DOI QR코드

DOI QR Code

Convergent Synthesis of PAMAM-like Dendrimers from Azide-functionalized PAMAM Dendrons

  • Lee, Jae-Wook (Department of Chemistry, Dong-A University) ;
  • Kim, Jung-Hwan (Department of Chemistry, Dong-A University) ;
  • Kim, Byung-Ku (Department of Chemistry, Dong-A University) ;
  • Kim, Ji-Hyeon (Department of Chemical & Biochemical Engineering, Dongguk University) ;
  • Shin, Won-Suk (Department of Chemistry Education & Center for Plastic Information System, Pusan National University) ;
  • Jin, Sung-Ho (Department of Chemistry Education & Center for Plastic Information System, Pusan National University) ;
  • Kim, Myung-hak (Inje Engineering Institute, Inje University)
  • 발행 : 2006.11.20

초록

The convergent synthesis of symmetric PAMAM-like dendrimers from azide-functionalized poly(amido- amine) (PAMAM) dendrons and two different multi-alkynes was investigated. The stitching method was based on the click chemistry protocol, i.e., the copper-catalyzed cycloaddition reaction between an alkyne and an azide.

키워드

참고문헌

  1. Grimsdale, A. C.; Müllen, K. Angew. Chem. Int. Ed. 2005, 44, 5592 https://doi.org/10.1002/anie.200500805
  2. Tomalia, D. A. Prog. Polym. Sci. 2005, 30, 294 https://doi.org/10.1016/j.progpolymsci.2005.01.007
  3. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638 https://doi.org/10.1021/ja00177a027
  4. Hawker, C. J.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun. 1990, 1010
  5. Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819 https://doi.org/10.1021/cr990116h
  6. Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. 1985, 17, 117 https://doi.org/10.1295/polymj.17.117
  7. Tomalia, D. A.; Naylor, A. M.; Goddard III, W. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 138 https://doi.org/10.1002/anie.199001381
  8. Majoros, I. J.; Myc, A.; Thomas, T.; Mehta, C. B.; Baker, J. R., Jr. Biomacromolecules 2006, 7, 572 https://doi.org/10.1021/bm0506142
  9. Gupta, U.; Agashe, H. B.; Asthana, A.; Jain, N. K. Biomacromolecules 2006, 7, 649 https://doi.org/10.1021/bm050802s
  10. Ambade, A. V.; Savariar, E. N.; Thayumanavan, S. Mol. Pharm. 2005, 2, 264 https://doi.org/10.1021/mp050020d
  11. Venditto, V. J.; Regino, C. A. S.; Brechbiel, M. W. Mol. Pharm. 2005, 2, 302 https://doi.org/10.1021/mp050019e
  12. McCarthy, T. D.; Karellas, P.; Henderson, S. A.; Giannis, M.; O'Keefe, D. F.; Heery, G.; Paull, J. R. A.; Matthews, B. R.; Holan, G. Mol. Pharm. 2005, 2, 312 https://doi.org/10.1021/mp050023q
  13. Pittelkow, M.; Christensen, J. B. Org. Lett. 2005, 7, 1295 https://doi.org/10.1021/ol050040d
  14. Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Synthesis, Applications; Wiley-VCH: Weinheim, 2001
  15. Frechet, J. M. J.; Tomalia, D. A. Dendrimers and Other Dendritic Polymers; John Wiely & Sons Ltd.: 2001
  16. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004
  17. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596 https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
  18. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057 https://doi.org/10.1021/jo011148j
  19. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51
  20. Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Fréchet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928 https://doi.org/10.1002/anie.200454078
  21. Helms, B.; Mynar, J. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 2004, 126, 15020 https://doi.org/10.1021/ja044744e
  22. Malkoch, M.; Schleicher, K.; Drockenmuller, E.; Hawker, C. J.; Russell, T. P.; Wu, P.; Fokin, V. V. Macromolecules 2005, 38, 3663 https://doi.org/10.1021/ma047657f
  23. Joralemon, M. J.; O'Reilly, R. K.; Matson, J. B.; Nugent, A. K.; Hawker, C. J.; Wooley, K. L. Macromolecules 2005, 38, 5436 https://doi.org/10.1021/ma050302r
  24. Lee, J. W.; Kim, B. K. Bull. Korean Chem. Soc. 2005, 26, 658 https://doi.org/10.5012/bkcs.2005.26.4.658
  25. Lee, J. W.; Kim, B. K.; Jin, S. H. Bull. Korean Chem. Soc. 2005, 26, 833 https://doi.org/10.5012/bkcs.2005.26.5.833
  26. Lee, J. W.; Kim, B. K.; Kim, J. H.; Shin, W. S.; Jin, S. H. Bull. Korean Chem. Soc. 2005, 26, 1790 https://doi.org/10.5012/bkcs.2005.26.11.1790
  27. Rijkers, D. T. S.; van Esse, G. W.; Merkx, R.; Brouwer, A. J.; Jacobs, H. J. F.; Pieters, R. J.; Liskamp, R. M. J. Chem. Commun. 2005, 4581
  28. Mynar, J. L.; Choi, T.-L.; Yoshida, M.; Kim, V.; Hawker, C. J.; Frechet, J. M. J. Chem. Commun. 2005, 5169
  29. Wu, P.; Malkoch, M.; Hunt, J. N.; Vestberg, R.; Kaltgrad, E.; Finn, M. G.; Fokin, V. V.; Sharpless, K. B.; Hawker, C. J. Chem. Commun. 2005, 5775
  30. Joosten, J. A. F.; Tholen, N. T. H.; Maate, F. A. E.; Brouwer, A. J.; van Esse, G. W.; Rijkers, D. T. S.; Liskamp, R. M. J.; Pieters, R. J. Eur. J. Org. Chem. 2005, 3182
  31. Lee, J. W.; Kim, B. K. Synthesis 2006, 615
  32. Lee, J. W.; Kim, J. H.; Kim, B. K.; Shin, W. S.; Jin, S. H. Tetrahedron 2006, 62, 894 https://doi.org/10.1016/j.tet.2005.10.039
  33. Lee, J. W.; Kim, B. K.; Kim, H. J.; Han, S. C.; Shin, W. S.; Jin, S. H. Macromolecules 2006, 39, 2418 https://doi.org/10.1021/ma052526f
  34. Lee, J. W.; Kim, J. H.; Kim, B. K. Tetrahedron Lett. 2006, 47, 2683 https://doi.org/10.1016/j.tetlet.2006.02.081
  35. Lee, J. W.; Kim, B. K.; Kim, J. H.; Shin, W. S.; Jin, S. H. J. Org. Chem. 2006, 71, 4988 https://doi.org/10.1021/jo0605905
  36. Lee, J. W.; Kim, J. H.; Kim, B. K.; Kim, J. H.; Shin, W. S.; Jin, S. H. Tetrahedron 2006, 62, 9193 https://doi.org/10.1016/j.tet.2006.07.030
  37. Mong, T. K.-K.; Niu, A.; Chow, H.-F.; Wu, C.; Li, L.; Chen, R. Chem. Eur. J. 2001, 7, 686 https://doi.org/10.1002/1521-3765(20010202)7:3<686::AID-CHEM686>3.0.CO;2-Z
  38. Wong, C.-H.; Chow, H.-F.; Hui, S.- K.; Sze, K.-H. Org. Lett. 2006, 8, 1811 https://doi.org/10.1021/ol0603716
  39. Sun, H.; Kaifer, A. E. Org. Lett. 2005, 7, 3845 https://doi.org/10.1021/ol051245p

피인용 문헌

  1. Synthesis of dendrimers via Staudinger/aza-Wittig reaction of Fréchet-type dendritic benzyl azides and Fréchet-type dendritic benzaldehydes vol.20, pp.10, 2012, https://doi.org/10.1007/s13233-012-0149-4
  2. Synthesis of Dendrimer Containing Dialkylated-fluorene Unit as a Core Chromophore via Click Chemistry vol.33, pp.1, 2012, https://doi.org/10.5012/bkcs.2012.33.1.137
  3. Synthesis of Unsymmetrical Fréchet-type Dendrimers via Double Click Chemistry vol.33, pp.4, 2012, https://doi.org/10.5012/bkcs.2012.33.4.1393
  4. Convergent Synthesis of Carbazole Core PAMAM Dendrimer via Click Chemistry vol.34, pp.3, 2013, https://doi.org/10.5012/bkcs.2013.34.3.971
  5. Synthesis and complexation study of new ExTTF-based hosts for fullerenes vol.12, pp.24, 2014, https://doi.org/10.1039/c3ob42477d
  6. A Convenient Method for the Synthesis of (Prop-2-Ynyloxy)Benzene Derivatives via Reaction with Propargyl Bromide, Their Optimization, Scope and Biological Evaluation vol.9, pp.12, 2014, https://doi.org/10.1371/journal.pone.0115457
  7. Synthesis of Diblock Codendrimers by Fusion of the Fréchet-Type and the PAMAM Dendrons vol.249-250, pp.1, 2007, https://doi.org/10.1002/masy.200750404
  8. Designing poly(amido amine) dendrimers containing core diversities by click chemistry of the propargyl focal point poly(amido amine) dendrons vol.46, pp.3, 2008, https://doi.org/10.1002/pola.22451
  9. Dendrimer design using CuI-catalyzed alkyne–azide “click-chemistry” pp.42, 2008, https://doi.org/10.1039/b809870k
  10. Polymer “Clicking” by CuAAC Reactions vol.29, pp.12–13, 2008, https://doi.org/10.1002/marc.200800159
  11. Formation of Rotaxane Dendrimers by Supramolecular Click Chemistry vol.28, pp.10, 2006, https://doi.org/10.5012/bkcs.2007.28.10.1837
  12. Efficient One-pot Synthesis of Dendritic Benzyl Azides from Their Alcohols vol.29, pp.5, 2008, https://doi.org/10.5012/bkcs.2008.29.5.1055
  13. Facile Synthesis of Dendritic-Linear-Dendritic Materials by Click Chemistry vol.17, pp.7, 2006, https://doi.org/10.1007/bf03218898
  14. Staudinger /Aza-Wittig Click Chemistry for Synthesis of Dendrimers Using Frechet Type Dendritic Benzyl Azides vol.30, pp.5, 2006, https://doi.org/10.5012/bkcs.2009.30.5.1001
  15. Synthesis of Poly(benzyl ether) Dendrimers Containing Core Diversitiesby Click Chemistry vol.30, pp.1, 2006, https://doi.org/10.5012/bkcs.2009.30.1.157
  16. Synthesis of Dendrimers by Homocoupling of Alkyne-focal Frechet Type Dendrons vol.30, pp.9, 2006, https://doi.org/10.5012/bkcs.2009.30.9.1925
  17. A New Efficient Convergent Synthesis of Conjugated Aryl-containing Dendrimers vol.31, pp.6, 2006, https://doi.org/10.5012/bkcs.2010.31.6.1757
  18. Synthesis of Dendrimers from Alkyne-focal Dendrons by Oxidative Homo-coupling of Terminal Acetylene vol.32, pp.11, 2011, https://doi.org/10.5012/bkcs.2011.32.11.3899
  19. Convergent Synthesis and Characterization of Dumbbell Type Dendritic Materials by Click Chemistry vol.32, pp.11, 2011, https://doi.org/10.5012/bkcs.2011.32.11.3933
  20. Synthesis of Dendrimers via Sonogashira Coupling Reaction of Alkyne-focal Fréchet Type Dendrons vol.32, pp.9, 2006, https://doi.org/10.5012/bkcs.2011.32.9.3211
  21. Facile Synthesis of Aldehyde-focal Fréchet Type Dendrons and Dendrimers via Staudinger/Aza-Wittig Reactions vol.32, pp.10, 2006, https://doi.org/10.5012/bkcs.2011.32.10.3624
  22. Synthesis of [3]-Rotaxane Dendrimers by Host-mediated Click Chemistry vol.32, pp.10, 2006, https://doi.org/10.5012/bkcs.2011.32.10.3809
  23. Synthesis of Dendrimer Containing Carbazole Unit as a Core Chromophore vol.33, pp.10, 2006, https://doi.org/10.5012/bkcs.2012.33.10.3451
  24. Convergent Synthesis of PAMAM Dendrimers Containing Tetra(ethyleneoxide) at Core Using Click Chemistry vol.33, pp.10, 2012, https://doi.org/10.5012/bkcs.2012.33.10.3501
  25. Synthesis of Diblock Codendrimer by Double Click Chemistry vol.33, pp.12, 2006, https://doi.org/10.5012/bkcs.2012.33.12.4103
  26. Efficient Synthesis of Carbazole Core Diblock Dendrimer by Double Click Chemistry vol.599, pp.1, 2006, https://doi.org/10.1080/15421406.2014.935969