21860-84-4Relevant academic research and scientific papers
Cyclomaltooligosaccharide-assisted spectroscopic discrimination of phthalimido-derived amino acids through the formation of molecular aggregates
Jursic, Branko S.,Patel, Paresh K.
, p. 2858 - 2866 (2006)
Spectroscopic evidence was used to demonstrate the formation of molecular associates in an aqueous solution of phthalimido tryptophan. These molecular associates are loosely formed through π-π aromatic stacking, properties that are not sufficient to cause NMR spectroscopic enantiomeric discrimination. A cyclomaltooligosaccharide with a larger cavity, such as cyclomaltooctaose (γ-cyclodextrin), is capable of forming a ternary complex with these molecular associates and enhances π-π aromatic stacking interactions, resulting in NMR enantiomeric discrimination. Electrospray-ionization mass spectroscopy (ESIMS) and NOESY two-dimensional NMR spectroscopic methods were used to study these complexes. Association constants and thermodynamic data for these cyclomaltooligosaccharide complexes were also estimated.
Palladium-Catalyzed Decarbonylation of Amino Acid Derivatives via C-C Bond and C-N Bond Dual Activations
Deng, Gongtao,Jiang, Yaojia,Jiao, Yongjuan,Li, Yingmei,Wu, Jiamin,Zhang, Jinli,Zhang, Zhengyu
, p. 17462 - 17470 (2021/12/02)
A unique decarbonylation of an amino acid derivative catalytic system has been established via palladium-catalyzed C-C bond and C-N bond dual activations. By employing 8-aminoquinoline as the directing group, this transformation has been found to facilitate the high chemoselectivity to decarbonylation of amino acid derivatives rather than intramolecular deamination or cross-dehydrogenative coupling reactions. This method provides a straightforward avenue for constructing diverse functionalized amide compounds in good to excellent yields. We proposed a possible reaction pathway that may go through the C-C bond and C-N bond dual activations on the basis of the mechanistic studies.
A Novel Class of 7-Membered Heterocyclic Compounds
Bauer, Adriano,Borsos, Eszter,Maulide, Nuno
supporting information, p. 3971 - 3974 (2020/05/25)
The work presented herein describes the synthesis of a formerly inaccessible class of heterocyclic compounds. The reaction relies on α-phthalimido-amides, which are readily prepared from amino acids in 2 simple reactions steps. Under amide activation conditions in which classical keteniminium ions are not formed, the nitrile solvent is incorporated into the new fused 7-membered ring system. Due to the absence of a keteniminium intermediate, the stereogenic information in the α-position is fully retained.
Tetrasubstituted Furans by Nucleophile-Induced Cleavage of Carbonyl Ylide-DMAD Cycloadducts
Dobesch, Matthias,Greiner, Julian,Maas, Gerhard
, p. 2987 - 3000 (2020/08/10)
Compounds incorporating a 4-aza-8-oxabicyclo[3.2.1]oct-6-en-2-one moiety, which were prepared by a tandem carbenoid carbonyl ylide cyclization/[3+2]-cycloaddition reaction from ethyl 2-diazo-3-oxo-4-phthalimidobutanoates, undergo a nucleophile-induced two-bond ring cleavage when treated with protic heteronucleophiles. In this manner, tetrasubstituted furantricarboxylates, tethered with α-amino acids, esters, thioesters, and amides by a 2-carbonylphenyl moiety, are obtained.
Enantioselective Synthesis of N-Benzylic Heterocycles: A Nickel and Photoredox Dual Catalysis Approach
Pezzetta, Cristofer,Bonifazi, Davide,Davidson, Robert W. M.
supporting information, p. 8957 - 8961 (2019/11/11)
Reported herein is a dual nickel- and photoredox-catalyzed modular approach for the preparation of enantioenriched N-benzylic heterocycles. α-Heterocyclic carboxylic acids, easily obtainable from common commercial material, are reported as suitable substrates for a decarboxylative strategy in conjunction with a chiral pyridine-oxazoline (PyOx) ligand, providing quick access to enantioenriched drug-like products. The presence of a directing group on the heterocyclic moiety is shown to be beneficial, affording improved stereoselectivity in a number of cases.
Synthesis and study of modified polyvinyl alcohol containing amino acid moieties as anticancer agent
Samir, Ali H.,Saeed, Ruwaidah S.,Matty, Fadhel S.
, p. 286 - 294 (2018/03/21)
A series of new phthalimides compounds[3-7]a-i were synthesized from reaction of Malic anhydride, phthalic anhydride, nitro phthalic anhydride, 2-phenyl-4H-benzo[d][1,3]oxazin-4-one, 2-(4-nitrophenyl)-4H-benzo[d][1,3]oxazin-4-one with different amino acids as glycine, alanine, valine, leucine, isoleucine, serine, threonine, tyrosine and Phenyl alanine [1]a-i under fusion conditions. Compounds [3-7]a-i react with SOCl2 in the presence of benzene to produce compounds [8-12]a-i. Chemical modification of Poly(vinyl alcohol)were obtained by reaction of PVA with compounds [8-12]a-i using the dimethyl formamide to give compounds [13-17]a-i. The structure of the synthesized compounds was characterized by their analytical and spectral data as, IR spectra, 1H, 13C-NMR, Elemental analysis (CHN), UV-Vis Spectroscopy, Scanning electron microscopy (SEM), Antibacterial activity were screened via two kinds of bacteria. Also, anticancer activity were examined for most of the modified polyvinyl alcohol.
Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp3)-H Direct Fluorination
Wei, Qiang,Ma, Yao,Li, Li,Liu, Qingfei,Liu, Zijie,Liu, Gang
supporting information, p. 7100 - 7103 (2018/11/24)
A coordinating, copper-catalyzed direct α-C(sp3)-H fluorination method has been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. A Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled Cu(II) charge transfer complex. The protocol can tolerate a rich variety of α-amino acids, for which the auxiliary group is removed in high yield and substituted for the direct preparation of dipeptide derivatives with detachable, single absolute configurations of the target compounds.
General Synthesis of Amino Acid Salts from Amino Alcohols and Basic Water Liberating H2
Hu, Peng,Ben-David, Yehoshoa,Milstein, David
supporting information, p. 6143 - 6146 (2016/06/09)
An atom-economical and environmentally friendly method to transform amino alcohols to amino acid salts using just basic water, without the need of pre-protection or added oxidant, catalyzed by a ruthenium pincer complex, is developed. Water is the solvent, the source of the oxygen atom of the carboxylic acid group, and the actual oxidant, with liberation of dihydrogen. Many important and useful natural and unnatural amino acid salts can be produced in excellent yields by applying this new method.
Pd-Catalyzed sequential β-C(sp3)-H arylation and intramolecular amination of δ-C(sp2)-H bonds for synthesis of quinolinones: Via an N,O-bidentate directing group
Guan, Mingyu,Pang, Yubo,Zhang, Jingyu,Zhao, Yingsheng
supporting information, p. 7043 - 7046 (2016/06/09)
The pharmacological importance of 2-quinolinone derivatives is well known. Herein, we developed an effective protocol for the synthesis of 2-quinolinone derivatives by palladium-catalyzed sequential β-C(sp3)-H arylation and selective intramolecular C(sp2)-H/N-H amination starting with aryl iodides and carboxylic acids. A novel directing group, glycine dimethylamide, was used in the synthesis. We synthesized various quinolinone derivatives, including 5-substituted quinolinones, which are difficult to obtain using the traditional pathway. The directing group could be easily removed and could be readily transformed into other useful functional groups.
Design, synthesis and anti-cancer activity evaluation of podophyllotoxin-norcantharidin hybrid drugs
Han, Hong-Wei,Qiu, Han-Yue,Hu, Cui,Sun, Wen-Xue,Yang, Rong-Wu,Qi, Jin-Liang,Wang, Xiao-Ming,Lu, Gui-Hua,Yang, Yong-Hua
supporting information, p. 3237 - 3242 (2016/07/12)
In this study, we designed and synthesized eighteen podophyllotoxin-norcantharidin hybrid drugs which could exhibit more potent anti-cancer activity than the parent drugs. Through the anti-proliferation assay, the most potent anti-cancer agent was screened out, namely Q9 (IC50?=?0.88?±?0.18?μM against MCF-7 cell line), and it showed lower cytotoxicity against non-cancer cells, human embryonic kidney cells (293T) (IC50?=?54.38?±?3.78?μM). Additionally, based on the flow cytometry analysis result, it can cause a remarkable cell cycle arrest at G2/M phase and induce apoptosis in MCF-7 cells more significantly than podophyllotoxin or norcantharidin per se. Moreover, the expression of cell cycle relative protein CDK1 was up regulated while a protein required for mitotic initiation, Cyclin B1 was down regulated. Furthermore, according to the confocal microscopy observation results, it was shown that Q9 was a potent tubulin polymerization inhibitor and the effect is comparable to that of colchicine. For further investigation on the aforementioned mechanisms, we performed western blot experiments, thus finding the increase of the cleavage of PARP. Consistent with these new findings, molecular docking observations suggested that compound Q9 could be developed as a potential anticancer agent.
