932-17-2Relevant articles and documents
New coumarin-based fluorescent melatonin ligands. Design, synthesis and pharmacological characterization
De La Fuente Revenga, Mario,Herrera-Arozamena, Clara,Fernández-Sáez, Nerea,Barco, Gema,García-Orue, Itxaso,Sugden, David,Rivara, Silvia,Rodríguez-Franco, María Isabel
, p. 370 - 373 (2015)
The design and synthesis of a series of new fluorescent coumarin-containing melatonin analogues is presented. The combination of high-binding affinities for human melatonergic receptors (h-MT1R and h-MT2R) and fluorescent properties, derived from the inclusion of melatonin pharmacophoric elements in the coumarin scaffold, yielded suitable candidates for the development of MT1R and MT2R fluorescent probes for imaging in biological media.
Design, synthesis, biological evaluation, homology modeling and docking studies of (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene) pyrrolidin-2-one derivatives as potent anticonvulsant agents
Wang, Tiantian,Dong, Shiyang,Chen, Xiaodong,Qian, Kun,Wang, Huayu,Quan, Hexiu,Zhang, Zhongli,Zuo, Yueming,Huang, Liping,Li, Dongxun,Yang, Ming,Yang, Shilin,Jin, Yi,Wang, Zengtao
supporting information, p. 1324 - 1329 (2018/03/21)
A series of (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)pyrrolidin-2-one derivatives were designed, synthesized, and evaluated for their anticonvulsant activities. In the preliminary screening, compounds 5, 6a–6f and 6h–6i showed promising anticonvulsant activities in MES model, while 6f and 6g represented protection against seizures at doses of 100 mg/kg and 0.5 h in scPTZ model. The most active compound 6d had a high-degree protection against the MES-induced seizures with ED50 value of 4.3 mg/kg and TD50 value of 160.9 mg/kg after intraperitoneal (i.p.) injection in mice, which provided 6d in a high protective index (TD50/ED50) of 37.4 comparable to the reference drugs. Beyond that, 6d has been selected and evaluated in vitro experiment to estimate the activation impact. Apparently, 6d clearly inhibits the Nav1.1 channel. Our preliminary results provide new insights for the development of small-molecule activators targeting specifically Nav1.1 channels to design potential drugs for treating epilepsy. The computational parameters, such as homology modeling, docking study, and ADME prediction, were made to exploit the results.
Palladium-Catalyzed Hydroamidocarbonylation of Olefins to Imides
Li, Haoquan,Dong, Kaiwu,Neumann, Helfried,Beller, Matthias
supporting information, p. 10239 - 10243 (2015/09/01)
Carbonylation reactions allow the efficient synthesis of all kinds of carbonyl-containing compounds. Here, we report a straightforward synthesis of various imides from olefins and CO for the first time. The established hydroamidocarbonylation reaction affords imides in good yields (up to 90%) and with good regioselectivity (up to 99:1) when applying different alkenes and amides. The synthetic potential of the method is highlighted by the synthesis of Aniracetam by intramolecular hydroamidocarbonylation.
CATALYSTS AND PROCESSES FOR THE HYDROGENATION OF AMIDES
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Paragraph 0181, (2014/06/24)
There is provided a process for the reduction of one or more amide moieties in a compound comprising contacting the compound with hydrogen gas and a transition metal catalyst in the presence or absence of a base under conditions for the reduction an amide bond. The presently described processes can be performed at low catalyst loading using relatively mild temperature and pressures, and optionally, in the presence or absence of a base or high catalyst loadings using low temperatures and pressures and high loadings of base to effect dynamic kinetic resolution of achiral amides.
Chemoselective palladium-catalyzed oxidation of vinyl ether to acetate using hydrogen peroxide
Kon, Yoshihiro,Tanaka, Shinji,Nakashima, Takuya,Sato, Kazuhiko,Shimada, Hiromichi
, p. 749 - 756 (2014/07/22)
A practical and environmental-friendly method was developed to convert vinyl ether into acetate by using a palladium complex with phosphine ligand and hydrogen peroxide. The only by-product is water. Chemoselective oxidation of vinyl ether and tert-enamides to form acetate and N-acetyl amide with hydrogen peroxide in the presence of palladium complex having phosphine ligand was developed under mild reaction conditions. This process is environmentally friendly because it uses hydrogen peroxide as a clean oxidant, with water being the only byprocuct.
Oxidative transformation of cyclic ethers/amines to lactones/lactams using a DIB/TBHP protocol
Zhao, Yi,Ang, Jascelyn Qian Lin,Ng, Angela Wan Ting,Yeung, Ying-Yeung
, p. 19765 - 19768 (2013/11/06)
A novel C-H oxidation of cyclic ethers and amines to the corresponding lactones and lactams was developed using a DIB/TBHP protocol. The reaction is mild and no metallic reagent is involved. In addition, study shows that the electronic properties of the substituents could affect the selectivity of oxidation. The Royal Society of Chemistry 2013.
Structural modifications of (Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene) thiazolidine-2,4-dione that improve selectivity for inhibiting the proliferation of melanoma cells containing active ERK signaling
Jung, Kwan-Young,Samadani, Ramin,Chauhan, Jay,Nevels, Kerrick,Yap, Jeremy L.,Zhang, Jun,Worlikar, Shilpa,Lanning, Maryanna E.,Chen, Lijia,Ensey, Mary,Shukla, Sagar,Salmo, Rosene,Heinzl, Geoffrey,Gordon, Caryn,Dukes, Troy,MacKerell Jr., Alexander D.,Shapiro, Paul,Fletcher, Steven
, p. 3706 - 3732 (2013/07/05)
We herein report on the pharmacophore determination of the ERK docking domain inhibitor (Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4- dione, which has led to the discovery of compounds with greater selectivities for inhibiting the proliferation of melanoma cells containing active ERK signaling. The Royal Society of Chemistry 2013.
Biomimetic aerobic oxidation of amino alcohols to lactams
Babu, Beneesh P.,Endo, Yoshinori,Baeckvall, Jan-E.
supporting information, p. 11524 - 11527,4 (2012/12/11)
The right path: N-Protected amino alcohols undergo aerobic and biomimetic oxidation to the corresponding lactams in the presence of a ruthenium catalyst and a combination of electron-transfer mediators under air (see scheme). The reaction was used for the synthesis of five-, six-, and seven-, membered lactams and showed good tolerance to a number of N-protecting groups. Copyright
A highly active catalyst for the hydrogenation of amides to alcohols and amines
John, Jeremy M.,Bergens, Steven H.
supporting information; experimental part, p. 10377 - 10380 (2011/12/04)
Amide-zing: The reaction between 2 equivalents of Ph2P(CH 2)2NH2 and cis-[Ru(CH3CN) 2(η3-C3H5)(cod)]BF4 (cod=1,5-cyclooctadiene) forms a highly active catalyst precursor for the selective hydrogenation of amides. The reaction proceeds with excellent atom economy, yield, and turnover numbers (TONs) under moderate reaction conditions. The technology offers a greener, practical approach to the use of metal hydride reagents commonly employed in both academia and industry. Copyright
Iridium-catalyzed highly enantioselective hydrogenation of exocyclic α,β-unsaturated carbonyl compounds
Tian, Fengtao,Yao, Dongmei,Liu, Yuanyuan,Xie, Fang,Zhang, Wanbin
supporting information; experimental part, p. 1841 - 1845 (2010/10/21)
By using the iridium complex of a phosphine-oxazoline ligand with an axis-unfixed biphenyl backbone, a highly enantioselective hydrogenation of the C=C bond of exocyclic α,β-unsaturated carbonyl compounds to afford α-chiral cyclic ketones, lactones and lactams was developed.
