86-96-4Relevant articles and documents
Synthesis of quinazoline-2,4(1H,3H)-dione from carbon dioxide and 2-aminobenzonitrile using mesoporous smectites incorporating alkali hydroxide
Fujita, Shin-Ichiro,Tanaka, Masahiro,Arai, Masahiko
, p. 1563 - 1569 (2014)
A series of magnesium containing mesoporous smectites has been prepared with and without incorporation of alkali hydroxide (NaOH, KOH or LiOH) and employed for the reaction of CO2 with aminobenzonitrile to produce quinazoline-2,4(1H,3H)-dione. The effects of the quantity and kind of the incorporated alkali atoms on the catalytic properties of the smectites were investigated. Characterization of the smectites has shown that the incorporation of alkali atoms reduces their surface area and total pore volume but enhances the amount and strength of their basic sites. The product yield increases with the amount of alkali atoms incorporated. The incorporation of Li was less effective than that of Na and K for the enhancement of the yield. It has been suggested that weak and/or moderate base sites are responsible for the reaction. The active sites should be alkali hydroxide particles existing between the smectite layers for the alkali incorporated smectites, while for the un-incorporated smectite, the active sites should be the Mg atoms and/or the neighboring O atoms. The Na incorporated smectite was deactivated by repeated catalyst recycling, while such deactivation was not observed with the un-incorporated smectite. The reason for the deactivation was discussed in connection with the structures of the active sites and the actions of the reaction intermediate. This journal is the Partner Organisations 2014.
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Lange,Sheibley
, p. 79 (1943)
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Delineating the Mechanism of Ionic Liquids in the Synthesis of Quinazoline-2,4(1H,3H)-dione from 2-Aminobenzonitrile and CO2
Hulla, Martin,Chamam, Sami M. A.,Laurenczy, Gabor,Das, Shoubhik,Dyson, Paul J.
, p. 10559 - 10563 (2017)
Ionic liquids (ILs) are versatile solvents and catalysts for the synthesis of quinazoline-2,4-dione from 2-aminobenzonitrile and CO2. However, the role of the IL in this reaction is poorly understood. Consequently, we investigated this reaction and showed that the IL cation does not play a significant role in the activation of the substrates, and instead plays a secondary role in controlling the physical properties of the IL. A linear relationship between the pKa of the IL anion (conjugate acid) and the reaction rate was identified with maximum catalyst efficiency observed at a pKa of >14.7 in DMSO. The base-catalyzed reaction is limited by the acidity of the quinazoline-2,4-dione product, which is deprotonated by more basic catalysts, leading to the formation of the quinazolide anion (conjugate acid pKa 14.7). Neutralization of the original catalyst and formation of the quinazolide anion catalyst leads to the observed reaction limit.
UNEXPECTED FORMATION OF 2,4-QUINAZOLINEDIONE IN THE REACTION OF α-CYANO-β-DIMETHYLAMINOCROTONAMIDE WITH ETHYL ANTHRANILATE
Yalysheva, N. Z.,Granik, V. G.
, p. 1186 (1984)
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Design, synthesis, in silico ADMET, docking, and antiproliferative evaluations of [1,2,4]triazolo[4,3-c]quinazolines as classical DNA intercalators
Alesawy, Mohamed S.,Eissa, Ibrahim H.,El-Adl, Khaled,Ibrahim, Mohamed-Kamal
, (2022/01/13)
Eleven novel [1,2,4]triazolo[4,3-c]quinazolines were designed, synthesized, and evaluated against HepG2 and HCT-116 cells. The molecular design was performed to investigate the binding mode of the proposed compounds with the DNA active site. The data obtained from biological testing highly correlated with that obtained from molecular modeling. HCT-116 was found to be the most sensitive cell line to the influence of the new derivatives. In particular, compounds 6f and 6e were found to be the most potent derivatives over all the tested compounds against the two HepG2 and HCT116 cancer cell lines, with IC50 = 23.44 ± 2.9, 12.63 ± 1.2, and 25.80 ± 2.1, and 14.32 ± 1.5 μM, respectively. Although compounds 6f and 6e displayed less activity than doxorubicin (IC50 = 7.94 ± 0.6 and 8.07 ± 0.8 μM, respectively), both could be useful as a template for future design, optimization, and investigation to produce more potent anticancer analogs. The most active derivatives 6a, 6c, 6e, and 6f were evaluated for their DNA-binding activities. Compound 6f displayed the highest binding affinity. This compound potently intercalates DNA at a decreased IC50 value (54.08 μM). Compounds 6a, 6c, and 6e exhibited good DNA-binding affinities, with IC50 values of 79.35, 84.08, and 59.35 μM, respectively. Furthermore, ADMET (absorption, distribution, metabolism, excretion, and toxicity) profiles were calculated for the four most active compounds in comparison to doxorubicin as a reference drug. Our derivatives 6a, 6c, 6e, and 6f displayed very good in-silico-predicted ADMET profiles. Doxorubicin violates three of Lipinski's rules, our derivatives 6a, 6c, 6e, and 6f do not violate any rule.
Method for efficiently catalytically converting carbon dioxide into quinazoline diketone compound by using eutectic solvent under room temperature and atmospheric pressure conditions
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Paragraph 0026-0031; 0036-0037, (2021/07/17)
The invention relates to a method for efficiently catalytically converting carbon dioxide into quinazoline diketone compounds by using a deep eutectic solvent under room temperature and atmospheric pressure conditions. According to the method, the deep eutectic solvent synthesized by adopting carbon dioxide and o-aminobenzonitrile with different substituent groups as raw materials, adopting ethylene glycol as a hydrogen bond donor, and adopting 1,5-diazabicyclo[4.3.0] non-5-ene (DBN) as a hydrogen bond acceptor, with the molar ratio of the hydrogen bond donor to the hydrogen bond receptor being 1:4, 1:1 and 4:1 is adopted as a catalyst, and the quinazoline diketone compound is synthesized at room temperature under atmospheric pressure for 1-24 h with the ratio of the substrate dosage to the catalyst dosage being 0.4: 3, 0.7: 3 and 1: 3. The invention provides the method for efficiently catalytically converting carbon dioxide into quinazoline diketone compounds by using the eutectic solvent under the conditions of room temperature and atmospheric pressure, and the method is simple and convenient, high in yield, low in cost, low in energy consumption, green and environment-friendly, avoids the use of a transition metal catalyst, and has very high practical application value.
