In 1950,Proceedings of the Royal Irish Academy, Section B: Biological, Geological and Chemical Science included an article by Barry, Vincent C.; Belton, J. G.; Conalty, M. L.; O’Rourke, L.; Twomey, D.. Safety of 2-Amino-2,4-dichlorodiphenyl ether. The article was titled 《Antituberculous substances. VII. Derivatives of diphenyl ether》. The information in the text is summarized as follows:
An attempt is made to relate antitubercular activity to chem. structure among Ph2O derivatives The dilution which completely inhibits the growth of Mycobacterium tuberculosis for 6 wk was determined in each case. The compounds tested and their effective dilution (in the presence and in the absence of blood serum, resp.) are given as follows: Ph2O, -, 1000. Derivatives containing 1 solubilizing group: 4-H2N, -, 35,000; 4-HO, -, 100,000; 4-HO2C, -, <5,000; 4-HO3S, -, <1,000; 4-guanyl, 10,000, 25,000; and 2-H2N, -, 10,000. Derivatives containing 1 halogen atom: 4-chloro-4'-amino, 10,000, 200,000; 2-chloro-4'-amino, -, 250,000; 2-chloro-4-amino, 10,000, 250,000; 2-chloro-4'-guanyl, 10,000, 50,000; 2-chloro-4-guanyl, 25,000, 25,000; 4-chloro-4'-guanyl, 50,000, 150,000; 4-chloro-4'-hydroxy, -, 300,000; 4-chloro-4'-carboxy, -, 50,000; 4,4'-diguanyl, 1,000, 10,000; 2-chloro-4,4'-diguanyl, 10,000, 25,000; 4-chloro-2'-amino, -, 10,000; and 4-chloro-2',4'-diamino, -, 10,000. Dihalogenated derivatives: 2,4'-dichloro-4-guanyl, 50,000, 100,000; 2,4-dibromo-4'-amino, -, 400,000; 2,4-dichloro-4'-amino, 10,000, 600,000; 4-amino-2,4'-dichloro, 25,000, 1,000,000; 4-amino-2,2'-dichloro, 10,000, 400,000; 2-amino-2',4-dichloro, -, 100,000; 2-amino-4,4'-dichloro, 10,000, 150,000; 4-amino-2',4'-dichloro, 5,000, 400,000; and 2,3-diiodo-4-amino, -, 600,000. Trihalogenated derivatives: 2,2-diiodo-4-amino-4'-chloro, 25,000, 1,000,000; 2,4,5-trichloro-4'-amino, 50,000, 500,000; 2,4,6-trichloro-4'-amino, 25,000, 500,000; 2,4,5-trichloro-4'-hydroxy, -, 400,000; 2,4,5-trichloro-2',4'-diamino, -, 25,000; 2,2',4-trichloro-4'-amino, 10,000, 1,000,000. Miscellaneous derivatives and other compounds: 3,4-dimethyl-4'-amino, 10,000, 50,000; 2-chloro-4-isobutyl-4'-amino, 10,000, 750,000; 3,5-dimethyl-4-chloro-4'-amino, 25,000, 500,000; 2-methyl-4-amino-4'-chloro, -, 300,000; 2-amino-4-methyl-2'-bromo, -, 25,000; 2-bromo-4-methyl-2'-amino, -, 25,000; 2-amino-4-nitro-4'-chloro, 5,000, 10,000; 2,2',4,5-tetrachloro-4'-amino-, 25,000, 1,000,000; 4,4'-diamino, -, 1,000; 4-amino-4'-hydroxy, 10,000, 50,000; 4-amino-4'-carboxy, -, 5,000; and 4-nitro-4'-carboxy, -, 25,000; 2-hydroxy-4-aminobenzoic acid (PAS), 200, 300; sulphetrone, <1000, <1000; and streptomycin, 500,000, 1,000,000. Similar tests were run to determine the dilution needed to inhibit growth of M. smegmatus for 6 days and data are given. The most active compounds are those in which the hydrophilic group occupies the para position to the O bridge and its basic or acidic character is not significant. A grouping which possesses high water solubility depresses biol. activity, as when 2 HO, 2 H2N, or 2 guanyl groups are present. Introduction of 1 or 2 Cl substituents increases the antitubercular activity; further halogenation has little addnl. effect. The greatest activity is shown by compounds in which the halogens are shared by both Bz nuclei. Compounds which most strongly depress O uptake of yeast cells have the highest antitubercular activity. All of the Ph2O derivatives tested required a dilution of 50,000 or less in the presence of serum (in vivo) as compared to an active dilution of 1:500,000 for streptomycin.2-Amino-2,4-dichlorodiphenyl ether(cas: 56966-48-4Safety of 2-Amino-2,4-dichlorodiphenyl ether) was used in this study.
2-Amino-2,4-dichlorodiphenyl ether(cas: 56966-48-4) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Safety of 2-Amino-2,4-dichlorodiphenyl ether
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics