Hydroxy derivatives of S-2-(3-aminopropylamine)ethyl dihydrogen phosphorothioate and related compounds as antiradiation agents

Journal Article · Wed Jan 01 04:00:00 EST 1975 · J. Med. Chem.; (United States)

DOI:https://doi.org/10.1021/jm00242a009· OSTI ID:7147884

Piper, J R; Rose, L M; Johnston, T P

The high antiradiation activity and low toxicity of sodium 3-amino-2-hydroxypropyl hydrogen phosphorothioate (1) suggested the introduction of hydroxyl groups into other types of radioprotective phosphorothioates. A number of such compounds were synthesized, including S-3-(3-aminopropylamino)-2-hydroxypropyl dihydrogen phosphorothioate (11, n = 3), S-2-(3-amino-2-hydroxypropylamino)ethyl dihydrogen phosphorothioate (20) and its propyl homolog 26, N,N'-(2-hydroxytrimethylene)bis(S-2-aminoethyl dihydrogen phosphorothioate) (40), S-2-(3-(2-hydroxyethylamino)propylamino)ethyl dihydrogen phosphorothioate (44), and sodium S-2-amino-2-(hydroxymethyl)-3-hydroxypropyl hydrogen phosphorothioate (49). Compounds 11 (n = 3), 20, 26, and 49 were highly protective when administered intraperitoneally but were generally ineffective when given perorally, as were the other hydroxylated phosphorothioates prepared. The introduction of hydroxyl groups significantly enhanced the radioprotective properties of nonhydroxylated parent compounds, however, only in the case of intraperitoneally administered 1.

• Research Organization: Kettering-Meyer Lab., Birmingham, AL
• OSTI ID: 7147884
• Journal Information: J. Med. Chem.; (United States), Journal Name: J. Med. Chem.; (United States) Vol. 18:8; ISSN JMCMA
• Country of Publication: United States
• Language: English

Related Subjects

560152* -- Radiation Effects on Animals-- Animals
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
BIOSYNTHESIS
DRUGS
EFFICIENCY
HYDROXYL RADICALS
INJECTION
INTAKE
INTRAPERITONEAL INJECTION
ORGANIC COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
ORGANIC SULFUR COMPOUNDS
RADICALS
RADIOPROTECTIVE SUBSTANCES
RESPONSE MODIFYING FACTORS
SYNTHESIS
THIOLS
TOXICITY