Synthesis of novel chlorin e6 derivatives containing organophosphorus groups

Synthesis

Volumn , Issue 14, 2010, Pages 2451-2455

  Minaeva, Lidiya I ^a   Kabachnik, Maria M ^a   Ponomarev, Gelii V ^b   Morozova, Julia V ^b   Beletskaya, Irina P ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b INSTITUTE OF BIOMEDICAL CHEMISTRY   (Russian Federation)

Author keywords

amino phosphonates; antitumor agents; bisphosphonates; chlorin e6; phosphoramidates; phosphorylations; photodynamic therapy

Indexed keywords

AMINOPHOSPHONATES; ANTI-TUMOR AGENTS; BISPHOSPHONATES; CHLORINS; PHOSPHORAMIDATES;

MICROWAVE IRRADIATION; PHOSPHORYLATION; PLASMONS;

PHOTODYNAMIC THERAPY;

CHLORIN E6 13(1) N [2 [N [(DIETHOXYPHOSPHORYL)(ETHYL)METHYL]AMINO]ETHYL]AMIDE 15(2),17(3) DIMETHYL ESTER; CHLORIN E6 13(1) N [2 [N [(DIETHOXYPHOSPHORYL)(ISOPROPYL)METHYL]AMINO]ETHYL]AMIDE 15(2),17(3) DIMETHYL ESTER; CHLORIN E6 13(1) N [2 [N [(DIETHOXYPHOSPHORYL)METHYL]AMINO]ETHYL]AMIDE 15(2),17(3) DIMETHYL ESTER; CHLORIN E6 13(1) N [2 [N [BIS(DIETHOXYPHOSPHORYL)METHYL]AMINO]ETHYL]AMIDE 15(2),17(3) DIMETHYL ESTER; CHLORIN E6 13(1) N BENZYLAMIDE 15(2),17(3) DIMETHYL ESTER; CHLORIN E6 DERIVATIVE; CHLORINE DERIVATIVE; METHYL 13(1) (N BENZYLAMINO) 13(1) (DIETHOXYPHOSPHORYL) 13(1) DEOXOPHEOPHORBIDE A; ORGANOPHOSPHORUS COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 77954615902     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218781     Document Type: Article

References (35)

1. Nyman E S., Hynninen P H., J. Photochem. Photobiol., B 2004 73 1
2. Haeubl M, Schuerz S, Svejda B, Reith L M., Gruber B, Pfragner R, Schoefberger W, Eur. J. Med. Chem. 2010 45 760
3. Renno R Z., Miller J W., Adv. Drug Delivery Rev. 2001 52 63
4. Hayashi K, Ohno-Matsui K, Teramukai T, Shimada N, Moriyama M, Hara W, Yoshida T, Tokoro T, Mochizuki M, J. Mol. Struct. 2008 875 167
5. Tajiri H, Yokoyama K, Boku N, Ohtsu A, Fujii T, Yoshida S, Sato T, Hakamata K, Hayashi K, Sakata I, Cancer Lett. 1997 111 215
6. Mody T D., J. Porphyrins Phthalocyanines 2000 4 362
7. Ali H, vanLier J E., Chem. Rev. 1999 99 2379
8. Pandey R K., J. Porphyrins Phthalocyanines 2000 4 368
9. Wainwright M, Anti-Cancer Agents Med. Chem. 2008 8 820
10. Robertson C A., HawkinsEvans D, Abrahamse H, J. Photochem. Photobiol., B 2009 96 1
11. Shternberg E D., Dolfin D, Brukner C, Tetrahedron 1998 54 4151
12. Olshevskaya V A., Savchenko A N., Zaitsev A V., Kononova E G., Petrovskii P V., Ramonova A A., Tatarskiy V V. Jr., Uvarov O V., Moisenovich M M., Kalinin V N., Shtil A A., J. Organomet. Chem. 2009 694 1632
13. Giard D, Weagle G, Gupta A, Berube G, Chapados C, Bioorg. Med. Chem. Lett. 2008 18 360
14. Belykh D V., Tarabukina I S., Gruzdev I V., Kutchin A V., Mendeleev Commun. 2007 17 340
15. Szurko A, Rams M, Sochanik A, Siero-Stotny K, Kozielec A M., Montforts F.-P, Wrzalik R, Ratuszna A, Bioorg. Med. Chem. 2009 17 8197
16. Bregadze V I., Sivaev I B., Lobanova I A., Titeev R A., Brittal D I., Grin M A., Mironov A F., Appl. Radiat. Isot. 2009 67 S101
17. Smith K M., Bisset G M. F., Bushell M J., [nl]J. Org. Chem. 1980 45 2218
18. 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. Pharmaceutics 2007 4 448
19. Hu D.-Y, Wan Q.-Q, Yang S, Song B.-A, Bhadury P S., Jin L.-H, Yan K, Liu F, Chen Z, Xue W, J. Agric. Food Chem. 2008 56 998
20. Wittine K, Benci K, Raji Z, Zorc B, Kralj M, Marjanovi M, Paveli K, DeClercq E, Andrei G, Snoeck R, Balzarini J, Mintas M, Eur. J. Med. Chem. 2009 44 143
21. Zlatev I, Giraut A, Morvan F, Herdewijn P, Vasseur J.-J, Bioorg. Med. Chem. 2009 17 7008
22. Morioka M, Kamizono A, Takikawa H, Mori A, Ueno H, Kadowaki S, Nakao Y, Kato K, Umezawa K, Bioorg. Med. Chem. 2010 18 1143
23. Kabachnik M I., Medved T Ya, Dokl. Akad. Nauk SSSR 1952 689; Chem. Abstr. 1953, 47, 2724b
24. Fields E K., J. Am. Chem. Soc. 1952 74 1528
25. Ranu B C., Hajra A, Jana U, Org. Lett. 1999 1 1141
26. Chandrasekhar S, Prakash S J., Jagadeshwar V, Narsihmulu C, Tetrahedron Lett. 2001 42 5561
27. Qian C, Huang T, J. Org. Chem. 1998 63 4125
28. Kabachnik M M., Zobnina E V., Beletskaya I P., Synlett 2005 1393
29. Kabachnik M M., Zobnina E V., Pavlov V Ya, Konstantinov I O., Beletskaya I P., Russ. Chem. Bull. 2005 54 262; Chem. Abstr. 2006, 144, 432906
30. Yashin N V., Villemson E V., Chemagin A V., Averina E B., Kabachnik M M., Kuznetsova T S., Synthesis 2008 464
31. Kabachnik M M., Minaeva L I., Beletskaya I P., Synthesis 2009 2357
32. Atherton F R., Openshaw H T., Todd R R., J. Chem. Soc. 1945 660
33. Minaeva L I., Patrikeeva L S., Orlinson B S., Novakov I A., Kabachnik M M., Beletskaya I P., Russ. J. Org. Chem. 2010 46 172
34. Takeuchi M, Sakamoto S, Yoshida M, Abe T, Isomura Y, Chem. Pharm. Bull. 1993 41 688
35. Kotsikorou E, Song Y, Chan J M. W., Faelens S, Tovian Z, Broderick E, Bakalara R, Docampo R, Oldfield E, J. Med. Chem. 2005 48 6128