Mannich bases of conjugated styryl ketones

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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546217, 546221, A61K 31445, C07D21148

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active

060179333

ABSTRACT:
Mannich bases of conjugated styryl ketones have been developed which are effective as cytotoxicity and anticancer agents, and which also have antifungal activity. Preferred compounds are those of the formula ##STR1## where R.sub.1 is Cl, CH.sub.3 or OCH.sub.3 and R.sub.2 is H or Cl. A compound of particular interest is (3-[3-(4-chlorophenyl)-2-propenoyl]-4-[2-(4-chlorophenyl)vinylene]-1-ethyl -4-piperidinol hydrochloride.

REFERENCES:
patent: 3655533 (1972-04-01), Page
patent: 3887568 (1975-06-01), Leir
80th Canadian Society for Chemistry Conference, Jun. 1-4, 1997, 534 "Synthesis, Cytotoxicity and Anticancer Activities of Some Acyclic and Cyclic Mannich Bases," J.R. Dimmock et al., College of Pharmacy and Nutrition, University of Saskatchewan.
Elias K. Manavathu et al., "In vitro antifungal activity of some Mannich bases of conjugated styryl ketones," Can. J. Microbiol. 44: 74-79 (1998).
Mohammed Jaffar et al., "Improved Stereospecific Syntheses of Novel 1-alkyl-3-benzoyl-4-hydroxy-4-phenylpiperidines," J. Pharm. Pharmacol. 1996, 48: 444-447.
B. V. Unkovskii et al., "Steric Structure of 1-alkyl-3-benzoyl-4-piperidinols and the stereochemistry of their synthesis," M. V. Lomonosov Moscow Institute of Fine Chemical Technology, pp. 1483-1487. Translated from Zhurnal Organicheskoi Khimii, vol. 2, No. 8, pp. 1501-1507, Aug., 1966.
John T. Plati et al., "1,3,4-Trisubstituted Piperidine Derivatives from Mannich Bases," J. Org. Chem. 14, 873-878 (1949).
J.R. Dimmock et al., "Activity of some Mannich bases of conjugated styryl ketones against Candida albicans," Pharmazie 49 (1994), H. 12., pp. 909-912.
SciFinder, Oct. 9, 1997, Answers 1-21, pp. 1-10.

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