Synthesis and characterization of pyrrolo[1,2-a]quinoline derivatives for their larvicidal activity against Anopheles arabiensis

Uppar, Vijayakumar; Chandrashekharappa, Sandeep; Venugopala, Katharigatta N.; Deb, Pran Kishore; Kar, Supratik; Alwassil, Osama I.; Gleiser, Raquel M.; Garcı́a, Daniel A.; Odhav, Bharti; Mohan, Mahendra K.; Venugopala, Rashmi; Padmashali, Basavaraj

doi:10.1007/s11224-020-01516-w

Cited by 28 publications

(8 citation statements)

References 43 publications

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“…Construction of the title compounds 4a-k was achieved by a two-step chemical synthesis (Scheme 1). Purification was completed by column chromatography and the yield was 54-67% after purification [19,23]. The purity of the compounds was ascertained by high-performance liquid chromatography (HPLC) and was found to be >99%.…”

Section: Chemistrymentioning

confidence: 99%

“…Synthesis of a series of ethyl 1-(substituted benzoyl)-5-methylpyrrolo[1,2-a]quinoline-3-carboxylate 4a-f and dimethyl 1-(substituted benzoyl)-5-methylpyrrolo[1,2-a]quinoline-2,3-dicarboxylate 4g-k analogues were achieved at 54-67% yield (Scheme 1 and Figure 2). The characterization of the title compounds 4a-k is completed by instrumental techniques such as FT-IR, 1 H-NMR, and 13 C-NMR ( Figures S1-S33 are available as supplementary with experimental details) [19,23]. The purity of the compounds was confirmed by HPLC and it was found to be more than 99%.…”

Section: Chemistry Of Compoundsmentioning

confidence: 99%

“…These scaffolds have attracted the attention of medical chemists, as they exhibit a wide variety of pharmacological properties [15]. The pyrrolo [1,2-a]quinoline derivatives possess antioxidant [16], anti-inflammatory [17,18], larvicidal [19], and antiviral [20] activities. 4-Amino-pyrrolo [2,3-b]quinoline has also been tested as a potential treatment for Alzheimer's disease [21].…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxicity and Antimycobacterial Properties of Pyrrolo[1,2-a]quinoline Derivatives: Molecular Target Identification and Molecular Docking Studies

et al. 2020

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A series of ethyl 1-(substituted benzoyl)-5-methylpyrrolo[1,2-a]quinoline-3-carboxylates 4a–f and dimethyl 1-(substituted benzoyl)-5-methylpyrrolo[1,2-a]quinoline-2,3-dicarboxylates 4g–k have been synthesized and evaluated for their anti-tubercular (TB) activities against H37Rv (American Type Culture Collection (ATCC) strain 25177) and multidrug-resistant (MDR) strains of Mycobacterium tuberculosis by resazurin microplate assay (REMA). Molecular target identification for these compounds was also carried out by a computational approach. All test compounds exhibited anti-tuberculosis (TB) activity in the range of 8–128 µg/mL against H37Rv. The test compound dimethyl-1-(4-fluorobenzoyl)-5-methylpyrrolo[1,2-a]quinoline-2,3-dicarboxylate 4j emerged as the most promising anti-TB agent against H37Rv and multidrug-resistant strains of Mycobacterium tuberculosis at 8 and 16 µg/mL, respectively. In silico evaluation of pharmacokinetic properties indicated overall drug-likeness for most of the compounds. Docking studies were also carried out to investigate the binding affinities as well as interactions of these compounds with the target proteins.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistry Of Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cytotoxicity and Antimycobacterial Properties of Pyrrolo[1,2-a]quinoline Derivatives: Molecular Target Identification and Molecular Docking Studies

et al. 2020

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“…For instance, recent publications from V. Uppar et al (2020) and others shows that pyrrolo[1,2-a]quinoline derivatives effectively inhibit the activity of microbial pathogens such as bacteria (both Gram-positive and Gram-negative) [ 44 , 53 , 54 , 55 , 56 ], and fungus [ 57 ], followed by various disease conditions such as cancer [ 58 ], malaria [ 59 ], inflammation [ 60 ] and Alzheimer disease [ 61 ]. In addition, these derivatives possess antioxidant activity [ 44 , 54 , 55 , 56 ]. Further, ethyl-1-(subbenzoyl)-5-methylpyrrolo[1,2-a]quinoline-3-carboxylate and dimethyl 1-(subbenzoyl)-5-methylpyrrolo[1,2-a]quinoline-2,3-dicarboxylate derivatives have been tested for their larvicidal activity against Anopheles arabiensis [ 56 ].…”

Section: Introductionmentioning

confidence: 99%

Investigation of Antifungal Properties of Synthetic Dimethyl-4-Bromo-1-(Substituted Benzoyl) Pyrrolo[1,2-a] Quinoline-2,3-Dicarboxylates Analogues: Molecular Docking Studies and Conceptual DFT-Based Chemical Reactivity Descriptors and Pharmacokinetics Evaluation

et al. 2021

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Candida albicans, an opportunistic fungal pathogen, frequently colonizes immune-compromised patients and causes mild to severe systemic reactions. Only few antifungal drugs are currently in use for therapeutic treatment. However, evolution of a drug-resistant C. albicans fungal pathogen is of major concern in the treatment of patients, hence the clinical need for novel drug design and development. In this study, in vitro screening of novel putative pyrrolo[1,2-a]quinoline derivatives as the lead drug targets and in silico prediction of the binding potential of these lead molecules against C. albicans pathogenic proteins, such as secreted aspartic protease 3 (SAP3; 2H6T), surface protein β-glucanase (3N9K) and sterol 14-alpha demethylase (5TZ1), were carried out by molecular docking analyses. Further, biological activity-based QSAR and theoretical pharmacokinetic analysis were analyzed. Here, in vitro screening of novel analogue derivatives as drug targets against C. albicans showed inhibitory potential in the concentration of 0.4 µg for BQ-06, 07 and 08, 0.8 µg for BQ-01, 03, and 05, 1.6 µg for BQ-04 and 12.5 µg for BQ-02 in comparison to the standard antifungal drug fluconazole in the concentration of 30 µg. Further, in silico analysis of BQ-01, 03, 05 and 07 analogues docked on chimeric 2H6T, 3N9K and 5TZ1 revealed that these analogues show potential binding affinity, which is different from the therapeutic antifungal drug fluconazole. In addition, these molecules possess good drug-like properties based on the determination of conceptual Density Functional Theory (DFT)-based descriptors, QSAR and pharmacokinetics. Thus, the study offers significant insight into employing pyrrolo[1,2-a]quinoline analogues as novel antifungal agents against C. albicans that warrants further investigation.

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“…Such properties are well co-related previously to the existence of certain phytochemicals. Hence, medicinal plants play an active role in cancer prophylaxis and management [3].…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial, anti-inflammatory, and anticancer activities of leaves extracts of Filicium decipiens

Basarikatti¹,

Mishra²,

Uppar³

et al. 2021

J App Biol Biotech

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Filicium decipiens (fern-tree) belongs to the family Sapindaceae. It grows in Asia and Africa region and is traditionally used for diabetes treatment in India. The plant has been documented to have molluscicidal, diabetic nephropathy, and anti-inflammatory properties. In the present study, experimental data on different leaves extracts of F. decipiens were collected for their preliminary phytochemical investigations along with antimicrobial, anti-inflammatory, and anticancer activities using in-vitro assays. The phytochemical investigations display the existence of alkaloids, tannins, flavonoids, saponins, glycosides, steroids, triterpenoids, and carbohydrates in the extracts prepared using three different solvents. Antimicrobial property was established against six bacterial and fungal strains. Petroleum ether extract exhibited higher antimicrobial activity as compared to chloroform and water extract. Anti-inflammatory assay was performed on RAW264.7 murine macrophage cells and petroleum ether extract exhibited reduced nitrite oxide production having IC 50 value 493.7 µg/ml. Cytotoxicity was determined against MCF-7 (Breast) and A-549 (Lung) cancer cells and paclitaxel was used as a standard drug, whereas cytocompatibility was assessed against mouse fibroblast cells (L929). Different sensitivities were observed against different study cell lines in a dosedependent manner. These study findings may provide biological evidence for the application of Filicium decipiens extract.

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Synthesis and characterization of pyrrolo[1,2-a]quinoline derivatives for their larvicidal activity against Anopheles arabiensis

Cited by 28 publications

References 43 publications

Cytotoxicity and Antimycobacterial Properties of Pyrrolo[1,2-a]quinoline Derivatives: Molecular Target Identification and Molecular Docking Studies

Cytotoxicity and Antimycobacterial Properties of Pyrrolo[1,2-a]quinoline Derivatives: Molecular Target Identification and Molecular Docking Studies

Investigation of Antifungal Properties of Synthetic Dimethyl-4-Bromo-1-(Substituted Benzoyl) Pyrrolo[1,2-a] Quinoline-2,3-Dicarboxylates Analogues: Molecular Docking Studies and Conceptual DFT-Based Chemical Reactivity Descriptors and Pharmacokinetics Evaluation

Antimicrobial, anti-inflammatory, and anticancer activities of leaves extracts of Filicium decipiens

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