Method of inhibiting lung tumors, arylalkyl isothiocyanates, and

Details Method of inhibiting lung tumors, arylalkyl isothiocyanates, and Method of inhibiting lung tumors, arylalkyl isothiocyanates, and

1991-12-13

1993-07-27

Nutter, Nathan M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Isothiocyanate esters

585 24, C07C33100, C07C 1300

Patent

active

052312097

ABSTRACT:
A method of inhibiting lung tumor multiplicity and/or incidence by treating mammals with relatively long chain arylalkyl isothiocyanates, especially effective with respect to tumors induced by exposure to tobacco-specific nitrosamine. Among the isothiocyanates are 4-phenylbutyl isothiocyanate, phenylpentyl isothiocyanate and phenylhexyl isothiocyanate, which are synthesized by adding hydrochloride of phenylbutylamine, phenylpentylamine, or phenylhexylamine in water to thiophosgene in an inert organic solvent. For comparison testing, oxo-pyridyl butyl isothiocyanate is synthesized by dissolving myosmine in HCl to obtain a hydrochloride salt, suspending the salt in dry chloroform, adding thiophosgene, and adding chloroform containing triethylamine.

REFERENCES:
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Wattenberg, "Inhibition of Carcinogen-induced Neoplasia by Sodium Cyanate, tert-Butyl Isocyanate, and Benzyl Isothiiocyanate" Can. Res. 41, 2991-2994, Aug. 1981.
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Morse et al "Inhibition of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA Adduct Formation and Tumorigenicity in the Lung of F344 Rats by Dietary Phenethyl Isothiocyanate" Cancer Research 49, 549-553, Feb. 1, 1989.
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Effects of Aromatic Isothiocyanates on Tumorigenicity, O.sup.6 -Methylguanine Formation, and Metabolism of the Tabacco-specific Nitrosamine 4-(Methylnitrosamino)-1-Cancer Research 49, 2894-2897, Jun. 1, 1989.
Effects of alkyl chain length on the inhibition of NNK-induced lung neoplasia in A/J mice by arylalkyl isothiocyanates Carcinogenesis vol. 10, No. 9, pp. 1757-1759, 1989.
Morse et al, Structure-Acitivity Relationships For Inhibition of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone Lung Tumorigenesis by Arylalkyl Isothiocyanates in A/J Mice, Apr. 1, 1991, Cancer Research 51, pp. 1846-1850.

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