Quinoline Carboxylate Research Articles

Switchable Selectivity in the Annulation ofo-Trifluoroacetylanilines and Activated Terminal Alkynes Based on Transition Metal and Phosphine Catalysis.

In this work, we have developed selective methods for the synthesis of quinoline-2-carboxylates and quinoline-3-carboxylates as well as (indolin-2-ylidene)acetates through copper-, silver-, or phosphine-catalyzed reaction of propiolates with 2'-amino-2,2,2-trifluoroacetophenones. The approaches proposed ensure synthesis of substituted quinoline carboxylates and (indolin-2-ylidene)acetates in good yields. Introduction of alkynones into the reaction with 2'-amino-2,2,2-trifluoroacetophenones gives acyl substituted derivatives in good yields.

Fluorescent quinoline carboxylate derivative: Study on the optical properties and photo diode application

Thin films of HPQC were processed using thermal deposition technique. The optical properties of the HPQC films were studied for application as optical sensor. The effect of film thickness and the effect of ultraviolet radiation on optical properties were studied. The emission properties of HPQC thin film are studied and it is found to have blue color emission. It was found that UV irradiation decreased the bandgap of HPQC film. A heterojunction device with the structure Au/HPQC/p-Si/Al was fabricated to perform as a photo diode. The characteristics of the heterogenous device were studied. The device was found to respond to temperature and illumination. The applicability of current limitation mechanisms in the reverse bias were studied. The responsivity and detectivity of the device to illumination were also studied and were found to act as functions of illumination power and voltage.

Synthesis of Proposed Structure of Aaptoline A, a Marine Sponge-Derived 7,8-Dihydroxyquinoline, and Its Neuroprotective Properties in C. elegans.

A concise and efficient synthesis of the proposed structure of aaptoline A, a 7,8-dihydroxyquinoline derived from a marine sponge, was accomplished in seven steps with a 52% overall yield. A key feature of the synthesis is the high-yielding Ag(I)-catalyzed cycloisomerization of the N-propargylaniline precursor to afford the quinoline carboxylate skeleton from acid-labile methyl aminobenzoate. However, the spectral data of the synthesized aaptoline A were not consistent with those of previous studies. The structure of the synthesized aaptoline A was confirmed by combined 2D NMR analysis. Additional studies on the bioactivity of the synthesized aaptoline A revealed that it has the ability to protect dopaminergic neurons against MPP+-induced neurotoxicity in C. elegans. In addition, impaired food-sensing ability and travel distance capability in C. elegans were significantly ameliorated by aaptoline A treatment, suggesting that aaptoline A can protect dopaminergic neurons both morphologically and functionally.

Synthesis and SAR of a series of mGlu7 NAMs based on an ethyl-8-methoxy-4-(4-phenylpiperazin-1-yl)quinoline carboxylate core

A High-Throughput Screening (HTS) campaign identified a fundamentally new mGlu7 NAM chemotype, based on an ethyl-8-methoxy-4-(4-phenylpiperazin-1-yl)quinolone carboxylate core. The initial hit, VU0226390, was a potent mGlu7 NAM (IC50 = 647 nM, 6% L-AP4 min) with selectivity versus the other group III mGlu receptors (>30 μM vs. mGlu4 and mGlu8). A multi-dimensional optimization effort surveyed all regions of this new chemotype, and found very steep SAR, reminiscent of allosteric modulators, and unexpected piperazine mimetics (whereas classical bioisosteres failed). While mGlu7 NAM potency could be improved (IC50s ~ 350 nM), the necessity of the ethyl ester moiety and poor physiochemical and DMPK properties precluded optimization towards in vivo tool compounds or clinical candidates. Still, this hit-to-lead campaign afforded key medicinal chemistry insights and new opportunities.

Synthesis and catalytic applications of Ru and Ir complexes containing N,O-chelating ligand

A series of monometallic complexes (Ru1–3, Ir1–3) which have N,O-chelating ligand (pyrazine-2-carboxylate (1), pyridine-2-carboxylate (2), quinoline carboxylate(3) and bimetallic complexes (Ru4,5, Ir4,5) bridged by pyrazine-2,3- dicarboxylate (4) and imidazole-4,5-dicarboxylate(5) were synthesized and characterized by 1H-, 13C NMR, FT-IR, and elemental analysis. The crystal structure of Ir2 was determined by X-ray crystallography. The complexes (Ru1–5, Ir1–5) were applied to investigate the electronic and steric effect of ligand in their catalytic activities in transfer hydrogenation and alpha(α)-alkylation reaction of ketones with alcohols. The activities of iridium complexes (Ir1–5) were much more efficient than ruthenium complexes (Ru1–5). The highest activity for both reactions was observed for the complex (Ir2) with pyridine-2-carboxylate. The Ir hydride species was monitored for both reactions.

Encapsulating Au-Fe3 O4 Nanodots into AIE-active Supramolecular Assemblies: Ambient Visible-light Harvesting "Dip-Strip" Photocatalyst for C-C/C-N Bond Formation Reactions.

The present study demonstrates the development of a supramolecular porous ensemble consisting of hetero-oligophenylene derivative 6 and Au-Fe3 O4 nanodots. Supramolecular assemblies of AIE-active hetero-oligophenylene derivative 6 served as reactors for the generation of Au-Fe3 O4 nanodots. The as prepared supramolecular ensemble functioned as an efficient recyclable photocatalytic system for C(sp2 )-H bond activation of anilines for the construction of quinoline carboxylates. Interestingly, the "dip catalyst" prepared by depositing PTh-co-PANI-6: Au-Fe3 O4 nanodots on a filter paper served as a recyclable strip (up to 10 cycles) for C-C/C-N bond formation reaction.

Synthesis, Characterization, Cytotoxic Activity, and Interactions with CT-DNA and BSA of Cationic Ruthenium(II) Complexes Containing Dppm and Quinoline Carboxylates.

The complexes cis-[Ru(quin)(dppm)2]PF6 and cis-[Ru(kynu)(dppm)2]PF6 (quin = quinaldate; kynu = kynurenate; dppm = bis(diphenylphosphino)methane) were prepared and characterized by elemental analysis, electronic, FTIR, 1H, and 31P{1H} NMR spectroscopies. Characterization data were consistent with a cis arrangement for the dppm ligands and a bidentate coordination through carboxylate oxygens of the quin and kynu anions. These complexes were not able to intercalate CT-DNA as shown by circular dichroism spectroscopy. On the other hand, bovine serum albumin (BSA) binding constants and thermodynamic parameters suggest spontaneous interactions with this protein by hydrogen bonds and van der Waals forces. Cytotoxicity assays were carried out on a panel of human cancer cell lines including HepG2, MCF-7, and MO59J and one normal cell line GM07492A. In general, the new ruthenium(II) complexes displayed a moderate to high cytotoxicity in all the assayed cell lines with IC50 ranging from 10.1 to 36 µM and were more cytotoxic than the precursor cis-[RuCl2(dppm)2]. The cis-[Ru(quin)(dppm)2]PF6 were two to three times more active than the reference metallodrug cisplatin in the MCF-7 and MO59J cell lines.

Synthesis, Structure Evaluation, Spectroscopic and Antibacterial Investigation of Metal Complexes with 2-(Pyridin-4-yl)quinoline-4-carboxylic Acid.

Four metal complexes based on quinoline carboxylate ligand from 2-(pyridin-4-yl)quinoline-4-carboxylic acid (HL), [ML2(H2O)2] · 2H2On (M = MnII, 1; M = CoII, 2; M = CdII, 3) and [Ag2L2(H2O)2] · 3H2On (4) have been synthesized under hydrothermal conditions. Their structures were determined by elemental analyses, IR spectra, and further characterized by single-crystal X-ray diffraction analysis. Complexes 1-3 feature a 1D chain structure which is further linked together to construct the 3D supramolecular network through hydrogen bonds. Complex 4 exhibits a 3D configuration. The fluorescent behavior and antibacterial activities of these compounds have been investigated.

ChemInform Abstract: Rhodium‐Catalyzed ortho C—H Bond Activation of Arylamines for the Synthesis of Quinoline Carboxylates.

AbstractA regioselective annulation of anilines with alkynic esters allowing for the synthesis of quinoline carboxylates using rhodium catalysts is proposed to proceed via rhodacycle of in situ generated amide and enamine ester followed by ortho C—H activation of arylamines.

Rhodium-catalyzed ortho C-H bond activation of arylamines for the synthesis of quinoline carboxylates.

The rhodium catalyzed annulation of anilines with alkynic esters allowing for the high-yield synthesis of quinoline carboxylates with excellent regioselectivity is described. This unprecedented reaction employs either formic acid as the C1 source and reductant or copper(ii) as the oxidant and is proposed to proceed via rhodacycle of in situ generated amide and enamine ester followed by ortho C-H activation of arylamines with rhodium as the catalyst.

Structure variations of a series of lanthanide complexes constructed from quinoline carboxylate ligands: photoluminescent properties and PMMA matrix doping

A series of lanthanide complexes constructed from H2qldc are synthesized and the luminescence properties discussed.

Crystal Structure, Multiplex Photoluminescence, and Magnetic Properties of a Series of Lanthanide Coordination Polymers Based on Quinoline Carboxylate Ligand

A series of novel one-dimensional (1D) lanthanide coordination polymers, [Ln(pqc)(Hpqc)(NO3)2]n (Ln = Sm (1), Eu (2), Gd (3), Tb (4), Dy (5), Ho (6), Er (7), Tm (8), Yb (9), or Lu (10); Hpqc = 2-phenyl-4-quinolinecarboxylic acid), have been synthesized via solvothermal reaction at low temperature and then characterized by single-crystal X-ray diffraction. Polymers 1–10 are isostructural and feature a 1D chain based on binuclear units in which Ln3+ polyhedra are interconnected by bridging Hpqc ligands and terminal nitrates. The infinite chains are further extended to a three-dimensional supramolecular framework through π···π stacking and hydrogen bonding interactions. This series affords an opportunity to study the lanthanide contraction effect, demonstrating that the sum of Ln–O distances proportional to this contraction follow a quadratic decay as a function of the number n of f electrons. The photoluminescence spectra show that these complexes are highly sensitized by Hpqc and exhibit characteristic Ln3+ (Sm (1), Eu (2), Tb (4), Er (7), and Yb (9)) and ligand centered (Dy (5), Ho (6), Tm (8), and Lu (10)) luminescence in both visible and near-infrared (NIR) regions. The magnetic properties of 4–7 have also been investigated.

Ruthenium(II) complexes with quinoline carboxylate as a co-ligand

Ruthenium(II) complexes with the general formulas [Ru(H/Cl)(CO)(PPh3)2(L)] and cis/trans-[Ru(PPh3)2(L)2] (L=isoquinoline-1-carboxylate or quinoline-2-carboxylate) were synthesized and characterized by IR, 1H, 13C and 31P NMR, UV–Vis spectroscopy and X-ray crystallography. The experimental studies were completed by quantum chemical calculations, which were used to describe the nature of the interactions between the ligands and the central ion, and the orbital compositions in the frontier electronic structures. Based on a molecular orbital scheme, the calculated results allowed the interpretation of the UV–Vis spectra obtained at an experimental level. The luminescence properties of the complexes were determined.

Copper(ii) triflate-catalyzed reactions for the synthesis of novel and diverse quinoline carboxylates

An efficient one-pot synthesis of a variety of quinoline carboxylates was accomplished by Cu(OTf)2-catalyzed reactions of Michael addition/cyclization/aromatization between 2-aminoaryl carbonyls and alkynyl carboxylates. This methodology offers several significant advantages, namely, ease of handling, mild reaction conditions, enhanced reaction rates, and use of an effective and non-toxic catalyst. The synthesized compounds were further transformed into highly functionalized novel quinoline carboxylates bearing aromatic rings on the quinoline skeleton using the Suzuki reaction.

Synthesis and Anticoccidial Activities of Quinoline Carboxylate Derivatives with Methyl (E)-2-(3-methoxy)acrylate Moiety

Synthesis and Anticoccidial Activities of Quinoline Carboxylate Derivatives with Methyl (E)-2-(3-methoxy)acrylate Moiety

ChemInform Abstract: A Mild Palladium‐Catalyzed Suzuki Coupling Reaction of Quinoline Carboxylates with Boronic Acids.

AbstractA variety of substituted 4‐hydroxyquinoline benzoates reacts with arylboronic acids or cyclopropylboronic acid (V) to afford the corresponding 4‐substituted derivatives.

Pyridoquinolones containing azetidinones: synthesis and their biological evaluation

A series of pyridoquinolone 4-oxo-1,4-dihydro(4′-methyl-6′-chloropyrido[2,3-h])quinoline-3-[N-(substituted phenyl methylidine)]carbohydrazide 3a–j and 4-oxo-1,4-dihydro(4′-methyl-6′-chloropyrido[2,3-h])-3-[N-{(3-chloro-2-oxo-4-(substituted phenyl) azetidine-1-yl)amino}carbonyl] quinoline 4a–j have been synthesized via 4-oxo-1,4-dihydro-(4′-methyl-6′-chloropyrido[2,3-h])quinoline carboxylate 1. All the compounds were proved by IR, 1H-NMR, 13C-NMR spectral studies and elemental analysis. Antibacterial activities (MIC) against E. coli, P. aeruginosa, S. aureus and S. pyogenes, and antifungal activities against C. albicans, A. niger and A. clavatus were screened, whereas selected compounds were screened against Mycobacterium tuberculosis H37Rv and compared with standard drugs.

A Mild Palladium‐Catalyzed Suzuki Coupling Reaction of Quinoline Carboxylates with Boronic Acids

AbstractA palladium‐catalyzed cross‐coupling between aryl carboxylates and boronic acids has been achieved for the first time by taking advantage of the enhanced reactivity of quinoline 4‐carboxylates. Also for the first time a Suzuki coupling reaction via a self‐activation of boronic acids without addition of base is described. The reactions proceed under mild conditions (25–65 °C) to give excellent yields, and a wide range of functionalities is tolerated.

Two 2-D copper(II) azido compounds: catena -poly[ di -μ1,1- azido, di -μN,O-(quinolinecarboxylato)(aqua)copper(II)] and 1-D catena -poly[ di -μN,N′-(quinoxaline)copper(II)nitrate

We synthesized three copper(II) complexes with two structurally related polydentate ligands, quinoline-4-carboxylic acid (quCOOH) and quinoxaline (qux). The structures of these complexes were determined using X-ray single crystal crystallography. Complex 1, [Cu(quCOO)(N3)(H2O)] n , has a 2-D polymeric structure through di-μ1,1 azido groups forming (Cu2N2) dimeric units and di-μN,O quinoline carboxylate bridging the binuclear copper units. [Cu(quCOO)(N3)(H2O)] n · 0.87MeOH, (2), has the same structure as 1 in addition to MeOH molecules separating the 2-D sheets of [Cu(quCOO)(N3)(H2O)] n . [Cu(qux)(NO3)2] n , (3), has no coordinated azido groups, but the quinoxaline is a bidentate bridging ligand giving a 1-D chain, while the μO,O′ chelating nitrato groups stabilize the chain structure by forming a square planar coordination sphere around copper. IR and UV–Vis spectra of the complexes are in agreement with the crystal structures.