40848-52-0Relevant articles and documents
Synthesis and in vitro anti-proliferative activity of some novel isatins conjugated with quinazoline/phthalazine hydrazines against triple-negative breast cancer MDA-MB-231 cells as apoptosis-inducing agents
Eldehna, Wagdy M.,Almahli, Hadia,Al-Ansary, Ghada H.,Ghabbour, Hazem A.,Aly, Mohamed H.,Ismael, Omnia E.,Al-Dhfyan, Abdullah,Abdel-Aziz, Hatem A.
, p. 600 - 613 (2017/11/10)
Treatment of patients with triple-negative breast cancer (TNBC) is challenging due to the absence of well- defined molecular targets and the heterogeneity of such disease. In our endeavor to develop potent isatin-based anti-proliferative agents, we utiliz
Synthesis of 4-substituted chlorophthalazines, dihydrobenzoazepinediones, 2-pyrazolylbenzoic acid, and 2-pyrazolylbenzohydrazide via 3-substituted 3-hydroxyisoindolin-1-ones
Nguyen, Hanh Nho,Cee, Victor J.,Deak, Holly L.,Du, Bingfan,Faber, Kathleen Panter,Gunaydin, Hakan,Hodous, Brian L.,Hollis, Steven L.,Krolikowski, Paul H.,Olivieri, Philip R.,Patel, Vinod F.,Romero, Karina,Schenkel, Laurie B.,Geuns-Meyer, Stephanie D.
experimental part, p. 3887 - 3906 (2012/06/30)
Figure Persented: Herein we describe a general three-step synthesis of 4-substituted chlorophthalazines in good overall yields. In the key step, N,N-dimethylaminophthalimide (8a) directs the selective monoaddition of alkyl, aryl, and heteroaryl organometallic reagents to afford 3-substituted 3-hydroxyisoindolinones 9b, 9i-9am. Many of these hydroxyisoindolinones are converted to chlorophthalazines 1b-1v via reaction with hydrazine, followed by chlorination with POCl3. We have also discovered two novel transformations of 3-vinyl- and 3-alkynyl-3-hydroxyisoindolinones. Addition of vinyl organometallic reagents to N,N-dimethylaminophthalimide (8a) provided dihydrobenzoazepinediones 15a-15c via the proposed ring expansion of 3-vinyl-3-hydroxyisoindolinone intermediates. 3-Alkynyl-3-hydroxyisoindolinones react with hydrazine and substituted hydrazines to afford 2-pyrazolyl benzoic acids 16a-16d and 2-pyrazolyl benzohydrazides 17a-17g rather than the expected alkynyl phthalazinones.