Synthesis, Topoisomerase I and II Inhibitory Activity, Cytotoxicity, and Structure-activity Relationship Study of Rigid Analogues of 2,4,6-Trisubstituted Pyridine Containing 5,6-Dihydrobenzo[h]quinoline Moiety

Jeong, Byeong Seon; Choi, Ho-Young; Thapa, Pritam; Karki, Radha; Lee, Eun-Young; Nam, Jung Min; Na, Younghwa; Ha, Eun Mi; Kwon, Young Joo; Lee, Eung Seok

doi:10.5012/bkcs.2011.32.1.303

Cited by 23 publications

(4 citation statements)

References 22 publications

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“…Different pyridine derivatives were studied for a variety of human cancer cell lines as a tool for novel anticancer drugs through the topoisomerase inhibitory activity. These results show various reports regarding different derivatives, such as bioisosteres of α-terthiophene as a potent for protein kinase C inhibitor [ 5 ], promising topoisomerase I and/or II inhibitory activity, as well as cytotoxicity against a variety of human cancer cell lines [ 6 , 7 , 8 , 9 , 10 ].…”

Section: Introductionsupporting

confidence: 79%

Synthesis, Molecular Docking Study, and Cytotoxicity Evaluation of Some Novel 1,3,4-Thiadiazole as Well as 1,3-Thiazole Derivatives Bearing a Pyridine Moiety

et al. 2022

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Pyridine, 1,3,4-thiadiazole, and 1,3-thiazole derivatives have various biological activities, such as antimicrobial, analgesic, anticonvulsant, and antitubercular, as well as other anticipated biological properties, including anticancer activity. The starting 1-(3-cyano-4,6-dimethyl-2-oxopyridin-1(2H)-yl)-3-phenylthiourea (2) was prepared and reacted with various hydrazonoyl halides 3a–h, α-haloketones 5a–d, 3-chloropentane-2,4-dione 7a and ethyl 2-chloro-3-oxobutanoate 7b, which afforded the 3-aryl-5-substituted 1,3,4-thiadiazoles 4a–h, 3-phenyl-4-arylthiazoles 6a–d and the 4-methyl-3- phenyl-5-substituted thiazoles 8a,b, respectively. The structures of the synthesized products were confirmed by spectral data. All of the compounds also showed remarkable anticancer activity against the cell line of human colon carcinoma (HTC-116) as well as hepatocellular carcinoma (HepG-2) compared with the Harmine as a reference under in vitro condition. 1,3,4-Thiadiazole 4h was found to be most promising and an excellent performer against both cancer cell lines (IC50 = 2.03 ± 0.72 and 2.17 ± 0.83 µM, respectively), better than the reference drug (IC50 = 2.40 ± 0.12 and 2.54 ± 0.82 µM, respectively). In order to check the binding modes of the above thiadiazole derivatives, molecular docking studies were performed that established a binding site with EGFR TK.

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Section: Introductionsupporting

confidence: 79%

Synthesis, Molecular Docking Study, and Cytotoxicity Evaluation of Some Novel 1,3,4-Thiadiazole as Well as 1,3-Thiazole Derivatives Bearing a Pyridine Moiety

et al. 2022

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“…They are also used as selective and potent human neurokinin-3 receptor antagonists (HNK-3) 27 . Furthermore, synthetic and drug chemists are attracted by functionalized dihydrobenzo[ h ]quinolines because they are possess some pharmacological activities, including, but not limited to, anti-tumor 28 , anti-cancer 29 , and anti-bacterial activity 30 . As a result of these elegant applications and features and in the continuation of our efforts to develop novel protocols for synthesizing N -containing heterocycles 31 – 42 , 6,7-dihydro-5 H -benzo[6,7]cyclohepta[1,2- b ]pyridine and 5,6-dihydrobenzo[ h ]quinoline have attracted our attention.…”

Section: Introductionmentioning

confidence: 99%

High pressure assisted synthetic approach for novel 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine and 5,6-dihydrobenzo[h]quinoline derivatives and their assessment as anticancer agents

Behbehani

Aryan

Dawood

et al. 2020

Sci Rep

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A novel, expedient and effective methodology for the synthesis of distinctly substituted 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine and 5,6-dihydrobenzo[h]quinoline systems has been developed with a new synthetic platform. This process includes ammonium acetate-mediated cyclocondensation reactions of 3-oxo-2-arylhydrazonopropanals with benzosuberone and tetralone precursors, respectively, using the high-pressure Q-tube reactor, which has been found to be superior to both conventional heating and microwave irradiation. The novel protocol benefits from its high atom efficiency, economy, ease of workup, broad substrate scope and is also applicable to gram-scale synthesis. To identify and confirm the newly synthesized targeted compounds, the X-ray single-crystal as well as all possible spectroscopic methods were utilized. The cytotoxicity of the newly synthesized 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine 4a–j and 5,6-dihydrobenzo-[h]quinolines derivatives 6a–e were preliminary examined toward three cell lines of human cancer; lung cancer (A549), breast cancer (MCF-7) and colon cancer (HCT-116), by applying the MTT colorimetric assay. The achieved results reflected the promising profile of the prepared compounds in this study against cancer cells and have shown that members from the synthesized 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine 4a–j exhibited promising cytotoxicity’s against MCF-7, and A549 cancer cells respectively, while the HCT-116 (colon) cancer cells were inhibited by certain examples of 5,6-dihydrobenzo[h]quinoline derivatives 6c,d. These promising results could serve as a good primary base for further research into the design of anticancer drugs.

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“…Some pyridine derivatives were contemplated for their topoisomerase inhibitory action and cytotoxicity against a few human malignant growth cell lines, thus marking them as novel anticancer agents [10]. Accordingly, it has been accounted those different pyridine derivatives, as bioisosteres of α-terthiophene (protein kinase C inhibitor) [11], have significant topoisomerase I and II inhibitory activity and cytotoxicity against many human cancer cell lines [12–15].…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis and antiproliferative activity of new 3-cyanopyridines

et al. 2019

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BackgroundPyridines have been reported to possess various pharmacological activities.ResultsSodium 3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-en-1-olate (2) and sodium 3-oxo-3-(3-oxo-3H-benzo[f]chromen-2-yl)prop-1-en-1-olate (7) were prepared and reacted with 2-cyano-N’-(1-aryl(heteryl)ethylidene)acetohydrazides 3a–d to produce 2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives 5a–d and 9a–d, respectively, in good yields. Also, 3a–d reacted with sodium (2-oxocyclopentylidene)methanolate (11a) or sodium (2-oxocyclohexylidene) methanolate (11b) to yield 2-oxo-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitriles 13a–d and 2-oxo-hexahydroquinoline-3-carbonitriles 13e–h, respectively. The mechanisms that account for the formation of the products are discussed. Additionally, the structures of all the newly synthesized products are confirmed, based on elemental analysis and spectral data. Several of the newly synthesized compounds are evaluated for their antitumor activity against HEPG2 and their structure activity relationship (SAR) was studied.ConclusionsThe results revealed that the pyridine derivatives 5c and 5d (IC50 = 1.46, 7.08 µM, respectively) have promising antitumor activity against liver carcinoma cell line (HEPG2), compared to the reference drug, doxorubicin.

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Synthesis, Topoisomerase I and II Inhibitory Activity, Cytotoxicity, and Structure-activity Relationship Study of Rigid Analogues of 2,4,6-Trisubstituted Pyridine Containing 5,6-Dihydrobenzo[h]quinoline Moiety

Cited by 23 publications

References 22 publications

Synthesis, Molecular Docking Study, and Cytotoxicity Evaluation of Some Novel 1,3,4-Thiadiazole as Well as 1,3-Thiazole Derivatives Bearing a Pyridine Moiety

Synthesis, Molecular Docking Study, and Cytotoxicity Evaluation of Some Novel 1,3,4-Thiadiazole as Well as 1,3-Thiazole Derivatives Bearing a Pyridine Moiety

High pressure assisted synthetic approach for novel 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine and 5,6-dihydrobenzo[h]quinoline derivatives and their assessment as anticancer agents

Facile synthesis and antiproliferative activity of new 3-cyanopyridines

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