Antiradiation compounds. XXII. Methyl 3-amino-2-phenyldithiopropenoates and 1,1-bis(methylthio)-3-amino-2-phenyl-1-propenes

Journal Article · Thu Oct 01 04:00:00 EDT 1987 · J. Pharm. Sci.; (United States)

DOI:https://doi.org/10.1002/jps.2600761012· OSTI ID:5441116

Foye, W O; Jones, R W; Ghoshal, P K

The title compounds were prepared in the attempt to provide methylthio and bis(methylthio) analogues of the radioprotective pyridinium- and quinolinium-2-dithioacetic acid derivatives in which the methylthio function is attached to an amino group through an aliphatic chain. The methyl 3-amino-2-phenyldithiopropenoates were obtained by the reaction of amines with 4-phenyl-3-methylthio-1,2-dithiolium iodide, and the 1,1-bis(methylthio)-3-amino-2-phenyl-1-propenes were obtained by methylation and reduction of the dithiopropenoates. The methyl dithiopropenoates with aliphatic substituents on the nitrogen gave only fair or poor radiation protection in mice, and one example of the reduced bis(methylthio) derivatives tested was inactive. The precursor 1,2-dithiole-3-thione and its methiodide, predicted to be radiation protective, were found inactive in this test.

• Research Organization: Massachusetts College of Pharmacy and Allied Health Sciences, Boston (USA)
• OSTI ID: 5441116
• Journal Information: J. Pharm. Sci.; (United States), Journal Name: J. Pharm. Sci.; (United States) Vol. 76:10; ISSN JPMSA
• 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.
ALKENES
ANIMALS
CHEMICAL REACTIONS
DISULFIDES
DRUGS
HYDROCARBONS
MAMMALS
METHYLATION
MICE
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PRECURSOR
RADIATION PROTECTION
RADIOPROTECTIVE SUBSTANCES
RADIOSENSITIVITY EFFECTS
RODENTS
STRUCTURE-ACTIVITY RELATIONSHIPS
VERTEBRATES