40288-70-8Relevant academic research and scientific papers
A convenient route to biologically important quinazolines using N-arylamino-1,3-diazabuta-1,3-dienes
Kumar, Vipan,Bhargava, Gaurav,Dey, Promita D.,Mahajan
, p. 3059 - 3062 (2005)
A potential and convenient protocol for the synthesis of 4-arylquinazolines and 4-aminoquinazolines by electrocyclisation of N-arylamino-1,3-diazabuta-1,3- dienes is described. Georg Thieme Verlag Stuttgart.
Rhodium(III)-catalyzed [4?+?2] annulation of N-arylbenzamidines with 1,4,2-dioxazol-5-ones: Easy access to 4-aminoquinazolines via highly selective C[sbnd]H bond activation
Ren, Jie,Huang, Yanzhen,Pi, Chao,Cui, Xiuling,Wu, Yangjie
supporting information, p. 2592 - 2596 (2021/03/09)
A novel approach for the synthesis of 4-aminoquinazolines has been developed via rhodium(III)-catalyzed [4 + 2] annulation of N-arylbenzamidines with 1,4,2-dioxazol-5-ones. This reaction features excellent regioselectivity, broad substrate scope and high step economy, which would provide the reference for the construction of the fused 4-aminoquinazolines with biologically and pharmacologically active compounds.
Metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates at room temperature
Chen, Jiewen,Liang, En,Shi, Jie,Wu, Yinrong,Wen, Kangmei,Yao, Xingang,Tang, Xiaodong
, p. 4966 - 4970 (2021/02/06)
Herein, we describe the novel reactivity of hexafluoroisopropyl 2-aminobenzoates. The metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates has been developed at room temperature. These procedures feature
Synthesis method of 2-aryl-4-aminoquinazoline
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Paragraph 0109-0128, (2020/02/27)
The invention relates to a synthesis method of 2-aryl-4-aminoquinazoline. The method comprises the steps: under the protection of inert gas, mixing 2-chloro-4-aminoquinazoline, arylboronic acid, a catalyst N-heterocyclic carbene-palladium complex, an alka
N-heterocyclic carbene-Pd(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of 2-chloro-4-aminoquinazolines with arylboronic acids
Bao, Zhen,Zhou, Zhi-Yuan,Mao, Ye-Ting,Shao, Li-Xiong
, (2020/09/16)
The Suzuki-Miyaura coupling between 2-chloro-4-aminoquinazolines and arylboronic acids catalyzed by the well-defined N-heterocyclic carbene-PdCl2-1-methylimidazole complex was performed at room temperature, giving the desired products in good t
Synthesis, 2D-QSAR studies and biological evaluation of quinazoline derivatives as potent anti-trypanosoma cruzi agents
Battini, Leandro,Bollini, Mariela,Bruno, Ana M.,Casal, Juan J.,Lombardo, María E.,Ni?o, María E.,Puente, Vanesa R.,Sasiambarrena, Leandro D.,Valdez, Damián A. G.
, p. 265 - 276 (2019/07/12)
Background: Chagas disease affects about 7 million people worldwide. Only two drugs are currently available for the treatment for this parasite disease, namely, benznidazol (Bzn) and nifurtimox (Nfx). Both drugs have limited curative power in the chronic phase of the disease. Therefore, continuous research is an urgent need so as to discover novel therapeutic alternatives. Objective: The development of safer and more efficient therapeutic anti-T. cruzi drugs continues to be a major goal in trypanocidal chemotherapy. Method: Synthesis, 2D-QSAR and drug-like physicochemical properties of a set of quinazolinone and quinazoline derivatives were studied as trypanocidal agents. All compounds were screened in vitro against Trypanosoma cruzi (Tulahuen strain, Tul 2 stock) epimastigotes and bloodstream trypomastigotes. Results: Out of 34 compounds synthesized and tested, six compounds (5a, 5b, 9b, 9h, 13f and 13p) displayed significant activity against both epimastigotes and tripomastigotes, without exerting toxicity on Vero cells. Conclusion: The antiprotozoal activity of these quinazolinone and quinazoline derivatives represents an interesting starting point for a medicinal chemistry program aiming at the development of novel chemotherapies for Chagas disease.
2,4,6-Substituted Quinazolines with Extraordinary Inhibitory Potency toward ABCG2
Krapf, Michael K.,Gallus, Jennifer,Namasivayam, Vigneshwaran,Wiese, Michael
, p. 7952 - 7976 (2018/09/06)
Several members of the ABC transporter superfamily play a decisive role in the development of multidrug resistance (MDR) in cancer. One of these MDR associated efflux transporters is ABCG2. One way to overcome this MDR is the coadministration of potent in
Development of a New Synthetic Method for Quinazolinones via Aerobic Oxidation in dimethylsulfoxide
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Paragraph 0231-0234, (2021/03/30)
The present invention relates to a method for preparing quinazoline derivatives by aerobic oxidation using oxygen as an oxidizing agent in dimethylsulfoxide (DMSO) solvent wherein metal and base are excluded. The method for preparing quinazoline derivatives according to the present invention does not require any metal catalyst such as palladium or iridium, and thus does not cause toxicity problem of residual metal; and does not require demanding processes such as strong acid, or base conditions, low temperature reactions, or reactions of anhydrous conditions and thus, it is possible to simply and economically prepare quinazoline derivatives by reacting anthranilamide derivatives and an aldehyde source.
Synthesis of quinazolinones from anthranilamides and aldehydes via metal-free aerobic oxidation in DMSO
Kim, Na Yeun,Cheon, Cheol-Hong
, p. 2340 - 2344 (2014/05/06)
A highly environmentally benign protocol for the synthesis of quinazolinones from anthranilamides and aldehydes via aerobic oxidation was developed in wet DMSO. This protocol is operationally simple, exhibits broad substrate scope, and does not need toxic metal catalysts and bases. In addition, the utility of this transformation was further demonstrated by converting the resulting quinazolinones into other useful products in the same-pot without their isolation.
Investigation of quinazolines as inhibitors of breast cancer resistance protein (ABCG2)
Juvale, Kapil,Gallus, Jennifer,Wiese, Michael
, p. 7858 - 7873 (2014/01/06)
Chemotherapy is one of the major forms of cancer treatment. Unfortunately, tumors are prone to multidrug resistance leading to failure of treatment. Breast cancer resistance protein (BCRP), the second member of ABC transporter subfamily G, has been found to play a major role in drug efflux and hence multidrug resistance. Until now, very few potent and selective BCRP inhibitors like Ko143 have been identified. In the search for more potent and selective BCRP inhibitors, we synthesized and investigated a series of differently substituted quinazoline compounds. Several variations at positions 2, 4, 6 and 7 of the quinazoline scaffold were carried out to develop a structure-activity- relationship analysis for these compounds. It was found that compounds bearing a phenyl substituent at position 2 of the 4-anilinoquinazoline scaffold were most potent. On the aniline ring at position 4 of the quinazoline moiety substituents like NO2, CN, CF3 led to very high BCRP inhibition potencies. The most potent compounds were further investigated for their intrinsic cytotoxicity and their ability to reverse the multidrug resistance. Compound 20, an anilinoquinazoline bearing a phenyl ring at position 2 and meta-nitro substitution on the 4-anilino ring, was found to have the highest therapeutic ratio. The most active compounds from each variation were also investigated for their effect on BCRP expression. It was found that compound 20 has no significant effect on BCRP expression, while compound 31 decreased the surface BCRP expression. The only difference in the two compounds was the presence of a 3,4-dimethoxyphenyl ring in compound 31 instead of phenyl substitution at position 2 of the quinazoline moiety. From the study of all target compounds, compound 20 was the most prominent compound having inhibitory potency even higher than Ko143, the most potent BCRP inhibitor known. Compound 20 was also found to be selective towards BCRP with a very high therapeutic ratio.
