21092-27-3Relevant academic research and scientific papers
Remarkable conversion of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones into the corresponding quinazoline-2,4(1H,3H)-diones: Spectroscopic analysis and X-ray crystallography
El-Azab, Adel S.,Khalil, Nasr Y.,Abdel-Aziz, Alaa A.-M.
, (2021/04/26)
A simple and efficient new synthetic method to obtain 3-substituted quinazolin-2,4-diones 9.16 by the reaction of 3-substituted 2- thioxo-quinazolin-4-ones 1.8 with sodamide under mild conditions was presented. The structure of the newly synthesized compounds was determined by infrared spectroscopy, UV-visible spectroscopy, nuclear magnetic resonance, and single-crystal X-ray crystallographic analysis. The crystal structure of 6-methyl-3-phenylquinazoline-2,4(1H,3H)-dione (11) [C15H12N2O2: MF. 252.27, triclinic, P-1, a = 7.8495 (13) ?, b= 12.456 (2) ?, c = 13.350 (2) ?, α = 103.322 (3)°, β = 90.002 (3)°, γ = 102.671 (4)°, V. 1237.5 (3) ?3, Z= 4, R = 0.0592, wR= 0.1699, S= 1.039] was determined. In the crystal cell, two identical conformers of compound 11 were found connected by intramolecular hydrogen bonds, responsible for the favourable occurrence of these two independent molecules.
Divergent 2-Chloroquinazolin-4(3H)-one Rearrangement: Twisted-Cyclic Guanidine Formation or Ring-Fused N-Acylguanidines via a Domino Process
Yan, Gang,Zekarias, Bereket L.,Li, Xiaoyu,Jaffett, Victor A.,Guzei, Ilia A.,Golden, Jennifer E.
, p. 2486 - 2492 (2020/02/13)
A highly efficient 2-chloroquinazolin-4(3H)-one rearrangement was developed that predictably generates either twisted-cyclic or ring-fused guanidines in a single operation, depending on the presence of a primary versus secondary amine in the accompanying diamine reagent. Exclusive formation of twisted-cyclic guanidines results from pairing 2-chloroquinazolinones with secondary diamines. Use of primary amine-containing diamines permits a domino quinazolinone rearrangement/intramolecular cyclization, gated through (E)-twisted-cyclic guanidines, to afford ring-fused N-acylguanidines. This scalable, structurally tolerant transformation generated 55 guanidines and delivered twisted-cyclic guanidines with robust plasma stability and an abbreviated total synthesis of an antitumor ring-fused guanidine (4 steps, 55 % yield).
Development of (E)-2-((1,4-Dimethylpiperazin-2-ylidene)amino)-5-nitro-N-phenylbenzamide, ML336: Novel 2-Amidinophenylbenzamides as Potent Inhibitors of Venezuelan Equine Encephalitis Virus
Schroeder, Chad E.,Yao, Tuanli,Sotsky, Julie,Smith, Robert A.,Roy, Sudeshna,Chu, Yong-Kyu,Guo, Haixun,Tower, Nichole A.,Noah, James W.,McKellip, Sara,Sosa, Melinda,Rasmussen, Lynn,Smith, Layton H.,White, E. Lucile,Aubé, Jeffrey,Jonsson, Colleen B.,Chung, Donghoon,Golden, Jennifer E.
, p. 8608 - 8621 (2014/12/11)
Venezuelan equine encephalitis virus (VEEV) is an emerging pathogenic alphavirus that can cause significant disease in humans. Given the absence of therapeutic options available and the significance of VEEV as a weaponized agent, an optimization effort wa
