Effect of substituents in directing the formation of benzochlorins and isobacteriochlorins in porphyrin and chlorin systems

被引：16

作者：

Mettath, S

Li, GL

Srikrishnan, T

Mehta, R

Grossman, ZD

Dougherty, TJ

Pandey, RK ^{[1
]}

机构：

[1] Roswell Pk Canc Inst, Chem Sect, Photodynam Therapy Ctr, Buffalo, NY 14263 USA

[2] Roswell Pk Canc Inst, Dept Nucl Med, Buffalo, NY 14263 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 12期

关键词：

D O I：

10.1021/ol990311i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A first synthesis of free-base fluorinated benzochlorins by acid catalyzed cyclization of 20-(2-trisiloxy-trifluoromethylvinyl)octaethylporphyrin is achieved, Under similar reaction conditions, the purpurin-18-N-hexylimide analogues produced the corresponding fluorinated and nonfluorinated ethylidene-substituted isobacteriochlorins and fluorinated chlorin, respectively. The structure of the porphyrin based fluorinated benzochlorin was also confirmed by X-ray analysis.

引用

收藏

页码：1961 / 1964

页数：4

相关论文

共 18 条

[1] Photoproduct formation from a zinc benzochlorin iminium salt detected by fluorescence microscopy [J].

Amit, I ;

Malik, Z ;

Kessel, D .

PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1999, 69 (06) :700-702

[2] WITTIG CONDENSATION PRODUCTS FROM NICKEL MESO-FORMYL-OCTAETHYLPORPHYRIN AND MESO-FORMYL-AETIOPORPHYRIN-I AND SOME CYCLIZATION REACTIONS [J].

ARNOLD, DP ;

GAETEHOLMES, R ;

JOHNSON, AW ;

SMITH, ARP ;

WILLIAMS, GA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (12) :1660-1670

[3] Photodynamic therapy [J].

Dougherty, TJ ;

Gomer, CJ ;

Henderson, BW ;

Jori, G ;

Kessel, D ;

Korbelik, M ;

Moan, J ;

Peng, Q .

JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1998, 90 (12) :889-905

[4] Purpurins and benzochlorins as sensitizers for photodynamic therapy [J].

Garbo, GM .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 1996, 34 (2-3) :109-116

[5]

Henderson BW, 1997, CANCER RES, V57, P4000

[6] Syntheses of chlorins possessing fused nitrogen-containing rings [J].

Johnson, CK ;

Dolphin, D .

TETRAHEDRON LETTERS, 1998, 39 (26) :4619-4622

[7] Syntheses of emeraldin and purpurin-18 analogs as target-specific photosensitizers for photodynamic therapy [J].

Kozyrev, AN ;

Zheng, G ;

Lazarou, E ;

Dougherty, TJ ;

Smith, KM ;

Pandey, RK .

TETRAHEDRON LETTERS, 1997, 38 (19) :3335-3338

[8] Application of Ruppert's reagent in preparing novel perfluorinated porphyrins, chlorins and bacteriochlorins [J].

Li, GL ;

Chen, YH ;

Missert, JR ;

Rungta, A ;

Dougherty, TJ ;

Grossman, ZD ;

Pandey, RK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (13) :1785-1787

[9] Synthesis and spectroscopic properties of novel benzochlorins derived from chlorophyll a [J].

Mettath, S ;

Shibata, M ;

Alderfer, JL ;

Senge, MO ;

Smith, KM ;

Rein, R ;

Dougherty, TJ ;

Pandey, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1646-1656

[10] SYNTHESIS OF BENZOCHLORIN IMINIUM SALTS WITH IMPROVED PHOTOSENSITIZING PROPERTIES [J].

MORGAN, AR ;

GUPTA, S .

TETRAHEDRON LETTERS, 1994, 35 (30) :5347-5350