Pyrazolo[3,4-h]quinolines promising photosensitizing agents in the treatment of cancer

Spanò, Virginia; Parrino, Barbara; Carbone, Anna; Montalbano, Alessandra; Salvador, Alessia; Brun, Paola; Vedaldi, Daniela; Diana, Patrizia; Cirrincione, Girolamo; Barraja, Paola

doi:10.1016/j.ejmech.2015.08.003

Cited by 60 publications

(34 citation statements)

References 66 publications

(48 reference statements)

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“…The quinoline ring occurs in various natural products and represents a key motif in medicinal chemistry [9][10][11][12], and its derivatives, quinoline-4-carboxylic acids, are a group of compounds associated with different biological activities, such asantiviral [13], anti-inflammatory [14], antimicrobial [15], anti-atherothrombosis [16], antiemetic [17], anxiolytic [18], antimalarial and antileishmanial [19]. Although quinoline-4-carboxylic acid derivatives exhibit various bioactivities, the research of new quinoline-4-carboxylic acid-based antibacterial drugs has developed slowly.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives

et al. 2016

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A series of new 2-phenyl-quinoline-4-carboxylic acid derivatives was synthesized starting from aniline, 2-nitrobenzaldehyde, pyruvic acid followed by Doebner reaction, amidation, reduction, acylation and amination. All of the newly-synthesized compounds were characterized by 1 H-NMR, 13 C-NMR and HRMS. The antibacterial activities of these compounds against Gram-negative (Escherichia coli, Pseudomonas aeruginosa) and Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis), as well as one strain of methicillin-resistant Staphylococcus aureus (MRSA) bacteria were evaluated by the agar diffusion method (zone of inhibition) and a broth dilution method (minimum inhibitory concentration (MIC)), and their structure-activity relationships were obtained and discussed. The results revealed that some compounds displayed good antibacterial activity against Staphylococcus aureus, and Compounds 5a 4 and 5a 7 showed the best inhibition with an MIC value of 64 µg/mL against Staphylococcus aureus and with an MIC value of 128 µg/mL against Escherichia coli, respectively. The results of the MTT assay illustrated the low cytotoxicity of Compound 5a 4 .

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives

et al. 2016

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“…Pyrazolo [4,3-c]quinoline derivatives serve as photosensitizing anti-cancer agents [7], benzodiazepine antagonists [8], selective cyclooxygenase-2 (COX-2) inhibitors [9] and others exhibit anti-inflammatory properties [6]. Interest in pyrazolo [4,3-c]quinoline-based compounds is (9) 0.0300 (9) not only limited to the synthesis or development of more diverse and complex bioactive derivatives for structureactivity relationship evaluations, but has since been extended to focus on their photophysical properties as potential photosensitizing anti-cancer agents and fluorescence probes.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(4-chlorophenyl)-6,8-diphenyl-1H-pyrazolo[4,3-c]quinoline, C₂₈H₁₈ClN₃

Maluleka

Mphahlele

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound was previously prepared by the reaction of 6,8-dibromo-4-chloroquinoline-3-carbaldehyde with 4-chlorophenylhydrazine hydrochloride (1.5 equiv.) in ethanol in the presence of triethylamine (1.5 equiv.) to afford the corresponding (6,8-dibromo-4-chloroquinolin-3-yl Experimental detailsData reduction was carried out using SAINT+ software, and SADABS was used to make empirical absorption corrections [2]. The crystal structure was solved through direct methods using SHELXS-97 [3]. Hydrogen atoms were positioned geometrically and allowed to ride on their respective parent atoms with d(C-H) = 0.95 Å and U iso (H) = 1.2Ueq(C). Diagrams and publication material were generated using WinGX

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“…On the basis of source and action mechanisms, the anticancer drugs are classified as alkylating agents, antimetabolites, natural products, hormones and antagonistic, miscellaneous agents. Many scientists are intensively engaged in the development of new anticancer active agents that reveal a selective cytotoxicity for cancer cells over normal cells which is undoubtedly needed to treat the severe cancer disease more efficiently and is also less toxic, since many of the marketed anticancer drugs are toxic in nature [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

“…During recent years, there have been intense investigations of fused thiadiazole and pyrimidine systems. Literature survey revealed that (1,3,4)thiadiazolo(3,2-α)pyrimidine nucleus is associated with diverse pharmacodynamic and chemotherapeutic activities [18,19], including antimicrobial [19][20][21] and antitumor activities [18,20], herbicidal, antifungal, neuramidase inhibitors. 1,3,4-thiadiazolo(3,2-α)pyrimidines have been used as key building blocks for the preparation of a variety of novel bioactive agents [22], therefore, we thought it worthwhile to explore this coupled heterocyclic system for evaluation of anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound Mediated One-Pot, Three Component Synthesis, Docking and ADME Prediction of Novel 5-Amino-2-(4-chlorophenyl)-7-Substituted Phenyl-8,8a-dihydro-7H-(1,3,4)thiadiazolo(3,2-α)pyrimidine-6-carbonitrile Derivatives as Anticancer Agents

Tiwari¹,

Seijas

Vázquez-Tato

et al. 2016

Molecules

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Herein, we report an environmentally friendly, rapid, and convenient one-pot ultrasoundpromoted synthesis of 5-amino-2-(4-chlorophenyl)-7-substituted phenyl-8,8a-dihydro-7H-(1,3,4) thiadiazolo(3,2-α)pyrimidine-6-carbonitrile derivatives. The in-vitro anticancer activities of these compounds were evaluated against four human tumor cell lines. Among all the synthesized derivatives, compound 4i, which has substituent 3-hydroxy-4-methoxyphenyl is found to have the highest GI 50 value of 32.7 µM, 55.3 µM, 34.3 µM, 28.9 µM for MCF-7, K562, HeLa and PC-3 cancer cell lines respectively. A docking study of the newly synthesized compounds were performed, and the results showed good binding mode in the active site of thymidylate synthase enzyme. ADME properties of synthesized compounds were also studied and showed good drug like properties.

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Pyrazolo[3,4-h]quinolines promising photosensitizing agents in the treatment of cancer

Cited by 60 publications

References 66 publications

Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives

Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives

Crystal structure of 1-(4-chlorophenyl)-6,8-diphenyl-1H-pyrazolo[4,3-c]quinoline, C₂₈H₁₈ClN₃

Ultrasound Mediated One-Pot, Three Component Synthesis, Docking and ADME Prediction of Novel 5-Amino-2-(4-chlorophenyl)-7-Substituted Phenyl-8,8a-dihydro-7H-(1,3,4)thiadiazolo(3,2-α)pyrimidine-6-carbonitrile Derivatives as Anticancer Agents

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Pyrazolo[3,4-h]quinolines promising photosensitizing agents in the treatment of cancer

Cited by 60 publications

References 66 publications

Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives

Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives

Crystal structure of 1-(4-chlorophenyl)-6,8-diphenyl-1H-pyrazolo[4,3-c]quinoline, C28H18ClN3

Ultrasound Mediated One-Pot, Three Component Synthesis, Docking and ADME Prediction of Novel 5-Amino-2-(4-chlorophenyl)-7-Substituted Phenyl-8,8a-dihydro-7H-(1,3,4)thiadiazolo(3,2-α)pyrimidine-6-carbonitrile Derivatives as Anticancer Agents

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Crystal structure of 1-(4-chlorophenyl)-6,8-diphenyl-1H-pyrazolo[4,3-c]quinoline, C₂₈H₁₈ClN₃