19078-72-9Relevant articles and documents
Systematic study on alkyl iodide initiators in living radical polymerization with organic catalysts
Lei, Lin,Tanishima, Miho,Goto, Atsushi,Kaji, Hironori,Yamaguchi, Yu,Komatsu, Hiroto,Jitsukawa, Takuya,Miyamoto, Michihiko
, p. 6610 - 6618 (2014)
Several low-molar-mass alkyl iodides were studied as initiating dormant species in living radical polymerization with organic catalysts. Primary, secondary, and tertiary alkyl iodides with different stabilizing groups (ester, phenyl, and cyano groups) were systematically studied for the rational design of initiating alkyl iodides. The activation rate constants of these alkyl iodides were experimentally determined for quantitative comparison. These alkyl iodides were used in the polymerizations of methyl methacrylate and butyl acrylate to examine their initiation ability in these polymerizations. A telechelic polymer was prepared using an alkyl iodide with a functional group. Alkyl iodides with multi-initiating sites were also studied.
L-(+)-α-Bromobenzeneacetic Acid (-)-Menthyl Ester
Kolev, Tsonko,Preut, Hans,Koniczek, Lothar,Bleckmann, Paul,Juchnovski, Ivan,Mladenova, Margarita
, p. 1634 - 1636 (1995)
The crystal structure of L-(+)-α-bromobenzeneacetic acid (-)-menthyl ester (C18H25BrO2) is reported.The Br atom and the O(carbonyl) atom are in trans positions.The 1-methyl-4-isopropylcyclohexane ring has a chair conformation.The dihedral angle between th
COMPOUNDS FOR USE IN TREATING NEUROLOGICAL DISORDERS
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Paragraph 00110-00111, (2021/02/05)
Provided are methods for treating neurological disorders using compounds of Formula (I), and pharmaceutically acceptable salts and compositions thereof.
Metal-free ATRP "grafting from" technique for renewable cellulose graft copolymers
Lu, Chuanwei,Wang, Chunpeng,Yu, Juan,Wang, Jifu,Chu, Fuxiang
, p. 2759 - 2770 (2019/06/03)
Photoinduced metal-free "grafting from" atom transfer radical polymerization (ATRP) has been successfully applied to the fabrication of renewable cellulose graft copolymers with the aid of 2-bromo-2-phenylacetyl ester-modified ethyl cellulose as the macro
Iron-Catalyzed Intramolecular C-H Amination of α-Azidyl Amides
Zhao, Xiaopeng,Liang, Siyu,Fan, Xing,Yang, Tonghao,Yu, Wei
supporting information, p. 1559 - 1563 (2019/03/20)
Iron-catalyzed intramolecular C-H amination of aliphatic azides has recently emerged as a powerful tool for the preparation of nitrogen heterocycles. This paper reports that α-azidyl amides can be converted in high efficacy to imidazolinone compounds via intramolecular C(sp3)-H amination by the action of a simple catalytic system composed of FeCl2 and a β-diketiminate ligand. The reactions provide a simple and atom-economical approach toward polysubstituted imidazolinones.
Benzoxazinone-containing 3,5-dimethylisoxazole derivatives as BET bromodomain inhibitors for treatment of castration-resistant prostate cancer
Xue, Xiaoqian,Zhang, Yan,Wang, Chao,Zhang, Maofeng,Xiang, Qiuping,Wang, Junjian,Wang, Anhui,Li, Chenchang,Zhang, Cheng,Zou, Lingjiao,Wang, Rui,Wu, Shuang,Lu, Yongzhi,Chen, Hongwu,Ding, Ke,Li, Guohui,Xu, Yong
, p. 542 - 559 (2018/05/24)
The bromodomain and extra-terminal proteins (BET) have emerged as promising therapeutic targets for the treatment of castration-resistant prostate cancer (CRPC). We report the design, synthesis and evaluation of a new series of benzoxazinone-containing 3,5-dimethylisoxazole derivatives as selective BET inhibitors. One of the new compounds, (R)-12 (Y02234), binds to BRD4(1) with a Kd value of 110 nM and blocks bromodomain and acetyl lysine interactions with an IC50 value of 100 nM. It also exhibits selectivity for BET over non-BET bromodomain proteins and demonstrates reasonable anti-proliferation and colony formation inhibition effect in prostate cancer cell lines such as 22Rv1 and C4-2B. The BRD4 inhibitor (R)-12 also significantly suppresses the expression of ERG, Myc and AR target gene PSA at the mRNA level in prostate cancer cells. Treatment with (R)-12 significantly suppresses the tumor growth of prostate cancer (TGI = 70%) in a 22Rv1-derived xenograft model. These data suggest that compound (R)-12 is a promising lead compound for the development of a new class of therapeutics for the treatment of CRPC.
Highly Enantioselective Hydrogenation of Amides via Dynamic Kinetic Resolution Under Low Pressure and Room Temperature
Rasu, Loorthuraja,John, Jeremy M.,Stephenson, Elanna,Endean, Riley,Kalapugama, Suneth,Clément, Roxanne,Bergens, Steven H.
supporting information, p. 3065 - 3071 (2017/03/11)
High-throughput screening and lab-scale optimization were combined to develop the catalytic system trans-RuCl2((S,S)-skewphos)((R,R)-dpen), 2-PrONa, and 2-PrOH. This system hydrogenates functionalized α-phenoxy and related amides at room temperature under 4 atm H2 pressure to give chiral alcohols with up to 99% yield and in greater than 99% enantiomeric excess via dynamic kinetic resolution.
Searching for New Leads for Tuberculosis: Design, Synthesis, and Biological Evaluation of Novel 2-Quinolin-4-yloxyacetamides
Pitta, Eleni,Rogacki, Maciej K.,Balabon, Olga,Huss, Sophie,Cunningham, Fraser,Lopez-Roman, Eva Maria,Joossens, Jurgen,Augustyns, Koen,Ballell, Lluis,Bates, Robert H.,Van Der Veken, Pieter
, p. 6709 - 6728 (2016/08/05)
In this study, a new series of more than 60 quinoline derivatives has been synthesized and evaluated against Mycobacterium tuberculosis (H37Rv). Apart from the SAR exploration around the initial hits, the optimization process focused on the improvement of the physicochemical properties, cytotoxicity, and metabolic stability of the series. The best compounds obtained exhibited MIC values in the low micromolar range, excellent intracellular antimycobacterial activity, and an improved physicochemical profile without cytotoxic effects. Further investigation revealed that the amide bond was the source for the poor blood stability observed, while some of the compounds exhibited hERG affinity. Compound 83 which contains a benzoxazole ring instead of the amide group was found to be a good alternative, with good blood stability and no hERG affinity, providing new opportunities for the series. Overall, the obtained results suggest that further optimization of solubility and microsomal stability of the series could provide a strong lead for a new anti-TB drug development program.
Tert-Butyl Hydroperoxide and Tetrabutylammonium Iodide-Promoted Free Radical Cyclization of α-Imino-N-arylamides and α-Azido-N-arylamides
Li, Dianjun,Yang, Tonghao,Su, Hailin,Yu, Wei
supporting information, p. 2529 - 2539 (2015/08/18)
The oxidizing system of tert-butyl hydroperoxide (TBHP) and tetrabutylammonium iodide (TBAI) is capable of generating α-(arylaminocarbonyl)iminyl radicals from ethyl 2-(N-arylcarbamoyl)-2-iminoacetates. These iminyl radicals preferably undergo intramolecular ipso attack on the benzene ring to give azaspirocyclohexadienyl radicals, which are readily captured by molecular oxygen under an oxygen atmosphere to yield azaspirocyclohexadienones. In the absence of oxygen, the reaction affords quinoxalin-2-one products. This oxidizing system is also effective to convert α-aryl-α-azido-N-arylamides to the corresponding iminyl radicals under basic conditions (sodium tert-butoxide, t-BuONa), and the subsequent cyclization of these iminyl radicals results in the formation of azaspirocyclohexadienone products in high yields under an oxygen atmosphere. Plausible mechanisms are proposed to rationalize the experimental results, and factors influencing the reactions are discussed.
Rhodium-catalyzed coupling of α-lactams with indole derivatives
Box, Hannah K.,Upul Kumarasinghe,Nareddy, Radhika R.,Akurathi, Gopalakrishna,Chakraborty, Amarraj,Raji, Babatunde,Rowland, Gerald B.
, p. 9709 - 9717 (2015/02/02)
We report herein a method that allows for the formation of a C-N bond between the C-3 carbon of α-lactams and the nitrogen atom of indoles. A general procedure for the coupling of indoles and α-lactams in only 25 min with high yield is reported. The scope of the reaction was extended by the development of a method for the in situ generation of less stable phenyl-substituted α-lactams. The developed method provides an atom-economical method for the formation of substituted α-amino amides that are found in a variety of biologically-active compounds.
