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Phosphorus-nitrogen compounds. 20. Thiophosphorus hydrazones

L A Cates, Y M Cho, L K Smith

Journal of Medicinal Chemistry

|September 1, 1976

Summary

New copper chelates and hydrazones show promise against Ehrlich ascites carcinoma in mice. Concurrent administration with copper ions significantly enhanced survival times, highlighting a potential therapeutic strategy.

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Area of Science:

Medicinal Chemistry
Pharmacology
Cancer Research

Background:

Pyridine derivatives and thiophosphoric hydrazones are classes of compounds with potential biological activity.
Ehrlich ascites carcinoma is a widely used murine model for evaluating anticancer agents.

Purpose of the Study:

To synthesize and evaluate novel pyridine-based hydrazones, hydrazides, and their metal chelates for anticancer activity.
To investigate the synergistic effects of copper or ferrous ions with these compounds against Ehrlich ascites carcinoma.

Main Methods:

Synthesis of six pyridine-2-carboxaldehydes, one pyridine N-oxide 2-carboxaldehyde, five diketone thiophosphoric hydrazones, three thiophosphoric hydrazides, and two cupric chelates.
In vivo testing of synthesized compounds and their combinations with metal salts against Ehrlich ascites carcinoma in mice.

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In vitro evaluation of enzyme inhibition against alkaline phosphatase and E. coli.

Main Results:

The chelate 'dimethyl pyridine-2-carboxaldehyde phosphorothioic hydrazone-copper (1:1)' exhibited the greatest anticancer activity.
Concurrent administration of cupric ion with the hydrazones significantly increased survival times in tumor-bearing mice.
Two thiosemicarbazones inhibited alkaline phosphatase activity, similar to previous findings.

Conclusions:

Copper chelates derived from pyridine-based hydrazones demonstrate significant potential as anticancer agents.
Co-administration with copper ions can potentiate the therapeutic efficacy of certain hydrazone compounds.
Further research into these metal complexes may lead to novel cancer therapies.