Synthesis, topoisomerase I inhibition and structure–activity relationship study of 2,4,6-trisubstituted pyridine derivatives

Zhao, Longxuan; Moon, Yoon‐Soo; Basnet, Arjun; Kim, Eun-kyung; Jahng, Yurngdong; Park, Jae Gyu; Jeong, Tae Cheon; Cho, Won‐Jea; Choi, Sang‐Un; Lee, Chong Ock; Lee, Sun-Young; Lee, Chong-Soon; Lee, Eung-Seok

doi:10.1016/j.bmcl.2003.11.084

Cited by 90 publications

(24 citation statements)

References 20 publications

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“…Further experiments investigated the fluorescence of NQD in the presence of CTP. Diaryl-substituted pyridine derivatives are bioisosteres of terpyridine that are known to exhibit a strong cytotoxicity against several human cancer cell lines through the inhibition of topoisomerase I [44][45][46][47][48]. An analog of such diaryl-substituted pyridines (CTP) was synthesized using 3-dimethylamino-1-(thiophen-2-yl)-1-propanone hydrochloride 1 (a ke- tonic Mannich base), 4-chlorophenacylpyridinium bromide 2 and ammonium acetate as starting materials in an one-pot approach (Figure 8).…”

Section: Results and Discussion 41 Morphologies And Structuresmentioning

confidence: 99%

Fluorescence detection system based on silicon quantum dots–polysilane nanocomposites

Săcărescu¹,

Roman²,

Săcărescu³

et al. 2016

Express Polym. Lett.

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Abstract.A dual channel fluorescence system that combines the optical properties of silicon quantum dots-polysilane nanocomposites with those of 2-(4-chlorophenyl)-6-(thiophen-2-yl)pyridine, a fluorescent cytotoxic agent, is presented. The system is capable to alternatively trigger emission signals at two different wavelengths by excitation at a single wavelength. For this purpose a highly stable colloidal dispersion of silicon quantum dots-polysilane nanocomposite is prepared by a one-pot synthetic method using microwave-activated Wurtz coupling of organochlorosilanes. The size and shape of the silicon quantum dots within the polysilane thin film are studied by TEM. The colloidal dispersions are investigated by SAXS, which evidences that polysilane plays also a role as stabilizing agent to prevent aggregation. UV-vis spectrophotometry of the silicon quantum dots-polysilane nanocomposites in the presence of 2-(4-chlorophenyl)-6-(thiophen-2-yl)pyridine is used to define the active wavelength range and establish the fluorescence detection method.

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Section: Results and Discussion 41 Morphologies And Structuresmentioning

confidence: 99%

Fluorescence detection system based on silicon quantum dots–polysilane nanocomposites

Săcărescu¹,

Roman²,

Săcărescu³

et al. 2016

Express Polym. Lett.

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“…37 It is interesting to note that the above procedure, when carefully adjusted, gave access to pyridine ring systems with variously substituted aryl substituents. The same group demonstrated the high activity of a catalytic system consisting of Pd 2 (dba) 3 and di(1-adamantyl)-n-butylphosphine as ligand for Suzuki cross coupling of tetrachloropyridine with a wide variety of arylboronic acids. 38 Also in this case, careful optimization of reaction conditions led to the regioselective step-wise arylation of the pyridine ring system.…”

Section: Resultsmentioning

confidence: 99%

“…Application of the classical Suzuki catalytic system based on Pd[PPh 3 ] and PdCl 2 [PPh 3 ] 2 in the presence of a medium-strong (Na 2 CO 3 ) or a weak base (K 3 PO 4 ) brought about the formation of 2a in low yield (entries 1-3). The GC-MS analysis indicated significant amounts of chloropyridine 7 and by-products A-C. Interestingly, when more bulky ligand P(o-tol) 3 was used instead of PPh 3 , the arylation occurred predominantly at 3 and 5 positions of 9 leading selectively to compound 7 in 92% yield (entry 4). Similar results were obtained when Pd(dppf)Cl 2 ×CH 2 Cl 2 (4) and a catalytic system consisting of Pd(OAc) 2 / tricyclohexylphosphine was used in the presence of a weak base K 3 PO 4 (entries 9 and 6, respectively).…”

Section: Resultsmentioning

confidence: 99%

“…[3][4][5][6] A typical example is pyridinitril, a well-known fungicide which exhibits the ability to block the action of cytochrome P450-dependent 14α-demethylase, preventing the formation of ergosterol, an important intermediate in the construction of fungal-cell membranes. [7][8][9] Many aryl-substituted pyridines are essential building blocks of pharmaceutical agents showing anti-inflammatory, 10 antibacterial, 11 and antimalarial 12 activities.…”

Section: Introductionmentioning

confidence: 99%

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Efficient synthesis of differently substituted triarylpyridines with the Suzuki-Miyaura cross-coupling reaction

Błachut¹,

Szawkało²,

Pomarański³

et al. 2016

Arkivoc

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A library of differently substituted 3,4,5-triaryl-2,6-dimethylpyridines and 2,3,5-triaryl-4,6-dimethylpyridines were synthesized and characterized using the Suzuki-Miyaura cross-coupling reaction with accordingly selected tribromodimethylpyridines and arylboronic acids. The optimized coupling conditions were found to be general for both isomeric tribromodimethylpyridines and a wide range of arylboronic acids substituted with electro-donating and electro-withdrawing groups.

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“…Some pyridine derivatives were studied for their topoisomerase inhibitory activity and cytotoxicity against several human cancer cell lines for the development of novel anticancer agents. As a result, it has been reported that various pyridine derivatives, as bioisosteres of α-terthiophene (potent protein kinase C inhibitor) [23], have significant topoisomerase I and/or II inhibitory activity, and cytotoxicity against several human cancer cell lines [24][25][26][27][28]. Early reports on the ability of α-terpyridine to form metal complexes [29] and to and to bind with DNA/RNA [30] have been the base for the study on pyridine derivatives as antitumor agents.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Novel Pyrazole-Based Heterocycles as Potential Antitumor Agents

et al. 2017

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Abstract:A new series of pyrazolylpyridines was prepared by reaction of ethyl-3-acetyl-1,5-diphenyl-1H-pyrazole-4-carboxylate with the appropriate aldehyde, malononitrile, or ethyl acetoacetate and an excess of ammonium acetate under reflux in acetic acid. Similarly, two novel bipyridine derivatives were prepared by the above reaction using terephthaldehyde in lieu of benzaldehyde derivatives. In addition, a series of 1,2,4-triazolo[4,3-a]pyrimidines was synthesized by a reaction of 6-(pyrazol-3-yl)pyrimidine-2-thione with a number of hydrazonoyl chlorides in dioxane and in the presence of triethylamine. The structure of the produced compounds was established by elemental analyses and spectral methods, and the mechanisms of their formation was discussed. Furthermore, the pyrazolyl-pyridine derivatives were tested as anticancer agents and the results obtained showed that some of them revealed high activity against human hepatocellular carcinoma (HEPG2) cell lines.

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Synthesis, topoisomerase I inhibition and structure–activity relationship study of 2,4,6-trisubstituted pyridine derivatives

Cited by 90 publications

References 20 publications

Fluorescence detection system based on silicon quantum dots–polysilane nanocomposites

Fluorescence detection system based on silicon quantum dots–polysilane nanocomposites

Efficient synthesis of differently substituted triarylpyridines with the Suzuki-Miyaura cross-coupling reaction

An Efficient Synthesis of Novel Pyrazole-Based Heterocycles as Potential Antitumor Agents

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