EFFECT OF HYDRATE WATER ON THE HYDROGEN BOND FORMATION IN DIMETHYLAMINOARGLABINE SALTS WITH HYDROCHLORIDE AND HYDRONITRA
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EFFECT OF HYDRATE WATER ON THE HYDROGEN BOND FORMATION IN DIMETHYLAMINOARGLABINE SALTS WITH HYDROCHLORIDE AND HYDRONITRATE K. M.Turdybekov1*, E. S. Mustafin1, D. M. Turdybekov2, and S. M. Adekenov3
The crystal structure of crystalline hydrates of dimethylaminoarglabine hydrochloride and dimethylaminoarglabine hydronitrate is determined by single crystal X-ray diffraction. It is established that in a crystal, water breaks the hydrogen bond between the anion and the cation in dimethylaminoarglabin hydrochloride and weakens it in dimethylaminoarglabin hydronitrate, which improves the solubility of salts in water. DOI: 10.1134/S0022476620070124 Keywords: dimethylaminoarglabine hydrochloride, dimethylaminoarglabine hydrochloride hydrate, dimethylaminoarglabine hydronitrate hydrate, hydrogen bond.
INTRODUCTION Many organic compounds exhibiting biological activity are insoluble or poorly soluble in water. Therefore, drugs based on them have been usually prepared with their water soluble derivatives. Biologically active compounds occur sometimes in the ion form in nature, e.g., В1 vitamin (thiamine) and its phosphorus derivatives, and do not require its conversion into the water soluble form [1]. A drug form is most often obtained based on a salt of the respective physiologically active compound. For instance, the antispastic drug adapromine (α-propyl-1-adamantylethylamine hydrochloride) or the antiviral drug dimedrochinum (1,2α-dimethyl-4е-ethinyl-trans-decahydroquinolol-4α hydrochloride) [2]. A new sesquiterpene lactone arglabine has been previously extracted from Artemisia glabella, which exhibited a pronounced antitumor activity in vitro [3]. In order to further test the biological activity of arglabine, well water-soluble dimethylamino arglabine hydrochloride (1) (Scheme 1) was synthesized [4]. The in vivo tests of 1 have shown the good clinical efficacy of the drug [5, 6]. The analysis of the structure of compound 1 revealed that a strong hydrogen bond between the cation and the anion was observed in the crystal. To study the effect of water molecules on the interaction between counterions a single crystal X-ray diffraction analysis of the crystal structures of crystal hydrates of dimethylamino arglabineа hydrochloride (2) and dimethylamino arglabine hydronitrate (3) was performed (Scheme 1).
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Buketov Karaganda State University, Karaganda, Republic of Kazakhstan; *[email protected]. 2Karaganda State Technical University, Karaganda, Republic of Kazakhstan. 3International Research and Production Holding “Phytochemistry”, Karaganda, Republic of Kazakhstan. Original article submitted September 6, 2019; revised January 23, 2020; accepted February 12, 2020. 0022-4766/20/6107-1097 © 2020 by Pleiades Publishing, Ltd.
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Scheme 1. Structural formulas of compounds 1-3.
EXPERIMENTAL Synthesis. A solution of 1 g arglabine in 10 mL of ethanol was treated with 10 mL of aqueous dimethylamine until the complete consumption of the starting material (controlled by thin-layer chromatography). Ethanol was distilled off in va
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