Chinese Journal of Organic Chemistry >
C(12)-Nomethylation of Pyropheophorbide-a and Synthesis of Chlorophyllous Chlorins Derivatives
Received date: 2014-02-28
Revised date: 2014-04-04
Online published: 2014-06-09
Supported by
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Research Centre of Gold Nanotechnology (2011).
Pyropheophorbide-a methyl ester, as a degradation product from chlorophyll-a, was used as a starting material, and the formyl group was introduced at 12-position by allomerization. The transformations of C(12)-functional group, including the structural rebuilding of E-ring, were carried out by classic reactions such as oxygenation, reduction, Grignard reaction, Knoevenagel reaction, Cannizzaro reaction and 1,3-dipolar cyclocaddition. The acyl, ester and substituted alkyl groups, which could conjugated with macrocyclic chromophore at various degrees, were established at 12-position. The synthesis of a series of unreported chlorins related to chlorophyll was accomplished and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. The different fluences on the chlorophyllous tetrapyrrole molecule by C(12)-nomethylation were also discussed.
Key words： chlorophyll-a; chlorin; chemical modification; C(12)-nomethylation; synthesis
Ji Jianye , Yin Jungang , Zhang Qian , Liu Chao , Qi Caixia , Wang Jinjunc . C(12)-Nomethylation of Pyropheophorbide-a and Synthesis of Chlorophyllous Chlorins Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(10) : 2047 -2056 . DOI: 10.6023/cjoc201402041
[1] (a) Chen, Y. H.; Li, G. L.; Pandey, R. K. Curr. Org. Chem. 2004, 8, 1105.
(b) Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese).
(王进军, 有机化学, 2005, 25, 1353.)
(c) Ethrivannan, M.; Chen, Y.-H.; Joshi, P.; Pandey, K. R. Chem. Soc. Rev. 2011, 40, 340.
(d) Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393.
[2] (a) Pandey, S. K.; Zheng, X.; Morgan, J.; Missert, J. R.; Liu, T.-H.; Shibata, M.; Bellnier, D. A.; Oseroff, A. R.; Henderson, B. W.; Dougherty, T. J.; Pandey, R. K. Mol. Pharm. 2007, 4, 448.
(b) Kozyrey, A. N.; Chen, Y.-H.; Goswami, L. N.; Tabaczynaki, W. A.; Pandey, R. K. J. Org. Chem. 2006, 71, 1949.
[3] (a) Wang, J.-J.; Yin, Y.-F.; Yang, Z. J. Iran. Chem. Soc. 2013, 10, 583.
(b) Wang, L.-M.; Wang, P.; Liu, C.; Jin, Y.-X.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 1700 (in Chinese).
(王鲁敏, 王朋, 刘超, 金英学, 王进军, 有机化学, 2012, 32, 1700.)
(c) Wang, J.-J.; Wang, P.; Li, J.-Z.; Jakus, J.; Shin, Y.-K. Bull. Korean Chem. Soc. 2011, 32, 3473.
(d) Liu, R.-R.; Wang, L.-M.; Yin, J.-G.; Wu, J.; Liu, C.; Zhang, P.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 318 (in Chinese).
(刘冉冉, 王鲁敏, 金英学, 武进, 刘超, 王朋, 王进军, 有机化学, 2012, 32, 318.)
(e) Li, J.-Z.; Wang, J.-J.; Yoon, L.; Cui, B.-C.; Shim, Y.-K. Bioorg. Med. Chem. Lett. 2012, 22, 1846.
(f) Yang, Z.; Wang, Z.; Liu, Y.; Xu, X.-S.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2013, 33, 116 (in Chinese).
(杨泽, 王振, 刘洋, 徐希森, 祁彩霞, 王进军, 有机化学, 2013, 33, 116.)
[4] Li, J.-Z.; Liu, W.-H.; Li, F.-G.; Wang, J.-J.; Suo, Y.-R.; Liu, Y.-J. Chin. J. Org. Chem. 2007, 27, 1594 (in Chinese).
(李家柱, 刘万卉, 李付国, 王进军, 索有瑞, 刘永军, 有机化学, 2007, 27, 1594.)
[5] Wang, J.-J.; Li, J.-Z.; Li, Y.-W.; Jakus, J.; Shim, Y.-K. J. Porphyrins Phthalocyanines 2010, 14, 859.
[6] Yu, S.-S.; X, X.-S.; Liu, Y.; Li, J.-Z.; Jin, Y.-X.; Qi, C.-X.; Wang, J.-J. Chin. J. Org. Chem. 2014, 34, 362 (in Chinese).
(于沙沙, 徐希森, 刘洋, 李家柱, 金英学, 祁彩霞, 王进军, 有机化学, 2014, 34, 362.)
[7] Tamiaki, H.; Monobe, R.; Koizumi, S.; Miyatake, T.; Kinoshita, Y. Tetrahedron: Asymmerty 2013, 24, 966
[8] Srivatsan, A.; Wang, Y.-F.; Joshi, P.; Sajjad, M.; Chen, Y.-H.; Liu, C.; Thankcppan, K.; Missert, J. R.; Tracy, E.; Morgan, J.; Rigual, N.; Baumann, H.; Pandey, R. K. J. Med. Chem. 2011, 54, 6859.
[9] Li, J.-Z.; Zhang, P.; Yao, N.-N.; Zhao, L.-L.; Wang, J.-J.; Shim, Y.-K, Tetrahedron Lett. 2014, 55, 1086
[10] Yin, J.-G.; Wang, Z.; Yang, Z.; Liu, C.; Zhao, L.-L.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 360 (in Chinese).
(殷军港, 王振, 杨泽, 刘超, 赵丽丽, 王进军, 有机化学, 2012, 32, 360.)
[11] Wu, J. M.S. Thesis, Yantai University, Yantai, 2011 (in Chinese).
(武进, 硕士论文, 烟台大学, 烟台, 2011.)
[12] Wang, J.-J.; Zhao, Y.; Wu, X.-R.; Han, G.-F.; Shin, R.-K. Chin. J. Org. Chem. 2002, 22, 565 (in Chinese).
(王进军, 赵岩, 邬旭然, 韩光范. 沈荣基, 有机化学, 2002, 22, 565.)
[13] Tamiaki, H.; Miyatake, T.; Tanikaga, R. Tetrahedron Lett. 1997, 38, 267.
[14] Wang, L.-M.; Yao, N.-N.; Yang, Z.; Wang, Z.; Shim, Y.-K.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 1899 (in Chinese).
(王鲁敏, 姚楠楠, 杨泽, 王振, 沈荣基, 王进军, 有机化学, 2012, 32, 1899.)
[15] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
/
| 〈 |
|
〉 |
