Synthesis and antitumor activity of simplified ecteinascidin-saframycin analogs

被引：50

作者：

Liu, ZZ ^{[1
]}

Wang, Y

Tang, YF

Chen, SZ

Chen, XG

Li, HY

机构：

[1] Peking Union Med Coll, Inst Mat Med, Beijing 100050, Peoples R China

[2] Chinese Acad Med Sci, Beijing 100050, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2006年 / 16卷 / 05期

关键词：

Et; 743; antitumor; alkaloid; L-DOPA; synthesis; tetrahydroisoquinoline;

D O I：

10.1016/j.bmcl.2005.11.069

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Two series of simplified analogs of the ecteinascidin-saframycin type alkaloids were prepared from L-DOPA. Their in vitro antitumor activity was tested against three human cancer cell lines (HCT-8 colon carcinoma, Bel-7402 liver carcinoma, and BGC-823 gastric carcinoma). Among these compounds, the ester analogs have stronger activities than those of amide analogs in general. Among them, 1-naphthalene carboxylate ester analog 31 has the strongest activity against BGC-823 cells. F (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1282 / 1285

页数：4

共 21 条

[1] Ecteinascidin 743: a novel anticancer drug with a unique mechanism of action [J].

Aune, GJ ;

Furuta, T ;

Pommier, Y .

ANTI-CANCER DRUGS, 2002, 13 (06) :545-555

[2] Enantioselective total synthesis of ecteinascidin 743 [J].

Corey, EJ ;

Gin, DY ;

Kania, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) :9202-9203

[3] Synthesis of ecteinascidin ET-743 and phthalascidin Pt-650 from cyanosafracin B [J].

Cuevas, C ;

Pérez, M ;

Martín, MJ ;

Chicharro, JL ;

Fernández-Rivas, C ;

Flores, M ;

Francesch, A ;

Gallego, P ;

Zarzuelo, M ;

de la Calle, F ;

García, J ;

Polanco, C ;

Rodríguez, I ;

Manzanares, I .

ORGANIC LETTERS, 2000, 2 (16) :2545-2548

[4] Total synthesis of ecteinascidin 743 [J].

Endo, A ;

Yanagisawa, A ;

Abe, M ;

Tohma, S ;

Kan, T ;

Fukuyama, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6552-6554

[5] Phase II and pharmacokinetic study of ecteinascidin 743 in patients with progressive sarcomas of soft tissues refractory to chemotherapy [J].

Garcia-Carbonero, R ;

Supko, JG ;

Manola, J ;

Seiden, MV ;

Harmon, D ;

Ryan, DP ;

Quigley, MT ;

Merriam, P ;

Canniff, J ;

Goss, G ;

Matulonis, U ;

Maki, RG ;

Lopez, T ;

Puchalski, TA ;

Sancho, MA ;

Gomez, J ;

Guzman, C ;

Jimeno, J ;

Demetri, GD .

JOURNAL OF CLINICAL ONCOLOGY, 2004, 22 (08) :1480-1490

[6]

GUAN Y, 1993, J BIOMOL STRUCT DYN, V10, P793

[7] Diketopiperazines as advanced intermediates in the biosynthesis of ecteinascidins [J].

Jeedigunta, S ;

Krenisky, JM ;

Kerr, RG .

TETRAHEDRON, 2000, 56 (21) :3303-3307

[8] Asymmetric total syntheses of (-)-jorumycin, (-)-renieramycin G, 3-epi jorumycin, and 3-epi-renieramycin G [J].

Lane, JW ;

Chen, YY ;

Williams, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) :12684-12690

[9] Phase II study of ecteinascidin 743 in heavily pretreated patients with recurrent osteosarcoma [J].

Laverdiere, C ;

Kolb, EA ;

Supko, JG ;

Gorlick, R ;

Meyers, PA ;

Maki, RG ;

Wexler, L ;

Demetri, GD ;

Healey, JH ;

Huvos, AG ;

Goorin, AM ;

Bagatell, R ;

Ruiz-Casado, A ;

Guzman, C ;

Jimeno, J ;

Harmon, D .

CANCER, 2003, 98 (04) :832-840

[10] Synthesis of the tetrahydroisoquinoline alkaloid (±)-renieramycin G and a (±)-lemonomycinone analogue from a common intermediate [J].

Magnus, P ;

Matthews, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) :12476-12477

← 1 2 3 →