63-64-9Relevant academic research and scientific papers
Thiol-Ene Networks from Sequence-Defined Polyurethane Macromers
Alabi, Christopher A.,De Hoe, Guilhem X.,Hillmyer, Marc A.,Hoff, Emily A.,Mulvaney, Christopher M.
supporting information, p. 6729 - 6736 (2020/04/30)
To date, scalability limitations have hindered the exploration and application of sequence-defined polymers in areas such as synthetic plastics, fibers, rubbers, coatings, and composites. Additionally, the impact of sequence on the properties of cross-lin
Design, synthesis, and biological evaluation of a series of resorcinol-based N-benzyl benzamide derivatives as potent Hsp90 inhibitors
Park, Sun You,Oh, Yong Jin,Lho, Yunmee,Jeong, Ju Hui,Liu, Kwang-Hyeon,Song, Jaeyoung,Kim, Soong-Hyun,Ha, Eunyoung,Seo, Young Ho
, p. 390 - 401 (2017/12/07)
Heat shock protein 90 (Hsp90) is a ubiquitous molecular chaperone that is responsible for the stabilization and maturation of many oncogenic proteins. Therefore, Hsp90 has emerged as an attractive target in the field of cancer chemotherapy. In this study, we report the design, synthesis, and biological evaluation of a series of Hsp90 inhibitors. In particular, compound 30f shows a significant Hsp90α inhibitory activity with IC50 value of 5.3 nM and an excellent growth inhibition with GI50 value of 0.42 μM against non-small cell lung cancer cells, H1975. Compound 30f effectively reduces the expression levels of Hsp90 client proteins including Her2, EGFR, Met, Akt, and c-Raf. Consequently, compound 30f promotes substantial cleavages of PARP, Caspase 3, and Caspase 8, indicating that 30f induces cancer cell death via apoptotic pathway. Moreover, cytochrome P450 assay indicates that compound 30f has weak inhibitory effect on the activities of five major P450 isoforms (IC50 > 5 μM for 1A2, 2C9, 2C19, 2D6, and 3A), suggesting that clinical interactions between 30f and the substrate drugs of the five major P450 isoforms are not expected. Compound 30f also inhibits the tumor growth in a mouse xenograft model bearing subcutaneous H1975 without noticeable abnormal behavior and body weight changes. The immunostaining and western immunoblot analysis of EGFR, Met, Akt in xenograft tissue sections of tumor further demonstrate a good agreement with the in vitro results.
Multigram synthesis of 1-O-acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-l-pyrrolosamine
Burk, Matthew,Wilson, Nolan,Herzon, Seth B.
supporting information, p. 3231 - 3234 (2015/02/19)
The synthesis of 1-O-acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-l-pyrrolosamine (7), which constitutes a protected form of the N,N-dimethyl-l-pyrrolosamine residues found within the antiproliferative bacterial metabolites (-)
Synthesis of new verapamil analogues and their evaluation in combination with rifampicin against Mycobacterium tuberculosis and molecular docking studies in the binding site of efflux protein Rv1258c
Singh, Kawaljit,Kumar, Malkeet,Pavadai, Elumalai,Naran, Krupa,Warner, Digby F.,Ruminski, Peter G.,Chibale, Kelly
, p. 2985 - 2990 (2014/06/24)
New verapamil analogues were synthesized and their inhibitory activities against Mycobacterium tuberculosis H37Rv determined in vitro alone and in combination with rifampicin (RIF). Some analogues showed comparable activity to verapamil and exhibited better synergies with RIF. Molecular docking studies of the binding sites of Rv1258c, a M. tuberculosis efflux protein previously implicated in intrinsic resistance to RIF, suggested a potential rationale for the superior synergistic interactions observed with some analogues.
2-aminobenzaldehydes as versatile substrates for rhodium-catalyzed alkyne hydroacylation: Application to dihydroquinolone synthesis
Castaing, Matthias,Wason, Sacha L.,Estepa, Beatriz,Hooper, Joel F.,Willis, Michael C.
supporting information, p. 13280 - 13283 (2014/01/06)
Amine for it! A cationic rhodium catalyst, which was assembled insitu from commercial components, promoted the reaction of a range of simple 2-aminobenzaldehydes with terminal and internal alkynes in a series of intermolecular hydroacylation reactions. The products of this reaction, amino-substituted enones, were efficiently converted into the corresponding dihydro-4-quinolones.
A novel construction of 2-benzazepine scaffold based on TiCl 4-mediated tandem Mannich reaction - Aromatic electrophilic substitution
Li, Liangxi,Li, Zhiming,Wang, Quanrui
experimental part, p. 2754 - 2761 (2010/04/02)
A novel construction of 2-benzazepine derivatives based on TiCl 4-mediated tandem Mannich reaction of electron-rich benzyl iminium ions with alkenyl ethers and Friedel - Crafts-type alkylation is described. The protocol is amenable to provide the tricyclic furo[3,2-d][2]benzazepine and pyrano[3,2-d][2]benzazepine derivatives, respectively, with 2,3-dihydrofuran or 3,4-dihydro-2H-pyran as the substrates.
SAR studies of capsazepinoid bronchodilators. Part 1: The importance of the catechol moiety and aspects of the B-ring structure
Dalence-Guzman, Maria F.,Berglund, Magnus,Skogvall, Staffan,Sterner, Olov
, p. 2499 - 2512 (2008/09/21)
Capsazepine as well as its derivatives and analogues are general inhibitors of constriction of human small airways. From a systematic variation of the capsazepine structure, divided into four regions, SARs were established. This part concerns the catechol moiety of the A-ring as well as the 2,3,4,5-tetrahydro-1H-2-azepine moiety (the B-ring) of capsazepine. It is revealed that a conformational constrain (as a fused ring) is important and that compounds with a six-membered B-ring (as a 1,2,3,4-tetrahydroisoquinoline) in general are more potent than the corresponding isoindoline, 2,3,4,5-tetrahydro-1H-2-benzazepine and 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives.
One-pot synthesis and hydroxylaminolysis of asymmetrical acyclic nitrones
Coskun, Necdet,Parlar, Aydin
, p. 2445 - 2451 (2007/10/03)
Aromatic aldehydes 1 were reductively aminated to the corresponding secondary amines 2 using NaBH4 in methanol in good yields. Amines 2 were oxidized with H2O2-WO42- regioselectively to nitrones 3, the structures of which were easily determined by reacting them with hydroxylamine hydrochloride as well as by spectral means. The products of hydroxylaminolysis in ether proved to be the corresponding benzaldehyde oximes 4 and benzyl or methyl hydroxylamine hydrochlorides 5. Copyright Taylor & Francis, Inc.
HETEROCYCLIC COMPOUNDS, METHODS OF MAKING THEM AND THEIR USE IN THERAPY
-
Page 87, (2010/02/07)
In part, the present invention is directed to antibacterial compounds of formula (I) wherein A is a bicyclic heteroaryl ring or a tricyclic ring and R2 is an heterocyclic residue; L is a bond, or L is alkyl, alkenyl or cycloalkyl.
Synthesis of N-methyl secondary amines
Kumpaty, Hephzibah J.,Williamson, John S.,Bhattacharyya, Sukanta
, p. 1411 - 1416 (2007/10/03)
A diverse set of N-methyl secondary amines are obtained in high yields by an expedient reductive alkylation of commercially available methanolic methylamine.
