Discovery of Pyrazolo[4,3-c]quinolines Derivatives as Potential Anti-Inflammatory Agents through Inhibiting of NO Production

Tseng, Chih Hua; Tung, Chun Wei; Peng, Shin I.; Chen, Yeh Long; Tzeng, Cherng Chyi; Cheng, Chih Mei

doi:10.3390/molecules23051036

Cited by 17 publications

(11 citation statements)

References 39 publications

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“…A quinoline scaffold is a versatile synthetic building block in various natural products [1][2][3][4][5], exceptional pharmaceuticals [6][7][8], physical materials [9][10][11][12][13], and is an important intermediate for asymmetric synthesis [14][15][16][17][18]. Functionalized quinolines are broadly used in agrochemicals [19,20], dyes [21,22], and some biologically active molecules for antimalarial [23][24][25], anticancer [26][27][28][29][30], antiviral [31], antifungal [32], anti-bacterial [33], and anti-inflammatory functions [34,35]. In particular, since the 17th century, the quinoline alkaloid quinine has been viewed historically as the first cure for treating or preventing malaria, [36,37].…”

Section: Introductionmentioning

confidence: 99%

Environmentally Friendly Nafion-Catalyzed Synthesis of Substituted 2-Ethyl-3-Methylquinolines from Aniline and Propionaldehyde under Microwave Irradiation

2021

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Herein, we report a facile synthetic methodology for the preparation of 2,3-dialkylquinolines from anilines and propionaldehydes. This cyclization involved environmentally friendly Nafion® NR50 as an acidic catalyst with microwave irradiation as the heating source. A series of substituted 2-ethyl-3-methylquinolines were prepared from various anilines and propionaldehyde derivatives through this protocol with good to excellent yields. Some new chemical structures were confirmed by X-ray single-crystal diffraction analysis and the related data were provided. The plausible reaction mechanism studies are also discussed.

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Section: Introductionmentioning

confidence: 99%

Environmentally Friendly Nafion-Catalyzed Synthesis of Substituted 2-Ethyl-3-Methylquinolines from Aniline and Propionaldehyde under Microwave Irradiation

2021

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“…2 Quinoline or 1-aza-naphthalene is nitrogen containing heterocyclic aromatic compound. The quinoline core is significant heterocyclic moiety that is found in numerous naturally occurring quinoline alkaloids, therapeutic and synthetic compounds with wide range of biological activities such as antimalarial, antidiabetic 3 anti-inflammatory 4 antihypertensive and antibacterial agents. Due to their pivotal role in various biological processes, the quinoline derivatives are well explored as therapeutic agents and some of them have displayed antihyperglycemic activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antidiabetic Evaluation and Bioisosteric Modification of Quinoline Incorporated 2-pyrazoline Derivatives

Kumar¹,

Kumar²,

Shetty³

et al. 2021

IJPER

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Background: Diabetes mellitus is a pervasive illness worldwide with many progressively increasing complications day by day. The quinoline nucleus is important heterocyclic moiety with different biological activities. Due to their pivotal role in different biological processes they are well explored as therapeutic agents and some of them have exhibited antihyperglycemic activity. Different substituted pyrazoles have been accounted for their in vivo antidiabetic activity, but we concentrated to substituted pyrazoline derivatives in the quest for novel basic classes of medications inhibiting the action of the ATP-K + beta cell pancreatic membrane channel, prompting the release of insulin. Materials and Methods: In the present study, 1-(4-(7-Chloroquinolin-4-yl oxy) phenyl ethanone and 1-(4-(7-Chloroquinolin-4-yl amino) phenyl ethanone was synthesized by nucleophilic substitution of 4-Chloro of 4,7-dichloroquinoline with substituted 4-hydroxy acetophenone and 4-amino acetophenone in DMF and KOH respectively. The amino linked chalcones and oxo linked chalcones was synthesized by Clasein Schmidt condensation with different substituted aromatic aldehydes. Finally substituted pyrazolines (ACP1-ACP10) was synthesized upon cyclisation of oxo linked and amino linked chalcones with hydrazine hydrate. The structures of the final synthesized compounds were characterized by IR, 1 H NMR and mass spectra. Results: The final synthesized compounds were evaluated for their in vitro antidiabetic activity by alpha glucosidase inhibition assay. Most of the compounds showed good antidiabetic activity compared to the standard drug acarbose. Conclusion:In-vitro results revealed that a large number of synthesized compounds having good antidiabetic activity. So these compounds are found to be interesting lead molecules for further synthesis as antidiabetic agents.

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“…Among N ‐containing heterocycles, the quinoline nucleus was found in nature, and many biologically active derivatives were extensively explored in different therapeutic areas such as antimalarial, [ 7 ] antibacterial, [ 8 ] antifungal, [ 9 ] anti‐inflammatory, [ 10 ] antimicrobial, [ 11 ] and antituberculosis. [ 12 ] Quinoline derivatives isolated from natural products also exhibited substantial antitubercular activity.…”

Section: Introductionmentioning

confidence: 99%

Quinoline‐Proline, Triazole Hybrids: Design, Synthesis, Antituberculosis, Molecular Docking, and ADMET Studies

Ganesan¹,

Raja²,

Murugesan

et al. 2021

Journal of Heterocyclic Chem

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A series of novel quinoline‐proline hybrids (11a‐g) and quinoline‐proline‐1,2,3‐triazole hybrids (12‐14) were synthesized by click chemistry based on molecular hybridization concept and were characterized by NMR, mass spectrometry, and elemental analysis. All the titled target compounds were tested for antitubercular activity by MABA and LORA methods by in vitro. Interestingly, two compounds (2R,4S)‐1‐((2‐cyclopropyl‐4‐(4‐fluorophenyl)‐quinolin‐3‐yl)‐methyl)‐4‐(4‐nitrobenzamido)‐N‐phenylpyrrolidine‐2‐carboxamide (11b) and (2R,4S)‐1‐((2‐cyclopropyl‐4‐(4‐fluorophenyl)‐quinolin‐3‐yl)‐methyl)‐4‐(4‐fluorobenzamido)‐N‐phenylpyrrolidine‐2‐carboxamide (11c) exhibited significant activity against the tested Mycobacterium tuberculosis H37Rv strain. Further, the cytotoxicity (CC50) profile of the titled compounds against the Vero cell was performed and discussed. A molecular docking study of the hit compounds (11b and 11c) was also performed to find their putative binding interaction with the active site of the target proteins. Finally, in silico ADMET properties were also predicted for all the synthesized molecules to evaluate their drug‐likeness behavior.

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Discovery of Pyrazolo[4,3-c]quinolines Derivatives as Potential Anti-Inflammatory Agents through Inhibiting of NO Production

Cited by 17 publications

References 39 publications

Environmentally Friendly Nafion-Catalyzed Synthesis of Substituted 2-Ethyl-3-Methylquinolines from Aniline and Propionaldehyde under Microwave Irradiation

Environmentally Friendly Nafion-Catalyzed Synthesis of Substituted 2-Ethyl-3-Methylquinolines from Aniline and Propionaldehyde under Microwave Irradiation

Synthesis, Antidiabetic Evaluation and Bioisosteric Modification of Quinoline Incorporated 2-pyrazoline Derivatives

Quinoline‐Proline, Triazole Hybrids: Design, Synthesis, Antituberculosis, Molecular Docking, and ADMET Studies

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