9-Methoxyacridine

Quinacrine Quinacrine, 6-chloro-9-(4-diethylamino-l-methylbntylamino)-2-methoxy-acridine (37.1.4.3), is synthesized from 6,9-dichloro-2-methoxyacridine (37.1.4.2) and aforementioned 4-diethylamino-l-methylbutylamine (37.1.1.2). The 6,9-dichloro-2-methoxyacridine (37.1.4.2) necessary for the synthesis is made in two stages. The initial reaction of 2,4-dichlorobenzoic acid and p-anizidine in the presence of copper dnst and potassium carbonate gives 2-(4-methoxyanilino)-4-chlorobenzoic acid (37.1.4.1), which upon reaction with phosphorus oxychloride turns into the necessary 6,9-dichloro-2-methoxyacridine (37.1.4.2) [33-38]. 

SYNS ACRICHINE ACRLNAMINE ACRIQUINE AKRICHIN ANTIMALARINA 6-CHLORO-9-((4-(DIETHYL AMINO)-l-METHYL BUTYL)AMINO)-2-METHOXYACRIDINE 3-CHLORO-7-METHOXY-9-(l-METHYL-4-DIETHYLAMINOBUTYUMvnNO)ACRlDINE... 

SYNS 9-(4-BIS(2-CHLOROETHYL)AMINO-l-iMETHYL-BUTYLAMINO)-6-CHLORO-2-METHOXYACRIDINE DIHYDROCHLORIDE ICR 10 2-METHOXY-6-CHLORO-9-(4-BIS(2-CHLOROETHYL)AMINO-l-iMETHYLBUTYLAiMINO)ACRIDINE DIHYDROCHLORIDE 2-METHOXY-6-CHLORO-9-(3-(ETHYL-2-CHLOROETHYL)AMINOPROPYLAMINO)ACRIDINE DIHYDROCHLORIDE QUINACRINE MUSTARD... 

BIS-(CHLOROETHYLAMINO)-1,6-DIDEOXY-d-MANNITOLDIHYDROCHLORIDE see MAW750 4 -(BIS(2-CHLOROETHYL)AMINO)-2-FLUORO ACETANILIDE see BHP750 l-(3-(BIS(2-CHLOROETHYL)AMINO-4-METHYLBENZOYL)AZIRIDINE) see BHQ760 l-(3-(BIS(2-CHLOROETHYL)AMINO)-4-METHYLBENZOYL)MORPHOLINE see BHR400 9-(4-BIS(2-CHLOROETHYL)AMINO-l-METHYLBUTYLAMINO)-6-CHLORO-2-METHOXYACRIDINE DIHYDROCHLORIDE see QDSOOO... 

Acyl-2,5-bis(arylamino)-l,A-benzoquinones (2) undergo cyclisation in either sulphuric acid or methanolic Itydrogen chloride to yield acridinequinones (3) (K. Joos, M. Pardo and W. Schafer, J. chem. Research (M), 1978, 4901). 2-Methoxyacridine is the starting point for the... 

Girault, S., Grellier, R, Berecibar, A., Maes, L., Mouray, E., Lemiere, R, Debreu, M.-A., Davioud-Charvet, E., Sergheraert, C. Antimalarial, antitrypanosomal, and antileishmanial activities and cytotoxiciy of bis(9-amino-6-chloro-2-methoxyacridines) influence of the linker. J. Med. Chem. 2000, 43, 2646-2654. 

A library of fe(6-chloro-2-methoxyacridin-9-yl) and fe(7-chloro-2-met-hoxybenzo[Z>][l,5]naphthyridin-10-yl) analogs was synthesized to explore the effect of structurally diverse linkers on PrPSe replication in scrapie-infected neuroblastoma cells (2003MI4). 

Nitrene insertion. A nitrene insertion reaction is central to many syntheses of pyridoacridine alkaloids and their analogues. For example, Labarca et al. [87JCS(P1)927] have reported a three-step synthesis of a pyridoacridine 169 starting from 2-methoxyacridine-9-carboxaldehyde 165 (Scheme 26). Cyclization of the vinyl azide 166 by thermolysis is believed to involve a nitrene insertion reaction, to give either 167 or 168. 

Quinacrine. N4-(6-Chloro-2-methoxy-9-acridin-ylt-N. N -diethyl-l.d-pentanediamine 6-chloro-9-[[4-(di-ethylaminot-1-methylbutylJaminoJ-2-methoxyacridine 3-... 

Publications about oligonucleotides linked to acridine derivatives have been summarized by several authors [246,275-277], The intercalating properties of acridine derivatives have been shown by NMR-studies [278, 279], 9-Amino-6-chloro-2-methoxyacridine is mostly used, which differs only slightly in size from the important intercalator drug, psoralen. Acridine-... 

Other Names Acridine, 9-amino-6-chlQro-2-methoxy- 2-Methoxy-6-chloro-9-aminoacridine 3-Chloro-7-methoxy-9-aminoacridme 6-Chloro-9-amino-2-methoxyacridine 9-Amino-3-chloro-7-methoxyacridine 9-Amino-6-chloro-2-methoxyacridme G 185 NSC 15300 CA Index Name 9-Acridinamine, 6-chloro-2-methoxy-CAS Registry Number 3548-09-2 Merck Index Number Not listed Chemical Structure... 

C23H2sBrN30, Ethidium bromide ethanol solvate, 40B, 278 C23H25CIN3O, Ethidium chloride ethanol solvate, 40B, 278 C2 3H36CI3N3O, 6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine dihydrochloride dihydrate, 39B, 216 C2 uNg, 1,14 7,8-Diethenotetrapyrido[1,3,5,8,10,12Ihexaazacyclo-tetradecine, 45B, 304... 

Casadio, R. Measurements of transmembrane pH differences of low extents in bacterial chromatophores. Study with the fluorescent probe 9-amino-6-chloro-2-methoxyacridine. Eur. Biophys. J. 1991,19,189-201. 

Dufour, J. R Goffeau, A. Tsong, T. Y. Active proton uptake in lipid vesicles reconstituted with the purified yeast plasma membrane ATPase. Eluorescence quenching of 9-amino-6-chloro-2-methoxyacridine. J. Biol. Chem. 1982, 257, 9365-9371. 

---