23853-10-3Relevant academic research and scientific papers
FLUORIDE INDUCED ALKYLATION OF α-SILOXYAMINES. A NEW METHOD FOR TRANSALKYLATION OF TERTIARY AMINES VIA THEIR N-OXIDES
Tokitoh, Norihiro,Okazaki, Renji
, p. 1937 - 1938 (1984)
α-Siloxyamines obtained from tertiary amines via their N-oxides react with alkyl halides to give the corresponding α-siloxyammonium salts, which can be converted into new tertiary amines by fluoride induced desilylation reaction.
Selective 1,2-Aryl-Aminoalkylation of Alkenes Enabled by Metallaphotoredox Catalysis
Chen, Zimin,Hu, Yuanyuan,Li, Weirong,Liao, Zixuan,Xi, Xiaoxiang,Yuan, Weiming,Zheng, Songlin
supporting information, p. 17910 - 17916 (2020/08/21)
A highly chemo- and regioselective intermolecular 1,2-aryl-aminoalkylation of alkenes by photoredox/nickel dual catalysis is described here. This three-component conjunctive cross-coupling is highlighted by its first application of primary alkyl radicals, which were not compatible in previous reports. The readily prepared α-silyl amines could be transferred to α-amino radicals by photo-induced single electron transfer step. The radical addition/cross-coupling cascade reaction proceeds under mild, base-free and redox-neutral conditions with good functional group tolerance, and importantly, provides an efficient and concise method for the synthesis of structurally valuable α-aryl substituted γ-amino acid derivatives motifs.
A de novo peroxidase is also a promiscuous yet stereoselective carbene transferase
Stenner, Richard,Steventon, Jack W.,Seddon, Annela,Anderson, J.L. Ross
, p. 1419 - 1428 (2020/01/28)
By constructing an in vivo-assembled, catalytically proficient peroxidase, C45, we have recently demonstrated the catalytic potential of simple, de novo-designed heme proteins. Here, we show that C45's enzymatic activity extends to the efficient and stereoselective intermolecular transfer of carbenes to olefins, heterocycles, aldehydes, and amines. Not only is this a report of carbene transferase activity in a completely de novo protein, but also of enzyme-catalyzed ring expansion of aromatic heterocycles via carbene transfer by any enzyme.
Carbene insertion into N-H bonds with size-selectivity induced by a microporous ruthenium-porphyrin metal-organic framework
Chen, Lianfen,Cui, Hao,Wang, Yanhu,Liang, Xiang,Zhang, Li,Su, Cheng-Yong
supporting information, p. 3940 - 3946 (2018/03/21)
A stable and porous porphyrinic metal-organic framework, Ru-PMOF-1(Hf), has been prepared through the self-assembly of [5,10,15,20-tetrakis(4-carboxyphenyl)porphyrinato](monocarbonyl)ruthenium (Ru(TCPP)(CO)) and HfCl4. Single-crystal X-ray diff
Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement
Spoehrle, Stéphanie S. M.,West, Thomas H.,Taylor, James E.,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information, p. 11895 - 11902 (2017/09/07)
A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of α-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammonium salt generation from the allylic phosphate and the glycine aryl ester. Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea benzotetramisole forms syn-α-amino acid derivatives with high diastereo- and enantioselectivity. This methodology is most effective using 4-nitrophenylglycine esters and tolerates a variety of substituted cinnamic and styrenyl allylic ethyl phosphates. The use of challenging unsymmetrical N-allyl-N-methylglycine esters is also tolerated under the catalytic relay conditions without compromising stereoselectivity.
Development of a series of bis-triazoles as G-quadruplex ligands
Saleh, Maysaa M.,Laughton, Charles A.,Bradshaw, Tracey D.,Moody, Christopher J.
, p. 47297 - 47308 (2017/10/19)
Maintenance of telomeres-specialized complexes that protect the ends of chromosomes-is provided by the enzyme complex telomerase, which is a key factor that is activated in more than 80% of cancer cells, but absent in most normal cells. Targeting telomere maintenance mechanisms could potentially halt tumour growth across a broad spectrum of cancer types. Telomeric ends of chromosomes consist of noncoding repeat sequences of guanine-rich DNA. These G-rich ends can fold into structures called G-quadruplexes. Stabilization of G-quadruplexes by small binding molecules called G4 ligands can prevent telomerase enzyme from maintaining telomere integrity in cancer cells. G-quadruplexes can exist in other parts of the genome too, especially within promoter sequences of oncogenes, and also be interesting drug targets. Here, we describe the development of a new series of novel bis-triazoles, designed to stabilize G-quadruplex structures selectively as G4 ligands. FRET assays showed two compounds to be moderately effective G4 binders, with particular affinity for the quadruplex formed by the Hsp90a promoter sequence, and good selectivity for G-quadruplex DNA vs. duplex DNA. However, CD spectroscopy failed to provide any information about the folding topology of the human telomeric G-quadruplex resulting from its interaction with one of the ligands. All the new ligands showed potent cell growth inhibitory properties against human colon and pancreatic cancer cell lines, as evidenced by the MTT assay; notably, they were more potent against cancer cells than in fetal lung fibroblasts. Docking studies were performed to rationalize the affinity of these ligands for binding to the telomeric parallel G-quadruplex DNA.
Dual role of Cu2O nanocubes as templates and networking catalysts for hollow and microporous Fe-porphyrin networks
Kang, Daye,Ko, Ju Hong,Choi, Jaewon,Cho, Kyoungil,Lee, Sang Moon,Kim, Hae Jin,Ko, Yoon-Joo,Park, Kang Hyun,Son, Seung Uk
supporting information, p. 2598 - 2601 (2017/03/09)
Cu2O nanocubes were used for the synthesis of hollow and microporous Fe porphyrin networks (H-MFePN). In this synthesis, Cu2O nanocubes performed not only as networking catalysts but also as shape controlling templates. MFePN were formed on the surface of the Cu2O nanocubes through azide-alkyne cycloaddition of tetrakis(4-ethynylphenyl) Fe-porphyrin with 1,4-diazidobenzene. H-MFePN showed excellent catalytic activities in carbene insertion into N-H bonds, maintaining their activities during five recycle tests.
NH insertion reactions catalyzed by reusable water-soluble ruthenium(II)-hm-phenyloxazoline complex
Abu-Elfotoh, Abdel-Moneim
supporting information, p. 4750 - 4754 (2017/11/29)
A water-soluble Ru(II)-hm-pheox complex was efficiently catalyzed NH insertion of EDA with a broad class of amine derivatives in water/ether biphasic medium to deliver the biologically active precursors α-aminoester products with excellent yields (up to >99%). The products were separated by decantation and the catalyst was washed and reused several times (at least 8 times) without any specific loss of its catalytic activity. The plausible mechanism of the reaction was explained. Additionally, In case of ethylene diamine, the NH insertion product could be transformed to biological active piperazinone compound in high yield. The asymmetric version of this catalytic reaction is under investigation.
PROTEIN KINASE INHIBITORS
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Paragraph 0164; 0174, (2015/02/18)
A compound of formula (I), wherein R3, R4, G, B, M, and Z are as defined in the claims, and pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as FGFR inhibitors and are useful in the treatment of a condition, where FGFR kinase inhibition is desired, such as cancer.
P-Tolylimido rhenium(v) complexes-synthesis, X-ray studies, spectroscopic characterization, DFT calculations and catalytic activity
Machura, Barbara,Gryca, Izabela,Malecki, Jan Grzegorz,Alonso, Francisco,Moglie, Yanina
, p. 2596 - 2610 (2014/02/14)
Novel p-tolylimido rhenium(v) complexes trans-(Cl,Cl)-[Re(p-NC 6H4CH3)Cl2(py-2-COO)(PPh 3)]·MeCN (1a), trans-(Cl,Cl)-[Re(p-NC6H 4CH3)Cl2(py-2-COO)(PPh3)] (1b), trans-(Br,Br)-[Re(p-NC6H4CH3)Br 2(py-2-COO)(PPh3)] (2), cis-(Cl,Cl)-[Re(p-NC 6H4CH3)Cl2(py-2-COO)(PPh 3)] (3), cis-(Br,Br)-[Re(p-NC6H4CH 3)Br2(py-2-COO)(PPh3)]·H2O (4), trans-(Cl,Cl)-[Re(p-NC6H4CH3)Cl 2(OMe)] (5) and trans-(Br,Br)-[Re(p-NC6H 4CH3)Br2(OMe)(PPh3) 2]·1/2H2O (6) were synthesized. The compounds were identified by elemental analysis, IR, NMR (1H, 13C and 31P), UV-Vis spectroscopy and X-ray crystallography. Calculations at the DFT level were undertaken in order to elucidate the structural, spectroscopic and bonding properties of the trans-(Cl,Cl) and cis-(Cl,Cl) isomers of [Re(p-NC6H4CH3)Cl 2(py-2-COO)(PPh3)]. In the first step, extended tests of the ability of different DFT methods (B3LYP, BP86, and PBE1PBE) were performed to find the best overall performer in describing the geometry of the imido Re(v) complexes; then, the electronic spectra of the trans and cis isomers of [Re(p-NC6H4CH3)Cl2(py-2-COO) (PPh3)] were investigated at the TDDFT level employing the PBE1PBE functional. Additional information about bonding in the compounds [Re(p-NC 6H4CH3)Cl2(py-2-COO)(PPh 3)] was obtained by NBO analysis. The catalytic activity of the complexes incorporating the picolinate ligand was studied and compared in the synthesis of N-substituted ethyl glycine esters from ethyl diazoacetate and amines.
