
We report a data-driven, physical organic approach to the development of new methionine-selective bioconjugation reagents with tunable adduct stabilities. Statistical modeling of structural features described by intrinsic physical organic parameters was applied to the development of a predictive model and to gain insight into features driving the stability of adducts formed from the chemoselective coupling of oxaziridine and methionine thioether partners through Redox Activated Chemical Tagging (ReACT). From these analyses, a correlation between sulfimide stabilities and sulfimide ν (C=O) stretching frequencies was revealed. We exploited the rational gains in adduct stability exposed by this analysis to achieve the design and synthesis of a bis-oxaziridine reagent for peptide stapling. Indeed, we observed that a macrocyclic peptide formed by ReACT stapling at methionine exhibited improved uptake into live cells compared to an unstapled congener, highlighting the potential utility of this unique chemical tool for thioether modification. This work provides a template for the broader use of data-driven approaches to bioconjugation chemistry and other chemical biology applications.
Selective Synthesis of Secondary Arylcarbamates via Efficient and Cost Effective Copper-Catalyzed Mono Arylation of Primary Carbamates with Aryl Halides and Arylboronic Acids
Sardarian, Ali Reza,DindarlooInaloo, Iman,Zangiabadi, Milad
, p. 642 - 652 (2018/01/11)
Abstract: An efficient, selective and cost-effective procedure has been developed for mono N-arylation of primary alkyl and benzyl carbamates with aryl iodides and bromides by incorporating CuI as an inexpensive and commercially available catalyst. Despite previous reports on C–N coupling reactions, this process does not need expensive ligands and takes advantage of readily available and inexpensive ethylenediamine (EDA) as the ligand. Reaction times were relatively short and related N-arylated carbamates were obtained in excellent yields. Interestingly, replacing CuI with Cu(OAc)2 allowed us to use arylboronic acids as coupling partner for this reaction. All products are well characterized by 1H- and 13C-NMR, MS, melting point, IR and CHNS techniques.
Acid–base sites synergistic catalysis over Mg–Zr–Al mixed metal oxide toward synthesis of diethyl carbonate?
Yan, Tingting,Bing, Weihan,Xu, Ming,Li, Yinwen,Yang, Yusen,Cui, Guoqing,Yang, Lan,Wei, Min
, p. 4695 - 4702 (2018/02/07)
In heterogeneous catalysis processes, development of high-performance acid–base sites synergistic catalysis has drawn increasing attention. In this work, we prepared Mg/Zr/Al mixed metal oxides (denoted as Mg2ZrxAl1x–MMO) derived from Mg–Zr–Al layered double hydroxides (LDHs) precursors. Their catalytic performance toward the synthesis of diethyl carbonate (DEC) from urea and ethanol was studied in detail, and the highest catalytic activity was obtained over the Mg2Zr0.53Al0.47MMO catalyst (DEC yield: 37.6%). By establishing correlation between the catalytic performance and Lewis acid–base sites measured by NH3-TPD and CO2-TPD, it is found that both weak acid site and medium strength base site contribute to the overall yield of DEC, which demonstrates an acid–base synergistic catalysis in this reaction. In addition, in situ Fourier transform infrared spectroscopy (in situ FTIR) measurements reveal that the Lewis base site activates ethanol to give ethoxide species; while Lewis acid site facilitates the activated adsorption of urea and the intermediate ethyl carbamate (EC). Therefore, this work provides an effective method for the preparation of tunable acid–base catalysts based on LDHs precursor approach, which can be potentially used in cooperative acid–base catalysis reaction.
