LIU Minghui, LIU Junhong, HAN Guiyan, ZHANG Xingjie, SHENG Chunquan, YAO Jianzhong. Design and synthesis of photosensitizer,13,15-cycloimides chlorin p6[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(1): 26-30,35. doi: 10.3969/j.issn.1006-0111.2017.01.007
| Citation:
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LIU Minghui, LIU Junhong, HAN Guiyan, ZHANG Xingjie, SHENG Chunquan, YAO Jianzhong. Design and synthesis of photosensitizer,13,15-cycloimides chlorin p6[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(1): 26-30,35. doi: 10.3969/j.issn.1006-0111.2017.01.007
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Design and synthesis of photosensitizer,13,15-cycloimides chlorin p6
- 1.
School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, China
- 2.
School of Pharmacy, Second Military Medical University, Shanghai 200433, China
- 3.
School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, China;School of Pharmacy, Second Military Medical University, Shanghai 200433, China
- Received Date: 2016-11-16
- Rev Recd Date:
2016-12-12
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Abstract
Objective To design and prepare 13,15-cycloimides chlorin p6 ( 1 ),a class of chlorin related antitumor photosensitizers,which contain a more stable six-membered cyclic imide comparing to the exocyclic anhydride ring of purpurin-18 ( 2 ). Compounds ( 1 ) exhibit strong absorption at long wavelengths near λmax 700 nm to take full advantage of greater tissue penetration. Methods Pheophorbide a ( 3 ) was obtained by acid hydrolysis of chlorophylla,which was from crude chlorophyll extracts of Chinese traditional herb named Silkworm excrement. Purpurin-18 ( 2 ) was prepared by air oxidation and alkali open loop simultaneously on five-membered beta-keto carboxylic ester ring of pheophorbide a ( 3 ). Finally,the target compounds 1a ~ 1j were synthesized via condensation of its anhydride ring with various amines including carboxyl-protected amino acids. Results Target compounds 1a ~ 1j were successfully synthesized in yields ranged from 32.6% to 65.2%. Their structures were confirmed by elemental analysis,ESI-MS and 1H NMR spectra. Conclusion Treatment of purpurin-18 ( 2 ) with amines can produce target compounds 1a ~ 1j . The starting raw material was inexpensive and readily available. The reaction conditions were mild and workup was convinient.
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