Synthesis and Properties of Two Antineoplastic Methanesulfonate Agents Utilizing Folic Acid and Triethanolamine

R.   L.   Bartzatt

Abstract

The synthesis of two antineoplastic compounds is accomplished by placing threemethanesulfonate groups on folic acid (I) and triethanolamine (II). Methane-sulfonate agents (I) and (II), alkylate an aqueous nucleophilic primary amine group at physiological pH 7.4 and 37 °C. Compound (I) utilizes folic acid as a drug carrier for highly specific delivery into tumor cells that have increased folic acid receptors. There are three reactive sites within (I) and (II) for alkylation of nucleophilic targets within tumor cells. Alkylation activity of compounds (I) and (II) showed first-order and second-order reaction kinetics, respectively. Molecular properties such as Log P,molar refractivity, aqueous solubility, polar surface area, halflife of reaction, and Log BB are determined.

Keywords: methanesulfonate, antineoplastic, folic acid, alkylation

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