14-membered macrocyclic ring-derived toolbox: The identification of small molecule inhibitors of angiogenesis and early embryo development in zebrafish assay

Organic Letters

Volumn 15, Issue 3, 2013, Pages 436-439

  Aeluri, Madhu ^a   Pramanik, Chinmoy ^a,e   Chetia, Lakshindra ^a,f   Mallurwar, Naveen Kumar ^a   Balasubramanian, Sridhar ^b   Chandrasekar, Gayathri ^c   Kitambi, Satish Srinivas ^c,d   Arya, Prabhat ^a  

^a INSTITUTE OF LIFE SCIENCES   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^c SÖDERTÖRN UNIVERSITY   (Sweden)

^d KAROLINSKA INSTITUTE   (Sweden)

^e Emcure Pharmaceuticals   (India)

^f SYNGENE INTERNATIONAL LTD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENESIS INHIBITOR; MACROCYCLIC COMPOUND;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; DRUG EFFECT; EMBRYO DEVELOPMENT; FEMALE; MORPHOGENESIS; NEOVASCULARIZATION (PATHOLOGY); PREGNANCY; PRENATAL DEVELOPMENT; STRUCTURE ACTIVITY RELATION; SYNTHESIS; ZEBRA FISH;

ANGIOGENESIS INHIBITORS; ANIMALS; DRUG DESIGN; EMBRYONIC DEVELOPMENT; FEMALE; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; MORPHOGENESIS; NEOVASCULARIZATION, PATHOLOGIC; PREGNANCY; STRUCTURE-ACTIVITY RELATIONSHIP; ZEBRAFISH;

EID: 84873370245     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3032126     Document Type: Article

References (34)

1. Driggers, E. M.; Hale, S. P.; Lee, J.; Terrett, N. K. Nat. Rev. Drug Discovery 2008, 7, 608
2. Arkin, M. R.; Wells, J. A. Nat. Rev. Drug Discovery 2004, 3, 301
3. Wells, J. A.; McClendon, C. L. Nature 2007, 450, 1001
4. Scott, J. D.; Pawson, T. Science 2009, 326, 1220
5. Pawson, T.; Warner, N. Oncogene 2007, 26, 1268
6. Schreiber, S. L. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 6699
7. Dandapani, S.; Marcaurelle, L. A. Nat. Chem. Biol. 2010, 6, 861
8. Thomas, G. L.; Wyatt, E. E.; Spring, D. R. Curr. Opin. Drug Discovery Dev. 2006, 9, 700
9. Dandapani, S.; Lowe, J. T.; Comer, E.; Marcaurelle, L. A. J. Org. Chem. 2011, 76, 8042
10. Marcaurelle, L. A.; Comer, E.; Dandapani, S.; Duvall, J. R.; Gerard, B.; Kesavan, S.; Lee, M. D. t.; Liu, H.; Lowe, J. T.; Marie, J. C.; Mulrooney, C. A.; Pandya, B. A.; Rowley, A.; Ryba, T. D.; Suh, B. C.; Wei, J.; Young, D. W.; Akella, L. B.; Ross, N. T.; Zhang, Y. L.; Fass, D. M.; Reis, S. A.; Zhao, W. N.; Haggarty, S. J.; Palmer, M.; Foley, M. A. J. Am. Chem. Soc. 2010, 132, 16962
11. Ajay, A.; Sharma, S.; Gupt, M. P.; Bajpai, V.; Hamidullah; Kumar, B.; Kaushik, M. P.; Konwar, R.; Ampapathi, R. S.; Tripathi, R. P. Org. Lett. 2012, 14, 4306
12. Dockendorff, C.; Nagiec, M. M.; Weiwer, M.; Buhrlage, S.; Ting, A.; Nag, P. P.; Germain, A.; Kim, H. J.; Youngsaye, W.; Scherer, C.; Bennion, M.; Xue, L.; Stanton, B. Z.; Lewis, T. A.; Macpherson, L.; Palmer, M.; Foley, M. A.; Perez, J. R.; Schreiber, S. L. ACS Med. Chem. Lett. 2012, 3, 808
13. Moretti, J. D.; Wang, X.; Curran, D. P. J. Am. Chem. Soc. 2012, 134, 7963
14. Stanton, B. Z.; Peng, L. F.; Maloof, N.; Nakai, K.; Wang, X.; Duffner, J. L.; Taveras, K. M.; Hyman, J. M.; Lee, S. W.; Koehler, A. N.; Chen, J. K.; Fox, J. L.; Mandinova, A.; Schreiber, S. L. Nat. Chem. Biol. 2009, 5, 154
15. Peng, L. F.; Stanton, B. Z.; Maloof, N.; Wang, X.; Schreiber, S. L. Bioorg. Med. Chem. Lett. 2009, 19, 6319
16. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483
17. Bender, A.; Fergus, S.; Galloway, W. R.; Glansdorp, F. G.; Marsden, D. M.; Nicholson, R. L.; Spandl, R. J.; Thomas, G. L.; Wyatt, E. E.; Glen, R. C.; Spring, D. R. Ernst Schering Res. Found Workshop 2006, 47
18. Winssinger, N.; Barluenga, S. Chem. Commun. (Camb.) 2007, 22
19. Moulin, E.; Barluenga, S.; Winssinger, N. Org. Lett. 2005, 7, 5637
20. Barluenga, S.; Jogireddy, R.; Koripelly, G. K.; Winssinger, N. ChemBioChem 2010, 11, 1692
21. Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 3760
22. Grubbs, R. H. Tetrahedron 2004, 60, 7117
23. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446
24. Peterson, R. T.; Fishman, M. C. Methods Cell Biol. 2011, 105, 525
25. Schoft, V. K.; Beauvais, A. J.; Lang, C.; Gajewski, A.; Prufert, K.; Winkler, C.; Akimenko, M. A.; Paulin-Levasseur, M.; Krohne, G. J. Cell Sci. 2003, 116, 2505
26. Martin, C. S.; Moriyama, A.; Zon, L. I. Genome Med. 2011, 3, 83
27. Konantz, M.; Balci, T. B.; Hartwig, U. F.; Dellaire, G.; Andre, M. C.; Berman, J. N.; Lengerke, C. Ann. N.Y. Acad. Sci. 2012, 1266, 124
28. Evensen, L.; Link, W.; Lorens, J. B. Curr. Pharm. Des. 2010, 16, 3958
29. Kitambi, S. S.; Malicki, J. J. Developmental dynamics: an official publication of the American Association of Anatomists 2008, 237, 3870
30. Kitambi, S. S.; Nilsson, E. S.; Sekyrova, P.; Ibarra, C.; Tekeoh, G. N.; Andang, M.; Ernfors, P.; Uhlen, P. BMC Physiology 2012, 12, 3
31. Murphey, R. D.; Zon, L. I. Methods 2006, 39, 255
32. Zhang, Q.; Li, Q.; Chen, Y.; Huang, X.; Yang, I. H.; Cao, L.; Wu, W. K.; Tan, H. M. Frontiers in Bioscience 2012, 4, 2525
33. Hao, J.; Ho, J. N.; Lewis, J. A.; Karim, K. A.; Daniels, R. N.; Gentry, P. R.; Hopkins, C. R.; Lindsley, C. W.; Hong, C. C. ACS Chem. Biol. 2010, 5, 245
34. Vogt, A.; McPherson, P. A.; Shen, X.; Balachandran, R.; Zhu, G.; Raccor, B. S.; Nelson, S. G.; Tsang, M.; Day, B. W. Chem. Biol. Drug Des. 2009, 74, 358