Synthesis and Photophysical Property Studies of the  2,6,8-Triaryl-4-(phenylethynyl)quinazolines

The extraordinary richness of push-pull molecules that incorporate pyrimidine rings as electron-withdrawing moieties in their structure is illustrated in this review. Interest in these pextended systems has increased dramatically over the last two decades due to their fluorescence properties and potential applications in sensing and as luminescent materials. As many as 422 different molecules are presented in an effort to establish structure-property relationships, which are often difficult to elucidate.[a] Dr.

show abstract

“…4‐Arylethynylquinazolines can be obtained by Sonogashira cross‐coupling reaction from 4‐chloroquinazoline derivatives (Figure ) ,,…”

Section: Arylethynylquinazolinesmentioning

confidence: 99%

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

2018

View full text Add to dashboard Cite

show abstract

“…Compound IV reacted with formamide to afford compound V [22] (Scheme 1). The reaction of urea, thiourea, aniline, p-toluidine, p-aminoacetophenone with benzoxazine derivative IV by fusion at high temperature afforded the corresponding quinazoline-4-one derivatives VI-X (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis of novel quinazolin-4-one derivatives and biological evaluation against human MCF-7 breast cancer cell line

Ahmed

Hashim

2015

Res Chem Intermed

View full text Add to dashboard Cite

A new series of 6,8-dibromo-2-(4-chlorophenyl)quinazolin-4(3H)-one derivatives VI-XIII were synthesized. Their chemical structures were confirmed by spectral and elemental analysis. The cytotoxic effect of the newly synthesized compounds was tested in vitro against human breast cancer cell line (MCF-7). Most of the tested compounds have shown promising cytotoxic activity. Compounds X and XIIIb exerted a powerful cytotoxic effect against MCF-7 with a very low IC50 (0.0015 and 0.0047 lmol/ml), while compounds VI, VII, VIII, XIIb, XI, XIIIc and IX exerted a moderate cytotoxic effect (IC50 0.01523, 0.0213, 0.031, 0.0478, 0.049, 0.068 and 0.079 lmol/ml respectively), compared to doxorubicin (0.0025 lmol/ml). Exploring their apoptotic effect; interestingly,all compounds activated apoptotic cascade in MCF-7. Compounds VI, XIIIb, XIIb, XI, XIIa, VII, V and VIII showed potent effect even much more than doxorubicin by 12.87-5.91 folds, while compounds XIIIc, IX, XIIIa, XIIc and X showed moderate increase in CASP3 activity by 4.96-3.22 folds relative to untreated cells more or less similar to doxorubicin (5.57 folds).

show abstract

“…Hitherto, the 4-alkynyl-2-aryl-6,8-dibromoquinazolines [23] and the 6,8-dibromo-2,4-diaminoquinazoline [24,25] have been found to undergo Suzuki-Miyaura cross-coupling at the 6-and 8-positions without selectivity due to comparable We decided to take advantage of the trend in reactivity of the C-sp 2 -X bonds in transition metal catalyzed cross-coupling (trend: C-sp 2 -I > C(4)-Cl > C-sp 2 -Br > C(2)-Cl > C-sp 2 -Cl) [18] and subjected compounds 1a-d to one-pot successive two-and three-step reaction sequences involving initial amination and subsequent Pd catalyzed cross-coupling reactions to afford novel unsymmetrical polycarbo-substituted 4-anilinoquinazolines. Table 2).…”

Section: One-pot Two-mentioning

confidence: 99%

“…Table 2). Hitherto, the 4-alkynyl-2-aryl-6,8-dibromoquinazolines [23] and the 6,8-dibromo-2,4-diaminoquinazoline [24,25] have been found to undergo Suzuki-Miyaura cross-coupling at the 6-and 8-positions without selectivity due to comparable Csp 2 -Br bond dissociation energies. Crystals of quality suitable for X-ray diffraction were obtained for 3d by slow evaporation of acetonitrile and the molecular structure of compounds 3 was further confirmed by single crystal X-ray crystallography.…”

Section: One-pot Two-mentioning

confidence: 99%

Synthesis and In Vitro Cytotoxic Properties of Polycarbo-Substituted 4-(Arylamino)quinazolines

2016

Self Cite

View full text Add to dashboard Cite

Herein, we describe the synthesis of novel unsymmetrical polycarbo-substituted 4-anilinoquinazolines derived from the 2-aryl-6-bromo-8-iodoquinazolines via one-pot three-step reaction sequences involving initial amination and subsequent double cross-coupling (bis-Suzuki, Sonogashira/Stille or Sonogashira/Suzuki-Miyaura) reactions with different cross coupling partners for the two carbon-carbon bond formation steps. The 4-anilinoquinazolines were evaluated for potential cytotoxicity against three cancer cell lines, namely, human breast adenocarcinoma (MCF-7) cells, human cervical cancer (HeLa) and human lung cancer (A549) cells. The most active compounds, 2b, 2c, 3c, 4a, 4c and 5a, were found to be more selective against the MCF-7 and HeLa cell lines than the human lung carcinoma (A549) cells. We selected compounds 2c, 3c and 7a as representatives for further evaluation for potential to induce apoptosis and/or necrotic properties in the three cancer cell lines. Compound 2c induced apoptosis of MCF-7 cells through cell membrane alteration. Treatment of Hela and A549 cell lines with compounds 3c and 7a, respectively, led to caspase-3 activation in both cell lines. Compound 3c, on the other hand, caused more necrosis than apoptosis induction in the membrane alteration assay.

show abstract

Synthesis and Photophysical Property Studies of the 2,6,8-Triaryl-4-(phenylethynyl)quinazolines

Cited by 26 publications

References 34 publications

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

Design, synthesis of novel quinazolin-4-one derivatives and biological evaluation against human MCF-7 breast cancer cell line

Synthesis and In Vitro Cytotoxic Properties of Polycarbo-Substituted 4-(Arylamino)quinazolines

Contact Info

Product

Resources

About