Chinese Journal of Organic Chemistry >
Synthesis and Antibacterial, Antitumor Activity of 2,6,6-Thrimethyl- bicyclo[3,1,1]heptan-3-(4-aryl-2-thiazoyl)hydrazones
Received date: 2014-04-26
Revised date: 2014-05-22
Online published: 2014-06-11
Supported by
Project supported by the National Natural Science Foundation of China (No. 31170538) and the Forestry Public Sector Research Found of State Forestry Administration of China (No. 201104015)
Twelve new 2,6,6-thrimethyl-bicyclo[3,1,1]heptan-3-(4-aryl-2-thiazoyl)hydrazones were synthesized by using α-pinene as starting material in four steps reaction including addition, oxidation, condensation, and reaction with α-bromo- acetophenone under room temperature. The yields of products were in the range from 52.4% to 88.9%. All synthesized new compounds were confirmed by 1H NMR, 13C NMR, IR, LC/MS spectra and elemental analysis. The preliminary bioassay showed that some of the target compounds exhibited significant antibacterial activity and certain antitumor activity.
Bao Mingkai , Yang Yiqing , Gu Wen , Xu Xu , Cao Mingzhen , Wang Shifa . Synthesis and Antibacterial, Antitumor Activity of 2,6,6-Thrimethyl- bicyclo[3,1,1]heptan-3-(4-aryl-2-thiazoyl)hydrazones[J]. Chinese Journal of Organic Chemistry, 2014 , 34(10) : 2146 -2151 . DOI: 10.6023/cjoc201404049
[1] Khare, M.; Keady, D. Expert Opin. Pharm. 2003, 4, 165
[2] Vicini, P.; Geroniki, A.; Anastasia, K. Bioorg. Med. Chem. 2006, 14, 3859.
[3] Bell, F. W.; Cantrell, A. S.; Hoegberg, M. J. Med. Chem. 1995, 38, 4929
[4] Sharma, P. K.; Sawheny, S. N. Bioorg. Med. Chem. Lett. 1997, 7, 2427.
[5] Vicini, P.; Geronikakib, A.; Incertia, M. Bioorg. Med. Chem. 2003, 11, 4785.
[6] Lu, Y. Y.; Li, C. M.; Wang, Z. J. Med. Chem. 2009, 52, 1701.
[7] Turan, G. Z.; Kaplancikli, A.; Yildiz, M. T.; Chevallet, P.; Kaya, D. Eur. J. Med. Chem. 2005, 40, 607.
[8] Cukurovali, A.; Yilmaz, I.; Gur, S.; Kazaz, C. Eur. J. Med. Chem. 2006, 41, 201.
[9] Shi, H. B.; Zhang, S. J.; Ge, Q. F.; Guo, D. W.; Cai, C. M.; Hu, W. X. Bioorg. Med. Chem. Lett. 2010, 20, 6555.
[10] Khan, S. A. Eur. J. Med. Chem. 2008, 43, 2040.
[11] Merlani, M. I.; Amiranashvili, L. S.; Mulkidzhanyan, K. G.; Shelar, A. R.; Manvi, F. V. Chem. Nat. Compd. 2008, 44, 618.
[12] Iványi, Z.; Wölfling, J.; Görbe, T.; Szécsi, M.; Wittmann, T.; Schneider, G. Steroids 2010, 75, 450.
[13] Bizzarri, B.; Chimenti, F.; Secci, D.; Bolsaco, A. Granese, A. Bioorg. Med. Chem. 2007, 17, 4635.
[14] Gulhan, T. Z.; Ahmet, O.; Zafer, A. K.; Kadriye, B.; Pierre, C.; Gulsen, A. Eur. J. Med. Chem. 2008, 43, 981.
[15] Caputto, M. E.; Ciccarelli, A.; Frank, F.; Moglioni, A. G. Eur. J. Med. Chem. 2012, 35, 155.
[16] Yuan, M. Y.; Liu, W. H.; Zhang, Y, Q.; Yan, H. F.; Zhang, D. N.; Liu, H. M.; Wang, J. P. Chin. J. Org. Chem. 2013, 33, 1108 (in Chinese).
(袁明月, 刘伟华, 张英群, 闫红飞, 张冬暖, 刘卉闵, 王建平, 有机化学, 2013, 33, 1108.)
[17] Wang, S. F.; Li, Y. P.; Zhang M. G. J. Org. Chem. 2007, 27, 1612 (in Chinese).
(王石发, 李艳苹, 张明光, 有机化学, 2007, 27, 1612.)
/
〈 |
|
〉 |