Chinese Journal of Organic Chemistry >
Solvent-Free Synthesis of Novel Schiff Base Type Molecular Tweezers Based on Chenodeoxycholic Acid Promoted by Microwave Irradiation
Received date: 2013-09-01
Revised date: 2013-11-01
Online published: 2013-11-14
Supported by
Project supported by the Science and Technology Department of Sichuan Province (No. 2012SZ0160) and the Fundamental Research Funds of Central Universities, Southwest University for Nationalities (No. 13NZYQN12).
Ten new steroidal molecular tweezers were efficiently synthesized via a method employing microwave irradiation by using chenodeoxycholic acid as spacer and Schiff base unit as arm through the condensation of amines and different aromatic aldehydes. Compared with a conventional method, the yields were increased from 30%~75% to 85%~94% and the reaction times were reduced from 300~480 min to 0.5~1.5 min. The structures of these novel molecular tweezers were characterized by 1H NMR, IR, ESI-MS techniques and elemental analysis. The recognition properties of these molecular tweezers for organic molecules were investigated by UV-vis spectra. The results indicated that this type of molecular tweezers has good binding properties for organic molecules.
Shi Zhichuan , Zhao Zhigang , Li Hui , Tan Jiong . Solvent-Free Synthesis of Novel Schiff Base Type Molecular Tweezers Based on Chenodeoxycholic Acid Promoted by Microwave Irradiation[J]. Chinese Journal of Organic Chemistry, 2014 , 34(3) : 572 -577 . DOI: 10.6023/cjoc201309002
[1] Ali, H.; Steven, T.; Gianluca, A.; Nicola, A.; Christopher, A. R.; Peter, D. W. B. J. Am. Chem. Soc. 2006, 128, 15903.
[2] Jeffrey, P. P.; Timothy, E. G. Org. Lett. 2006, 8, 2163.
[3] Hardouin-Lerouge, M.; Hudhomme, P.; Salle, M. Chem. Soc. Rev. 2011, 40, 30.
[4] Fernandez-Herrera, M. A.; Lopez-Munoz, H.; Hernandez-Vazquez, J. M. V.; Sanchez-Sanchez, L.; Escobar-Sanchez, M. L.; Pinto, B. M.; Sandoval-Ramirez, J. Eur. J. Med. Chem. 2012, 54, 721.
[5] Leblond, J.; Petitjean, A. Chem. Phys. Chem. 2011, 12, 1043.
[6] Ghodratbeigi, M.; Rashidi-Ranjbar, P.; Abbasi, A. J. Mol. Struct. 2011, 990, 140.
[7] Klarner, F. G.; Kahlert, B. Acc. Chem. Res. 2003, 36, 919.
[8] Kihel, L. E.; Clement, M.; Bazin, M. A.; Descamps, G.; Khalid, M.; Rault, S. Bioorg. Med. Chem. 2008, 16, 8737.
[9] Fernandez-Herrera, M. A.; Lopez-Munoz, H.; Hernandez-Vazquez, J. M. V.; Sanchez-Sanchez, L.; Escobar-Sanchez, M. L.; Pinto, B. M.; Sandoval-Ramirez, J. Eur. J. Med. Chem. 2012, 54, 721.
[10] Xiong, X. Q.; Cai, L.; Tang, Z. K. Chin. J. Org. Chem. 2012, 32, 1410 (in Chinese).
(熊兴泉, 蔡雷, 唐忠科, 有机化学, 2012, 32, 1410.)
[11] Xiao, S. Y.; Zhu, J.; Mu, X. J.; Li, Z. H. Chin. J. Org. Chem. 2013, 33, 1668 (in Chinese).
(肖尚友, 朱俊, 穆小静, 李正华, 有机化学, 2013, 33, 1668.)
[12] Nguyen, H. H.; Kurth, M. J. Org. Lett. 2013, 15, 362.
[13] Troegel, B.; Lindel, T. Org. Lett. 2012, 14, 468
[14] Read, M. L.; Gundersen, L. L. J. Org. Chem. 2013, 78, 1311.
[15] Collados, J. F.; Toledano, E.; Guijarro, D.; Yus, M. J. Org. Chem. 2012, 77, 5744.
[16] Kandre, S.; Bhagat, P. R.; Sharma, R.; Gupte, A. Tetrahedron Lett. 2013, 54, 3526
[17] Mahindra, A.; Sharma, K. K.; Jain, R. Tetrahedron Lett. 2012, 53, 6931
[18] Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
[19] Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008, 41, 629.
[20] Zhao, Z. G.; Shi, Z. C.; Liu, M.; Liu, X. L. Bioorg. Med. Chem. Lett. 2012, 22, 7730.
[21] Li, G. H.; Shi, Z. C.; Li, X. R.; Zhao, Z. G. J. Chem. Res. 2011, 35, 278.
[22] Shi, Z. C.; Zhao, Z. G.; Liu, X. L.; Wu, L. L. J. Chem. Res. 2011, 35, 198.
[23] Dayal, B.; Speck, J.; Bagan, E.; Tint, G. S.; Salen, G. Steroids 1981, 37, 239.
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