101005-04-3Relevant academic research and scientific papers
Simple Analogues of Quaternary Benzo[ c]phenanthridine Alkaloids: Discovery of a Novel Antifungal 2-Phenylphthalazin-2-ium Scaffold with Excellent Potency against Phytopathogenic Fungi
Cui, Zhi-Ming,Zhou, Bo-Hang,Fu, Chao,Chen, Liu,Fu, Juan,Cao, Fang-Jun,Yang, Xin-Juan,Zhou, Le
, p. 15418 - 15427 (2021/01/09)
Inspired by sanguinarine and chelerythrine, a novel antifungal 2-phenylphthalazin-2-ium scaffold as a simple analogue was designed. Most of the 30 compounds showed excellent inhibition activity against almost all eight phytopathogenic fungi, far superior to sanguinarine and chelerythrine. A third of the compounds were more active than azoxystrobin in most cases. Compounds 26 and 27 showed the highest total activity against all the fungi with EC50 means of ca. 4.6 μg/mL. Fusarium solani showed the highest susceptibility with an EC50 mean of 3.62 μg/mL to 19 compounds. A concentration of 25.0 μg/mL 27 can fully control the Colletotrichum gloeosporioides infection in apples over 9 days. Electron microscopic observations showed that 27 was able to damage the structures of the hypha and cell membrane. The structure-activity relationship showed that the presence of electron-withdrawing groups on the C-ring increases the activity against most of the fungi. Thus, 2-phenylphthalazin-2-ium compounds represent promising leads for the development of novel fungicides.
A trans-Folded Alkene System: Synthesis, Structure and Isomerization of 2,2'-Diaryl-1,1'-bi(1,2-dihydrophthalazinylidenes)
Butler, Richard N.,Gillan, Ann M.,Lysaght, Fiona A.,McArdle, Patrick,Cunningham, D.
, p. 555 - 564 (2007/10/02)
A series of 2,2'-diaryl-1,1'-bi(1,2-dihydrophthalazinylidenes) have been synthesized from 1-hydroxy-2-aryl-1,2-dihydrophthalazines.An X-ray crystal structure showed relief of strain in these new ylidenes by a trans-folding of the alkene linkage.The mechanism of their formation was probed with additives such as sulphur, N-phenylmaleimide, and dimethyl acetylenedicarboxylate which interacted with intermediates in the reaction and gave further interesting new ylidene structures.The mechanism of trans-cis isomerization of the biphthalazinylidenes was studied using 270 MHz 1 H-NMR spectroscopy to measure the kinetics and activation parameters for the isomerization.X-Ray crystal structures of the following compounds are reported: 2,2'(p-bromophenyl)-trans-1,1'-bi--4--1-phenyl-3,4-dihydropyrrole-2,5-dione, (10d); dimethyl 3-(2-phenyl-1,2-dihydrophthalazin-1-ylidene)-2-oxobutanedioate (11), and dimethyl 2-acetoxy-3-(2-phenyl-1,2-dihydrophthalazin-1-yl)but-2-ene-1,4-dioate (12).
1,1'-Bi-(2-aryl-1,2-dihydrophthalazinylidenes): Potential New Pigments. Relief of Strain by a trans-Folded Alkene Linkage
Butler, Richard N.,Gillan, Ann M.,McArdle, Patrick,Cunningham, Desmond
, p. 1016 - 1017 (2007/10/02)
1-Hydroxy-2-aryl-1,2-dihydrophthalazines are dimerized to give 1,1'-bi-(2-aryl-1,2-dihydrophthalazinylidenes); an X-ray crystal structure shows a relief of strain in these compounds by a trans-folded alkene linkage and a buckling of the phthalazinyl ring.
A Simple One-step Synthesis of N-Substituted Isoindolin-1-ones. Diastereofacially Selective Protonation of an Intermediate Isoindolinol
Grigg, Ronald,Gunaratne, H. Q. Nimal,Sridharan, Visuvanathar
, p. 1183 - 1184 (2007/10/02)
α-Amino acids and their methyl esters, arylamines, heterocyclic amines and, less efficiently, aryl substituted aliphatic amines, react with o-phthaldialdehyde in the presence of acetic acid to give N-substituted isoindolin-1-ones in excellent yield; deute
