Crystal structures of 5-Bromo-2-hydroxybenzaldehyde, 2-hydroxy-3-methoxybenzaldehyde, and 2-hydroxynaphthalene-1-carbald
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CTURE OF ORGANIC COMPOUNDS
Crystal Structures of 5Bromo2Hydroxybenzaldehyde, 2Hydroxy3Methoxybenzaldehyde, and 2Hydroxynaphthalene 1Carbaldehyde 4(2Pyridyl) Thiosemicarbazones Yu. M. Chumakova, P. A. Petrenkoa, T. B. Coditab, V. I. Tsapkovb, D. Poirierc, and A. P. Guleab a
Institute of Applied Physics, Academy of Sciences of Moldova, Akademicheskaya ul. 5, Kishinev, MD2028 Moldova email: [email protected] b Moldova State University, ul. A. Mateevici 60, Kishinev, MD2009 Moldova c Laval University, rue de l’Université 2325, Quebec, 1506 Canada Received March 14, 2013
Abstract—5Bromo2hydroxybenzaldehyde, 2hydroxy3methoxybenzaldehyde, and 2hydroxynaph thalene1carbaldehyde 4(2pyridyl) thiosemicarbazones (I–III, respectively) were synthesized and their crystal structures were determined by Xray diffraction. All these molecules are almost planar. The presence of bulky substituents at the terminal nitrogen atoms of these molecules does not lead to changes in the con formation of the thiosemicarbazide moiety. Depending on the nature of substituents in the phenol rings, the crystals are composed of either centrosymmetric dimers (I) or infinite chains (II and III). In the concentra tion range of 10–5–10–7 mol/L, thiosemicarbazones I–III selectively inhibit the growth of human myeloid leukemia HL60 cells. DOI: 10.1134/S1063774514020072
INTRODUCTION Thiosemicarbazide derivatives are widely used in medicine for the treatment of different diseases [1]. All these derivatives have a wide range of reactive atoms and form biologically active compounds with different compositions and properties [2–5]. In many cases, the biological activity of these compounds correlates well with their structure. Hence, the synthesis of thiosemi carbazide derivatives and investigation of their struc
tural features are both of scientific and practical interest. The goal of the present study is to synthesize 5bromo2hydroxybenzaldehyde, 2hydroxy3meth oxybenzaldehyde, and 2hydroxynaphthalene1car baldehyde 4(2pyridyl) thiosemicarbazones (I–III, respectively) and determine their crystal structures by Xray diffraction.
R1 HO
HO S N
N NH NH I, II
S
;
R2
N
N NH NH III
I: R1 = H, R2 = Br; II: R1 = CH3O, R2 = H
EXPERIMENTAL Synthesis Compound I was synthesized accord ing to the following procedure. A solution of 4(2 pyridyl)thiosemicarbazide (10 mmol) in ethanol (35 mL) was added with stirring and heating (50– 55°С) on a water bath to a solution of 5bromosali cylic aldehyde (10 mmol) in ethanol (15 mL). The resulting pale orange solution was refluxed on a water
bath for 50–60 min. After slow evaporation of the solution overnight, a finely crystalline pale yellow compound precipitated (in 84% yield). The precipi tate was washed with a small amount of ethanol and dried in air. Its composition was determined by ele mental analysis. For C13H11BrN4OS anal. calcd. (%): C, 44.46; H, 3.16; Br, 22.75; N, 15.95; S, 9.13. Found (%): C, 44.37; H, 3.07; Br, 22.55; N, 15.67; S, 9.07. The melting point is 214–2
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