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1.
PLoS One ; 19(1): e0296191, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38271445

RESUMEN

This systematic review and meta-analysis aimed to assess and compare the therapeutic outcomes of cutting balloon angioplasty and high-pressure balloon angioplasty for arteriovenous fistula stenosis in hemodialysis patients. All studies indexed in PubMed, Embase, and Cochrane Library Web of Science were retrieved. The retrieval deadline was July 15, 2023. Risk of bias 2.0 was used to evaluate the quality of the included studies. Revman 5.4 software was used for data analysis. This review included three studies and 180 patients, with 90 patients in the cutting balloon angioplasty group and 90 patients in the high-pressure balloon angioplasty group. The results of the meta-analysis suggested that compared with high-pressure balloon angioplasty, cutting balloon angioplasty can improve primary lesion patency rates of internal arteriovenous fistulas at 6 months (relative risk, 1.45; 95% confidence interval, 1.08-1.96; P = 0.01). However, there were no significant differences between the technical success rate (relative risk, 0.99; 95% confidence interval, 0.93-1.05; P = 0.72) and clinical success rate (relative risk, 1.01; 95% confidence interval, 0.95-1.07; P = 0.73). Therefore, cutting balloon angioplasty is likely to increase primary lesion patency rates at 6 months. However, more high-quality, large-sample, multicenter, randomized controlled trials are needed for further validation due to the limited number of included studies.


Asunto(s)
Angioplastia de Balón , Fístula Arteriovenosa , Derivación Arteriovenosa Quirúrgica , Humanos , Oclusión de Injerto Vascular/etiología , Oclusión de Injerto Vascular/terapia , Grado de Desobstrucción Vascular , Constricción Patológica/etiología , Constricción Patológica/cirugía , Resultado del Tratamiento , Derivación Arteriovenosa Quirúrgica/efectos adversos , Angioplastia de Balón/métodos , Diálisis Renal , Fístula Arteriovenosa/terapia , Estudios Multicéntricos como Asunto
2.
Angew Chem Int Ed Engl ; 62(41): e202308836, 2023 Oct 09.
Artículo en Inglés | MEDLINE | ID: mdl-37643998

RESUMEN

The direct catalytic asymmetric hydrogenation of pyridines for the synthesis of piperidines remains a challenge. Herein, we report a one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Brønsted acid activation strategy. Catalyzed by an iridium-BINAP complex, the substrates undergo ketone reduction, cyclization and pyridine hydrogenation in sequence to form indolizidines and quinolizidines. The absolute configuration of the stereocenter of the alcohol is retained and influences the formation of the second stereocenter. Experimental and theoretical mechanistic studies reveal that the chloride anion and certain noncovalent interactions govern the stereoselectivity of the cascade reaction throughout the catalytic process.

3.
Org Lett ; 24(49): 9033-9037, 2022 12 16.
Artículo en Inglés | MEDLINE | ID: mdl-36472575

RESUMEN

An efficient enantioselective reductive amination and amidation cascade reaction has been developed. Catalyzed by iridium or rhodium complexes and with the help of sets of additives, the coupling of simple alkyl diamines and α-ketoesters occurs smoothly to afford the chiral cyclic piperazinone products. For disubstituted and monosubstituted alkyl diamine substrates, the corresponding reactions proceed through distinctive types of intermediates and thus require different transition metals to achieve high enantioselectivity, namely, iridium for the former and rhodium for the latter. In this transformation, the applied highly modular phosphoramidite-phosphine hybrid ligands displayed preeminent versatility and tunability.


Asunto(s)
Rodio , Elementos de Transición , Aminación , Rodio/química , Iridio/química , Catálisis , Elementos de Transición/química
4.
Org Lett ; 24(31): 5646-5650, 2022 08 12.
Artículo en Inglés | MEDLINE | ID: mdl-35916628

RESUMEN

The sturdy chelation of 1,2-diamines and transition-metals would retard or even interrupt the routine catalytic cycles. In the amidation and asymmetric reductive amination (ARA) cascade reactions of diamines and ketoesters, we deployed sets of additives to ensure a smooth transformation catalyzed by the complexes of rhodium and versatile and highly modular phosphoramidite-phosphine ligands. The tunability of the ligands was fully exploited to accommodate various diamines and α-ketoesters for the efficient synthesis of chiral 3,4-dihydroquinoxalinones.


Asunto(s)
Rodio , Aminación , Aminas , Catálisis , Diaminas , Ligandos
5.
Nat Commun ; 13(1): 3344, 2022 06 10.
Artículo en Inglés | MEDLINE | ID: mdl-35688909

RESUMEN

Direct asymmetric reductive amination is one of the most efficient methods for the construction of chiral amines, in which the scope of the applicable amine coupling partners remains a significant challenge. In this study we describe primary alkyl amines effectively serve as the N-sources in direct asymmetric reductive amination catalyzed by the iridium precursor and sterically tunable chiral phosphoramidite ligands. The density functional theory studies of the reaction mechanism imply the alkyl amine substrates serve as a ligand of iridium strengthened by a (N)H-O(P) hydrogen-bonding attraction, and the hydride addition occurs via an outer-sphere transition state, in which the Cl-H H-bonding plays an important role. Through this concise procedure, cinacalcet, tecalcet, fendiline and many other related chiral amines have been synthesized in one single step with high yields and excellent enantioselectivity.


Asunto(s)
Aminas , Iridio , Aminación , Catálisis , Ligandos
6.
Artículo en Inglés | MEDLINE | ID: mdl-35328888

RESUMEN

In the context of rapid urbanisation and an emerging need for a healthy urban environment, revitalising urban spaces and its effects on the urban eco-environment in Chinese cities have attracted widespread attention. This study assessed urban vibrancy from the dimensions of density, accessibility, liveability, diversity, and human activity, with various indicators using an adjusted spatial TOPSIS (technique for order preference by similarity to an ideal solution) method. The study also explored the effects of urban vibrancy on the urban eco-environment by interpreting PM 2.5 and land surface temperature using "big" and "dynamic" data, such as those from mobile and social network data. Thereafter, spatial modelling was performed to investigate the influence of urban vibrancy on air pollution and temperature with inverted and extracted remote sensing data. This process identified spatial heterogeneity and spatial autocorrelation. The majority of the dimensions, such as density, accessibility, liveability, and diversity, are negatively correlated with PM 2.5, thereby indicating that the advancement of urban vibrancy in these dimensions potentially improves air quality. Conversely, improved accessibility increases the surface temperature in most of the districts, and large-scale infrastructure construction generally contributes to the increase. Diversity and human activity appear to have a cooling effect. In the future, applying spatial heterogeneity is advised to assess urban vibrancy and its effect on the urban eco-environment, to provide valuable references for spatial urban planning, improve public health and human wellbeing, and ensure sustainable urban development.


Asunto(s)
Planificación de Ciudades , Remodelación Urbana , China , Ciudades , Planificación de Ciudades/métodos , Humanos , Material Particulado , Urbanización
7.
Angew Chem Int Ed Engl ; 60(52): 27307-27311, 2021 12 20.
Artículo en Inglés | MEDLINE | ID: mdl-34699113

RESUMEN

Asymmetric reductive amination (ARA) is one of the most promising methods for the synthesis of chiral amines. Herein we report our efforts on merging two ARA reactions into a single-step transformation. Catalyzed by a complex formed from iridium and a steric hindered phosphoramidite, readily available and inexpensive aromatic ketones initially undergo the first ARA with ammonium acetate to afford primary amines, which serve as the amine sources for the second ARA, and finally provide the enantiopure C2 -symmetric secondary amine products. The developed process competently enables the successive coupling of inorganic and organic nitrogen sources with ketones in the same reaction system. The Brønsted acid additive plays multiple roles in this procedure: it accelerates the formation of imine intermediates, minimizes the inhibitory effect of N-containing species on the iridium catalyst, and reduces the primary amine side products.

8.
Nat Commun ; 11(1): 621, 2020 01 30.
Artículo en Inglés | MEDLINE | ID: mdl-32001706

RESUMEN

Asymmetric hydrogenation (AH) and direct reductive amination (DRA) are both efficient transformations frequently utilized in industry. Here we combine the asymmetric hydrogenation of prochiral olefins and direct reductive amination of aldehydes in one step using hydrogen gas as the common reductant and a rhodium-Segphos complex as the catalyst. With this strategy, the efficiency for the synthesis of the corresponding chiral amino compounds is significantly improved. The practical application of this synthetic approach is demonstrated by the facile synthesis of chiral 3-phenyltetrahydroquinoline and 3-benzylindoline compounds.

9.
Front Pharmacol ; 11: 610205, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-33519476

RESUMEN

Background: Oncogenic transformation is associated with elevated oxidative stress that promotes tumor progression but also renders cancer cells vulnerable to further oxidative insult. Agents that stimulate ROS generation or suppress antioxidant systems can drive oxidative pressure to toxic levels selectively in tumor cells, resulting in oxidative DNA damage to endanger cancer cell survival. However, DNA damage response signaling protects cancer cells by activating DNA repair and genome maintenance mechanisms. In this study, we investigated the synergistic effects of combining the pro-oxidative natural naphthoquinone alkannin with inhibition of DNA repair by PARP inhibitors. Methods and Results: The results showed that sublethal doses of alkannin induced ROS elevation and oxidative DNA damage in colorectal cancer but not normal colon epithelial cells. Blocking DNA repair with the PARP inhibitor olaparib markedly synergized with alkannin to yield synergistic cytotoxicity in colorectal cancer cells at nontoxic doses of both drugs. Synergy between alkannin and olaparib resulted from interrupted repair of alkannin-induced oxidative DNA damage and PARP-trapping, as it was significantly attenuated by NAC or by OGG1 inhibition and the non-trapping PARP inhibitor veliparib did not yield synergism. Mechanistically, the combination of alkannin and olaparib caused intense replication stress and DNA strand breaks in colorectal cancer cells, leading to apoptotic cancer cell death after G2 arrest. Consequently, coadministration of alkannin and olaparib induced significant regression of tumor xenografts in vivo, while each agent alone had no effect. Conclusion: These studies clearly show that combining alkannin and olaparib can result in synergistic cancer cell lethality at nontoxic doses of the drugs. The combination exploits a cancer vulnerability driven by the intrinsic oxidative pressure in most cancer cells and hence provides a promising strategy to develop broad-spectrum anticancer therapeutics.

10.
Chem Sci ; 10(16): 4509-4514, 2019 Apr 28.
Artículo en Inglés | MEDLINE | ID: mdl-31057780

RESUMEN

The secondary amine participating asymmetric reductive amination remains an unsolved problem in organic synthesis. Here we show for the first time that secondary amines are capable of effectively serving as N-sources in direct asymmetric reductive amination to afford corresponding tertiary chiral amines with the help of a selected additive set under mild conditions (0-25 °C). The applied chiral phosphoramidite ligands are readily prepared from BINOL and easily modified. Compared with common tertiary chiral amine synthetic methods, this procedure is much more concise and scalable, as exemplified by the facile synthesis of rivastigmine and N-methyl-1-phenylethanamine.

11.
Molecules ; 23(9)2018 Aug 31.
Artículo en Inglés | MEDLINE | ID: mdl-30200331

RESUMEN

In this article we demonstrate how asymmetric total synthesis of (S)-rivastigmine has been achieved using direct asymmetric reductive amination as the key transformation in four steps. The route started with readily available and cheap m-hydroxyacetophenone, through esterification, asymmetric reductive amination, N-diphenylmethyl deprotection and reductive amination, to provide the final (S)-rivastigmine in 82% overall yield and 96% enantioselectivity. In the asymmetric reductive amination, catalysed by the iridium⁻phosphoramidite ligand complex and helped by some additives, the readily prepared 3-acetylphenyl ethyl(methyl)carbamate directly reductively coupled with diphenylmethanamine to yield the chiral amine product in 96% ee and 93% yield.


Asunto(s)
Rivastigmina/síntesis química , Aminación , Evaluación Preclínica de Medicamentos , Ligandos , Oxidación-Reducción , Rivastigmina/química
12.
Org Lett ; 19(8): 1942-1945, 2017 04 21.
Artículo en Inglés | MEDLINE | ID: mdl-28362503

RESUMEN

The highly efficient direct catalytic reductive amination of ketones with diphenylmethanamine catalyzed by iridium-phosphoramidite complexes is described. As an effective coupling partner, diphenylmethanamine is suitable for a wide range of ketones to provide chiral amines in high yields and enantioselectivity. The chiral monodentate phosphoramidite ligands are tunable and competent to accommodate substrates with different structures.

13.
Angew Chem Int Ed Engl ; 56(10): 2725-2729, 2017 03 01.
Artículo en Inglés | MEDLINE | ID: mdl-28140506

RESUMEN

A one-pot N-Boc deprotection and catalytic intramolecular reductive amination protocol for the preparation of enantiomerically pure tetrahydroisoquinoline alkaloids is described. The iodine-bridged dimeric iridium complexes displayed superb stereoselectivity to give tetrahydroisoquinolines, including several key pharmaceutical drug intermediates, in excellent yields under mild reaction conditions. Three additives played important roles in this reaction: Titanium(IV) isopropoxide and molecular iodine accelerated the transformation of the intermediate imine to the tetrahydroisoquinoline product; p-toluenesulfonic acid contributed to the stereocontrol.

14.
Angew Chem Int Ed Engl ; 55(17): 5309-12, 2016 Apr 18.
Artículo en Inglés | MEDLINE | ID: mdl-26992130

RESUMEN

The highly efficient and direct asymmetric reductive amination of arylacetones catalyzed by an iridium complex for the preparation of enantiomerically pure ß-arylamines is described. The monodentate phosphoramidite ligand exhibits superb reactivity (TONs of up to 20 000) and enantioselectivity (up to 99 % ee). Additives played important roles in this reductive coupling reaction.

15.
Angew Chem Int Ed Engl ; 53(47): 12761-4, 2014 Nov 17.
Artículo en Inglés | MEDLINE | ID: mdl-25297378

RESUMEN

Iridium-catalyzed asymmetric hydrogenation of N-alkyl-2-alkylpyridinium salts provided 2-aryl-substituted piperidines with high levels of enantioselectivity. Simple benzyl and other alkyl groups successfully activated the challenging pyridine substrates toward hydrogenation. The use of the unusual chiral-phosphole-based MP(2) -SEGPHOS was the key to the success of this approach which provides a versatile and practical procedure for the synthesis of chiral piperidines.


Asunto(s)
Compuestos Heterocíclicos con 1 Anillo/química , Compuestos Organofosforados/química , Compuestos de Piridinio/química , Catálisis , Hidrogenación , Estructura Molecular , Sales (Química)/química
16.
Org Lett ; 15(17): 4354-7, 2013 Sep 06.
Artículo en Inglés | MEDLINE | ID: mdl-23937659

RESUMEN

A green method for chiral amine synthesis, the direct catalytic asymmetric reductive amination, was developed. Phenylhydrazide is an ideal nitrogen source for reductive amination. Molecular sieves play dual roles in this reaction. They help to remove H2O to form imine, as well as promote an imine reduction. f-Binaphane minimizes the inhibition effect from amines and helps the coordination of sterically demanding imines to the iridium center, thus leading to a smooth reaction.


Asunto(s)
Aminas/síntesis química , Iminas/síntesis química , Cetonas/química , Aminación , Aminas/química , Catálisis , Iminas/química , Iridio/química , Estructura Molecular , Fenilhidrazinas/síntesis química , Fenilhidrazinas/química , Estereoisomerismo
17.
Org Lett ; 15(3): 484-7, 2013 Feb 01.
Artículo en Inglés | MEDLINE | ID: mdl-23339282

RESUMEN

Rh-catalyzed enantioselective hydrogenation of oxime acetates was first reported, which afforded a new approach for chiral amine synthesis.


Asunto(s)
Acetatos/química , Aminas/síntesis química , Oximas/química , Rodio/química , Aminas/química , Catálisis , Hidrogenación , Estructura Molecular , Estereoisomerismo
18.
Org Lett ; 14(1): 102-5, 2012 Jan 06.
Artículo en Inglés | MEDLINE | ID: mdl-22149490

RESUMEN

A highly regioselective isomerization-hydroaminomethylation of internal olefins has been developed. A 95.3% amine selectivity and 36.2 n/i ratio were obtained for 2-octene with a Tetrabi ligand and Rh(acac)(CO)(2), and a TON of linear amine was achieved of 6837 with a 39.1 n/i ratio of amine. The m-CF(3)-Ph substituted ligand was the best of the applied Tetrabi-type phosphorus ligands for different internal olefins, as up to a 99.2% amine selectivity and 95.6 n/i ratio were obtained for 2-pentene.


Asunto(s)
Alquenos/química , Hidrógeno/química , Fósforo/química , Rodio/química , Aminación , Catálisis , Ligandos , Metilación , Estructura Molecular , Estereoisomerismo
19.
Chemistry ; 17(51): 14559-63, 2011 Dec 16.
Artículo en Inglés | MEDLINE | ID: mdl-22105788

RESUMEN

A highly regioselective hydroaminomethylation of terminal olefins catalyzed by Rh complexes with 2, 2', 6, 6'-tetrakis ((diphenylphosphino)methyl)-1, 1'-biphenyl (Tetrabi) ligand has been developed. Up to 99 % amine selectivity, 168 linear/branched amine product ratio (n/i), and 97.4 % linear amine yield has been obtained at a substrate/rhodium precursor ratio (S/Rh) of 1000 with this methodology. The turnover number was achieved 6930 at 10,000 S/Rh ratio, and the n/i can reach up to >525. Several different olefins and secondary amines have been applied successfully with high chemoselectivity (99 %), yield (>98 %), and regioselectivity (>120).


Asunto(s)
Alquenos/química , Aminas/síntesis química , Compuestos de Bifenilo/química , Compuestos Organometálicos/química , Compuestos Organofosforados/química , Rodio/química , Aminas/química , Catálisis , Ligandos , Estructura Molecular , Estereoisomerismo
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