- Polymorph-dependent solid-state fluorescence and selective metal-ion-sensor properties of 2-(2-hydroxyphenyl)-4(3H)-quinazolinone
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2-(2-Hydroxy-phenyl)-4(3H)-quinazolinone (HPQ), an organic fluorescent material that exhibits fluorescence by the excited-state intramolecular proton-transfer (ESIPT) mechanism, forms two different polymorphs in tetrahydrofuran. The conformational twist b
- Anthony, Savarimuthu Philip
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Read Online
- Synthesis and use of new fluorogenic precipitating substrates
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New fluorogenic esterase, glycosidase, aryl sulfatase, microsomal dealkylase, guanidinobenzoatase and alkaline phosphatase substrates have been prepared which precipitate at the site of enzyme activity, both in vitro and in vivo.
- Naleway, John J.,Fox, Christina M. J.,Robinhold, Daniel,Terpetschnig, Ewald,Olson, Nels A.,Haugland, Richard P.
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- Fluorescence turn-on detection of fluoride using HPQ-silyl ether reactive probes and its in vivo application
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Fluoride and its derivatives are implicated in a variety of pathological and physiological conditions and hence play an important role in our daily life. Thus a fluorescent probe that enables the detection and imaging of fluoride in living species is highly demanded. In this study, three turn-on fluorescent probes (HPQF1~HPQF3) were designed for detecting fluoride with their sensibilities verified by different steric hindrances around silyl ethers. The three HPQ-based probes could quantitatively detect fluoride anion in acetonitrile as well as in water. The fluorescent response time was only a few seconds in acetonitrile, and two different fluorescent sensing channels in acetonitrile (blue) and water (green) were observed by naked eyes. This work also provides a useful method to fluorescently image the presence of fluoride anions in both living cells and specific zebrafish organelles.
- Zhou, Yi,Liu, Meng-Meng,Li, Jing-Yun,Ye, Min-An,Yao, Cheng
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- A novel HPQ-based turn-on fluorescent probe for detection of fluoride ions in living cells
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2-(2′-Hydroxyphenyl)-4(3H)-quinazolinone (HPQ) has been reported as a precipitating fluorescent molecule with excellent optical properties, such as large Stokes shift and strong fluorescence intensity. HPQF, a novel HPQ-based turn-on probe for localizable detection of fluoride ions, was designed, synthesized and fully characterized by 1H NMR, 13C NMR and HRMS. As a chemogenic fluoride probe, the tert-butyldiphenylsilane moiety of HPQF can be easily cleaved by fluoride. After spontaneous 1,6-elimination, HPQ molecule was generated to emit fluorescence under the excitation light. Further study shows that HPQF exhibited high selectivity and sensitivity for detection of fluoride. In addition, HPQF was utilized for the detection of fluoride in living cells.
- Zhao, Zhou,Bi, Xinzhou,Mao, Wuxiang,Xu, Xiaowei
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Read Online
- Electrochemically induced synthesis of quinazolinonesviacathode hydration ofo-aminobenzonitriles in aqueous solutions
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An efficient and practical electrochemically catalyzed transition metal-free process for the synthesis of substituted quinazolinones from simple and readily availableo-aminobenzonitriles and aldehydes in water has been accomplished. I2/base and water play an unprecedented and vital role in the reaction. By electrochemically catalysed hydrolysis ofo-aminobenzonitriles, the synthesis of quinazolinones with benzaldehyde was first proposed. The synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactiveN-(2,5-dichlorophenyl)-6-(2,2,2-trifluoroethoxy) pteridin-4-amine, which enables straightforward, practical and environmentally benign quinazolinone formation.
- Yang, Li,Hou, Huiqing,Li, Lan,Wang, Jin,Zhou, Sunying,Wu, Mei,Ke, Fang
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supporting information
p. 998 - 1003
(2021/02/16)
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- Electrochemical synthesis of quinazolinone: via I2-catalyzed tandem oxidation in aqueous solution
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The development of protocols for synthesizing quinazolinones using biocompatible catalysts in aqueous medium will help to resolve the difficulties of using green and sustainable chemistry for their synthesis. Herein, using I2 in coordination with electrochemical synthesis induced a C-H oxidation reaction which is reported when using water as the environmentally friendly solvent to access a broad range of quinazolinones at room temperature. The reaction mechanism strongly showed that I2 cooperates electrochemically promoted the oxidation of alcohols, then effectively cyclizing amides to various quinazolinones.
- Hou, Huiqing,Ma, Xinhua,Lin, Yingying,Lin, Jin,Sun, Weiming,Wang, Lei,Xu, Xiuzhi,Ke, Fang
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p. 17721 - 17726
(2021/05/29)
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- Synthesis and evaluation of antioxidant properties of 2-substituted quinazolin-4(3H)-ones
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Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3H)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TEACCUPRAC, to obtain key information about the structure-antioxidant activity relationships of a diverse set of substituents at position 2 of the main quinazolinone scaffold. Regarding the antioxidant activity, ABTS and TEACCUPRAC assays were more sensitive and gave more reliable results than the DPPH assay. To obtain antioxidant activity of 2-phenylquinazolin-4(3H)-one, the presence of at least one hydroxyl group in addition to the methoxy substituent or the second hydroxyl on the phenyl ring in the ortho or para positions is required. An additional ethylene linker between quinazolinone ring and phenolic substituent, present in the second series (compounds 25a and 25b), leads to increased antioxidant activity. Furthermore, in addition to antioxidant activity, the derivatives with two hydroxyl groups in the ortho position on the phenyl ring exhibited metal-chelating properties. Our study represents a successful use of three different antioxidant activity evaluation methods to define 2-(2, 3-dihydroxyphenyl)quinazolin-4(3H)-one 21e as a potent antioxidant with promising metal-chelating properties.
- Hrast, Martina,Mravljak, Janez,Slavec, Lara,Sova, Matej
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- Antioxidant and ros inhibitory activities of heterocyclic 2-aryl-4(3h)-quinazolinone derivatives
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Background: Antioxidants are small molecules that prevent or delay the process of oxidations caused by highly reactive free radicals. These molecules are known for their ability to protect various cellular architecture and other biomolecules from oxidative stress and free radicals. Thus, antioxidants play a key role in the prevention of oxidative damages caused by highly reactive free radicals. Methods: In the present study, a series of previously synthesized heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 were screened for antioxidant activity by employing in vitro DPPH and superoxide anion radical scavenging activities. ROS inhibitory activities were also evaluated by serum-opsonized zymosan activated whole blood phagocytes and isolated neutrophils. Cytotoxicity studies were carried out by employing an MTT assay against the 3T3 cell line. Results: Most of the 2-aryl-4(3H)-quinazolinone derivatives showed potent antioxidant activities in superoxide anion radical scavenging assay with IC50 value ranging between 0.57 μM-48.93 μM, as compared to positive control quercetin dihydrate (IC50 = 94.1 ± 1.1 μM ). Compounds 5, 6, and 14 showed excellent activity in DPPH assay. Compounds 5-8, 12-15, 17, and 20 showed promising activities in the ROS inhibition assay. All compounds were found to be non-cytotoxic against the 3T3 cell line. Structure antioxidant activity has been established. Conclusion: It can be concluded that most of the heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 are identified as promising antioxidant agents that are capable of fighting against free radicals and oxidative stress. Thus, they can serve as a lead towards treating oxidative stress and related pathologies.
- Choudhary, Muhammad Iqbal,Khan, Khalid Mohammed,Perveen, Shahida,Saad, Syed Muhammad
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p. 806 - 815
(2021/11/17)
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- Synthesis of 2-(2-Hydroxyaryl)-4H-benzo[e][1,3]oxazin-4-ones by Palladium-Catalyzed C(sp2)?H Hydroxylation via Electro-chemical Oxidation
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An electrochemical direct ortho-hydroxylation of 2-aryl-4H-benzo[e][1,3]oxazin-4-ones was developed with Pd(OAc)2 as catalyst, oxazine ring as a directing group and Oxone as the hydroxylation reagent. A series of hydroxylation products were obtained under mild conditions, and the yields were from medium to good. This method is characterized by good functional group tolerance and a wide range of substrates. More importantly, use anodic oxidation to avoid the use of potentially toxic and polluting oxidants. A gram-scale direct electrochemical hydroxylation of 2-phenyl-4H-benzo[e][1,3]oxazin-4-one was performed, and the hydroxylation product was applied to synthesize the drug deferasirox. In addition, the single crystal of 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one was obtained and determined by X-ray diffraction. Finally, the reaction mechanism was proposed and verified by cyclic voltammetry (CV). This protocol also provides an alternative electrochemical hydroxylation methodology for the functionalization of molecules. (Figure presented.).
- Wu, Hongfeng,An, Qi,He, Chaoyin,Fan, Xiaodong,Guo, Weihao,Zuo, Minghui,Xu, Chunzhao,Guo, Rui,Chu, Wenyi,Sun, Zhizhong
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p. 2459 - 2465
(2020/04/29)
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- Cu-Catalyzed Direct Diversification of 2-(2-Bromophenyl)quinazolin-4(3 H)-ones through Orthogonal Reactivity Modulation
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A modular strategy to obtain three different products from a single substrate was developed. The present methodology unveils new step-economical and cost-efficient routes to access diverse fused quinazolinoquinazolinone derivatives which are not prevalent
- Chatterjee, Satadru,Srinath, Ravuri,Bera, Suvankar,Khamaru, Krishnendu,Rahman, Afifa,Banerji, Biswadip
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supporting information
p. 9028 - 9032
(2019/11/19)
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- Facile and solvent-free synthesis of quinazolin-4(3H)-ones under microwave condition promoted by SbCl3
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– Antimony trichloride (SbCl3) was found to be an effective catalyst (1 mol%) for one-pot synthesis of quinazolin-4(3H)-ones in good to excellent yields using anthranilamide and acyl chlorides under microwave irradiation. This method has the advantages of simplicity, mild reaction conditions, highly tolerant to several functional groups, as well as the avoidance of hazardous solvents.
- Li, Jun,Wang, Weili,Su, Xinglin,Zhang, Xiaoling,Zhang, Yan,Zhang, Xuewen,Cai, Mengmeng,Cao, Yuqian,Jin, Juan,Xu, Yanbin
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p. 2107 - 2110
(2019/04/04)
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- Fluorescent probe compound for detecting beta-galactosidase and preparation method thereof
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The invention discloses a fluorescent probe compound for detecting beta-galactosidase and a preparation method thereof. A fluorescent probe is a quinazolinone type derivate with a structural formula shown in the description; firstly, 2-(2-hydroxyphenyl)-4-(1H)-quinazolinone is synthetized; then, 4-(1H)-quinazolinone,2-[2-[2,3,4,6-tetraacetoxy-(alpha-D-pyrangalactosyl)oxyl]phenyl] is synthetized; finally, 4-(1H)-quinazolinone,2-[2-(beta-D-pyrangalactosyl)oxyl]phenyl] is synthetized. The synthetized probe molecule L can realize qualitative and quantitative recognition on beta-galactosidase by afluorescence spectra method; good anti-interference performance, high selectivity and high sensitivity are still realized under the condition of existence of other impurities such as inorganic salt, amino acid and enzyme.
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Paragraph 0037; 0040; 0041
(2018/08/28)
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- Microwave-assisted synthesis of quinazolin-4(3H)-ones catalyzed by SbCl
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Antimony(III) trichloride (SbCl3) is an effective catalyst (1 mol%) for the condensation of anthranilic amide with various aldehydes or ketones to quinazolin-4(3H)-one derivatives in good to excellent yields under microwave irradiation. The process is carried out within several minutes under solvent-free conditions. This general methodology has the advantages of simplicity, mild reaction conditions and high yields of products.
- Kang, Huaiyuan,Wang, Weili,Sun, Qinqiang,Yang, Shuya,Jin, Juan,Zhang, Xuewen,Ren, Xiaoliang,Zhang, Jiming,Zhou, Jianhua
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p. 293 - 296
(2018/11/27)
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- NEW COMPOUNDS AND USES THEREOF FOR DETECTION OF TARGET MOLECULES IN A SAMPLE
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The present invention relates to new profluorophores and conjugates thereof and their use for the detection of target molecule in a sample, in particular nucleic acid target molecules. The invention relates to new profluorophores and new fluorophores and methods of use thereof particularly useful in the fields of diagnostics and quality control.
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Page/Page column 45; 46
(2018/04/27)
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- For detection in living cells of fluorine fluorescence probe and its preparation method (by machine translation)
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The invention discloses a method for detecting in the living cell fluorine ion fluorescence probe and its preparation method. The probe has the structure of formula I shown, the probe itself almost without any fluorescent, however in the induction of fluorine ions, Si - O bond breaking, off the TBDPS protecting group, production phenol hydroxy, release the HPQ, thus generating excited state in the molecule proton transfer effect, generating fluorescent and greatly improve the phenomenon, so that the fluorescence "turn - on" detecting fluorinion strategy. When the fluoride ions at a low concentration 20 uM when, under the irradiation of ultraviolet light, can be observed by naked eyes to the probe fluorescent strong phenomenon; the probe has good biological compatibility, which is impermeable to the cell membrane, combined with the laser confocal microscope, can be observed on live cells in micromolar levels to produce a response to the fluoride ions. In addition, the synthesis method is simple, easy post treatment, without column chromatography purification, it can get the higher yield of final product. (by machine translation)
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Paragraph 0028-0029
(2018/03/13)
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- An ESIPT-based two-photon fluorescent probe detection of hydrogen peroxide in live cells and tissues
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A variety of diseases associated with human aging, which have a strong oxidative stress, but connecting age-related diseases and oxidative stress of the basic molecular mechanisms still insufficiently understood. Oxidative stress origins from the unregulated production of reactive oxygen species (ROS), and oxidative damaging to tissues and organs from subsequent oxidation-reduction chemistry by cellular mismanagement. In particular, H2O2 is a major by-product of ROS in live organisms and a common marker for oxidative stress, and its dynamic equilibrium can have various physiological and pathological consequences. H2O2 is a small molecule, but it is an essential oxygen metabolite in living systems and acts as an important compound in cellular signal transduction by reversible oxidation of proteins. To quantitatively detect of H2O2 in biosystems, herein, we adopted a 2-(2′-hydroxyphenyl)-4(3H)-quinazolinone (HPQ), a small organic fluorophore known for its luminescence mechanism through excited-state intramolecular proton transfer (ESIPT). HPQ was employed as a precursor to develop a turn-on probe (HPQ-H) for bioimaging applications. After cleavaging the boronic ester moiety by H2O2, HPQ-H releases a HPQ fluorophore which shows a 45-fold fluorescence intensity enhancement with high sensitivity and selectivity over other reactive oxygen species (ROS), and a high resolution imaging and large tissue-imaging depth (70–170?μm) in living cells and tissues images under two-photon excitation (720?nm).
- Zhou, Liyi,Peng, Yongbo,Wang, Qianqian,Lin, Qinlu
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p. 264 - 268
(2017/01/16)
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- Sulfonic acid ionic liquid catalyzing controlled synthesis method for dihydro-quinazolinone and quinazolinone derivatives
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The invention discloses a sulfonic acid ionic liquid catalyzing controlled synthesis method for dihydro-quinazolinone and quinazolinone derivatives. The dihydro-quinazolinone and quinazolinone derivatives are controllably prepared through a cascade reaction of anthranilamide or derivatives thereof and an aldehyde compound by taking sulfonic acid ionic liquid as a catalyst. Under the set catalytic reaction condition, the conversion rate of raw materials reaches up to 99%, and the yield of dihydro-quinazolinone and the yield of quinazolinone both can reach 95%. Compared with the prior art, the green solvent-ionic liquid is taken as the catalyst, no additional oxidizing agent or heavy metal catalyst is needed, the advantages that the reaction conditions are mild, environmental friendliness is achieved, the reaction selectivity and the product yield are high, controllable synthesis is achieved, and the catalyst can be recycled and reused conveniently are achieved, and the novel method is friendly to environment and efficient in synthesis.
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Paragraph 0068; 0069; 0070; 0071
(2017/08/28)
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- Simple preparation method of 4 (3H)-quinazolinone derivative
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The invention provides a simple preparation method of a 4 (3H)-quinazolinone derivative, the 4 (3H)-quinazolinone derivative can be synthesized in one step in a mixed solvent from anthranilamide and an aldehyde as raw materials under the catalysis effects of an ion catalyst, due to the use of the mixed solvent, the 4 (3H)-quinazolinone derivative can be postprocessed only by washing with ethanol and drying, postprocessing steps are simplified, the purity of the product is improved, and meanwhile time is saved.
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Paragraph 0010
(2018/02/04)
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- Aggregation-induced emission probe based on quinazolinones compound as well as preparation method and application of aggregation-induced emission probe
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The invention relates to a quinazolinones compound. The compound does not emit light under a solid state; however, an ester functional group -O-C(O)-R3 is subjected to ammonolysis reaction under the action of ammonia gas to realize hydroxyl; O-H of the hydroxyl and N of C=N in a quinazolinone ring have a mutual effect to form an intramolecular six-membered ring hydrogen bond; strong fluorescent light is emitted under the solid state due to an intramolecular rotation restricted and excited-state intramolecular proton transferring mechanism. The compound can be used as a fluorescent probe and is used for detecting the ammonia gas; furthermore, the compound can be used as a detection reagent for detecting the corrosion degree of foods and an invisible ink material with an AND logic gate.
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Paragraph 0115; 0116; 0117; 0118; 0119; 0120
(2017/07/15)
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- Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones
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An efficient and practical copper-catalyzed consecutive synthesis of quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones from easily available 2-halobenzamides (or 2-halonicotinamides), aldehydes, and sodium azide has been developed, which gave the corresponding target products in 50-95% yields for 29 examples. This remarkable consecutive process involved sequential copper-catalyzed SNAr, reduction, cyclization, and oxidation. Notably, this work would provide a novel synthetic strategy for bioactive molecules containing quinazolinone class skeletons.
- Li, Ting,Chen, Minglu,Yang, Lei,Xiong, Zhengxin,Wang, Yongwei,Li, Fei,Chen, Dongyin
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p. 868 - 874
(2016/01/20)
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- Mechanistic insights into a catalyst-free method to construct quinazolinones through multiple oxidative cyclization
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A novel one-pot benign oxidative cyclization of alcohols with 2-aminobenzamides was successfully developed without catalyst to afford the quinazolinones under O2. This one-pot protocol involved oxidations and cyclizations to construct the skeleton of quinazolinones through possibly three kinds of distinct reaction mechanisms.
- Wang, Zhen-Zhen,Tang, Yu
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p. 1330 - 1336
(2017/02/15)
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- In vitro antileishmanial activities of 2-aryl-4(3H)-quinazolinones
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A series of synthetic 2-aryl-4(3H)-quinazolinones (1-25) was evaluated for in vitro antileishmanial activities against promastigotes of Leishmania major. Compound 1, with nitro group installed at C-4′, was found to be the most active analog having the IC50 value of 35.8 ± 0.1 μM against the standard, pentamidine (IC50 = 5.09 ± 0.09 μM). Fourteen other derivatives i.e. 2, 5-8, 10-12, 14, 16, 19, 22, 24, ad 25, showed a moderate to weak antilieshmanial activity with IC50 values between 62.8-90.45 μM. The results indicate the potential of these compounds as leads for further studies towards the development of antileishmanial drugs.
- Perveen, Shama,Saad, Syed Muhammad,Perveen, Shahnaz,Hameed, Abdul,Alam, Muhammad Tanveer,Khan, Khalid Mohammed,Choudhary, M. Iqbal
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p. 352 - 357
(2016/08/20)
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- Methods for tumor diagnosis and therapy
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The present invention discloses a method for the enzyme-mediated, site-specific, in-vivo precipitation of a water soluble molecule in an animal. The enzyme is either unique to tumor cells, or is produced within a specific site (e.g., tumor) at concentrations that are higher than that in normal tissues. Alternatively, the enzyme is conjugated to a targeting moiety such as an antibody or a receptor-binding molecule.
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Page/Page column 6; 7
(2016/01/08)
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- Synthesis, structure and photoluminescent properties of BF2 and BPh2 complexes with N,O-benzazine ligands
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Novel N,O-bidentate BF2 and BPh2 complexes have been prepared in good to excellent yields through coordination of 8-hydroxy-2-methylquinolines and 2-(2-hydroxyphenyl)-3H-quinazolin-4-ones with boron trifluoride etherate or triphenylb
- Nosova, Emiliya V.,Moshkina, Tatyana N.,Lipunova, Galina N.,Baklanova, Inna V.,Slepukhin, Pavel A.,Charushin, Valery N.
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p. 145 - 151
(2015/06/08)
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- Iodine Catalyzed Oxidative Synthesis of Quinazolin-4(3H)-ones and Pyrazolo[4,3-d]pyrimidin-7(6H)-ones via Amination of sp3 C-H Bond
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Molecular iodine catalyzed oxidative coupling of 2-aminobenzamides with aryl methyl ketones produced 2-aryl quinazolin-4(3H)-ones. The reaction performed well in the absence of any metal or ligand. The quantity of iodine played a very crucial role in this transformation in order to selectively get 2-aryl quinazolin-4(3H)-ones. The utility of this protocol for synthesis of pyrazolo[4,3-d]pyrimidin-7(6H)-ones including a key intermediate involved in sildenafil synthesis has also been demonstrated.
- Mohammed, Shabber,Vishwakarma, Ram A.,Bharate, Sandip B.
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p. 6915 - 6921
(2015/10/06)
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- Y(OTf)3-catalyzed heterocyclic formation via aerobic oxygenation: An approach to dihydro quinazolinones and quinazolinones
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The Y(OTf)3-catalyzed aerobic oxidative cyclization reaction for the selective synthesis of dihydroquinazolinones and quinazolinones has been developed. This method provides a practical, effective and green synthetic approach to dihydroquinazolinones and quinazolinones which both are important units in many biologically active compounds.
- Shang, Ying-Hui,Fan, Li-Yan,Li, Xiang-Xiong,Liu, Meng-Xia
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supporting information
p. 1355 - 1358
(2015/10/28)
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- 2-Arylquinazolin-4(3H)-ones: A novel class of thymidine phosphorylase inhibitors
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Thymidine phosphorylase (TP) over expression plays an important role in several pathological conditions, such as rheumatoid arthritis, chronic inflammatory diseases, psoriasis, and tumor angiogenesis. In this regard, a series of twenty-five 2-arylquinazolin-4(3H)-one derivatives 1-25 were evaluated for thymidine phosphorylase inhibitory activity. Six compounds 5, 6, 20, 2, 23, and 3 were found to be active against thymidine phosphorylase enzyme with IC50 values in the range of 42.9-294.6 μM. 7-Deazaxanthine (IC50 = 41.0 ± 1.63 μM) was used as a standard inhibitor. Compound 5 showed a significant activity (IC50 = 42.9 ± 1.0 μM), comparable to the standard. The enzyme kinetic studies on the most active compounds 5, 6, and 20 were performed for the determination of their modes of inhibition, and dissociation constants Ki. All active compounds were found to be largely non-cytotoxic against the mouse fibroblast 3T3 cell line. This study identifies a novel class of thymidine phosphorylase inhibitors which may be further investigated as leads to develop therapeutic agents.
- Javaid, Sumaira,Saad, Syed Muhammad,Perveen, Shahnaz,Khan, Khalid Mohammed,Choudhary, M. Iqbal
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p. 142 - 151
(2015/11/18)
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- Direct synthesis of quinazolinones by acceptorless dehydrogenative coupling of o-aminobenzamide and alcohols by heterogeneous Pt catalysts
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HBEA zeolite-supported Pt metal nanoclusters (Pt/HBEA) effectively catalyze direct dehydrogenative synthesis of quinazolinones from o-aminobenzamide and alcohols under promoter-free conditions. This is the first heterogeneous catalytic system for this reaction, which has a turnover number (TON) more than 25 times higher than previous homogeneous catalysts as well as wide scope for aliphatic and aromatic alcohols. This journal is the Partner Organisations 2014.
- Hakim Siddiki,Kon, Kenichi,Touchy, Abeda Sultana,Shimizu, Ken-Ichi
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p. 1716 - 1719
(2014/06/09)
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- Synthesis and β-glucuronidase inhibitory activity of 2-arylquinazolin-4(3H)-ones
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2-Arylquinazolin-4(3H)-ones 1-25 were synthesized by reacting anthranilamide with various benzaldehydes using CuCl2·2H 2O as a catalyst in ethanol under reflux. Synthetic 2-arylquinazolin-4(3H)-ones 1-25 were evaluated for their β-glucuronidase inhibitory potential. A trend of inhibition IC50 against the enzyme in the range of 0.6-198.2 μM, was observed and compared with the standard d-saccharic acid 1,4-lactone (IC50 = 45.75 ± 2.16 μM). Compounds 13, 19, 4, 12, 14, 22, 23, 25, 15, 8, 17, 11, 21, 1, 3, 18, 9, 2, and 24 with the IC50 values within the range of 0.6-44.0 μM, indicated that the compounds have superior activity than the standard. The compounds showed no cytotoxic effects against PC-3 cells. A structure-activity relationship is established.
- Khan, Khalid Mohammed,Saad, Syed Muhammad,Shaikh, Nimra Naveed,Hussain, Shafqat,Fakhri, Muhammad Imran,Perveen, Shahnaz,Taha, Muhammad,Choudhary, Muhammad Iqbal
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p. 3449 - 3454
(2014/06/23)
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- CuO nanoparticles catalyzed simple and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones under ultrasound irradiation in aqueous ethanol under ultrasound irradiation in aqueous ethanol
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A CuO nanoparticle-catalyzed one-pot process has engineered for the preparation of diverse quinazolinones from the readily available isatoic anhydride, aldehydes and amine or ammonium. For amine substrates the reactions afford 2,3-dihydroquinazolin-4(1H)-ones in aqueous ethanol promoted by ultrasound irradiation. However, the ammonium substrates undergo intramolecular electron transfer and rearrangement yielding quinazolin-4(3H)-ones. The catalyst is recyclable four times without loss of substantial activity. Other remarkable features include the wide range of functional group tolerance (46 quinazolinones are synthesized and 9 of them are reported firstly), and providing moderate to excellent yield of the products under mild conditions.
- Zhang, Jin,Ren, Decheng,Ma, Yangmin,Wang, Weitao,Wu, Hao
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p. 5274 - 5282
(2014/07/08)
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- CuO nanoparticles catalyzed simple and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones under ultrasound irradiation in aqueous ethanol under ultrasound irradiation in aqueous ethanol
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A CuO nanoparticle-catalyzed one-pot process has engineered for the preparation of diverse quinazolinones from the readily available isatoic anhydride, aldehydes and amine or ammonium. For amine substrates the reactions afford 2,3-dihydroquinazolin-4(1H)-ones in aqueous ethanol promoted by ultrasound irradiation. However, the ammonium substrates undergo intramolecular electron transfer and rearrangement yielding quinazolin-4(3H)-ones. The catalyst is recyclable four times without loss of substantial activity. Other remarkable features include the wide range of functional group tolerance (46 quinazolinones are synthesized and 9 of them are reported firstly), and providing moderate to excellent yield of the products under mild conditions.
- Zhang, Jin,Ren, Decheng,Ma, Yangmin,Wang, Weitao,Wu, Hao
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p. 5274 - 5282
(2014/12/10)
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- QUINAZOLINES AS B-GLUCURONIDASE NOVEL INHIBITORS
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Quinazoline derivatives 1-25, (2-[3,4-bis(methyloxy)phenyl]quinazolin-4-(3H)-one) and 2-[2-(ethyloxy)phenyl]quinazoline-4-(3H)-one) are reported as β-glucuronidase inhibitors useful in the treatment of β-glucuronidase hyperactivity disorders.
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Paragraph 0019; 0020; 0021
(2014/09/29)
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- A simple one-pot synthesis of 2-substituted quinazolin-4(3 H)-ones from 2-nitrobenzamides by using sodium dithionite
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A simple one-pot procedure for the preparation of 2-(het)arylquinazolin- 4(3H)-ones starting from readily available 2-nitrobenzamides and (het)aryl aldehydes is described. Sodium dithionite is used as the reducing agent for the nitro group, and its decomposition in situ in aqueous N,N-dimethylformamide leads to the final oxidation step that gives the desired heterocyclic compounds. Georg Thieme Verlag Stuttgart, New York.
- Romero, Angel H.,Salazar, Jose,Lopez, Simon E.
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p. 2043 - 2050
(2013/07/26)
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- Iodine-catalyzed oxidative system for cyclization of primary alcohols with o-aminobenzamides to quinazolinones using DMSO as the oxidant in dimethyl carbonate
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The iodine catalyzed one-pot two-step oxidative system for cyclization of primary alcohols with o-aminobenzamides to quinazolinones using DMSO as the oxidant has been achieved, providing a convenient and efficient method for the synthesis of quinazolinones in good to excellent yields via in situ oxidation of primary alcohols to aldehydes. The reaction was carried out in the green solvent DMC, under atmospheric conditions. The procedure is suitable for aromatic or alkyl primary alcohols. The Royal Society of Chemistry 2013.
- Ge, Wenlei,Zhu, Xun,Wei, Yunyang
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p. 10817 - 10822
(2013/09/02)
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- A Cu (NO3)2.3H2O catalysed facile synthesis of substituted 4(3H)-quinazolinones and benzimidazoles
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One pot synthesis of alkyl, aryl, heteroaryl mono(2)substituted 4(3H)-quinazolinones and 2-aryl or heteroaryl, 1-arylmethyl or heteroarylmethyl -1H-benzimidazoles using a water soluble Cu (NO3)2.3H 2O catalyst at room/ambient temperature in excellent yield.
- Durgareddy,Ravikumar,Ravi,Adapa, Srinivas R.
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p. 175 - 182
(2013/04/24)
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- Amino acid-based ionic liquid immobilized on α-Fe2O 3-MCM-41: An efficient magnetic nanocatalyst and recyclable reaction media for the synthesis of quinazolin-4(3H)-one derivatives
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For the first time, we report the synthesis and the application of magnetic nanocatalyst (α-Fe2O3)-MCM-41-l-prolinium nitrate which was characterized by XRD, TEM, IR, X-ray energy diffraction (XED) spectra and nitrogen physisorption measurements. l-prolinium nitrate (fully green amino acid-based ionic liquid) inside the mesochannels of (α-Fe 2O3)-MCM-41 lead to prepare a new solid catalyst which was used as an efficient heterogeneous catalyst for the one-pot oxidative cyclization straight synthesis of quinazolin-4(3H)-one derivatives from isatoic anhydride, aldehyde or alkyl halide and primary amines under mild reaction conditions without using any oxidant with good to excellent yields. Moreover, it was proven that in these reactions, the use of such a hybrid material as a catalyst plays the role of rendering the reactions while neither the (α-Fe2O3)-MCM-41 nor the l-prolinium nitrate were not able to promote this reaction in the desired pathway toward the above mentioned product. The characteristic features of this catalyst are attributed to both acidic and oxidative behavior of the catalyst.
- Rostamizadeh, Shahnaz,Nojavan, Masoomeh,Aryan, Reza,Isapoor, Elyass,Azad, Mohammad
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p. 102 - 110
(2013/06/27)
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- Synthesis of quinazolinone analogues using sodium perborate as catalyst
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An environmentally benign approach for the synthesis of 2-aryl-3H-quinazolin-4-ones employing sodium perborate (SPB) as catalyst is described. SPB in water and acetone system is proved as selective catalyst of hydration for cyanides. The rate enhancement
- Kidwai, Mazaahir,Priya
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experimental part
p. 1876 - 1881
(2009/05/26)
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- A new efficient method for the three-component synthesis of 4(3H)-Quinazolinones
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4(3H)-Quinazolinones were efficiently synthesised by the three component cyclisation-oxidation of isatoic anhydride, ammonium acetate and aromatic aldehydes in the presence of ceric ammonium nitrate in ethanol. The Japan Institute of Heterocyclic Chemistry.
- Baghbanzadeh, Mostafa,Dabiri, Minoo,Salehi, Peyman
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experimental part
p. 2809 - 2815
(2011/04/17)
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- Enzymatic analysis using substrates that yield fluorescent precipitates
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Novel fluorescent precipitating substrates made from a class of fluorophores, generally including quinazolinones (quinazolones), benzimidazoles, benzothiazoles, benzoxazoles, quinolines, indolines, and phenanthridines, having the general formula: STR1 where carbon atoms of --C1 =C2 -- are further joined so as to complete a first 5- or 6-membered aromatic ring which may contain at least one of the hetero atoms N, O or S, where carbon atoms of --C4 --N=C3 -- are further joined so as to complete a second 5- or 6-membered aromatic ring that contains at least the nitrogen between C3 and C4 and may contain at least one additional hetero atom N, O or S, where the first and second aromatic rings may be joined by a 5- or 6-membered bridging ring that contains at least the C2 from the first aromatic ring and the C3 from the second aromatic ring, which bridging ring may be saturated or unsaturated and may contain a hetero atom N, O, or S, where each of the first and second aromatic rings may be fused to at least one additional aromatic ring that may contain at least one of the hetero atoms N, O or S, and where each of said aromatic rings may be further modified by substitution of any hydrogens on an aromatic carbon by substituents that are halogen, nitro, cyano, aryl, lower alkyl (1-4 carbons), perfluoroalkyl (1-4 carbons), or alkoxy (1-4 carbons), or any combination thereof; and Xfl is covalently linked to the oxygen --O-- at C1.
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- Reactions of 2-Hydroxybenzonitrile with Isocyanates
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Triethylamine catalyzes the reaction of 2-hydroxybenzonitrile (1) with arylisocyanates to form the corresponding carbamates 2a-c, as well as the cyclization of the latter compounds to either 4--3-aryl-2H-1,3-benzoxazin-2-ones 4a-c, or 4-arylamino-2H-1,3-benzoxazin-2-ones 7a-c, depending on the reaction temperature.Under analogous conditions, the carbamates obtained from 1 and 2-chloroethyl isocyanate, 3-chloropropyl isocyanate and ethyl isocyanatoacetate undergo a double cyclization yielding imidazo- and pyrimidobenzoxazinones 13a, b, 17.Upon heating in phenyl ether, compounds 7a-c, rearrange to 2-(2-hydroxyphenyl)-4(3H)-quinazolinones 10a-c.
- Petridou-Fischer, J.,Papadopoulos, E. P.
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p. 1159 - 1167
(2007/10/02)
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