TsCl-promoted sulfonylation of quinoline N-oxides with sodium sulfinates in water

An eco-friendly protocol for the synthesis of various 2-sulfonyl quinolines/pyridines through sulfonylation of heteroaromatic N-oxides with sodium sulfinates in water at ambient temperature under metal-and oxidant-free conditions has been developed.The mild reaction conditions,high reaction efficiency,operational simplicity,short reaction time and remarkable functional-group compatibility make the developed protocol very attractive for the preparation of 2-sulfonyl N-heteroaromatic compounds.

Rh(Ⅲ)-catalyzed C8 arylation of quinoline N-oxides with arylboronic acids

Herein,we report the first Rh~Ⅲ-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners.This procedure is simple,and the reaction shows perfect regioselectivity,a broad substrate scope,and isolated yields of up to 92%.We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide.

Assessing quinoline removal performances of an aerobic continuous moving bed biofilm reactor(MBBR) bioaugmented with Pseudomonas citronellolis LV1

This study evaluated the bioaugmentation potential of a quinoline-degrading strain Pseudomonas citronellolis LV1 inoculation into activated sludge for treating quinoline wastewater, and results indicated the inoculation of LV1 in aerobic continuous MBBR could substantially improve the quinoline removal performance with an improved removal efficiency of 34% averagely when quinoline was used as the sole carbon and nitrogen source. Additionally, efficient removal of quinoline in enhanced MBBR occurred at the influent p H of 7.0–8.0, hydraulic retention time(HRT) of 24–28 h and influent quinoline concentration of 100–700 mg·L^(-1). High-throughput sequencing analysis indicated that bioaugmentation could increase microbial diversity and shape the microbial community structure. Although the inoculant LV1 did not remain its dominance in stage Ⅲ, bioaugmentation indeed induced the formation of effective microbial community, and the indigenous microbes including Flavobacterium, Pseudoxanthomonas,Pseudomonas, Vermamoeba, Dyadobacter and Sphingomonas might play the key role in quinoline removal.According to the PICRUSt, the enhanced genes encoding aromatic ring-cleavage enzyme, especially for Nheterocyclic ring-cleavage enzymes, could lead to the improved removal performance of quinoline in bioaugmentation stage. Moreover, the enhanced MBBR treated well actual coking wastewater, as indicated by high removal performance of quinoline, phenol and COD.

Trimethylamine N-oxide generation process was influenced by the proportion and source of macronutrients in the diet

Trimethylamine N-oxide(TMAO)is a risk factor of various chronic diseases,which was produced by metabolism from precursors to trimethylamine(TMA)in gut and the oxidation from TMA in liver.The TMA generation was influenced by diet,mainly due to the rich TMAO precursors in diet.However,it was still unclear that the effects of different proportion and source of macronutrients in different dietary pattern on the production process of TMAO.Here,the generation of TMA from precursors and TMAO from TMA was determined after single oral choline chloride and intraperitoneal injection TMA,respectively,in mice fed with carbohydrates,proteins and fats in different proportion and sources.The results suggested that the generation of TMAO was increased by low non-meat protein and high fat via enhancing the production of TMAO from TMA,and decreased by plant protein and refined sugar via reducing TMA production from precursors in gut and TMAO transformation from TMA in liver.The high fat and high sugar diets accelerating the development of atherosclerosis did not increase the production of TMAO,the risk factor for atherosclerosis,which indicated that the dietary compositions rather than the elevated TMAO level might be a more key risk factor for atherosclerosis.

Trimethylamine N-oxide aggravates vascular permeability and endothelial cell dysfunction under diabetic condition:in vitro and in vivo study

AIM:To provide the direct evidence for the crucial role of trimethylamine N-oxide(TMAO)in vascular permeability and endothelial cell dysfunction under diabetic condition.METHODS:The role of TMAO on the in vitro biological effect of human retinal microvascular endothelial cells(HRMEC)under high glucose conditions was tested by a cell counting kit,wound healing,a transwell and a tube formation assay.The inflammation-related gene expression affected by TMAO was tested by real-time polymerase chain reaction(RT-PCR).The expression of the cell junction was measured by Western blotting(WB)and immunofluorescence staining.In addition,two groups of rat models,diabetic and non-diabetic,were fed with normal or 0.1%TMAO for 16wk,and their plasma levels of TMAO,vascular endothelial growth factor(VEGF),interleukin(IL)-6 and tumor necrosis factor(TNF)-αwere tested.The vascular permeability of rat retinas was measured using FITC-Dextran,and the expression of zonula occludens(ZO)-1 and claudin-5 in rat retinas was detected by WB or immunofluorescence staining.RESULTS:TMAO administration significantly increased the cell proliferation,migration,and tube formation of primary HRMEC either in normal or high-glucose conditions.RT-PCR showed elevated inflammation-related gene expression of HRMEC under TMAO stimulation,while WB or immunofluorescence staining indicated decreased cell junction ZO-1 and occludin expression after high-glucose and TMAO treatment.Diabetic rats showed higher plasma levels of TMAO as well as retinal vascular leakage,which were even higher in TMAO-feeding diabetic rats.Furthermore,TMAO administration increased the rat plasma levels of VEGF,IL-6 and TNF-αwhile decreasing the retinal expression levels of ZO-1 and claudin-5.CONCLUSION:TMAO enhances the proliferation,migration,and tube formation of HRMEC,as well as destroys their vascular integrity and tight connection.It also regulates the expression of VEGF,IL-6,and TNF-α.

Microbial Degradation of Quinoline: Kinetics Study With Burkholderia picekttii

Objective To investigate the kinetics of quinoline biodegradation by Burkholderia pickttii, a Gram negative rod-shaped aerobe, isolated in our laboratory. Methods HPLC (Hewlett-Packard model 5050 with an UV detector) was used for the analysis of quinoline concentration. GC/MS method was used to identify the intermediate metabolites of quinoline degradation. Results The biodegradation of quinoline was inhibited by quinoline at a high concentration, and the degradation process could be described by the Haldane model. The kinetic parameters based on Haldane substrate inhibition were evaluated. The values were v = 0.44 h-1,Ks=166.7 mg/L, Ki= 650 mg/L, respectively. The quinoline concentration to avoid substrate inhibition was inferred theoretically and determined to be 329 mg/L. Conclusion The biodegradation of quinoline conforms to the Haldane inhibition model and the main intermediate metabolite of quinoline biodegradation is 2-hydroxy-quinoline.

N-Oxides制备方法

综述了吡啶类衍生物、喹啉类衍生物等杂环含氮化合物,仲胺以及叔胺被氧化成为相应的氮氧化合物的方法。

Synthesis of 6-sulfamoyl-4-oxoquinoline-3-carboxylic acid derivatives as integrase antagonists with anti-HIV activity

A series of novel 6-sulfamoyl-4-oxoquinoline-3-carboxylic acids derivatives have been synthesized and screened for HIV integrase inhibition activity. Their structures were confirmed by ESI-MS, ^1H NMR and ^13C NMR. 2009 Li Ming Hu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

Synthesis and Crystal Structure of 3,7,7-Trimethyl-1-phenyl-4-(3-nitrophenyl)-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline-5(6H)-one

The title compound (C25H24N4O3) has been prepared by the cyclocondensation of 5-amino-3-methyl-1-phenypyrazol, m-nitrobenaldehyde and dimedone in glycol under microwave irradiation without catalyst. The crystal structure was determined by single-crystal X-ray diffraction to be orthorhombic, space group Pbca with a = 16.3331(10), b = 13.8329(9), c = 19.4163(12) ?, V = 4386.8(5) ?3, Z = 8, Dc = 1.298 g/cm3, μ = 0.087 mm-1, F(000) = 1808, Mr = 428.48, the final R = 0.0519 and wR = 0.1019. X-ray analysis revealed that the pyridine ring is of boat conformation and the six-membered ring fused with it adopts twist boat conformation.② Corresponding author. Tu Shu-Jiang, born in 1957, professor, majoring in the synthesis of organic and heterocycle compounds. E-mail: laotu2001@ 263.net

Bioaugmentation: a new strategy for removal of recalcitrant compounds in wastewater—a case study of quinoline

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Novel indole and quinoline alkaloids from Melodinus yunnanensis

6/7-Seco rearranged spiro-indolone alkaloids,meloyunines A(1)and B(2)and a monoterpenoid quinoline alkaloid meloyunine C(3)together with its possible intermediate 14,15-dehydromelohenine B(4),and their precursorΔ14-vincamenine(5)were isolated from Melodinus yunnanensis.All structures were elucidated based on NMR,FTIR,UV,and MS spectroscopic data.The isolation of monoterpenoid indole,quinoline,and its immediate from the same plant chemically supported the biosynthesis of quinoline from indole.Compound 2 was cytotoxic against several human cancer cell lines.

Preparation,Single-crystal Structure and Antibacterial Activity of N-((6-Bromine-2-methoxylquinoline-3-yl)benzyl)-3-morpho-line-N-(naphthalene-1-yl)propionamide

The halogenated hydrocarbon amination reaction between the original raw mate-rial N-（（6-bromine-2-methoxylquinoline-3-yl）benzyl）-3-chlorine-N-（naphthalene-1-yl）propionamide and morpholine produces the target molecule N-（（6-bromine-2-methoxylquinoline-3-yl）benzyl）-3-morpholine-N-（naphthalene-1-yl）propionamide （C34H32BrN3O3,Mr=610.54）,and its structure was characterized by 1H NMR,IR,H RMS and X-ray single-crystal diffraction.This crystal is of triclinic system,space group P1 with a=9.315（2）,b=10.3449（12）,c=15.901（3）,α=80.981（14）,β=76.996（17）,γ=74.917（13）°,V=1433.6（5）3,Z=2,Dc=1.414 g/cm3,F（000）= 632,μ（MoKα）=1.47 mm-1,the final R=0.0735 and wR=0.2457.In total,5585 independent reflections including 3727 observed ones with I 〉 2σ（I） were collected.The dihedral angle between naphthyl and substituted quinolyl and that between phenyl and substituted quinolyl are 61.2（1） and 108.2（1）°,respectively.Through C-H…O and C-H…N hydrogen bonds among molecules,the whole molecule is stacked into a three-dimensional structure.In addition,π-π stacking among adjacent naphthalene rings makes the molecule more stable,and the morpholine ring adopts a chair conformation.The target molecule exhibits good antibacterial activity.

Crystal Structure of 4-(4-chlorophenyl)-7,7-dimethyl-2,5- dioxo-1,2,3,4,5,6,7,8-octahydroquinoline

The crystal structure of the title compound (C17H18ClNO2) has been determined by single-crystal X-ray diffraction. The crystal is monoclinic with space group C2/c, a=23.677(5), b=9.5333(2), c=14.027(3)? b=98.06(3), V=313.5(1)?, Mr=303.77, Z=8, Dc=1.287g/cm3, l=0.71073, m(MoKa)=0.247mm-1, F(000)=1280. The structure was refined to R=0.0600, wR=0.1959 for 2020 reflections with I>2s(I). X-ray analysis reveals that the dihedral angle between plane 1 [C(1)~C(6)] and plane 2 [N(1), C(10), C(11), C(7)] is 78.8(1) , between plane 2 and plane 3 [C(10), C(11), C(12), C(13), C(15)] is 3.95(7) .

Syntheses of Tetrahydropyrrolizino[2,1-c]quinoline Derivatives

The three title compounds were prepared from 2-phenylaminomethyl-3H-1,2-dihydro-1-pyrrolizinols via an intramolecular Friedel-Crafts reaction. 2-Phenylaminomethyl-3H-1,2-dihydro-1-pyrrolizinols were prepared from 2-phenylaminomethyl-3H-1,2-dihydro-1-pyrrolizinones via reduction. The heterocyclic ring system of pyrrolizino[2,1-c]quinoline has not been found in literature.

Charge effects on quinoline hydrodenitrogenation catalyzed by Ni-Mo-S active sites-A theoretical study by DFT calculation

The charge distribution on Ni-Mo-S active sites can affect hydrodenitrogenation(HDN)activity.In this study,a series of model Ni-Mo-S were developed with various charge distributions.For comparison,the charge distribution effects on quinoline HDN were studied.The results show that a lack of electrons and extra protons can both lower the orbital eigenvalue of the Ni-Mo-S,leading to stronger adsorption of nitrogen-containing compounds and inhibition of ammonia desorption.Electron deficiency will improve the generation of active hydrogen on the active sites but inhibit hydrogen transfer to the nitrogen compounds;extra protons can provide H^(+)to the nitrogen compounds,which will flexibly transfer between the nitrogen compound and active sites,thus improving the cleavage of the C-N bond.

Syntheses, Crystal Structures and Photoluminescence Properties of Cadmium(Ⅱ) and Nickel(Ⅱ) Complexes with 2-(2-Benzimidazolyl)quinoline

Two novel complexes, [Cd2（BMQU）2Cl4] （1） and [Ni（BMQU）2HPO4]·1.5H2O （2） （BMQU = 2-（2-benzimidazolyl）quinoline）, were synthesized by the hydrothermal method and characterized by elemental analysis, IR, and TG-DTG. The crystal structures were determined by single-crystal X-ray diffraction. Both 1 and 2 crystallize in the triclinic system, space group P . The data for 1： a = 0.8342（7）, b = 0.9226（9）, c = 1.0646（8） nm, α = 90.819（2）, β = 97.466（2）, γ = 98.280（2）°. The Cd（Ⅱ） is coordinated with three chlorine atoms and two nitrogen atoms of a BMQU molecule, generating a distorted square-pyramidal geometry. The dinuclear Cd（Ⅱ） complex is formed by two chlorine bridge bonds, and the one-dimensional chain structure is constructed with the hydrogen bond N-H…Cl and π-π stacking interaction. The data for 2： a = 1.2251（1）, b = 1.2451（1）, c = 1.2868（1） nm, α = 107.510（2）, β = 98.630（1）, γ = 109.921（2）°. The Ni（Ⅱ） is coordinated with four nitrogen atoms of two BMQU molecules and two oxygen atoms of a HPO42-, forming a distorted-octahedral geometry. The two-dimensional layer structure is formed by the hydrogen bonds and π-π stacking interaction between neighboring molecules. Complex 1 shows a strong blue fluorescence emission （λmax= 456 nm） at solid state.

Corrosion behavior of aluminum alloy 2024-T3 by 8-hydroxy-quinoline and its derivative in 3.5% chloride solution

The corrosion behavior of aluminum alloy 2024-T3 was studied in 3.5% NaCl solution with two fluorescence quinoline compounds named 8-hydroxy-quinoline(8HQ) and 8-hydroxy-quinoline-5-sulfonic acid(HQS). The open circuit potential(OCP) test result indicates that both compounds change the alloy corrosion potential by adsorbing on the electrode surface. Polarization measurements show that 8HQ is a mixed type inhibitor by blocking the active sites of the metal surface, while HQS is a corrosion accelerator by activating the cathodic reaction. Changes of the impedance parameters in the electrochemical impedance spectroscopy(EIS) are related to the adsorption of 8HQ on the metal surface, which leads to the formation of a protective layer. The impedance diagram in the solution with HQS is similar to the one without additional organic compounds. The morphology and composition of the protective layer were studied by using SEM/EDS. The result confirms the function of the additions that the effect of 8HQ is due to the insoluble aluminum chelate, Al(HQ)3, to prevent adsorption of chloride ion, while the effect of HQS is to break down the oxide film.

Pyrolysis Mechanisms of Quinoline and Isoquinoline with Density Functional Theory

The pyrolysis mechanisms of quinoline and isoquinoline were investigated using the density functional theory of quantum chemistry,including eight reaction paths and a common tautomeric intermediate 1-indene imine.It is concluded that the conformational tautomerism of the intermediate decides the pyrolysis products(C6H6,HC≡C—C≡N,C6H5C≡N and HC≡CH)to be the same,and also decides the total disappearance rates of the reactants to be the same,for both original reactants quinoline and isoquinoline during the pyrolysis reaction.The results indicate that the intramolecular hydrogen migration is an important reaction step,which often appears in the paths of the pyrolysis mechanism.The activation energies of the rate determining steps are obtained.The calculated results are in good agreement with the experimental results.