Citation: SHI Xiu-Dong, GE Bing-Chen, XU Jiang-Ping, ZHOU Zhong-Zhen. Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole[J]. Chinese Journal of Structural Chemistry, ;2016, 35(1): 34-38. doi: 10.14102/j.cnki.0254-5861.2011-0857 shu

Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole

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a Neuropharmacology Group, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China;
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b Key Laboratory of New Drug Screening of Guangdong Province, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China

Received Date: 17 June 2015
Available Online: 14 October 2015
Fund Project: The project was supported by the National Natural Science Foundation of China (No. 21002048) (No. 21002048)

The title compound 6-chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-ben- zofuro[3,2-c]pyrazole (5, C₂₁H₁₃Cl₂N₃O, M_r = 394.26) was synthesized and characterized by elemental analysis, ¹H NMR,¹³C NMR and X-ray single-crystal diffraction. The structure reveals that the crystal belongs to the triclinic system, space group P1 with a = 7.8829(8), b = 10.3281(10), c = 11.7615(12) Å, α = 83.5552(2), β = 79.921(2), γ = 70.189(2)°, V = 885.54(15) Å³, Z = 2, D_c = 1.479 g/cm³, μ = 0.383 mm^-1, F(000) = 404, R = 0.0538 and wR = 0.1335 for 2453 observed reflections with I > 2σ(I). The result reveals that the crystal structure of the title compound 5 is stabilized by three C-Cl…π interactions and π…π stacking interaction. In addition, the preliminary investigation showed that 5 exhibits remarkably good antitumor activity against the MCF-7 and A549 cell lines.
- benzofuro[3,2-c]pyrazole,
- synthesis,
- crystal structure,
- antitumor activity
1. [1]
  (1) Pinna, G.; Loriga, G.; Lazzari, P.; Ruiu, S.; Falzoi, M.; Frau, S.; Pau, A.; Murineddu, G.; Asproni, B.; Pinna, G. A. Tricyclic pyrazoles. part 6. benzofuro[3,2-c]pyrazole: a versatile architecture for CB2 selective ligands. Eur. J. Med. Chem. 2014, 82, 281-292.
2. [2]
  (2) Atobe, M.; Naganuma, K.; Kawanishi, M.; Morimoto, A.; Kasahara, K. I.; Ohashi, S.; Suzuki, H.; Hayashi, T.; Miyoshi, S. SAR－based optimization of 2-(1H-pyrazol-1-yl)-thiazole derivatives as highly potent EP1 receptor antagonists. Bioorg. Med. Chem. Lett. 2013, 23, 6569-6576.
3. [3]
  (3) Rosen, M. D.; Woods, C. R.; Goldberg, S. D.; Hack, M. D.; Bounds, A. D.; Yang, Y.; Wagaman, P. C.; Phuong, V. K.; Ameriks, A. P.; Barrett, T. D.; Kanelakis, K. C.; Chang, J.; Shankley, N. P.; Rabinowitz, M. H. Discovery of the first known small-molecule inhibitors of heme-regulated eukaryotic initiation factor 2α (HRI) kinase. Bioorg. Med. Chem. Lett. 2009, 19, 6548-551.
4. [4]
  (4) Cools, J.; Mentens, N.; Furet, P.; Fabbro, D.; Clark, J. J.; Griffin, J. D.; Marynen, P.; Gilliland, D. G. Prediction of resistance to small molecule FLT3 inhibitors: implications for molecularly targeted therapy of acute leukemia. Cancer Res. 2004, 64, 6385-6389.
5. [5]
  (5) Murata, K.; Kumagai, H.; Kawashima, T.; Tamitsu, K.; Irie, M.; Nakajima, H.; Suzu, S.; Shibuya, M.; Kamihira, S.; Nosaka, T.; Asano, S.; Kitamura, T. Selective cytotoxic mechanism of GTP-14564, a novel tyrosine kinase inhibitor in leukemia vells expressing a constitutively active fms-like tyrosine kinase 3 (FLT3). J. Biol. Chem. 2003, 278, 32892-32898.
6. [6]
  (6) Zhou, Z. Z.; Zou, M.; Zhou, J.; Zhou, C. Q.; Deng, Y. H.; Chen, M. H.; Gu, C. P.; Jiang, Z. H.; Chen, W. H.; Liu, S. W. Synthesis, cytotoxicities and DNA-binding affinities of benzofuran-3-ols and their fused analogs. Chem. Pharm. Bull. 2011, 59, 1057-1061.
7. [7]
  (7) Yang, J. S.; Lee, C.; Cho, M.; Kim, H.; Kim, J. H.; Choi, S.; Oh, S. J.; Kang, J. S.; Jeong, J. H.; Kim, H. J.; Han, G. Discovery of orally available runt-related transcription factor 3 (RUNX3) modulators for anticancer chemotherapy by epigenetic activation and protein stabilization. J. Med. Chem. 2015, 58, 3512-3521.
8. [8]
  (8) Srungboonmee, K.; Songtawee, N.; Monnor, T.; Prachayasittikul, V.; Nantasenamat, C. Probing the origins of 17β-hydroxysteroid dehydrogenase type 1 inhibitory activity via QSAR and molecular docking. Eur. J. Med. Chem. 2015, 96, 231-237.
9. [9]
  (9) Zhou, Z. Z.; Deng, Y. H.; Jiang, Z. H.; Chen, W. H. Microwave-assisted dieckmann reaction: efficient one-step synthesis of 2-aroylbenzofuran-3-ols. Adv. Synth. Catal. 2010, 352, 1909-1913.
10. [10]
  (10) Sheldrick, G. M. SHELXS-97. Program for the Solution of Crystal Structure. University of Göttingen, Germany 1997.
11. [11]
  (11) Sheldrick, G. M. SHELXL-97. Program for the Refinement of Crystal Structure. University of Göttingen, Germany 1997.
12. [12]
  (12) Chen, X. B.; Li, K.; Shi, D. Q. Synthesis and crystal structure of N-(1,3,4-thiadiazol-2-yl)-1-[1-(6-chloropyridin-3-yl)methyl]-5-methyl-1H-[1,2,3] triazol-4-carboxamide. Chin. J. Struct. Chem. 2008, 27, 1389-1392.
13. [13]
  (13) Wang, Z.; Jian, F.; Duan, C.; Bai, Z.; You, X. 2-(2-Hydroxybenzylidene)-1-(2-picoloyl)hydrazine hemihydrate. Acta Crystallogr., Sect. C Cryst. Struct. Commun. 1998, C54, 1927-1929.
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沈阳化工大学材料科学与工程学院沈阳 110142