2-Ethoxy-6,9-diaminoacridine

Originator

Rivanol,Sopharma

The Uses of 2-Ethoxy-6,9-diaminoacridine

7-ethoxyacridine-3,9-diamine is used in biological studies for cancer regression by inducing a regeneration-like response by activating expression and/or function of YAP and/or TAZ.

Definition

ChEBI: Ethacridine is a member of acridines.

Manufacturing Process

A mixture of 250 parts by volume of ethylene glycol, 50 parts by weight of 6- nitro-9-chloro-2-ethoxyacridine (obtained by reaction of 52 parts by weight of 30 nitro-4-ethoxy-diphenylamine-6-carboxylic acid with phosphorous oxychloride), 10 parts by weight of ammonium chloride, and 11 parts by weight of urea were heated to 170°C and stirred for 1 hour at 170°-175°C. Subsequently, the whole was cooled to 100°C, the reaction mixture was introduced into 1000 parts by volume of water, rendered acidic to Congo paper by means of hydrochloric acid and the 6-nitro-9-amino-2-ethoxyacridine precipitated was filtered off. By reduction iron according to Bechamp, 6,9- diamino-2-ethoxy-acridine hydrochloride was obtained with yield of 83% as the yellow needles. The base was prepared by adding an equivalent of NaOH. MP: 124°C.
In practice it is usually used as lactate.

Therapeutic Function

Antiseptic, Antibacterial

Purification Methods

It crystallises from 50% EtOH or EtOH as orange-yellow crystals. It also crystallises as a monohydrate m 116-118o. It has a pK2 0 of 11.04 in 50% aqueous EtOH. The methiodide is soluble in H2O and has m 332-334o (dec) (from aqueous Me2CO). [Albert & Gledhill J Soc Chem Ind 61 159 1942, Foye et al. J Pharm Sci 57 1795 1968, Albert & Goldacre J Chem Soc 708 1946, Beilstein 22 II 458, 22 III/IV 6679, 22/12 V 243.]