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Fused tetracyclic systems containing a quinoline nucleus represent an important class of heterocyclic bioactive natural products and pharmaceuticals because of their significant and wide-spectrum biological properties. Several of these compounds have been obtained with diverse pharmacological and biological activities, such as antiplasmodial, antif...
Citations
... The fusion of quinoline to other different homo/heterocyclic rings results in novel scaffold which has earned strong reputation for having versatile pharmacological activities. [20] Hence, by placing emphasis on the importance of fused quinoline backbones, some reviews focus on tricyclic fused-quinoline, [21] fused tetracyclic quinoline [22] and quinoline-fused heterocycles with sulfur atom. [23] This review provides a comprehensive compilation of fused homo/heterocyclic rings to the quinoline backbone. ...
Fused quinolines have gained substantial attention due to their significant biological and wide‐spectrum synthetic applications. This review supplies an encyclopedic document regarding the approaches developed for the synthesis of fused‐cyclic quinolines based on ring volume size reported thus far. This collected information will be valuable for medicinal chemists to obtain knowledge regarding designing new approaches in order to access biological active compounds.
... Refluxing a solution of 5-substituted thiophene-3-carboxaldehydes 30 and malonic acid in pyridine produced 5-substituted 3-(3-thienyl)acrylic acids 31, which upon heating with SOCl 2 in chlorobenzene underwent cyclization to produce the corresponding 3-chloro-thieno[2,3-b]thiophene-2-carbonyl chlorides 32 (Scheme 15) [37]. Thereafter, reaction of 32 with aniline derivatives in refluxing toluene afforded the 3-cholorothieno[2,3-b]thiophene-2-carboxamides 33, which were photochemically dehydro-halogenated to give the respective products 34 (Scheme 15) [37]. ...
... Refluxing a solution of 5-substituted thiophene-3-carboxaldehydes 30 and malonic acid in pyridine produced 5-substituted 3-(3-thienyl)acrylic acids 31, which upon heating with SOCl 2 in chlorobenzene underwent cyclization to produce the corresponding 3-chloro-thieno[2,3-b]thiophene-2-carbonyl chlorides 32 (Scheme 15) [37]. Thereafter, reaction of 32 with aniline derivatives in refluxing toluene afforded the 3-cholorothieno[2,3-b]thiophene-2-carboxamides 33, which were photochemically dehydro-halogenated to give the respective products 34 (Scheme 15) [37]. Thienoquinolone 36 was synthesized as shown in Scheme 16. ...
The quinoline scaffold has become an important construction motif for the development of new drugs. The quinolones and their heteroannulated derivatives have high importance due to their diverse spectrum of biological activities as antifungal, anti-inflammatory, anti-diabetes, anti-Alzheimer’s disease, antioxidant and diuretic activities. This review summarizes the various new, efficient and convenient synthetic approaches to synthesize diverse quinolone-based scaffolds and their biological activities. We also dealt with the important mechanism, the route and type of reactions of the obtained products. The biological activities of some heteroannulated quinolones were also discussed.
Graphic abstract
... The antiviral zidovudine, the anticancer 5-fluorouracil and the antifungal flucytosine ( Fig. 2) are among the pyrimidine-containing chemotherapeutics currently in use, [15] in addition to several pharmacological properties such as anticancer [16][17][18] and selective inhibitors for multidrug resistance (MDR). [19] Given the promising properties of pyrimidines and quinolines and as a sequel to our work on the synthesis of biologically active fused quinolines, [20][21][22][23][24][25][26][27][28][29][30] we decided to study the effect of combining the pyrimidine and quinoline scaffolds in one molecule on the biological activity of such a ring system. Many attentions have been focused on the synthesis and bioactivities of pyrimido [5,4-c]quinolines. ...
A novel series of pyrimido[5,4-c]quinoline derivatives variously substituted at positions 2 and 5 have been synthesized, in good to excellent yields, via rapid base-catalyzed cyclization reaction of 2,4-dichloroquinoline-3-carbonitrile (5) with guanidine hydrochlorides 6a-c. All the synthesized compounds were screened for their in vitro antiproliferative activity. The most active hybrids 26a-d, 28a-d, and 30B were assessed against topoisomerase (topo) I, topo IIα, CDK2, and EGFR. The majority of the tested compounds exhibited selective topo I inhibitory activity while had weak topo IIα inhibitory action with compounds 30B and 28d, showed better topo I inhibitory activity than the reference camptothecin. Compound 30B, the most potent derivative as antiproliferative agent, exhibited moderate activity against CDK2 (IC50 = 1.60 µM). The results of this assay show that CDK2 is not a potential target for these compounds, implying that the observed cytotoxicity of these compounds is due to a different mechanism. Compounds 30B, 28d, and 28c were found to be the most potent against EGFR and their EGFR inhibitory activities (IC50 = 0.40±0.2, 0.49±0.2, and 0.64±0.3, respectively) relative to the positive control erlotinib (IC50 = 0.07 ± 0.03 µM). These results revealed that topo I and EGFR are attractive targets for this class of chemical compounds.
... Quinoline is a heterocyclic compound with few chemical applications on its own. However, several of its derivatives have numerous applications such as pharmaceutical preparations [1], agricultural chemistry [2], materials and dyes [3], as well as in medicine. Recently, the nucleus of quinoline and plenty of its derivatives grasped interest to chemists and biologists owing to their many and necessary applications within the field of medicine as a number of them are used as antituberculosis [1,4,5], antimalarial [6], anticancer [7], antibiotic [8], hypotensive, antiviral [1], antioxidant [9], and antifungal [10]. ...
... e main objective of the study in this manuscript is the spectroscopic investigations and computational calculations of compounds under study using the DFT method followed by the determination of the accurate functional as well as the basis set using TD-DFT to arrive at the accurate theoretical results and comparing them with the experimental ones. [1,3,2] diaazaborininodiquinoline acetonitrile (DDPA) were provided by Professor Dr. Ewald Daltrozzo of Konstanz University, Germany, and used without further purification. All solvents employed in this work were of chemical analysis grade and were preliminary checked for the absence of absorbing or fluorescent impurities among the scanned spectral ranges. ...
Quinoline derivatives such as 15,15-difluoro-[1,3,2] diaazaborininodiquinoline (DDP) and 15,15-difluoro-[1,3,2] diaazaborininodiquinoline acetonitrile (DDPA) have a range of biological and medical activities. So, it is vital to shed light on these
compounds in terms of their optical properties supported by quantum calculations. )e absorption and emission spectra of
studied compounds were measured within the laboratory, whereas the quantum calculations were performed utilizing the density
functional theory (DFT) calculations. Additionally, the time-dependent density functional theory (TD-DFT) was applied for the
comparison of some sensible results with the theoretical ones. )e molecular structures of these compounds were presented via
applying chemical analysis techniques. )e electronic absorption spectra of DDP and DDPA molecular structures were monitored
through an experiment in hosts such as carbon tetrachloride (CCl4), chloroform (CHCl3), methylene dichloride (CH2Cl2),
acetone, and dimethyl sulfoxide (DMSO). Also, the influence of pH on the absorption spectra of the DDP molecule was studied.
)e molecular structures of these quinoline derivatives have been optimized via utilizing the B3LYP/6-31G (d) level of theory. )e
electronic absorption and emission spectra of the DDP compound in gas, THF, and DMSO have been calculated utilizing TD-DFT
at the CAM-B3LYP/6-31G ++(d, p) level
... Currently, many quinoline-containing drugs are available on the market [3,4]. Recently, three 5a, 5b ...
A series of 1,3,4-oxadiazole bridged pyrazole/isoxazole bearing quinoline derivatives has been designed and synthesized by a clean and convenient method. Structures of the newly synthesized compounds have been confirmed by FTIR, 1H and 13C NMR, and HRMS spectral data. The titled compounds have been evaluated for their molecular docking guided antimicrobial and anti-inflammatory activity. One of 1,3,4-oxadiazole bridged quinolinyl-pyrazole derivatives has interacted efficiently with E. Coli protein (PDB file: 1KZN), and has been characterized by good antimicrobial activity against the majority of the tested pathogens. Another product has exhibited excellent anti-inflammatory activity.
... [24] Synthesized quinoline hetero-cyclic compounds are synthesis has become a powerful for making new molecules for drug discovery and development [25] and other hands, quinoline derivatives owe their popularity since quinoline ring is quickly available synthetic approaches have been reported. [26,27] Although modern methods of Conrad-Limpach, [28] Niementowski, [29,30] Doebner-Miller, [31] Vilsmeier-Haak reactions [32] Claisen condensation reaction of amines with carboxyl derivative followed by cyclization to produce the desired quinolines molecule. [33] The classical multistep reaction operations, not only results in an increase in efficiency and but also reduces the generating large quantities of waste. ...
An exclusive approach towards the synthesis of novel 3-(hydroxymethyl)-2-phenyl-2,3 dihydroquinolin-4(1H)-one and it's in-silico evaluation as inhibitor of COVID-19 main protease. The one-pot synthesis of an established procedure Claisen ester condensation reaction was sodium hydride mediated with intramolecular cyclization with solvent free conditions. The structures of the synthesized compound were confirmed by IR, 1H,13C NMR, and EI-MS spectral studies. Chemo-informatics study showed that the compound obeyed the Lipinski's rule, PASS, Swiss ADME. Computational docking analysis was performed using PyRx, AutoDock Vina option based on scoring functions. In-silico molecular docking study results demonstrated Greater binding energy and affinity to the active pocket the N3 binding site of the Coronavirus primary protease.
... Product 6c and 6d with chloro and nitro substituent at the para position of the aromatic aldehyde with ethyl cyanoacetate gave excellent yield 85 and 90% in 30 and 25 min, respectively (Table 3, entries 18 and 19). Next, we further examined the effect of the electron-donating group (EDG) on the aromatic aldehydes, we found that the reaction rate on these substituents contain EDG decreased than the EWG (Table 3, entries [10][11][12][13][14][15][16][17][18][19]. Methyl substituent at ortho and para position afforded compounds 5 g, 5j, and 6a with 86%, 87% and 84% yields, respectively (Table 3, entries 7, 10, 16). ...
A newer, convenient and efficient approach has been designed for the
diverse synthesis of 2-amino-4H-pyranoquinolines and achieved by a one-
pot three-component reaction of aromatic aldehydes with ethyl cyanoace-
tate/malononitrile and 8-hydroxyquinoline catalyzed by b-cyclodextrin as a
reusable supramolecular catalyst in an aqueous medium under ultrasound
irradiation. Target products were synthesized in a tandem process, which
meets their requirements of pharmaceutical chemistry.
... Cascade enzyme reactions have been utilized with different purposes, especially in the development of a more-efficient synthesis of chemical compounds, such as bioactive oligosaccharides, glycosylated molecules, or amoniacid derivatives [21][22][23][24][25][26]. ...
Cascade reactions have been described as efficient and universal tools, and are of substantial interest in synthetic organic chemistry. This review article provides an overview of the novel and recent achievements in enzyme cascade processes catalyzed by multi-enzymatic or chemoenzymatic systems. The examples here selected collect the advances related to the application of the sequential use of enzymes in natural or genetically modified combination; second, the important combination of enzymes and metal complex systems, and finally we described the application of biocatalytic biohybrid systems on in situ catalytic solid-phase as a novel strategy. Examples of efficient and interesting enzymatic catalytic cascade processes in organic chemistry, in the production of important industrial products, such as the designing of novel biosensors or bio-chemocatalytic systems for medicinal chemistry application, are discussed
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Isatins have been widely used in the preparation of a variety of heterocyclic compounds, where the skeletal editing of isatins has shown significant advantages for the construction of diverse heterocycles. This review highlights the progress made in the last decade (2013−2023) in the skeletal editing of the isatin scaffold. A series of ring expansion reactions for the construction of quinoline skeleton, quinolone skeleton, polycyclic quinazoline skeleton, medium‐sized ring skeleton, as well as a series of ring opening reactions for the generation of 2‐(azoly)aniline skeleton by the cleavage of C−C bond and C−N bond are highlighted. It is hoped that this review will provide some understanding of the chemical transformations of isatins and contribute to the further realization of its molecular diversity.
