Acridine hydroxy

Acridine, 9,10-dihydro-9,9-dimethyl-as antidepressant, 1, 169 Acridine, 9-formyl-synthesis, 2, 507 Acridine, 3-hydroxy-formylation, 2, 322 Acridine, 9-hydroxy-N-oxide... 

Proflavine — see Acridine, 3,6-diamino-Progesterone, 11 of-hydroxy-racemic... 

These compounds usually give many of the reactions characteristic of phenols and were long considered to exist completely in the hydroxy form (see, for example, reference 42). It has been noted that the ultraviolet spectra of aqueous ethanolic solutions of hydroxy-acridines varied with changes in the composition of the solvent, and this phenomenon has been interpreted in terms of the equilibria 132 133 and 134 135. Some compounds of these types show... 

The major class of topoisomerase I inhibitors comprise of the camptothecins, while topoisomerase II inhibitors fall into several classes - anthracyclines (e.g. doxorubicin), anthracenediones (mitoxantrone), anthrapyrazoles (bianthrazole), actinomycins (actinomycin D), acridines (m-AMSA), ellipticines (9-hydroxy-ellipticine) and epidophyllotoxins (Etoposide (VP-16) and VM-26). The chemical... 

Acridine-4,5-diol was converted to the corresponding 18-crown-6 ligand by alkylation of the hydroxy groups with tetraethylene glycol di-p-tosylate <99T1491>. 

For some time Tanasescu held the view that a group of compounds obtained by reaction of o-nitrobenzaldehydes with aromatic compounds in concentrated sulfuric acid, containing one oxygen atom more than the arylanthranils formed concurrently, were anthranil-A-oxides (e.g., 172).2QQ 201,206 Lehmstedt opposed this, and put forward the A-hydroxyacridone structure (173),213 312 which Tanasescu himself later adopted, although he preferred the tautomeric hydroxy-acridine- A-oxide structure (174).195 198 199 313... 

Acridin 2-Hydroxy-l,4,9-trioxo-1,4,9,10-tetrahydro- IV/lb, 695 Benzolgjquinolin 2,4-Dihydroxy- ... 

DIMETHYLHYDRAZINO)ACRIDINE MONOHYDROCHLORIDE see DSG330 2-(2,2-DIMETHYLHYDRAZINO)-4-(5-NTTRO-2-FURYL)THIAZOLE see DSG400 DIMETHYL HYDROGEN PHOSPHITE see DSG600 DIMETHYLHYDROGENPHOSPHITE see DSG600 DIMETHYL-2,5 (HYDROXY 4 BENZOYL) 3 FURANNE see DSClOO... 

Hydroxy-2-(trifluoromethyl)pyridine derivatives 80 (Scheme 31) were linked [53] to the acetamide moiety in the usual way. Pyridyloxy-acetamides 81 smoothly rearranged into the respective 4-aminopyridines 82 when heated with potassium carbonate in DMF at 150 °C. Acid hydrolysis provided amines 83. In a similar way, hydroxy-quinolines and hydroxy-acridines were transformed into the respective amines [50,54]. 

The acridinyl aniside amascrine (165) is useful in treatment of some cancers, including acute adult leukemia. The lactate of 7-ethoxy-3,9-acridine diamine, or ethacridine (166), is an abortifacient, used for induction of second trimester abortions. The antitumor drug mitozantrone (mitoxantrone, novantrone) (167), a bis(hydroxy)aminoanthraquinone... 

In some rigid planar systems snch as 34 photochemically induced proton transfer occurs in benzene as solvent, but this is followed by cyclization resulting in the formation of the acridine 35 . The cychzation is a common oxidative process in c -stilbenoid systems. The proton transfer is an essential feature in the cyclization, since it was demonstrated that the reaction fails with the methoxylated analogue. With the bis hydroxy compound 34, X = = OH, a second cyclization affords 36 albeit in lower yield (14%). 

Several routes to benz[c]acridines involve electrophilic aromatic substitution to form the heterocyclic ring. Thus, 9-nitrobenz[c]acridine results from the cyclisation of the 2-(l-naphtlylamino)benzaldehyde derived from 1-naphthylamine and 2-fluoro-5-nitrobenzaldehyde (J. Rosevear and J.F.K. Wilshire, Austral. J. Qiem., 1981, 34, 839). The reaction between a ff-aryl-l-naphthylamine and acetic anhydride has been used to synthesise 9- and ll-hydroxy-7-methylbenz[c]acridines and cyclisation of partially reduced 2-(l-naphtltylamino)benzoic acid by phosphorus oxychloride affords the 7-chloro-l,2,3,4-tetralydro derivative (B.V. Lap et ai,y J. heterocyclic Chem., 1983, 20, 281). 

The halogen atom of 7-chloro l,2,3.4-tetrahydrobenz [c]acridine is prone to nucleophilic displacement, as expected of a y-halogenopyridine system. Ready hydrolysis yields the 7-hydroxy compound and sodiomalononitrile affords the dicyanomethyl derivative both products exist as the keto-tautomers (B.V. Lap et at, 2. heterocyclic Chem., 1983, 20, 281). 

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