32889-11-5Relevant articles and documents
Ligand-free copper-catalyzed regio- And stereoselective 1,1-alkylmonofluoroalkylation of terminal alkynes
Lv, Yunhe,Pu, Weiya,Wang, Xiaoxing
, p. 12933 - 12936 (2020)
The copper-catalyzed highly regio- and stereoselective 1,1-alkylmonofluoroalkylation of terminal alkynes with α-chloroacetamides and dialkyl 2-fluoromalonate or 2-fluoro-N,N-dialkyl-3-oxobutanamide without an external ligand has been realized. With this novel methodology, (E)-β-monofluoroalkyl-β,γ-unsaturated amides containing quaternary C-F centers can be easily constructed in good to excellent yields. This journal is
A light activated CMP conjugated 8-aminoquinoline turn-on fluorescent optode for selective determination of Th4+ in an aqueous environment
Kumar R., Selva,Ashok Kumar
, p. 12607 - 12614 (2019)
A new dibutyl(2-oxo-2-(quinolin-8-ylamino)ethyl)phosphinate (L) was designed, synthesised and developed as a light activated optode for Th4+ determination. The sensing performance of L was studied in solution and in the polymeric membrane phase using absorbance and emission techniques. The neutral ion carrier L exhibits weak fluorescence at 400 nm in CH3CN : H2O (9 : 1, v/v). Upon complexation of L with Th4+, the emission intensity at 486 nm was increased 100-fold due to chelation induced enhanced fluorescence. The L-Th4+ binding interaction was studied using both Hill's and Job's plots. They indicate the formation of complex species in a 2 : 1 ratio with an estimated binding constant of 2.66 × 104 M-2. Complex formation between L and Th4+ was studied by NMR (1H, 31P), FTIR and LC-MS analyses. In order to synthesize a probe for the sensing of Th4+ in 100% aqueous medium, the optode was prepared by immobilizing L as a neutral ion carrier in a PVC support using dioctyl phthalate (DOP) as a membrane solvent. The best performance of the optode was observed with a membrane composition of PVC : L : NaTPB : DOP in proportions of 35 : 5 : 3 : 57 (%, w/w) in the pH range of 4.0-8.0. The optode can detect Th4+ concentrations down to 1.1 nM with a fast response time of 15 s and the optical response remains unaltered even after 3 months; the optode sensor can be regenerated using Na2EDTA solution. Finally, the optode was used for the quantification of Th4+ in various water samples, monazite sand, and gas mantle samples.
A highly sensitive and selective ratiometric fluorescent sensor for Zn 2+ ion based on ICT and FRET
Chen, Xiaoqiang,Ma, Yang,Chen, Haiyan,Wang, Fang,Kambam, Srinivasulu,Wang, Yong,Mao, Chun
, p. 301 - 307 (2014)
A ratiometric sensor (QA) for detecting Zn2+ with high sensitivity and selectivity was reported. The fluorescence changes of sensor upon the addition of Zn2+ were attributed to the conjugation of internal charge transfer and fluorescence resonance energy transfer mechanisms. There is a good linear relationship between the fluorescence ratio I 497nm/I420nm and the concentrations of Zn2+ ranging from 0 μM to 40 μM, which makes an effective ratiometric detection of Zn2+ ion. The limit of detection (LOD) was evaluated to be 33.6 nM. The imaging experiments indicated that QA is cell-permeable and can be used to detect Zn2+ within living cells with good selectivity over Cd2+.
New fluorogenic chemosensors derived from benzimidazole
Tikhomirova, Karina S.,Tolpygin, Ivan E.,Starikov, Andrey G.,Kaz’mina, Maria A.
, p. 179 - 185 (2017)
[Figure not available: see fulltext.] We report the synthesis of new 1-substituted N-(anthracen-9-ylmethyl)-1H-benzimidazol-2-amines and 1,2,3-trisubstituted 1H-benzimidazolium chlorides containing anthracene fluorophores. Benzimidazol-2-amine derivatives
1,3-Di-amidoquinoline conjugate of calix[4]arene (L) as a ratiometric and colorimetric sensor for Zn2+: Spectroscopy, microscopy and computational studies
Mummidivarapu, V. V. Sreenivasu,Tabbasum, Khatija,Chinta, Jugun Prakash,Rao, Chebrolu P.
, p. 1671 - 1674 (2012)
Carboxamidoquinoline appended calix[4]arene-1,3-di-conjugate (L) has been synthesized and characterized and its single crystal XRD structure has been established. L has been shown to act as selective ratiometric turn-on fluorescence sensor for Zn2+ up to a lowest concentration of 183 ± 18 ppb (2.82 μM) with a nine-fold enhancement by exhibiting blue-green emission. The coordination features of the species of recognition have been computationally evaluated by DFT methods and found to have distorted tetrahedral Zn2+ center in an N4 core. The spherical nano-structural features observed for L in TEM are being transformed into the Koosh nano-flower like structure when complexed with Zn2+ and hence these two can be easily differentiated. Even the features observed in AFM can distinctly differentiate L from its Zn2+ complex.
Rhodamine based derivative and its zinc complex: Synthesis and recognition behavior toward Hg(II)
Zhou, Xin,Yan, Wei,Zhao, Tong,Tian, Zhexi,Wu, Xue
, p. 9535 - 9539 (2013)
A simple fluorescent probe, which contains rhodamine and aminoquinoline moieties, was designed and prepared for selective detection of Hg2+ in acetonitrile. RbQ exhibited high selectivity and sensitivity toward Hg 2+ over other common metal ions. The recognition of RbQ toward Hg2+ can be detected by fluorescence spectra, absorption spectra, and even by naked eyes. The binding ratio of the RbQ-Hg2+ complex was found to be 1:1 according to Job plot experiment, and the limit of detection was 1.05×10-7 M. Moreover, the prepared complex RbQ-Zn 2+ (RbQZ) could detect Hg2+ in a ratiometric way and showed lower limit of detection (2.95×10-8 M) than RbQ in the same condition. Finally, we also demonstrated that the aminoquinoline-zinc complex could be served as a new and effective FRET donor for rhodamine derivatives.
Quinoline-functionalized norbornene for fluorescence recognition of metal ions
Yao, Pei-Shui,Cao, Qian-Yong,Peng, Rong-Peng,Liu, Jing-Hua
, p. 11 - 18 (2015)
A quinoline-functionalized norbornene (1) and its homopolymer (P1) for metal ions recognition have been synthesized and characterized. In CH3CN solution, 1 exhibited fluorescence enhancement response toward Hg2+, Zn2+ and Cu2+, with Hg2+ resulting in a green emission at 465 nm, and Zn2+/Cu2+ increasing 1's original emission at 406 nm. NMR titrations and DFT calculations results indicated that 1 bound Hg2+ in an imidic acid tautomeric form of the amide quinoline receptor, while Zn2+ and Cu2+ were bound to 1 in an amide tautomeric form. In addition, owing to the strong imidic acid tautomeric binding mode of 1-Hg2+ complex, 1 can recognized Hg2+ from Zn2+/Cu2+ and other competitive metal ions. In contrast, the homopolymer P1, which was obtained by ring opening metathesis polymerization (ROMP) method, exhibited only fluorescence enhancement sensing to Hg2+ and Cu2+ in an amide tautomeric binding mode with increasing emission at 416 nm.
A highly selective fluorescent sensor for distinguishing cadmium from zinc ions based on a quinoline platform
Zhou, Xiaoyan,Li, Pengxuan,Shi, Zhaohua,Tang, Xiaoliang,Chen, Chunyang,Liu, Weisheng
, p. 9226 - 9231 (2012)
A fluorescent sensor, N-(quinolin-8-yl)-2-(quinolin-8-yloxy)acetamide (HL), based on 8-aminoquinoline and 8-hydroxyquinoline platforms has been synthesized. This sensor displays high selectivity and sensitive fluorescence enhancement to Cd2+ in ethanol. Moreover, sensor HL can distinguish Cd2+ from Zn2+ via two different sensing mechanisms (photoinduced electron transfer for Cd2+; internal charge transfer for Zn2+). The composition of the complex Cd2+/HL or Zn2+/L- has been found to be 1:1, based on the fluorescence/absorption titration and further confirmed by X-ray crystallography.
Copper-Catalyzed Regio- And Stereoselective 1,1-Dicarbofunctionalization of Terminal Alkynes
Lv, Yunhe,Pu, Weiya,Shi, Lihan
, p. 6034 - 6039 (2019)
The copper-catalyzed highly regio- and stereoselective 1,1-dicarbofunctionalization of terminal alkynes is realized for the first time. Using a removable, bidentate 8-aminoquinoline auxiliary, the three-component, selective 1,1-arylalkylation of alkynes with α-haloacetamides and organoboronic acids by the addition of both alkyl and aryl groups to the terminal carbon of alkynes was achieved. Mechanistic investigations suggest that the reaction likely proceeds via the copper-catalyzed cross-coupling of terminal alkynes with α-haloamides, rearrangement, transmetalation, syn-carbocupration, and protonolysis.
A 18F radiolabelled Zn(II) sensing fluorescent probe
Price, Thomas W.,Firth, George,Eling, Charlotte J.,Kinnon, Michelle,Long, Nicholas J.,Sturge, Justin,Stasiuk, Graeme J.
, p. 3227 - 3230 (2018)
A selective fluorescent probe for Zn(ii), AQA-F, has been synthesized. AQA-F exhibits a ratiometric shift in emission of up to 80 nm upon binding Zn(ii) ([AQA-F] = 0.1 mM, [Zn(ii)Cl2] = 0-300 μM). An enhancement of quantum yield from Φ = 4.2% t
A selective and sensitive fluorescent sensor for cysteine detection based on bi-8-carboxamidoquinoline derivative and Cu2+ complex
Chai, Guoping,Liu, Qingwen,Fei, Qiang,Zhang, Jinling,Sun, Xiaoxiao,Shan, Hongyan,Feng, Guodong,Huan, Yanfu
, p. 153 - 160 (2018)
In this paper, a novel fluorescent sensor 1 for selective and sensitive detection of cysteine was developed based on a complex between bi-8-carboxamidoquinoline derivative ligand (L) and Cu2+. The interaction of Cu2+ with the ligand causes a dramatic fluorescence quenching most likely due to its high affinity towards Cu2+ and a ligand–metal charge transfer (LMCT) process. The in situ generated L–Cu2 complex was utilized as a chemosensing ensemble for cysteine. In the presence of cysteine, the fluorophore, L, was released from L–Cu2 complex because of the strong affinity of cysteine to Cu2+ via the Cu–S bond, leading to the fluorescence recovery of the ligand. The proposed displacement mechanism was confirmed by the results of mass spectrometry (MS) study. Under optimized conditions, the recovered fluorescence intensity is linear with cysteine concentrations in the range 1?×?10?6?mol/l to 8?×?10?6?mol/l. The detection limit for cysteine is 1.92?×?10?7?mol/l. Furthermore, the established method showed a highly sensitive and selective response to cysteine among the 20 fundamental α-amino acids used as the building blocks of proteins, after Ni2+ was used as a masking agent to eliminate the interference of His. The proposed sensor is applicable in monitoring cysteine in practical samples with good recovery rate.
A switch-off fluorescence probe towards Pb(II) and cu(II) ions based on a calix[4]pyrrole bearing amino-quinoline group
Bhatt, Keyur D.,Shah, Hemangini D.,Panchal, Manthan
, p. 1398 - 1404 (2017)
A new fluorescence receptor calix[4]pyrrole-N-(quinoline-8-yl) acetamide (CAMQ) containing a pyrrolic ring connected via the meso-position was synthesized, purified and characterized by elemental analysis, NMR and mass spectroscopy. This compound was exam
Dipodal quinoline-tethered fluorescent probe synthesis and investigation of spectroscopic properties
Obal?, Asl?han Y?lmaz,Yilmaz, Menzeher Serkan,U?an, Halil ?smet
, p. 192 - 196 (2017)
Novel quinoline-tethered fluorescent probe was designed and synthesized as multidentate ligand. Their sensing actions were confirmed by UV–Vis absorbance and emission spectroscopic studies in presence of perchlorate salts of Co2+, Li+, Fe2+, K+, Pb2+, Cu2+, Zn2+, Ni2+, Hg2+, Ag+ cations in acetonitrile (1 × 10?5 M for absorption studies, 1 × 10?7 M for fluorescence studies). It was found that the dipodal compounds can selectively bind to Cu2+ and Ag+ metal ions with a significant quenching in their emissions. The capture of Cu2+ and Ag+ by the probe resulted in deprotonation of the secondary amine conjugated to the quinoline-tethered probe, so that the electron-donation ability of the ‘N’ atom would be greatly enhanced and the probe (2) showed blue-shift in emission and exhibited an on-off fluorescent response. The binding study was explored by using fluorescence spectroscopy with Job plot method.
Synthesis and Evaluation of Bakuchiol Derivatives as Potent Anti-inflammatory Agents in Vitro and in Vivo
Bai, Chunmei,Bian, Ming,Du, Huan-Huan,Gong, Guohua,Liu, Chunyan,Ma, Qianqian,Quan, Zhe-Shan,Wei, Chengxi
supporting information, p. 15 - 24 (2022/01/27)
Bakuchiol, a prenylated phenolic monoterpene derived from the fruit of Psoralen corylifolia L. (Buguzhi), is widely used to treat tumors, viruses, inflammation, and bacterial infections. In this study, we designed and synthesized 30 bakuchiol derivatives
Improving the solubility of anti-proliferative thieno[2,3-b]quinoline-2-carboxamides
Haverkate, Natalie A.,van Rensburg, Michelle,Kumara, Sisira,Reynisson, Jóhannes,Leung, Euphemia,Pilkington, Lisa I.,Barker, David
supporting information, (2021/03/16)
Thieno[2,3-b]pyridines are a class of compounds known for their potent anti-proliferative activities against a range of human cancer cell lines. In this research, a number of strategies to generate analogues that have improved aqueous solubility whilst retaining the potent anti-proliferative actions, compared to previously-explored compounds in this class, were made. Herein we report the synthesis of 80 novel compounds, comprising two series, all based on the thieno[2,3-b]pyridine core structure. Overall, it was found that introducing alternative heterocycles did not notably improve the solubility or retain anti-proliferative activity seen in previously-reported analogues. However, pleasingly it was discovered, that the best strategy for improving the solubility was the alteration of the appended alkyl ring to introduce polar groups such as alcohols, ketones and substituted amine groups. In addition to this finding, we have discovered a thieno[2,3-b]pyridine, 15e, with greater aqueous solubility that has ever been seen for this class of compounds that is also a potent inhibitor of cancer cell growth, with IC50′s in the nanomolar range. This new lead structure will form the basis of future explorations into this class of compounds.
