610-24-2Relevant academic research and scientific papers
Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 catalyzed by N-heterocyclic carbene at atmospheric pressure
Xiao, Yunqing,Kong, Xianqiang,Xu, Zhicheng,Cao, Changsheng,Pang, Guangsheng,Shi, Yanhui
, p. 5032 - 5037 (2015/03/03)
Under atmospheric pressure, quinazoline-2,4(1H,3H)-diones were obtained from the reaction of 2-aminobenzonitriles with carbon dioxide (0.1 MPa) with a catalytic amount of N-heterocyclic carbene in DMSO. It was found that various electron-donating and electron-withdrawing groups such as -OMe, -F, -Cl, -Br, -CH3, -CF3 and -CN were well tolerated to give the products in almost quantitative yields.
Synthesis and QSAR of Quinazoline Sulfonamides As Highly Potent Human Histamine H4 Receptor Inverse Agonists
Smits, Rogier A.,Adami, Maristella,Istyastono, Enade P.,Zuiderveld, Obbe P.,Van Dam, Cindy M. E.,De Kanter, Frans J. J.,Jongejan, Aldo,Coruzzi, Gabriella,Leurs, Rob,De Esch, Iwan J. P.
supporting information; experimental part, p. 2390 - 2400 (2010/09/11)
Hit optimization of the class of quinazoline containing histamine H 4 receptor (H4R) ligands resulted in a sulfonamide substituted analogue with high affinity for the H4R. This moiety leads to improved physicochemical properties and is believed to probe a distinct H4R binding pocket that was previously identified using pharmacophore modeling. By introducing a variety of sulfonamide substituents, the H4R affinity was optimized. The interaction of the new ligands, in combination with a set of previously published quinazoline compounds, was described by a QSAR equation. Pharmacological studies revealed that the sulfonamide analogues have excellent H4R affinity and behave as inverse agonists at the human H4R. In vivo evaluation of the potent 2-(6-chloro-2-(4-methylpiperazin-1-yl)quinazoline4-amino)-N- phenylethanesulfonamide (54) (pki = 8.31 ± 0.10) revealed it to have anti-inflammatory activity in an animal model of acute inflammation.
Quinazolines and related heterocyclic compounds and their therapeutic use
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Page/Page column 17, (2009/07/18)
A compound of the formula wherein X is CR1 or N; Y is CR3 or N; R1, R3, R4, R5 and R6 are independently H, F, Cl, Br, I, or a hydrocarbon group which optionally contains one or more heteroatoms; R7 is a heterocyclic group including one or more N atoms; R' is Rx or NRyRz wherein Rx, Ry and Rz are each H or the same or different groups, including cyclic groups formed by Ry and Rz with the N atom, of up to 20 C atoms and optionally including up to 3 further heteroatoms selected from N, O and S; or a pharmaceutically acceptable salt, ester or solvate thereof, has therapeutic utility.
Discovery of alogliptin: A potent, selective, bioavailable, and efficacious inhibitor of dipeptidyl peptidase IV
Feng, Jun,Zhang, Zhiyuan,Wallace, Michael B.,Stafford, Jeffrey A.,Kaldor, Stephen W.,Kassel, Daniel B.,Navre, Marc,Shi, Lihong,Skene, Robert J.,Asakawa, Tomoko,Takeuchi, Koji,Xu, Rongda,Webb, David R.,Gwaltney II, Stephen L.
, p. 2297 - 2300 (2008/02/05)
Alogliptin is a potent, selective inhibitor of the serine protease dipeptidyl peptidase IV (DPP-4). Herein, we describe the structure-based design and optimization of alogliptin and related quinazolinone-based DPP-4 inhibitors. Following an oral dose, these noncovalent inhibitors provide sustained reduction of plasma DPP-4 activity and a lowering of blood glucose in animal models of diabetes. Alogliptin is currently undergoing phase 111 trials in patients with type 2 diabetes.
