Citation: HONG Yan-Ping, SHANGGUAN Xin-Chen, IQBAI Zafar, YIN Xiao-Li. Synthesis, X-ray Crystallographic Analysis and Bioactivities of α-Aminophosphonates Featuring Pyrazole and Fluorine Moieties[J]. Chinese Journal of Structural Chemistry, ;2014, 33(11): 1673-1682. doi: 10.14102/j.cnki.0254-5861.2011-0367 shu

Synthesis, X-ray Crystallographic Analysis and Bioactivities of α-Aminophosphonates Featuring Pyrazole and Fluorine Moieties

a.
a. Jiangxi Key Laboratory of Natural Product and Functional Food, College of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China;
b.
b. PCSIR Laboratories Complex, Feroze Pur Road Lahore 54000, Pakistan;
c.
c. Library of Jiangxi Agricultural University, Nanchang 330045, China

Corresponding author: HONG Yan-Ping,
Received Date: 9 May 2014
Available Online: 1 July 2014
Fund Project: This project was supported by the Future Talent Project of JXAU (No. 09003444) (No. 09003444)the Doctoral Research Foundation of JXAU (No. 09004065) (No. 09004065)

A series of novel α-aminophosphonates containing pyrazole and fluorine moieties was designed and synthesized through ultrasonic-assisted condensation and solvent-free addition reactions. Their structures were verified by IR, ¹H NMR, ¹³C NMR and elemental analysis. The crystal structure of diethyl[(4-cyano-1H-pyrazol-3-ylamino)(3,5-difluorophenyl)methyl]phosphonate (4a, C₁₅H₁₇F₂N₄O₃P) was determined by single-crystal X-ray diffraction. Compound 4a crystallizes in the triclinic system, space group P1, with a=8.381(3), b=10.103(5), c=11.268(3)Å, α=83.772(19), β=74.726(19), γ=70.964(18)°, V=869.9(6)Å³, M_r=370.30, D_c=1.414 g/cm³, Z=2, F(000)=384, μ=0.200 mm^-1, MoKa radiation (λ=0.71073Å), the final R=0.0487 and wR=0.0823 for 1582 observed reflections with I>2σ(I). X-ray diffraction analysis reveals that there are two planes in 4a, and the dihedral angle is 71.51°. Two intermolecular hydrogen bonds and a face-to-face π…π stacking interaction are observed in the crystal structure. The compounds were evaluated for their antifungal, antiviral and antitumor activities, respectively. Among them, 4b, 4c, 4g and 4h exhibit good activities on Sclerotium rolfsii Sacc at 200 μg/mL, while 4b, 4c, 4f and 4g possess good anti-TMV activities at 500 μg/mL. Unfortunately, all of the compounds showed weak antitumor activities.
- α-aminophosphonate,
- pyrazole and fluorine,
- crystal structure,
- bioactivities,
- synthesis
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