1769-24-0Relevant articles and documents
Aluminium-containing ring systems and N-heterocycle formation via nitrile insertions into Al-N bonds
Gibson,Redshaw,White,Williams
, p. 79 - 80 (2001)
Reactions of Me3Al with 1,2-diaminobenzene [1,2-(H2N)2C6H4] or anthranilic acid, [1,2-(H2N)(HO2-C)C6H4], followed by treatment with acetonitrile, afford tetranuclear and hexanuclear aluminium-containing ring systems; a single crystal X-ray structure on the hexametallic product reveals the construction of quinazoline ligands arising via insertion of acetonitrile into Al-N bonds.
A copper-catalyzed Ritter-type cascade via iminoketene for the synthesis of quinazolin-4(3H)-ones and diazocines
Abe, Takumi,Kida, Koshiro,Yamada, Koji
, p. 4362 - 4365 (2017)
We have developed a copper-catalyzed Ritter-type reaction/cyclization cascade of anthranilic acids and nitriles, affording the quinazolin-4(3H)-ones. The cascade proceeds through a Ritter-type reaction capturing the iminoketene intermediates by nitriles. Furthermore, we found a novel Ritter-type reaction/condensation/intramolecular anti-Markovnikov hydroamination cascade, providing access to functionalized diazocines in one-pot.
Infrared spectra, thermogravimetric analysis and antifungal studies of noval cr(iii), fe(iii) and cu(ii) 2-methyl-quinazolinone complexes
Sadeek,El-Attar,El-Lattif, N.S. Abd
, p. 53 - 66 (2014)
Some new solid complexes [CrCl3(L)3]×6H 23O, [FeCl3(L)3]×6H2O and [Cu(CH 3COO)2(L)3]×2H2O have been synthesized quantitatively by the interactions of 2-methyl-quinazolinone (L) with CrCl3.6H23O, FeCl3.6H2O and Cu(CH3COO)2. 2H2O in a mixture of an ethanol-bidistilled water (1:1), at 60 °C. They were characterized by melting point, molar conductivity, magnetic moment, elemental analysis, infrared spectra and thermal analyses. The results supported the formation of the complexes and indicated that the ligand reacted as a monodentate ligand bound to the metal ion through the oxygen atom. The antifungal activity of the free ligand and their metal complexes were evaluated against several species, such as Fusarium solani, Rizoctonia solani, Sclortium rolfsii and Botryodiplodia and they showed a good antifungal activity to some selected fungal strain as compared with free ligand.
2-Styryl-4-aminoquinazoline derivatives as potent DNA-cleavage, p53-activation and in vivo effective anticancer agents
Chen, Nan-Ying,Huang, Wan-Yun,Li, Xiao-Juan,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa,Wei, Xin-Wei,Yuan, Jing-Mei
, (2019)
Forty-eight analogues of CP-31398, an antitumor agent modulated the mutant p53 gene were synthesized and their cytotoxicities against four cancer cell lines with different p-53 status including bladder cell T24 (w-p53), gastric cell MGC-803 (m-p53), prostate cell DU145 (m-p53), prostate cell PC-3 (null-p53), lung cell A549 (w-p53) and normal liver cell line HL-7702 (w-p53) were examined. (E)-2-(4-Nitrostyryl)-4-(3-dimethylaminopropyl)-aminoquinazoline (10ah) was identified as the most potent compound in anti-proliferation against MGC-803 cells, with IC50 lowed to 1.73 μM, far potency than that of CP-31398. Molecular mechanism study revealed that 10ah and CP-31398 differ greatly in mechanism to exert their antitumor properties. 10ah could intercalate into DNA and resulted in significant DNA double-strand break. 10ah-treatment in MGC-803 cells increased the expression of p53, phosphorylated p53 (p-p53), CDK4, p21 to cause cell cycle arrest at G2/M phase, significantly up-regulated the levels of pro-apoptosis proteins Bak, Bax, Bim while down-regulated the anti-apoptosis proteins Bcl-2, Bcl-xL and the levels of cyclin B1, fluctuated the intracellular reactive oxygen species (ROS), Ca2+ and mitochondrial membrane potential, activated Caspase-9 and Caspase-3 to induce apoptosis. 10ah also displayed potent anticancer efficiency against MGC-803 xenograft tumors models, with tumor growth inhibition (TGI) up to 61.8% at 20 mg/kg without obvious toxicity.
Synthesis and biological evaluation of quinazolin-4(3 H)-one derivatives bearing dithiocarbamate side chain at C2-position as potential antitumor agents
Ding, Pan-Pan,Gao, Man,Mao, Bei-Bei,Cao, Sheng-Li,Liu, Cui-Huan,Yang, Chao-Rui,Li, Zhong-Feng,Liao, Ji,Zhao, Hongchang,Li, Zheng,Li, Jing,Wang, Hailong,Xu, Xingzhi
, p. 364 - 373 (2016)
A series of quinazolin-4(3H)-one derivatives bearing dithiocarbamate side chain at the C2-position were synthesized and evaluated for their antiproliferative activities against A549, MCF-7, HeLa, HT29 and HCT-116 cell lines. Most of the synthesized compounds exhibited broad spectrum antitproliferative activity against five cell lines, of which 5c was the most potent against HT29 cell line with an IC50 value of 5.53 μM, inducing a G2/M phase arrest in HT29 cells. Treatment of HT29 cells with 5c resulted in BubR1 phosphorylation and an increase of mitotic index in a time-dependent manner. Furthermore, 5c promoted tubulin polymerization in vitro. These results demonstrate that quinazolin-4(3H)-one derivatives bearing dithiocarbamate side chain at C2-position may be potentially novel antitumor agents targeting tubulin to activate the spindle assembly checkpoint.
Acylanthranils. 9. Influence of Hydrogen Bonding on the Reaction of Acetylanthranil with Ammonia
Errede, L. A.,Martinucci, P. D.,McBrady, J. J.
, p. 3009 - 3017 (1980)
It was shown that hydrogen bonding has a marked influence on the reaction of acetylanthranil (1) with ammonia.The product of the reaction in anhydrous benzene is 2-methylquinazolin-4-one (5, R = H) which is formed via pathway A as shown in Scheme I, but the rate of formation is unusually slow.The rate of this conversion is about 6 times faster in pyridine than in benzene.If water is added to the benzene system, the rate of reaction is increased by orders of magnitude, but the product is o-acetamidobenzamide (4, R = H) and not 5.In contrast to this result, the addition of water to the pyridine system causes a small decrease in rate and only a slight change in selectivity.These results are consistent with postulated mechanisms whereby 1 reacts with molecular clusters of ammonia, i.e. with (NH3)n in benzene, with N(H*S)3 in strong proton acceptor solvents S, and with (NH3)n*H2O in benzene plus added water.It was verified that cyclodehydration of 4 to give 5 occurs at an appreciable rate in aqueous solution at elevated temperatures and that this rate is accelerated considerably by the presence of strong base even at room temperature.It was also observed that o-acetamidobenzamide exists in at least two crystalline forms, α and β, which have different physical properties.
Incorporation of molecular nitrogen into organic compounds III. Reaction of titanium-nitrogen complexes with acid halides and acid anhydrides
Mori, Miwako,Uozumi, Yasuhiro,Shibasaki, Masakatsu
, p. 255 - 267 (1990)
The titanium-nitrogen complex 1, prepared from TiCl3 or TiCl4 and Mg in THF under nitrogen reacts with acid chloride to give amide and/or imide.The cyclic imides were obtained by the reaction of titanium-isocyanate complex 3, , made from titanium-nitrogen complex 1 and carbon dioxide, and the corresponding cyclic acid anhydrides.Benzoxazone derivatives afforded the corresponding quinazoline derivatives in a similar procedure.These results indicate that molecular nitrogen was incorporated into organic compounds via titanium nitrogen complexes.
Unexpected Products from Carbonylation of Lithiated Quinazolin-4(3H)-one Derivatives
Smith,El-Hiti,Abdel-Megeed
, p. 430 - 435 (2003)
Doubly lithiated 3-pivaloylaminoquinazolin-4(3H)-one reacts with carbon(II) oxide at 0°C to give 77% of a mixture of azetidinone and indole derivatives, each incorporating a diisopropylamide unit from lithium diisopropylamide used for lithiation. No analogous reaction occurs with doubly lithiated 3-acetyl-aminoquinazolin-4(3H)-one and 3-acyl-2-alkylquinazolin-4(3H)- one. Carbonylation of doubly lithiated 2-alkyl-3-aminoquinazolin-4(3H)-ones at 0°C results in deamination to give 2-alkylquinazolin-4(3H)-ones in good yields.
Microwave assisted synthesis of pyridin-1-ium salt of 6-nitroquinazolin-4-one and its 6-amino analog under ultrasonic irradiation
Hayun,Arrahman,Suryadi,Yanuar
, p. 7904 - 7906 (2014)
The new compounds of quinazolin-4-one derivative i.e., 2-methyl-6-nitroquinazolin-4-one substituted pyridin-1-ium salt at methyl group and its 6-amino analog have been synthesized. Microwave irradiation of solution of 2-bromomethyl-6- nitroquinazolin-4-one and pyridine in acetonitrile for 3 min afforded 1-[(6-nitroquinazolin-4-one-2-yl)methyl]pyridin-1-ium bromide; and nitro reduction of the product with iron in ethanol/acetic acid/water under ultrasonic irradiation afforded 1-[(6-aminoquinazolin-4-one-2-yl)methyl]pyridin-1-ium bromide. The structure of the synthesized compounds were confirmed on the basis of FT-IR, 1H NMR and 13C NMR data.
Linear-Organic-Polymer-Supported Iridium Complex as a Recyclable Auto-Tandem Catalyst for the Synthesis of Quinazolinones via Selective Hydration/Acceptorless Dehydrogenative Coupling from o-Aminobenzonitriles
Hao, Shushu,Yang, Jiazhi,Liu, Peng,Xu, Jing,Yang, Chenchen,Li, Feng
supporting information, p. 2553 - 2558 (2021/04/13)
A linear-organic-polymer-supported iridium complex Cp*Ir@P4VP, which is designed and synthesized by the coordinative immobilization of [Cp*IrCl2]2 on poly(4-vinylpyridine), was proven to be an efficient heterogeneous autotandem catalyst for synthesizing quinazolinones via selective hydration/acceptorless dehydrogenative coupling from o-aminobenzonitriles. Furthermore, the synthesized catalyst was recycled five times without an obvious decrease in the catalytic activity.
