2,6-Dithienyl-4-furyl pyridines: Synthesis, topoisomerase I and II inhibition, cytotoxicity, structure–activity relationship, and docking study

Basnet, Arjun; Thapa, Pritam; Karki, Radha; Choi, Ho-Young; Choi, Jae Hun; Yun, Minho; Jeong, Byeong‐Seon; Jahng, Yurngdong; Na, Younghwa; Cho, Won‐Jea; Kwon, Young Joo; Lee, Chong-Soon; Lee, Eung-Seok

doi:10.1016/j.bmcl.2009.11.041

Cited by 46 publications

(13 citation statements)

References 29 publications

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“…Some transition metal complexes of terpyridines have redox, magnetic and optical properties, photovoltaic applications and catalytic properties . Some terpyridine ligands and their complexes bind to RNA and DNA and have been investigated for antitumour activity against various human cell lines …”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, antimicrobial screening and DNA binding of novel silver(I)–thienylterpyridine and silver(I)–furylterpyridine complexes

Njogu

Martincigh

Omondi

et al. 2018

Applied Organom Chemis

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Six new silver(I) complexes, [(AgL1) 2 ](ClO 4 ) 2 (1), [(AgOTfL1) 2 ] (2), [(AgO 2 CF 3 L1) 2 ] (3), [AgL2](ClO 4 ) 2 (4), [(AgOTfL2) 2 ] (5) and [(AgO 2 CF 3 L2) 2 ] (6), were synthesized by reaction of 4′-(2-thienyl)-2,2′;6′,2″-terpyridine (L1)or 4′-(2-furyl)-2,2′;6′,2″-terpyridine (L2) with the respective silver salts, i.e. AgClO 4 , AgOTf or AgTFA. The complexes are dinuclear of the type Ag 2 L 2 in which the two ligands utilize the pyridinyl N atoms from the central rings and one of the peripheral rings to coordinate to one of the silver(I) centres while the remaining pyridinyl N atoms coordinate to the second silver(I) centre. Complexes 2 and 5 have the trifluoromethanesulfonate anion remotely coordinating via a single O atom while complex 3 has the trifluoroacetate anion coordinating to a single silver(I) centre in a bidentate mode. The perchlorate anion in complex 4 is excluded from the silver(I) coordination sphere.All complexes demonstrate moderate to high antimicrobial activity against the Gram-negative bacteria Escherichia coli and Salmonella typhimirium and the fungus Candida albicans. Complexes 1-6 interact strongly with salmon testes DNA as indicated by the steady increase in the relative viscosity of DNA solutions with increasing concentration of the silver(I) complexes and the relatively large intrinsic binding constants measured. There was substantial hyperchromism and hypsochromism recorded in solutions of complexes 1-6 with increasing concentration of salmon testes DNA. Complexes 1-6 interact with DNA via intercalation, and groove and external binding.

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Section: Introductionmentioning

confidence: 99%

“…Previous biological studies of furyl‐ and thienyl‐functionalised terpyridines have shown strong cytotoxicity against several human cancer cell lines and considerable topoisomerase I and II inhibitory activities . Incorporating a metal ion into such organic ligands influences their biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, antimicrobial screening and DNA binding of novel silver(I)–thienylterpyridine and silver(I)–furylterpyridine complexes

Njogu

Martincigh

Omondi

et al. 2018

Applied Organom Chemis

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“…Our study is aimed at designing and synthesizing topoisomerase-targeting anticancer agents. As a part of the study, we have previously designed, synthesized and reported several 2,4,6-triaryl pyridine derivatives as bioisosteres of terpyridine for the topoisomerase inhibitory activity and cytotoxicity against several human cancer cell lines [26][27][28][29][30][31][32][33][34]. Furthermore, we have introduced hydroxyl group(s) [24,25] into phenyl moiety to improve topo I and/or II inhibitory activities, and cytotoxicity against several human cancer cell lines.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Synthesis and biological activity of 2,4-di-p-phenolyl-6-2-furanyl-pyridine as a potent topoisomerase II poison

Karki

Park

Jun

et al. 2015

European Journal of Medicinal Chemistry

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“…It is well known that the incorporation of heterocyclic rings into prospective pharmaceutical candidates is a major tactic to gain activity and safety merits [21]. Heterocyclic rings such as thiophene are important pharmacophores in search of molecules with antiproliferation activity [22][23][24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative and in Silico Admet Study of New 4-(Piperidin-1-Ylmethyl)-2- (Thiophen-2-Yl) Quinoline Analogues

Harishkumar

2018

Asian J Pharm Clin Res

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Objective: Synthesis and antiproliferative study of novel 4-(piperidin-1-ylmethyl)-2-(thiophen-2-yl) quinoline 7(a-j) derivatives.Methods: 4-(piperidin-1-ylmethyl)-2-(thiophen-2-yl) quinolines were synthesized by the addition of 4-(chloromethyl)-2-(thiophen-2-yl) quinoline (0.01 mol), piperidine (0.01 mol) in DMF (10 v) and K 2 CO 3 ( 0.02 mol). The anticancer activity of the title compounds performed against T-47D, HeLa, HepG2, and MCF-7 human cancer cell lines growth was investigated by MTT assay. Results:The compounds 7b and 7g exhibited 90% of the growth inhibitory effect on T-47D, HeLa, and MCF-7 and also 80% growth inhibition in HepG2 when compared with standard drug paclitaxel. Conclusion:The synthesized compounds 4-(piperidin-1-ylmethyl)-2-(thiophen-2-yl) quinoline 7(a-j) exhibited a considerable degree of growth inhibition of human cancer cell lines. The synthesized molecules 7(a-j) are in acceptable range and are less toxic and can be considered as possible hits for drug discovery.In continuation of search on new compounds for antiproliferation treatment from our laboratory [28][29][30][31][32], we discovered that 2-(1-benzofuron-2-yl) quinoline-4-carboxylic acid and its esters [28] and 2-(benzofuran-2-yl)-4-(5-phenyl-4H-1,2,4-triazol-3-yl) quinoline and its derivatives [29] have possessed appreciable cytotoxic properties. Hence, the present work deals with the synthesis and antiproliferative potential of 4-(piperidin-1-ylmethyl)-2-(thiophen-2-yl) quinoline and its derivatives, along with detailed in silico pharmacokinetic and druglikeness properties Scheme 1. METHODS MaterialsCommercially available chemicals are used in the synthesis of compounds 7(a-j). The compounds were purified by column chromatography using silica gel 100-200 mesh with occasional monitoring by pre-coated aluminum thin layer chromatography (TLC) plates procured from Merck. Melting points were recorded by the open capillary method and are uncorrected by Raga Melting Point Apparatus. The 1 H-nuclear magnetic resonance (NMR) and 13 C-NMR spectra were recorded on a 400 MHz and 100 MHz, Bruker spectrometer using CDCl 3 as solvent and TMS as an internal standard. Mass spectra were recorded on the liquid chromatography-mass spectrometry Agilent mass spectrometer. Method 2-(1-thiophene-2-yl)quinoline-4-carboxylic acid 3(a-b)Isatin 1(a-b) (0.01 mol) and ethanol (10 v) were taken in a round bottom flask, to this 33% aq. KOH was added dropwise at 0-5°C followed by addition of 2-acetylthiophene 2 (0.01 mol). The reaction was refluxed at 75°C for 8 h. After completion, the reaction mixture was neutralized with dilute HCl. The precipitate, thus, formed was filtered, washed with ethyl acetate to remove impurities and dried to get compound 3(a-b). Methyl 2-(1-thiophene-2-yl) quinolone-4-carboxylates 4(a-b)2-(1-thiophene-2-yl) quinoline-4-carboxylic acid 3(a-b) (0.01 mol) was taken in methanol (10 v) in a round bottom flask, to this two drops of Conc. H 2 SO 4 was added. The reaction was refluxed at 75°C for 8 h. After completion, the reaction mixt...

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2,6-Dithienyl-4-furyl pyridines: Synthesis, topoisomerase I and II inhibition, cytotoxicity, structure–activity relationship, and docking study

Cited by 46 publications

References 29 publications

Synthesis, characterization, antimicrobial screening and DNA binding of novel silver(I)–thienylterpyridine and silver(I)–furylterpyridine complexes

Synthesis, characterization, antimicrobial screening and DNA binding of novel silver(I)–thienylterpyridine and silver(I)–furylterpyridine complexes

Synthesis and biological activity of 2,4-di-p-phenolyl-6-2-furanyl-pyridine as a potent topoisomerase II poison

Antiproliferative and in Silico Admet Study of New 4-(Piperidin-1-Ylmethyl)-2- (Thiophen-2-Yl) Quinoline Analogues

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