Citation: YANG Ping, GAO Hui, SONG Xin-Jian. Synthesis, Crystal Structure, and Antitumor Activity of 1-(4-Methoxybenzylidene)-2-(1-phenyl-6-trifluoromethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)hydrazine Monohydrate[J]. Chinese Journal of Structural Chemistry, ;2014, 33(8): 1129-1134. shu

Synthesis, Crystal Structure, and Antitumor Activity of 1-(4-Methoxybenzylidene)-2-(1-phenyl-6-trifluoromethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)hydrazine Monohydrate

YANG Ping ^a,b ,
GAO Hui ^a ,
SONG Xin-Jian ^a,b

a.
a. Key Laboratory of Biologic Resources Protection and Utilization of Hubei Province, Hubei Minzu University, Enshi 445000, China;
b.
b. College of Forestry and Horticultrue, Hubei Minzu University, Enshi 445000, China

Received Date: 20 March 2014
Available Online: 15 May 2014
Fund Project: Supported by the National Natural Science Foundation of China (No. 21262012) (No. 21262012) the Project for Cultivating Excellent Postgraduate's Dissertation of Hubei Minzu University (PY201402) (No. PKLHB1314) and the First-class Discipline of Forestry in Hubei Minzu University (PY201402)

The novel title compound 1-(4-methoxybenzylidene)-2-(1-phenyl-6-trifluoromethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)hydrazine monohydrate (C₂₀H₁₅F₃N₆O·H₂O, M_r=430.40) has been synthesized by a four-step procedure including the cyclization, chlorination, hydrazinolysis and condensation reaction, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to orthorhombic, space group Pbca with a=8.3779(13), b=17.607(3), c=26.774(4) Å, V=3949.2(11) Å³, Z=8, D_c=1.448 g/cm³, μ=0.117 mm^-1, F(000)=1776, the final R=0.0553 and wR=0.1516 for 2354 observed reflections with I>2σ(I). X-ray diffraction analysis reveals that the title compound is almost coplanar except for the trifluoromethyl and phenyl moieties. In the crystal packing, the molecules are linked by intermolecular O(1W)-H(1WA)…N(2), O(1W)-H(1WA)…N(4) and N(5)-H(5A)…O(1W) hydrogen bonds via water molecules and stacked through π-π stacking interactions. The preliminary bioassay suggested that the title compound exhibits relatively good antitumor activity against HepG2 and BCG-823.
- pyrazolo[3,4-d]pyrimidine,
- hydrazone,
- trifluoromethyl,
- antitumor activity
1. [1]
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2. [2]
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13. [13]
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14. [14]
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17. [17]
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