5260-41-3Relevant academic research and scientific papers
Detection of Isotopic Atropisomerism Based on ortho-H/D Discrimination
Saito, Kazuya,Miwa, Shota,Iida, Asumi,Fujimoto, Yuuki,Caytan, Elsa,Roussel, Christian,Kitagawa, Osamu
supporting information, p. 7492 - 7496 (2021/10/02)
Racemic and optically active 3-(2-deuteriophenyl)-2-(1-phenylpropan-2-yl)quinazoline-4-thiones were prepared. The nuclear magnetic resonance spectra clearly show that they exist as a 1:1 mixture of diastereomers due to the isotopic atropisomerism based on ortho-H/D discrimination (N-C axial chirality) and a chiral carbon.
Casein kinase 1[epsilon] inhibitor, pharmaceutical composition and application thereof
-
Paragraph 0207; 0210, (2021/01/11)
The invention discloses a novel substituted pyrazolopyrimidine compound for inhibiting the activity of casein kinase 1[epsilon] (CK1[epsilon]), a stereoisomer or a stereoisomer mixture of the novel substituted pyrazolopyrimidine compound, a pharmaceutically acceptable salt or solvate of the novel substituted pyrazolopyrimidine compound, and application of the compound to preparation of medicine for treating diseases, disorders or symptoms benefiting from the inhibition of the activity of casein kinase 1[epsilon] (CK1[epsilon]). The compound has inhibitory activity on CK1[epsilon] kinase, OCI-LY10 cells and Karpas299 cells, shows good anti-tumor activity in an OCI-LY10 subcutaneous xenogeneic model, shows excellent synergistic anti-tumor activity when being combined with a BTK inhibitor, has good pharmacokinetic properties, and can be applied to treatment of diseases, disorders or symptoms, including cancers, autoimmune diseases and the like, which benefit from inhibition of casein kinase 1[epsilon] activity, alone or in combination with other drugs.
Quinazolin-4(3H)-ones and 5,6-dihydropyrimidin-4(3H)-ones from β-aminoamides and orthoesters
Gavin, Joshua T.,Annor-Gyamfi, Joel K.,Bunce, Richard A.
, (2018/11/24)
Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12–24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110?C for 12–72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, 1H-NMR, 13C-NMR, and HRMS.
Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization
Hirai, Motohiro,Terada, Shumpei,Yoshida, Hiroaki,Ebine, Kenki,Hirata, Tomoaki,Kitagawa, Osamu
, p. 5700 - 5703 (2016/11/17)
In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH4 gave optically active N-C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmet
Copper-Catalyzed Tandem Reaction of 2-Aminobenzamides with Tertiary Amines for the Synthesis of Quinazolinone Derivatives
Xu, Wei,Zhu, Xiao-Rui,Qian, Peng-Cheng,Zhang, Xing-Guo,Deng, Chen-Liang
, p. 2851 - 2857 (2016/12/16)
We developed a copper-catalyzed tandem reaction of 2-aminobenzamides with tertiary amines for the formation of quinazolinone derivatives. The strategy includes two steps (cyclization and coupling) performed in one pot. A number of substrates reacted well under standard conditions to give the corresponding quinazolinone derivatives in moderate to good yields.
Functionalized carbodiimide mediated synthesis of 2,3-disubstituted quinazolin-4(3 H)-ones via the tandem strategy of C-nucleophilic addition and intramolecular NH-substitution cyclization
Nakano, Hayato,Kutsumura, Noriki,Saito, Takao
, p. 3179 - 3184 (2012/11/14)
A facile synthesis of quinazolin-4(3H)-ones possessing carbon substituents at positions 2 and 3 has been developed. Key to the synthesis is a tandem strategy involving introduction of a 2-substituent and construction of the quinazolinone framework via C-nucleophilic addition to the carbodiimide cumulenic carbon followed by intramolecular nucleophilic substitution by the newly formed NH moiety at the proximal ester group.
Synthesis of 3h-quinazolin-4-ones and 4h-3,1-benzoxazin-4-ones via benzylic oxidation and oxidative dehydrogenation using potassium iodide-tert-butyl hydroperoxide
Kumar, R. Arun,Maheswari, C. Uma,Ghantasala, Satheesh,Jyothi,Reddy, K. Rajender
, p. 401 - 410 (2011/04/18)
A simple and elegant method for benzylic activation was demonstrated employing the potassium iodide/tert-butyl hydrogen peroxide catalytic system. This methodology was further extended for the synthesis of biologically important heterocycles namely, 3H-quinazolin-4-ones and 4H-3,1-benzoxazin-4-ones including mecloqualone and etaqualone which are important quinazolinone-based drugs used for the treatment of insomnia in good yields.
Synthesis and structure-activity relationships of vasicine analogues as bronchodilatory agents
Mahindroo, Neeraj,Ahmed, Zabeer,Bhagat, Asha,Bedi, Kasturi Lal,Khajuria, Ravi Kant,Kapoor, Vijay Kumar,Dhar, Kanaya Lal
, p. 347 - 368 (2007/10/03)
The series of vasicine (1) analogues, an alkaloid from Adhatoda vasica Nees., were synthesized with changes in A, B or C rings. Compounds 3-19 were evaluated for in vitro bronchodilatory activity using isolated guinea pig tracheal chain. Compounds 3-8 were also synthesized in good yields using microwave-mediated synthesis under solvent free conditions. Compounds 5 and 8 with seven-member C ring were more active than etofylline and caused 100% relaxation of both the histamine and acetylcholine pre-contracted guinea pig tracheal chain. The structure-activity relationship studies showed that the quinazoline and oxo functionalities were essential for activity. The compounds without C ring and instead having aliphatic and phenyl substitutions in B ring showed relaxation against histamine pre-contracted tracheal chain only, 2-methyl substituted analogues, 12 and 13, being most active with 100% relaxation effect. Birkhaeuser Boston 2006.
Synthesis and structure-activity relationship of 3-phenyl-3H-quinazolin-4- one derivatives as CXCR3 chemokine receptor antagonists
Storelli, Stefania,Verdijk, Pauline,Verzijl, Dennis,Timmerman, Henk,Van De Stolpe, Andrea C.,Tensen, Cornelis P.,Smit, Martine J.,De Esch, Iwan J. P.,Leurs, Rob
, p. 2910 - 2913 (2007/10/03)
A series of 3-phenyl-3H-quinazolin-4-ones have been synthesized and tested for affinity and activity at the chemokine CXCR3 receptor. The most potent compound (1d) has been evaluated using radioligand binding and calcium mobilization assays and is considered a useful tool for further characterization of the CXCR3 receptor.
