• 약학회지
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• 제34권2호
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• pp.133-138
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• 1990

The reaction of 2-aminobenzamide with phthalic acid anhydride In dioxane produced a bicyclic product 2,8-dioxoisoindole(1,2,a) quinazoline (I) in addition to hydrolysis product 2(2-Carboxyphenyl)-1,2-2H-quinazoline-4-one (II). The yields were 64% and 30% respectively. On the other hand, the same reaction in DMF afforded compound (I) and 2(2N-dimethyl carbamyl phenyl)-1,4-2H-quinazoline-4-one (III) in 30% and 60% yield respectively. The compound III was also obtained by the reaction of compound II with dimethylamine. However the reaction of 2-aminobenzamide with neat succinic acid anhydride gave only bicyclic product 2,8-oxopyrrolidine (2,1,a)-1,4-2H-quinazoline (IV) in 93%.

• 약학회지
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• 제29권2호
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• pp.103-106
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• 1985

Reaction between 2-aminobenzamide and thionylchloride gave benzo-2-this-1,3[2H]-diazine-4-one-2-oxide (I) at room temperature. With other carbonyl derivatives quinazoline-4-one derivatives (II-VIII) were obtained.

• Bulletin of the Korean Chemical Society
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• 제31권11호
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• pp.3265-3271
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• 2010

A series of 6,7,8,9-tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted hydrazino thiazolo (2,3-b) quinazolines have been synthesized to meet the structural requirements essential for anti-inflammatory and antinociceptive properties. The synthesized series of heterocycles, 6,7,8,9-tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted hydrazino thiazolo (2,3-b) quinazoline by the reaction of 6,7,8,9-tetrahydro-5H-5-hydroxy phenyl thiazolo (2,3-b) quinazolin-3(2H)-one with appropriate hydrazine hydrate and ketones/aldehydes in the presence of anhydrous sodium acetate and glacial acetic acid as presented in Scheme 1. Their antinociceptive activity were evaluated by tailflick technique, anti-inflammatory was evaluated by carrageenan-induced paw edema test and their ulcerogenicity index determined by reported protocol. The compounds exhibited the lowest ulcer index ($0.51{\pm}1.63$, $0.48{\pm}1.28$ and $0.50{\pm}1.53$, respectively. The 6,7,8,9-tetrahydro-5H-5-hydroxy phenylhydroxy-2-benzylidine-3-(N'-3-pentylidenehydrazino) thiazolo (2,3-b) quinazoline and 6,7,8,9-tetrahydro-5H-5-hydroxy phenyl-2-benzylidine-3-(N'-2-pentylidene-hydrazino) thiazolo (2,3-b) quinazoline exhibited the most potent antinociceptive and anti-inflammatory activities.

• Bulletin of the Korean Chemical Society
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• 제32권6호
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• pp.2121-2124
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• 2011

• 약학회지
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• 제50권4호
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• pp.278-286
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• 2006

Classical dihydropyrrole[3,4-f]quinazoline antifolates 7,8 and 9, in which the tricyclic ring is structurally similar to the pteridine ring of $CH_2-THF(1)$, the cofactor of thymidylate synthase (TS), were synthesized, and their in vitro antitumor activity was evaluated by measuring the cell growth inhibitory activity against cancer cell lines. The target compounds were cytotoxic against CCRF-CEM, human T-cell acute lymphoblastic leukemia, with the cell growth inhibitory activity $(IC_{50})$ of $0.8{\sim}8.3\;{\mu}M$. Among the three compounds, 3-amino analog 7 was 10- and 3.5-fold more cytotoxic compared to the 3-methyl analogs 8 and 9, and its cytotoxicity was similar to that of the reference compound with the $IC_{50}$ value of $0.83\;{\mu}M$. This result was supposed as the consequence of the fact that dihydropyrroloquinazolinone ring with amino group was able to bind well in the active site of TS. In the case of 3-methyl analogs, analog 9, which has two-carbon bridge between the dihydropyrroloquinazolinone ring and benzoyl-L-glutamic acid, was 3-times more potent in cytotoxicity than analog 8 which has one-carbon bridge, and this result indicates that the distance and conformational orientation of the benzoyl-L-glutamic acid moiety with respect to the tricyclic ring may also be a crucial determinant of cell growth inhibitory activity.

• 통합자연과학논문집
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• 제8권3호
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• pp.214-220
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• 2015

Cancer has emerged as one of the leading cause of deaths worldwide. A three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis was performed on a series of quinazoline-based anticancer agents. Purpose of the study is to understand the structural basis for their inhibitory activity. Comparative molecular field analysis (CoMFA) technique was employed to develop 3D-QSAR model. Ligand-based alignment scheme was used to generate a reliable CoMFA model. The model produced statistically significant results with a cross-validated correlation coefficient ($q^2$) of 0.589 and a non-cross-validated correlation coefficient ($r^2$) of 0.928. Model was further validated by bootstrapping and progressive scrambling analysis. This study could assist in the design of novel and more potent anticancer agents.

• Natural Product Sciences
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• 제22권3호
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• pp.216-219
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• 2016

The microbial transformation of anthranilic acid (1) by the marine-mudflat-derived fungus Thielavia sp. produced an antibacterial polycyclic quinazoline alkaloid, thielaviazoline (2). The stereostructure of the metabolite was assigned based on detailed spectroscopic data analyses including comparison of the NMR ($^1H$ and $^{13}C$) data with those of reported compound (2). Compound 2 displayed in vitro antimicrobial activity against methicillin-resistant and multidrug-resistant Staphylococcus aureus (MRSA and MDRSA), with minimum inhibitory concentrations (MICs) of 6.25 and $12.5{\mu}g/mL$, respectively. Compound 2 also showed potent radical-scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) with an $IC_{50}$ of $11{\mu}M$, which was more active than the positive control, L-ascorbic acid ($IC_{50}$, $20.0{\mu}M$).

• 한국생명과학회:학술대회논문집
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• 한국생명과학회 2008년도 제49회 학술심포지움 및 국제학술대회
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• pp.56.1-56.1
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• 2008

• Journal of Applied Biological Chemistry
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• 제58권1호
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• pp.5-8
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• 2015

This study was to isolate an active component of the chloroform fraction from the methanol extract of Ruta chalepensis leaves and to measure inhibitory effects against ${\alpha}$-glucosidase or ${\alpha}$-amylase. The inhibitory compound of R. chalepensis leaves was isolated using chromatographic methods and identified as quinoline. Quinoline and its structurally related derivatives were tested for their inhibitory activities by evaluating the $IC_{50}$ values against ${\alpha}$-amylase or ${\alpha}$-glucosidase and were compared with that of acarbose. Based on the $IC_{50}$ values, quinazoline exhibited the greatest inhibitory activity ($20.5{\mu}g/mL$), followed by acarbose ($66.5{\mu}g/mL$), and quinoline ($80.3{\mu}g/mL$) against ${\alpha}$-glucosidase. In case of ${\alpha}$-amylase, quinazoline had potent inhibitory activity, followed by quinoline ($179.5{\mu}g/mL$) and acarbose ($180.6{\mu}g/mL$). These results indicate that R. chalepensis extract, quinoline, and quinazoline could be useful for inhibiting ${\alpha}$-glucosidase or ${\alpha}$-amylase.

• 약학회지
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• 제30권5호
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• pp.203-207
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• 1986

2-Aminobenzamide reacts with not only keton radical but also carbonyl group in carboxylic acid, to form easily -N-C-N-novel ring cyclization as a result I and V. In addition, it reacts with 1, 2-cyclohexadione or benzil, whitch are both 1, 2-diketone compounds, at the both ketone radical sites to give V or VII respectively. On the reaction with dimethone, however, which has 1, 3-diketone radical, it reacted with only one carbanyl group and VI was produced. We investigated the reaction with cr-ketoester such as ethyl pyruvate and diethyl rnesoxalate. In the reaction with ethylpyruvate, amine group in 2-aminobenzamide reacted not with ketone radical but carbonyl group in ester (product VIII). On the other hand, diethyl measoxalate reacted at the ketone radical site rather than the ester site (product IX).