13501-67-2Relevant articles and documents
Synthesis of new atropisomers derived from methoxychloroacridine. Preparation of enantiomerically pure (aR)-(-)-2,2′-dihydroxy-9,9′-biacridine
Tuan Lormier, Anh,Boyer, Gérard,Faure, Robert,Pierre Galy, Jean
, p. 449 - 463 (2002)
New biacridinyl atropisomers were obtained from symmetric ligand 2,2′-dihydroxy-9,9′-biacridine (4), prepared from 9-chloro-2-methoxyacridine. Alternative O-acylation and alkylation led to different polycycles and to a biacridinyl crown ether. The molecular structures of 2,2′-di(p-chlorobenzoyloxy)-9,9′-biacridinyl (5) and (9,9′-bisacridinyl)-2,2′-dihydroxy-bis-(camphanate) ester (13) were solved by X-Ray crystallography, showing a 'scissor-like' host conformation and guest inclusion of chloroform and acetonitrile. The determination of X-Ray structure of one diastereomer (13) allows to assign the absolute configuration of enantiomerically recovered (aR)-(-)-2,2′-dihydroxy-9,9′-biacridinyl.
Synthesis of N-phenylanthranilic acid derivatives using water as solvent in the presence of ultrasound irradiation
Docampo Palacios, Maite L.,Pellon Comdom, Rolando F.
, p. 1771 - 1775 (2003)
An improved synthesis of N-phenylanthranilic acid using water as solvent can be achieved by ultrasound irradiation. A number of N-phenylanthranilic acids were prepared in good yields in a very short reaction time.
Frameshift mutagenicity and DNA intercalation of 9-amino-2-hydroxyacridine, a rat liver S9 metabolite of 9-aminoacridine
Tomosaka, Hideyuki,Anzai, Kentaro,Hasegawa, Eietsu,Horigome, Tsuneyoshi,Omata, Saburo
, p. 714 - 716 (1996)
9-Amino-2-hydroxyacridine, a rat liver S9 metabolite of 9-aminoacridine (9-AA), was synthesized, and found to have lower frameshift mutagenicity and stronger DNA binding affinity than 9-AA.
Design, synthesis and biological evaluation of N-anthraniloyl tryptamine derivatives as pleiotropic molecules for the therapy of malignant glioma
Fan, Xiaohong,Li, Junfang,Long, Lin,Shi, Tao,Liu, Dan,Tan, Wen,Zhang, Honghua,Wu, Xiaoyan,Lei, Xiaoyong,Wang, Zhen
, (2021/06/09)
COX-2 and STAT3 are two key culprits in the glioma microenvironment. Herein, to inhibit COX-2 and block STAT3 signaling, we disclosed 27 N-anthraniloyl tryptamine compounds based on the combination of melatonin derivatives and N-substituted anthranilic acid derivatives. Among them, NP16 showed the best antiproliferative activity and moderate COX-2 inhibition. Of note, NP16 decreased the level of p-JAK2 and p-STAT3, and blocked the nuclear translocation of STAT3 in GBM cell lines. Moreover, NP16 downregulated the MMP-9 expression of BV2 cells in a co-culture system of BV2 and C6 glioma cells, abrogated the proliferative/invasive/migratory abilities of GBM cells, induced apoptosis by ROS and the Bcl-2-regulated apoptotic pathway, and induced obvious G2/M arrest in glioma cells in vitro. Furthermore, NP16 displayed favorable pharmacokinetic profiles covering long half-life (11.43 ± 0.43 h) and high blood-brain barrier permeability. Finally, NP16 effectively inhibited tumor growth, promoted the survival rate, increased the expression of E-cadherin and reduced overproduction of PGE2, MMP-9, VEGF-A and the level of p-STAT3 in tumor tissue, and improved the anxiety-like behavior in C6 glioma model. All these evidences demonstrated N-anthraniloyl tryptamine derivatives as multifunctional anti-glioma agents with high potency could drain the swamp to beat glioma.
N-o-substituted phenyl benzamide-4-methylamino acridine compound as well as preparation method and application thereof
-
Paragraph 0024; 0036, (2020/05/05)
The invention discloses an N-o-substituted phenyl benzamide-4-methylamino acridine compound as well as a preparation method and application thereof. The compound is characterized in that the compoundis a compound with a structural formula shown as a formula I or pharmaceutically acceptable salt, ester or solvate thereof, wherein R1 is H, OCH3, OCH2CH3, F, Cl, Br, CF3, NO2 or straight-chain alkylwith a carbon atom number of 1-5; R2 is H, OCH3, OCH2CH3, F, Cl, Br, CF3, NO2 or straight-chain alkyl with a carbon atom number of 1 to 5; R3 is NH2, NHCH3, NHCH2CH3, OH, COOH, and SH, and R4 is H, OCH3 or linear alkyl with 1-5 carbon atoms and the like. The compound has the advantages that the compound can effectively inhibit DNA topoisomerase I, and proliferation of I-type HDAC and/or eukaryotictumor cells, and prevents and/or treats tumors.
