Quinoline Amines Research Articles

Exploring the structure-activity relationship (SAR) of Schiff bases as effective compounds in scavenging free radicals

Naphthol-imine compounds containing N-phenylethylenediamine (1) and quinoline amine (2) moieties were synthesized and characterized. Density Functional Theory (DFT) calculations were performed aiming to obtain information on the chemical properties of these molecules. In silico ADME/Tox profile analyses were performed on molecules 1 and 2 using the web tools pkCSM-pharmacokinetics, Molinspiration, and Osiris Property Explorer. Drug-likeness levels of 1 and 2 were predicted according to the Lipinski rules. The radical scavenger activity of compounds 1 and 2 was determined by in vitro assays such as 1,1-diphenyl-2-picrylhydrazyl free radicals (DPPH.) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) radicals (ABTS.+). Molecules 1 and 2 were ineffective as radical scavengers in the DPPH radical capture assay at the test doses. However, 1 showed activity in eliminating ABTS+ radical with IC50 = 17.4 ± 0.9 µM. The neutral red assay determined the cytotoxicity of 1 and 2 against the V79 cell line. Molecule 1 was more cytotoxic than 2, with IC50 values ​​of 36.67 µM and 51.26 µM, respectively. The alkaline comet assay was used to investigate the in vitro genotoxicity of 1 and 2. After 24 h of exposure to a dose of 20 μM, 1 did not cause significant DNA damage compared to non-exposed cells. The compounds were tested for toxicity using Artemia saline assay.

The Anticancer Potentials of Substituted Indeno[1,2-b]quinoline Amines against HT29 and SW620: Experimental and In silico Approach

Background: This study aimed the determination of the antiproliferative and cytotoxic activities of recently prepared indeno [1,2-b]quinoline amines against colon carcinoma, HT29 and SW620 cell lines by using cell proliferation and cytotoxicity assays. Methods: In vitro inhibition of cell proliferation of indenoquinoline derivatives was determined with an MTT cell proliferation assay. On the other hand, their cell cytotoxicities and apoptotic potential were investigated by LDH cytotoxicity and DNA laddering assays. Moreover, molecular docking studies were performed between the compounds and PDB ID: 1OLG and 4LVT target proteins using virtual scanning techniques. Results: Most of the compounds (1, 3, and 7-9) exhibit much more potent antiproliferative activity than positive controls against HT29 and SW620 cell lines (IC50 values 1.1 - 4.1 μg/mL) and show slightly toxic properties (percent cytotoxicity 9.8% to 33.5%) to cells compared to positive control. On the other hand, it was determined that effective compounds 1, 2, 3 and 9 stimulated apoptosis on HT29 and SW620. Moreover, the anticancer effect of the recent indeno[1,2-b]quinoline amine derivatives was investigated with the help of molecular docking simulations for their pharmacokinetics. The molecular docking results displayed that mono bromo (1-3) and phenyl (7-9) substituted indeno [1,2-b]quinoline amines interact with mutated p53 and protein Blc-2 residues with hydrogen bonding and polar interactions, respectively. Conclusion: As a result, the preliminary experimental data and in silico studies indicated that the monosubstituted indenoquinoline amine derivatives, especially 1, 3, and 7-9, exhibit effective pharmacological properties.

Eaton's reagent is an alternative of PPA: Solvent free synthesis, molecular docking and ADME studies of new angular and linear carbazole based naphtho naphthyridines

An approach towards the preparation of novel angular and linear carbazole based naphtho naphthyridines are described in good yields. From schematic study on the condensation of 4-chloro-2-methylbenzo[h]quinoline and 3-amino-9-ethylcarbazole in presence of CuI as catalyst to N-(9-ethyl-9H-carbazol-3-yl)-2-methylbenzo[h]quinolin-4-amine was stated as starting synthon. Thus, this carbazole based quinoline amine on treatment with Eaton's reagent catalyzed cyclisation reaction with Aromatic carboxylic acids to yield the linear and angular 8-substituted naphtho[h]carbazol [1,6]naphthyridines. This Eaton's reagent is a precise catalyst for the reaction of cyclizing cum aromatization agent followed by dehydration of the conversion of angular and linear naphthyridines in excellent yields compared with Polyphosphoric acid (PPA). Further, the molecular docking studies were conducted to offer binding mode into the binding sites of phosphoinositide-dependent protein kinase 1 (PDK-1) receptors. The synthesized compounds showed better docking scores and binding energies, when compared with reference drugs ARC-111 and Ellipticine. Pharmacokinetic (ADME) parameters of the potent derivatives have also been found to an acceptable range.

Synthesis and characterization of fluorine functionalized graphene oxide dispersed quinoline‐based polyimide composites having low‐k and UV shielding properties

AbstractPolyimide nanocomposites having low‐k and UV shielding properties have been developed using fluorine functionalized graphene oxide and bis(quinoline amine) based polyimide. The polyimide was synthesized using bis(quinoline amine) and pyromellitic dianhydride at appropriate experimental conditions, and its molecular structure was confirmed through various spectral analysis such as FTIR and NMR. The polyimide (PI) composites were prepared using bis(quinoline amine), pyromellitic dianhydride, and separately filled with 1, 5, 10 wt% of fluorinated graphene oxide (FGO) through in situ polymerization. The polymer composites were characterized using thermo gravimetric analysis (TGA), X‐ray powder diffraction (XRD), and scanning electron microscopy (SEM). In addition, the water contact angle, dielectric behavior, and UV–Vis shielding behavior of FGO/PI composites were evaluated. The value of the water contact angle of the polyimide was increased with increment of FGO in the polyimide matrix. The highest water contact angle of polyimide composites observed 108° was obtained for 15 wt% FGO reinforced polyimide composite. The value of the dielectric constant for neat, 1, 5, and 15 wt% FGO reinforced polyimide composites was obtained as 4.5, 3.7, 2.6, and 2.0, respectively. It is also observed from by UV–Vis spectroscopy analysis that the FGO reinforced polyimide composites have good UV shielding behavior.

In–Vitro Anticancer and Antibacterial Activities of Brominated Indeno[1,2‐b]qinoline Amines Supported with Molecular Docking and MCDM**

AbstractThe present study describes mono substituted indeno[1,2‐b]quinolines (3 a–c and 5) have much more antiproliferative potentials than positive controls against A549, HeLa, MCF7 and Hep3B cell lines (IC50 values 1.1–29.6 μg/mL) and show similar cytotoxicity (14.3 % to 19.8 %) to cells such as controls. Moreover, the mono substituted indeno[1,2‐b]quinoline amines (3 a–c and 5) exhibit significant antimicrobial activity with MIC values between 15.62 μg/mL and 250 μg/mL. The compounds can also bind to DNA in the groove binding mode with a binding constant range of 1.1×103–1.1×105 M−1. The anticancer and antibacterial properties of compounds were confirmed with the molecular docking simulation for their pharmacokinetic. As a result, the preliminary experimental data and a multi‐criteria decision‐making methodology (MCDM) indicated that the mono substituted indeno[1,2‐b]quinoline amine derivatives, especially 3 a and 5, exhibit effective pharmacological properties. parameters and their interaction with related cells at the molecular level.

Low-k and UV shielding polybenzoxazine nanocomposites synthesised from quinoline amine and bio-silica

ABSTRACT Polybenzoxaines nanocomposites with low-k and UV shielding behaviour have been developed using a new bis(quinoline amine), cardanol and biosilica. The new bis(quinoline amine) was synthesized through acid catalysed Friedlander reaction and its molecular structure has been confirmed using FT-IR and 1H NMR. The bio-benzoxazine (C-bqa) was synthesised using cardanol, bis(quinoline amine) and paraformaldehyde at appropriate experimental conditions, and its molecular structure was confirmed from spectral analysis. Cardanol-based polybenzoxazine was reinforced with varying weight percentages of (5, 10, 15 wt%) of 3-glycidoxypropyltrimethoxysilane (GPTMS) functionalized bio-silica and were characterized using DSC, TGA, XRD, SEM and TEM. From the DSC analysis, it was observed that an exothermic peak maxima representing the ring opening polymerisation (curing) temperature of both neat cardanol based benzoxazine and 15 wt% of bio-silica reinforced cardanol-based benzoxazine composites are observed at 206°C and 216°C, respectively. The value of water contact angle of poly(C-bqa) was enhanced according to the increasing weight percentage of bio-silica reinforcement and the values observed for poly(C-bqa) matrix and 15 wt% of bio-silica reinforced poly(C-bqa) composites are 92° and 124° respectively. The values of dielectric constant obtained for neat poly(C-bqa) matrix and 15 wt% bio-silica reinforced poly(C-bqa) composites are 4.3 and 2.3 respectively. The UV shielding behaviour of bio-silica reinforced polybenzoxazine composites was also studied by UV-Vis spectroscopy technique and the results obtained infer that these materials possess good UV shielding behaviour.

Understanding the binding of quinoline amines with human serum albumin by spectroscopic and induced fit docking methods

Seven new quinoline-based bioorganic compounds were prepared by solvent-free synthesis and characterized using spectral techniques. The binding of these compounds with human serum albumin (HSA) was investigated by multi-spectroscopic methods. The quenching of Trp fluorescence upon addition of these compounds to HSA confirmed their significant binding. The quenching analysis at three different temperatures revealed that the complex formation is static and the reaction is entropy driven, spontaneous, and exothermic. Hydrogen bonds and van der Waals forces mainly contributed in the interactions as confirmed by the negative ΔH and ΔS values as well as molecular docking. The results from the circular dichroism (CD) spectroscopy indicated the minimal conformational changes of the protein upon binding with these quinoline compounds. The specific binding site and mode of interactions with HSA were also modeled using induced fit molecular docking procedure and their binding site was found to be in the interface of domains II and III, which is similar to the binding of the drug iodipamide with serum albumin.Communicated by Ramaswamy H. Sarma

Benzoquinoline amines – Key intermediates for the synthesis of angular and linear dinaphthonaphthyridines

A systematic study on the condensation reaction of 2,4-dichlorobenzo[h]quinoline and naphth-1-ylamine in the presence of CuI as catalyst to functionalised mono- and di-substituted (naphthalen-1-yl)benzo[h]quinoline amines was described. Subsequently these mono- and di-substituted amines on polyphosphoric acid catalysed cyclisation reaction with aromatic/heteroaromatic carboxylic acids led to the construction of angular and linear aromatic/heteroaromatic substituted dinaphthonaphthyridines in good yields.

Photoactive amorphous molecular materials based on quinoline amines and their synthesis by Friedländer condensation reaction

A new class of conjugated quinoline amines was prepared by Friedländer condensation reaction. They showed stable amorphous state below glass transition temperatures as examined by differential scanning calorimetry and X-ray diffraction studies. Additionally, they exhibited fluorescence properties in the blue to green region of visible spectrum in both solution and solid state. Their fluorescence quantum efficiencies in chloroform were in a broad range of 3–45%. Interestingly, they formed stable fibers with micrometer thickness drawn from melt, which were characterized by polarizing optical microscopy and scanning electron microscopy studies.

Interfering basic materials in urine from racing greyhounds

Three quinoline amines, 2-aminomethylquinoline, 2-hydroxymethylquinoline and quinaldine (2-methylquinoline), are identified in greyhound urine. These amines can interfere in the analysis of greyhound material for basic drugs. This is a special problem in ultraviolet spectrometry since their extinction coefficients are high. Reference analytical data for these quinoline amines and for six related compounds are given. The techniques used are infrared spectrometry, ultraviolet spectrometry, fluorometry, thin-layer chromatography, gas chromatography and mass spectrometry.

Interfering basic materials in urine from racing greyhounds

Three quinoline amines, 2-aminomethylquinoline, 2-hydroxymethylquinoline and quinaldine (2-methylquinoline), are identified in greyhound urine. These amines can interfere in the analysis of greyhound material for basic drugs. This is a special problem in ultraviolet spectrometry since their extinction coefficients are high. Reference analytical data for these quinoline amines and for six related compounds are given. The techniques used are infrared spectrometry, ultraviolet spectrometry, fluorometry, thin-layer chromatography, gas chromatography and mass spectrometry.

Sulfanilyl Derivatives of Pyridine and Quinoline Amines

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSulfanilyl Derivatives of Pyridine and Quinoline AminesRobert WinterbottomCite this: J. Am. Chem. Soc. 1940, 62, 1, 160–161Publication Date (Print):January 1, 1940Publication History Published online1 May 2002Published inissue 1 January 1940https://doi.org/10.1021/ja01858a045RIGHTS & PERMISSIONSArticle Views300Altmetric-Citations8LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (216 KB) Get e-Alerts Get e-Alerts