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Synthesis of novel 3-aryl isoindolinone derivatives

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Abstract

A library of novel 3-aryl isoindolinone derivatives with aromatic amino acid derivative fragments was designed and synthesized. Two synthetic routes were employed to construct 3-aryl isoindolinone ring system for different amino acid derivatives.

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References

  1. Kondo T., Yoshida K., Yoshimura Y., Tanayama S., Biopharm. Drug Dispos., 1995, 16(9), 755

    Article  CAS  Google Scholar 

  2. Linden M., Hadler D., Hofmann S., Human Psychopharmacology: Clinical and Experimental, 1997, 12(5), 445

    Article  CAS  Google Scholar 

  3. Stuk T. L., Assink B. K., Bates R. C., Erdman D. T., Fedij V., Jennings S. M., Lassig J. A., Smith R. J., Smith T. L., Organic Process Research & Development, 2003, 7(6), 851

    Article  CAS  Google Scholar 

  4. Belliotti T. R., Brink W. A., Kesten S. R., Rubin J. R., Wustrow D. J., Zoski K. T., Whetzel S. Z., Corbin A. E., Pugsley T. A., Heffner T. G., Wise L. D., Bioorganic & Medicinal Chemistry Letters, 1998, 8(12), 1499

    Article  CAS  Google Scholar 

  5. Zhuang Z. P., Kung M. P., Mu M., Kung H. F., J. Medicinal Chemistry, 1998, 41(2), 157

    Article  CAS  Google Scholar 

  6. Kanamitsu N., Osaki T., Itsuji Y., Yoshimura M., Tsujimoto H., Soga M., Chemical & Pharmaceutical Bulletin, 2007, 55(12), 1682

    Article  CAS  Google Scholar 

  7. Bernstein P. R., Aharony D., Albert J. S., Andisik D., Barthlow H. G., Bialecki R., Davenport T., Dedinas R. F., Dembofsky B. T., Koether G., Kosmider B. J., Kirkland K., Ohnmacht C. J., Potts W., Rumsey W. L., Shen L., Shenvi A., Sherwood S., Stollman D., Russell K., Bioorganic & Medicinal Chemistry Letters, 2001, 11(20), 2769

    Article  CAS  Google Scholar 

  8. Mertens A., Zilch H., Koenig B., Schaefer W., Poll T., Kampe W., Seidel H., Leser U., Leinert H., J. Medicinal Chemistry, 1993, 36(17), 2526

    Article  CAS  Google Scholar 

  9. Brooklyn V. K., Oreland E. A. G., Danbury S. R. M., Germering L. W., Isoindolone Compounds, Compositions Containing the Same, and Methods of Use Thereof for the Treatment of Viral Infections Related to the Etiology of Cancer US7705021, 2010

    Google Scholar 

  10. Wacker D. A., Varnes J. G., Malmstrom S. E., Cao X., Hung C. P., Ung T., Wu G., Zhang G., Zuvich E., Thomas M. A., Keim W. J., Cullen M. J., Rohrbach K. W., Qu Q., Narayanan R., Rossi K., Janovitz E., Lehman-McKeeman L., Malley M. F., Devenny J., Pelleymounter M. A., Miller K. J., Robl J. A., Journal of Medicinal Chemistry, 2007, 50(6), 1365

    Article  CAS  Google Scholar 

  11. Annika B., Jonas B., Oejvind D., Hans E., Ulrik G., Tommy I., Johan K., Roine O., Lars S., Gert S., Johan S., Yuan. Z. Q., Isoindoline Derivatives for the Treatment of Arrhythmias, WO 2008008022, 2008

    Google Scholar 

  12. Honma T., Hayashi K., Aoyama T., Hashimoto N., Machida T., Fukasawa K., Iwama T., Ikeura C., Ikuta M., Suzuki-Takahashi I., Iwasawa Y., Hayama T., Nishimura S., Morishima H., J. Medicinal Chemistry, 2001, 44(26), 4615

    Article  CAS  Google Scholar 

  13. Hardcastle I. R., Ahmed S. U., Atkins H., Farnie G., Golding B. T., Griffin R. J., Guyenne S., Hutton C., Kaellblad P., Kemp S. J., Kitching M. S., Newell D. R., Norbedo S., Northen J. S., Reid R. J., Saravanan K., Willems H. M. G., Lunec J., J. Medicinal Chemistry, 2006, 49(21), 6209

    Article  CAS  Google Scholar 

  14. Hardcastle I. R., Liu J., Valeur E., Watson A., Ahmed S. U., Blackburn T. J., Bennaceur K., Clegg W., Drummond C., Endicott J. A., Golding B. T., Griffin R. J., Gruber J., Haggerty K., Harrington R. W., Hutton C., Kemp S., Lu X., McDonnell J. M., Newell D. R., Noble M. E. M., Payne S. L., Revill C. H., Riedinger C., Xu Q., Lunec J., J. Medicinal Chemistry, 2011, 54(5), 1233

    Article  CAS  Google Scholar 

  15. Watson A. F., Liu J., Bennaceur K., Drummond C. J., Endicott J. A., Golding B. T., Griffin R. J., Haggerty K., Lu X., McDonnell J. M., Newell D. R., Noble M. E. M., Revill C. H., Riedinger C., Xu Q., Zhao Y., Lunec J., Hardcastle I. R., Bioorganic & Medicinal Chemistry Letters, 2011, 21(19), 5916

    CAS  Google Scholar 

  16. Ghosh U., Bhattacharyya R., Keche A., Tetrahedron, 2010, 66(12), 2148

    Article  CAS  Google Scholar 

  17. Mi H. Y., Cui L. L., Zhang Q. L., Li F., Jiang T., Liang Y. T., Wang E. S., Chem. Res. Chinese Universities, 2011, 27(4), 614

    CAS  Google Scholar 

  18. David F., Robert R., Parallel Synthesis of Anticancer, Antiinflammatory, and Antiviral Agents Derived from L- and D-amino Acids, CRC Press, Boca Raton, 2008, 177

    Google Scholar 

  19. Romanova N. N., Tallo T. G., Rybalko I. I., Zyk N. V., Shvyadas V. K., Chemistry of Heterocyclic Compounds, 2011, 47(4), 395

    Article  CAS  Google Scholar 

  20. Deniau E., Enders D., Tetrahedron Letters, 2000, 41(14), 2347

    Article  CAS  Google Scholar 

  21. Mamouni A., Pigeon P., Daïch A., Decroix B., Journal of Heterocyclic Chemistry, 1997, 34(5), 1495

    Article  CAS  Google Scholar 

  22. Allin S. M., Northfield C. J., Page M. I., Slawin A. M. Z., Tetrahedron Letters, 1999, 40(1), 143

    Article  CAS  Google Scholar 

  23. Allin S. M., Northfield C. J., Page M. I., Slawin A. M. Z., J. Chemical Society, Perkin Trans. 1, 2000, 1715

    Google Scholar 

  24. Deniau E., Enders D., Couture A., Grandclaudon P., Tetrahedron: Asymmetry, 2003, 14(15), 2253

    Article  CAS  Google Scholar 

  25. Ruan Y. P., Chen M. D., He M. Z., Zhou X., Huang P. Q., Synthetic Communications, 2004, 34(5), 853

    Article  CAS  Google Scholar 

  26. Chen M. D., Zhou X., He M. Z., Ruan Y. P., Huang P. Q., Tetrahedron, 2004, 60(7), 1651

    Article  CAS  Google Scholar 

  27. Chen M. D., He M. Z., Zhou X., Huang L. Q., Ruan Y. P., Huang P. Q., Tetrahedron, 2005, 61(5), 1335

    Article  CAS  Google Scholar 

  28. Chen M. W., Chen Q. A., Duan Y., Ye Z. S., Zhou Y. G., Chemical Communications(Cambridge, U. K.), 2012, 48(11), 1698

    Article  CAS  Google Scholar 

  29. Osante I., Lete E., Sotomayor N., Tetrahedron Letters, 2004, 45(6), 1253

    Article  CAS  Google Scholar 

  30. Wakchaure P. B., Easwar S., Puranik V. G., Argade N. P., Tetrahedron, 2008, 64(8), 1786

    Article  CAS  Google Scholar 

  31. Wang E. C., Chen H. F., Feng P. K., Lin Y. L., Hsu M. K., Tetrahedron Letters, 2002, 43(50), 9163

    Article  CAS  Google Scholar 

  32. Maity A. K., Roy S., J. Organic Chemistry, 2012, 77(6), 2935

    Article  CAS  Google Scholar 

  33. Enders D., Braig V., Raabe G., Canadian Journal of Chemistry-revue Canadienne De Chimie, 2001, 79(11), 1528

    Article  CAS  Google Scholar 

  34. Campbell J. B., Dedinas R. F., Trumbower-Walsh S., Synlett., 2010, 3008

    Google Scholar 

  35. Clayden J., Turnbull R., Pinto I., Tetrahedron: Asymmetry, 2005, 16(13), 2235

    Article  CAS  Google Scholar 

  36. Wang Z. Q., Feng C. G., Xu M. H., Lin G. Q., J. Am. Chem. Soc., 2007, 129(17), 5336

    Article  CAS  Google Scholar 

  37. Lamblin M., Couture A., Deniau E., Grandclaudon P., Tetrahedron: Asymmetry, 2008, 19(1), 111

    Article  CAS  Google Scholar 

  38. Lorion M., Couture A., Deniau E., Grandclaudon P., Synthesis, 2009, 1897

    Google Scholar 

  39. Nguyen T. B., Wang Q., Guéritte F., Chemistry: A European Journal, 2011, 17(35), 9576

    Article  CAS  Google Scholar 

  40. He X., Design and Synthesis of Novel Cholesterol Absorption Inhibitors, Jilin University, Changchun, 2010

    Google Scholar 

  41. Ravi Kumar A., Bhaskar G., Madhan A., Venkateswara R. B., Synthetic Communications, 2003, 33(16), 2907

    Article  CAS  Google Scholar 

  42. O’Brien P. A., Osborne S. D., Parker D., J. Chemical Society, Perkin Trans. 1, 1998, (16), 2519

    Google Scholar 

  43. Nieto S., Sayago F. J., Laborda P., Soler T., Cativiela C., Urriolabeitia E. P., Tetrahedron, 2011, 67(23), 4185

    Article  CAS  Google Scholar 

  44. Drandarov K., Guggisberg A., Hesse M., Helv. Chim. Acta, 2002, 85(4), 979

    Article  CAS  Google Scholar 

  45. Hart D. J., Kanai K., Thomas D. G., Yang T. K., J. Organic Chemistry, 1983, 48(3), 289

    Article  CAS  Google Scholar 

  46. Stilz H. U., Guba W., Jablonka B., M. Just, Klingler O., König W., Wehner V., Zoller G., J. Medicinal Chemistry, 2001, 44(8), 1158

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Center for Combinatorial Chemistry and Drug Discovery, College of Chemistry and School of Pharmaceutical Sciences, Jilin University, Changchun, 130021, P. R. China

    Chen-ming Hu, Lian-you Zheng, Ya-zhong Pei & Xu Bai

Authors
  1. Chen-ming Hu
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  2. Lian-you Zheng
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  3. Ya-zhong Pei
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  4. Xu Bai
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Corresponding author

Correspondence to Xu Bai.

Additional information

Supported by the National Natural Science Foundation of China(No.81072526) and the Fund of the Department of Science and Technology of Jilin Province of China(No.20106039).

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Hu, Cm., Zheng, Ly., Pei, Yz. et al. Synthesis of novel 3-aryl isoindolinone derivatives. Chem. Res. Chin. Univ. 29, 487–494 (2013). https://doi.org/10.1007/s40242-013-2294-5

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  • DOI: https://doi.org/10.1007/s40242-013-2294-5

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