38215-36-0Relevant articles and documents
Strong in vitro and vivo cytotoxicity of novel organoplatinum(II) complexes with quinoline-coumarin derivatives
Qin, Qi-Pin,Wang, Zhen-Feng,Huang, Xiao-Ling,Tan, Ming-Xiong,Zou, Bi-Qun,Liang, Hong
, (2019)
A series of novel organoplatinum(II) complexes, [PtII(QC1)(H-QC1)Cl] (Pt1), [PtII(QC2)(H-QC2)Cl] (Pt2), [PtII(QC3)(H-QC3)Cl] (Pt3), [PtII(QC4)(H-QC4)Cl]?CH3OH (Pt4), [PtII(QC5)(H-QC5)Cl] (Pt5), [PtII(H-QC6)(DMSO)Cl2] (Pt6), [PtII(H-QC7)(DMSO)Cl2]?H2O (Pt7), [PtII(H-QC8)(DMSO)Cl2] (Pt8), [PtII(H-QC9)(DMSO)Cl2]?CH3OH (Pt9), [PtII(H-QC10)(DMSO)Cl2] (Pt10) and [PtII(H-QC11)(DMSO)Cl2] (Pt11), bearing quinoline-coumarin derivatives (H-QC1?H-QC11) have been first designed. Complexes Pt1–Pt11 selectively displayed obvious cytotoxicities in comparison to cisplatin for A549/DDP (cisplatin-resistant human lung adenocarcinoma) cells and HeLa cervical carcinoma cells, with IC50 values as low as 100 nM?10.33 μM. In addition, Pt4 and Pt5 display a green-colored luminescent properties, targeted mitochondrial membrane and, thereby induced mainly mitochondria-mediated cell apoptosis was in the following order: Pt4 > Pt5. The different anti-cancer activity of quinoline-coumarin complexes Pt4 (100 nM) and Pt5 (250 nM) were correlate with the presence of 3-(2′-quinolyl)-6-hydroxy-coumarin (H-QC4) ligand. The quinoline-coumarin complex Pt4 (2.0 mg/kg per 2 days) also displayed potent in vivo anti-tumor effect after 21 days-treated. In contrast, the H-QC4 ligand highly enhances the anti-tumor activity and selectivity of organoplatinum(II) complexes in comparison to other previously reported coumarin derivatives metal complexes.
Photoinduced formation of the laser dye coumarin 6 from its dihydro derivatives
Traven, Valerii F.,Cheptsov, Dmitrii A.,Solovjova, Natalya P.,Chibisova, Tatjana A.,Voronov, Ilya I.,Dolotov, Sergei M.,Ivanov, Ivan V.
, p. 159 - 168 (2017)
The dihydro form of the laser dye Coumarin 6 and its acylated derivatives undergo photoinduced transformations with Coumarin 6 formation. The reactions go easily both in organic solvents and in polymer films with a high increase of fluorescence. Irreversibility of the reaction provides potential use of the new photosensitive media for optical information recording and sensing technologies.
Fluorescent 7-Substituted Coumarin Dyes: Solvatochromism and NLO Studies
Bhagwat, Archana A.,Sekar, Nagaiyan
, p. 121 - 135 (2018/11/10)
The effect of three substituents N,N-diethylamine, carbazole and diphenylamine at the 7 position of coumarin on linear and nonlinear optical properties are studied using absorption and emission solvatochromism, and DFT. By varying the substituent 53?nm red shift is achieved in emission. The polarity plots with regression close to unity revealed good charge transfer in the system. Solvent polarizability and dipolarity are mainly responsible for solvatochromic shift as proved by multilinear regression analysis. General Mulliken Hush analysis shows diphenylamine substituent leads to more charge separation in compound 6c. The hyperpolarizabilities are evaluated by quantum mechanical calculations. Structure of the compounds are optimized at B3LYP/6-31G(d) level and NLO computations are done using range separated hybrid functionals with large basis sets. Second order hyperpolarizability (γ) found 589.27 × 10?36, 841.29 × 10?36 and 1043.00 × 10?36 e.s.u for the compounds 6a, 6b and 6c respectively.
Reinvestigation of the synthesis of “covalent-assembly” type probes for fluoride ion detection. Identification of novel 7-(diethylamino)coumarins with aggregation-induced emission properties
Quesneau, Valentin,Roubinet, Beno?t,Renard, Pierre-Yves,Romieu, Anthony
supporting information, (2019/11/05)
An unprecedented C-3 functionalization of 4-(diethylamino)salicylaldehyde through a Friedel-Crafts type alkylation reaction has been discovered during the synthesis of “covalent-assembly”-based fluorescent probes for detection of fluoride ions. The resulting Friedel-Crafts adduct was successfully used for the preparation of two novel 8-substituted 7-(diethylamino)coumarin dyes. The photophysical study of these fluorophores has enabled us to highlight their remarkable aggregation-induced emission (AIE) properties characterized by a yellow-orange emission of aggregates in water. Therefore, 4-(tert-butyldimethylsilyloxy)benzyl substituent was identified as a novel AIE-active moiety which could be seen as a possible alternative to popular tetraphenylethylene (TPE).