Citation: HE Dian, YANG Zhu-Qing, HOU Meng. Synthesis, Crystal Structure and Antitumor Activities of N-(2-(1H-indol-3-yl)ethyl)-2-nitroaniline[J]. Chinese Journal of Structural Chemistry, ;2014, 33(12): 1784-1788. doi: 10.14102/j.cnki.0254-5861.2011-0364 shu

Synthesis, Crystal Structure and Antitumor Activities of N-(2-(1H-indol-3-yl)ethyl)-2-nitroaniline

HE Dian ^a,b,, ,
YANG Zhu-Qing ^a ,
HOU Meng ^a

a.
a. Institute of Medicinal Chemistry, School of Pharmaceutical Science, Lanzhou University, Lanzhou 730000, China;
b.
b. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

Corresponding author: HE Dian,
Received Date: 6 May 2014
Available Online: 1 July 2014
Fund Project: This paper was supported by the Fundamental Research Funds for the Central Universities (lzujbky-2010-137) (lzujbky-2010-137)

The title compound, N-(2-(1H-indol-3-yl)ethyl)-2-nitroaniline (C₁₆H₁₅N₃O₂, M_r=281.31), has been synthesized by the multicomponent reaction of milder Ullmann, and its structure was characterized by ¹H NMR, ¹³C NMR, IR, H RMS (ESI) and single-crystal X-ray diffraction. It crystallizes in monoclinic, space group I2/c with a=15.0212(10), b=9.4911(6), c=20.3075(13)Å, β=100.776(7)°, V=2844.1(3)Å³, Z=8, D_c=1.314 g/cm³, F(000)=1184.0, μ=0.089 mm^-1, the final R=0.0574 and wR=0.1688 for 1701 observed reflections (I>2σ(I)). X-ray analysis indicates three major N(2)-H(2)…O(2), C(13)-H(13)…O(2), N(2)-H(2)…N(3) hydrogen bonds and π-π stacking interactions in the crystal structure. The preliminary biological test shows that the title compound has a good antitumor activity against A549 in vitro with the IC₅₀ value of 35 μmol/L.
- crystal structure,
- synthesis,
- N-(2-(1H-indol-3-yl)ethyl)-2-nitroaniline,
- biological activity
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