Citation: XU Ying-Shu, SHI Da-Bin. Synthesis, Crystal Structure and Antifungal Activities of 3-Methyl-1-(4-methylphenyl)-4-(N-4-trifluoromethylphenyl)-aminomethyl-5-(4-methoxyphenylthio)-1H-pyrazole[J]. Chinese Journal of Structural Chemistry, ;2014, 33(1): 37-42. shu

Synthesis, Crystal Structure and Antifungal Activities of 3-Methyl-1-(4-methylphenyl)-4-(N-4-trifluoromethylphenyl)-aminomethyl-5-(4-methoxyphenylthio)-1H-pyrazole

XU Ying-Shu ,
SHI Da-Bin

1.
School of Pharmaceutical Sciences, Zunyi Medical College, Zunyi 563003, China

Received Date: 14 June 2013
Available Online: 20 November 2013
Fund Project: This work was supported by Research Fund for the Doctoral Program of Zunyi Medical College (F-564) (F-564)Natural Science Foundation of Guizhou Province (No.J2011[2083]) (No.J2011[2083])

The title compound 3-methyl-1-(4-methylphenyl)-4-(N-4-trifluoromethylphenyl) aminomethyl-5-(4-methoxyphenylthio)-1N-pyrazole has been synthesized via a four-step reaction and characterized by IR, ¹H NMR, elemental analysis and X-ray crystallography. The compound crystallizes in monoclinic, space group P2₁/c with a=8.7170(15), b=18.355(3), c=15.292(3) Å, β=103.445(3)°, V=2379.7(7) Å³, D_c=1.350 g/cm³, Z=4, μ=0.184, F(000)=1008, and the final R=0.0491 and wR=0.1339 for 4160 observed reflections (I>2σ(I)). The results demonstrate that there is a face-to-face π-π stacking interaction between one benzene ring (C(19)~C(24)) and another (C(13)~C(18)) at a plane-plane distance of 3.3539 Å. The ring normal and vector between the ring centroids form an angle of 18.2° up to the centroid-to-centroid distance of 3.5273 Å. The crystal structure is stabilized by the intermolecular hydrogen bond of N(3)-H(3A)…N(2) (symmetry code:A-x+1,-y+1,-z). The preliminary biological test shows that the title compound has a moderate antifungal activity.
- pyrazole,
- crystal structure,
- thioether,
- synthesis,
- antifungal activity
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