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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 24
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Original Articles

Diversity-oriented TsOH catalysis-enabled construction of tanshinone-substituted bis(indolyl/pyrrolyl)methanes and their biological evaluation for anticancer activities

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Pages 2378-2386 | Received 18 Jun 2017, Published online: 10 Nov 2017

References

  • For selected examples, see: (a) Choi, S. K. Synthetic Multivalent Molecules; Wiley-Interscience: New York, 2004; (b) Nakagawa-Goto, K.; Yamada, K.; Nakamura, S.; Chen, T.-H.; Chiang, P.-C.; Bastow, K. F.; Wang, S. C.; Spohn, B.; Hung, M. C.; Lee, F. Y.; Bioorg. Med. Chem. Lett. 2007, 17, 5204–5209; (c) Samala, G.; Devi, P. B.; Nallangi, R.; Sridevi, J. P.; Saxena, S.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. 2014, 22, 1938–1947; (d) Sang, Z.; Li, Y.; Qiang, X.; Xiao, G.; Liu, Q.; Tan, Z.; Deng, Y. Bioorg. Med. Chem. 2015, 23, 668–680; (e) Kaminski, K.; Rapacz, A.; Łuszczki, J.; Latacz, G.; Obniska, J.; Kiec-Kononowicz, K.; Filipek, B. Bioorg. Med. Chem. 2015, 23, 2548–2561; (f) Wan, Z.-Y.; Tao, Y.; Wang, Y.-F.; Mao, T.-Q.; Yin, H.; Chen, F.-E.; Piao, H.-R.; Clercq, E. D.; Daelemans, D.; Pannecouque, C. Bioorg. Med. Chem. 2015, 23, 4248–4255; (g) Zhao, Y.; Su, J.; Goto, M.; Morris-Natschke, S. L.; Li, Y.; Zhao, Q.-S.; Yao, Z.-J.; Lee, K.-H. J. Med. Chem. 2013, 56, 4749–4757; (h) Zhang, Y.; Wei, B.-W.; Lin, H.; Zhang, L.; Liu, J.-X.; Luo, H.-Q.; Fan, X.-L. Green Chem. 2015, 17, 3266–3270; (i) MacClean, D.; Schullek, J. R.; Murphy, M. M.; Ni, Z.-J.; Gordon, E. M.; Gallop, M. A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 2805–2810; (j) Hanessian, S.; Bayrakdarian, M. Bioorg. Med. Chem. Lett. 2000, 10, 427–431; (k) Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441–9444; (l) Lo, M.-C.; Neimann, C. S.; Nagayama, S.; Perlstein, E. O.; Schreiber, S. L. J. Am. Chem. Soc. 2004, 126, 16077–16086; (m) Yu, J.-S.; Zhou, F.; Liu, Y.-L.; Zhou, J. Synlett 2015, 26, 2491–2504.
  • For selected examples, see: (a) Lee, W. Y.; Cheung, C. C.; Liu, K. W.; Fung, K. P.; Wong, J.; Lai, B. S.; Yeung, H. K. J. Nat. Prod. 2010, 73, 854–859; (b) Yin, H. Q.; Kim, Y. S.; Choi, Y. J.; Kim, Y. C.; Sohn, D. H.; Ryu, S. Y.; Lee, B. H. Arch. Pharm. Res. 2008, 31, 659–665; (c) You, Z.; Xin, Y.; Liu, Y.; Han, B.; Zhang, L.; Chen, Y.; Gu, L.; Gao, H.; Xuan, Y. Exp. Toxicol. Pathol. 2012, 64, 453–458; (d) Tan, X.; Li, J.; Wang, X.; Chen, N.; Cai, B.; Wang, G.; Shan, H.; Dong, D.; Liu, Y.; Li, X.; Yang, F.; Li, X.; Zhang, P.; Li, X.; Yang, B.; Lu, Y. Int. J. Biol. Sci. 2011, 7, 383–389; (e) Wang, X.; Wang, Y.; Jiang, M.; Zhu, Y.; Hu, L.; Fan, G.; Wang, Y.; Li, X.; Gao, X. J. Ethnopharmacol. 2011, 135, 662–671; (f) Wang, W.; Zheng, L. L.; Wang, F.; Hu, Z. L.; Wu, W. N.; Gu, J.; Chen, J. G. J. Ethnopharmacol. 2011, 134, 147–155; (g) Ahn, Y. M.; Kim, S. K.; Lee, S. H.; Ahn, S. Y.; Kang, S. W.; Chung, J. H.; Kim, S. D.; Lee, B. C. Phytother Res. 2010, 24, 1886–1892; (h) Tang, C.; Xue, H.; Bai, C.; Fu, R.; Wu, A. Phytomedicine. 2010, 17, 1145–1149.
  • (a) Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Chem. Rev. 2010, 110, 2250–2293; (b) Bell, R.; Carmeli, S.; Sar, N. J. Nat. Prod. 1994, 57, 1587–1590; (c) Fahy, E.; Potts, B. C. M.; Faulkner, D. J.; Smith, K. J. Nat. Prod. 1991, 54, 564–569; (d) Swetha, A.; MadhuBabu, B.; Meshram, H. M. Tetrahedron Lett. 2015, 56, 1775–1779; (e) Garbe, T. R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.; Yukawa, H. J. Nat. Prod. 2000, 63, 596–598.
  • (a) Kohmoto, S.; Kashman, Y.; McConnell, O. J.; Rinehart Jr., K. L.; Wright, A.; Koehn, F. J. Org. Chem. 1988, 53, 3116–3118; (b) Wright, A. E.; Pomponi, S. A.; Cross, S. S.; McCarthy, P. J. Org. Chem. 1992, 57, 4772–4775; (c) Capon, R. J.; Rooney, F.; Murray, L. M.; Collins, E.; Sim, A. T. R.; Rostas, J. A. P.; Butler, M. S.; Carroll, A. R. J. Nat. Prod. 1998, 61, 660–662; (d) Cutignano, A.; Bifulco, G.; Bruno, I.; Casapullo, A.; Gomez-Paloma, L.; Riccio, R. Tetrahedron 2000, 56, 3743–3748; (e) Shiri, M.; Ali-Zolfigol, M.; Kruger, H. G.; Tanbakouchain, Z. Chem. Rev. 2010, 110, 2250–2293; (f) Ryan, K. S., Drennan, C. L. Chem. Biol. 2009, 16, 351–364; (g) Wang, G.; Shang, L.; Burgett, A. W. G.; Harran, P. G.; Wang, X. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 2068–2073; (h) Williams, N. S.; Burgett, A. W. G.; Atkins, A. S.; Wang, X.; Harran, P. G.; McKnight, S. L. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 2074–2079.
  • Fischer, E.; Justus, L. Ann. Chem. 1887, 242, 372–383.
  • Noland, W. E.; Venkiteswaran, M. R. J. Org. Chem. 1961, 26, 4263–4269.
  • (a) Sharma, G. V. M.; Reddy, J. J.; Lakshmi, P. S.; Krishna, P. R. Tetrahedron Lett. 2004, 45, 7729–7732; (b) Xia, M.; Wang, S. H.; Yuan, W. B. Synth. Commun. 2004, 34, 3175–3182; (c) Ji, S. J.; Wang, S. Y.; Zhang, Y.; Loh, T. P. Tetrahedron 2004, 60, 2051–2055.
  • (a) Ji, S. J.; Zhou, M. F.; Gu, D. G.; Wang, S. Y.; Loh, T. P. Synlett 2003, 13, 2077–2079; (b) Mi, X.; Luo, S.; He, J.; Cheng, J. P. Tetrahedron Lett. 2004, 45, 4567–4570.
  • (a) Deb, M. L.; Bhuyan, P. J. Tetrahedron Lett. 2006, 47, 1441–1443; (b) Lin, X. F.; Cui, S. L.; Wang, Y. G. Synth. Commun. 2006, 36, 3153–3160.
  • (a) Pore, D. M.; Desai, U. V.; Thopate, T. S.; Wadgaonkar, P. P. Arkivoc 2006, 12, 75–80; (b) Zolfigol, M. A.; Velsi, H.; Farajollah, M.; Sedrpoushan, A. J. Heterocycl. Chem. 2011, 48, 977–986; (c) Zeng, X. F.; Ji, S. J. Lett. Org. Chem. 2006, 3, 374–378.
  • (a) Nie, J.; Zhang, G. W.; Wang, L.; Fu, A.; Zheng, Y.; Ma, J. A. Chem. Commun. 2009, 17, 2356–2358; (b) Fu, A.; Meng, W.; Li, H.; Nie, J.; Ma, J. A. Org. Biomol. Chem. 2014, 12, 1908–1918.
  • (a) Maiti, A. K.; Bhattacharyya, P. J. Chem. Res. Synop. 1997, 11, 424–425; (b) Chakrabarty, M.; Ghosh, N.; Basak, R.; Harigaya, Y. Tetrahedron Lett. 2002, 43, 4075–4078.
  • CCDC 1555819 contains the supplementary crystallographic datas for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • (a) Mosman, T. J. Immunol. Methods 1983, 65, 55–63; (b) Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Shoemaker, R. H.; Boyd, M. R. Cancer Res. 1988, 48, 589–601.

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