Synthesis, optical properties, and cellular imaging of novel quinazolin-2-amine nopinone derivatives

Yang, Jinlai; Xu, Haijun; Xu, Xu; Jian, Rui; Fang, Xianying; Cao, Xiaoqin; Wang, Shifa

doi:10.1016/j.dyepig.2016.01.016

Cited by 18 publications

(7 citation statements)

References 21 publications

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“…In recent years, the discovery and application of new chiral auxiliaries and catalysts have become a crucial question in stereoselective syntheses [ 1 , 2 , 3 , 4 ]. To achieve new, efficient, and commercially available chiral catalysts, natural chiral terpenes [ 5 ], including (+)-pulegone [ 6 , 7 , 8 ], α- and β-pinene [ 9 , 10 , 11 , 12 , 13 , 14 ], and fenchone-camphor [ 15 , 16 , 17 , 18 , 19 ] have proved to be excellent sources. Starting from these readily available natural sources, several powerful chiral catalysts, including various di- and trifunctional synthons, such as 1,3-aminoalcohols and aminodiols, have been applied in stereoselective syntheses [ 5 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Syntheses and Application of Chiral Bi- and Tridentate Ligands Derived from (+)-Sabinol

et al. 2018

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A library of bidentate diols, as well as tridentate triols and aminodiols, derived from (+)-sabinol, was synthesized in a stereoselective manner. Sabinol was transformed into allylic trichloroacetamide via Overman rearrangement of the corresponding trichloroacetimidate. After changing the protecting group to Boc, the enamine was subjected to stereospecific dihydroxylation with OsO4/NMO, resulting in the (1R,2R,3R,5R)-aminodiol diastereomer. The obtained primary aminodiol was transformed to a secondary analogue. The ring closure of the N-benzyl-substituted aminodiol with formaldehyde was investigated and regioselective formation of the spiro-oxazolidine ring was observed. Hydroboration or dihydroxylation of sabinol or its benzyl ether with OsO4/NMO resulted in the formation of sabinane-based diols and triols following a highly stereospecific reaction. Treatment of sabinol with m-CPBA afforded O-benzoyl triol as a diastereoisomer of the directly dihydroxylated product, instead of the expected epoxy alcohol. The resulting aminodiols, diol, and triols were applied as chiral catalysts in the reaction of diethylzinc and benzaldehyde from moderate to good selectivity.

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Section: Introductionmentioning

confidence: 99%

Stereoselective Syntheses and Application of Chiral Bi- and Tridentate Ligands Derived from (+)-Sabinol

et al. 2018

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“…In addition, new imidazo[1,5-a]pyridine and imidazo [5,1-a]isoquinoline derivatives were synthesized for cell imaging applications on Arabidopsis thaliana seedlings [8], and a low cytotoxicity fluorescent NTR probe based on the iminocoumarinbenzothiazole fluorophore (KC-NTR) was developed to monitor nitroreductase in the living HepG2 cells [9]. At the same time, a few of turpentine (natural product) derivatives had been synthesized for an imaging application in A549 cells and watermelon peel veins [10,11].…”

Section: Introductionmentioning

confidence: 99%

Extraction, Optical Properties and Bio-Imaging of Fluorescent Composition From Moso Bamboo Shoots

Yang¹,

Wu²,

Pan³

2019

Journal of Renewable Materials

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A novel fluorescent composition was firstly isolated from natural winter fresh Moso bamboo shoots, and its optical properties were fully investigated by fluorescence spectroscopy. It could emit strong blue light both in solid and solution state, providing high fluorescence intensity in ethanol. The solution's concentration and addition of water greatly affected the fluorescence intensity, high concentration and addition of much water could quench fluorescence. Apoptosis results showed that the fluorescent extract (0-25 mg/L) could not induce apoptosis of Hela cells. Confocal fluorescent microscopic imaging in human hepatocellular carcinoma cells (HepG2) was realized using the fluorescent extract, it could dye the whole cell well which was different from 4', 6-diamidino-2-phenylindole (DAPI) only dying cell nucleus. The fluorescent extract may be candidate for future natural fluorescent bio-imaging agent.

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“…In recent years, many nopinone derivatives have been synthesized such as 3-cyanopyridine derivatives, 39 chiral 1,3-aminoalcohols and 1,3-diols, 40 terpenyl diselenides, 41 quinazolin-2-amine nopinone derivatives. 42 However, there is no work about using the pinane frame to construct some new EL materials.…”

Section: Introductionmentioning

confidence: 99%

Nopinone-based aggregation-induced emission (AIE)-active difluoroboron β-diketonate complex: photophysical, electrochemical and electroluminescence properties

et al. 2018

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Four difluoroboron (BF 2 ) b-diketonate nopinone complexes 3a-3d that exhibited typical aggregationinduced emission (AIE) properties were synthesized using the natural renewable b-pinene derivative nopinone as the starting material. The thermal, photophysical, electrochemical and electroluminescent properties as well as the AIE properties of complexes 3a-3d were analyzed systematically. The data of photophysical and electrochemical demonstrated that compound 3b with a methoxy group exhibited the largest bathochromic shift, the highest absolute photoluminescence quantum yields and narrowest optical bandgap among 3a-3d. Using 3b as the emitter, electroluminescent (EL) device I exhibits bluegreen light with CIE coordinates of (0.2774, 0.4531) and showed a better performance with a luminous efficacy (h p ) of 7.09 lm W À1 and correlated color temperature (T C ) of 7028 K. The results demonstrate that new AIE compounds are promising solid-state luminescent materials with practical utility in electroluminescent materials. Scheme 1 Synthetic route of compounds 3a-3d. 30056 | RSC Adv., 2018, 8, 30055-30060 This journal is

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Synthesis, optical properties, and cellular imaging of novel quinazolin-2-amine nopinone derivatives

Cited by 18 publications

References 21 publications

Stereoselective Syntheses and Application of Chiral Bi- and Tridentate Ligands Derived from (+)-Sabinol

Stereoselective Syntheses and Application of Chiral Bi- and Tridentate Ligands Derived from (+)-Sabinol

Extraction, Optical Properties and Bio-Imaging of Fluorescent Composition From Moso Bamboo Shoots

Nopinone-based aggregation-induced emission (AIE)-active difluoroboron β-diketonate complex: photophysical, electrochemical and electroluminescence properties

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