Stereospecific synthesis of 9-substituted benzolactam-V8 from L-tyrosine via regioselective aromatic nitration

被引：8

作者：

Ma, DW ^{[1
]}

Tang, WJ ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 40期

关键词：

benzolactam-V8; aromatic nitration; protein kinase C;

D O I：

10.1016/S0040-4039(98)01598-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new protocol for the synthesis of 9-substituted benzolactam-V8, a class of potent protein kinase C activators, from L-tyrosine through regioselective aromatic nitration, is described (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7369 / 7372

页数：4

共 12 条

[1] CU-2+/BH4- REDUCTION SYSTEM - SYNTHETIC UTILITY AND MODE OF ACTION [J].

COWAN, JA .

TETRAHEDRON LETTERS, 1986, 27 (10) :1205-1208

[2]

Endo Y, 1996, CHEM PHARM BULL, V44, P1138

[3] Synthesis, conformation, and biological activity of teleocidin mimics, benzolactams. A clarification of the conformational flexibility problem in structure-activity studies of teleocidins [J].

Endo, Y ;

Ohno, M ;

Hirano, M ;

Itai, A ;

Shudo, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (08) :1841-1855

[4] QUANTITATIVE STRUCTURE ACTIVITY STUDIES ON INDOLE ALKALOID TUMOR PROMOTER INDOLACTAM CONGENERS [J].

IRIE, K ;

OKUNO, S ;

KAJIYAMA, S ;

KOSHIMIZU, K ;

NISHINO, H ;

IWASHIMA, A .

CARCINOGENESIS, 1991, 12 (10) :1883-1886

[5]

KAZANIETZ MG, 1993, MOL PHARMACOL, V44, P298

[6] Modeling chemistry, and biology of the benzolactam analogues of indolactam V (ILV) .2. Identification of the binding site of the benzolactams in the CRD2 activator-binding domain of PKC delta and discovery of an ILV analogue of improved isozyme selectivity [J].

Kozikowski, AP ;

Wang, SM ;

Ma, DW ;

Yao, JC ;

Ahmad, S ;

Glazer, RI ;

Bogi, K ;

Acs, P ;

Modarres, S ;

Lewin, NE ;

Blumberg, PM .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (09) :1316-1326

[7] SYNTHESIS, MOLECULAR MODELING, 2-D NMR, AND BIOLOGICAL EVALUATION OF ILV MIMICS AS POTENTIAL MODULATORS OF PROTEIN-KINASE-C [J].

KOZIKOWSKI, AP ;

MA, D ;

PANG, YP ;

SHUM, P ;

LIKIC, V ;

MISHRA, PK ;

MACURA, S ;

BASU, A ;

LAZO, JS ;

BALL, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3957-3965

[8] DESIGNED MOLECULES REPRODUCING THE 2 CONFORMATIONS OF TELEOCIDINS [J].

OHNO, M ;

ENDO, Y ;

HIRANO, M ;

ITAI, A ;

SHUDO, K .

TETRAHEDRON LETTERS, 1993, 34 (50) :8119-8122

[9]

OUERTANI M, 1982, TETRAHEDRON LETT, V23, P4315

[10] Iodide acceleration in the Pd-catalyzed coupling of aromatic 1,2-ditriflates with alkynes: Synthesis of enediynes [J].

Powell, NA ;

Rychnovsky, SD .

TETRAHEDRON LETTERS, 1996, 37 (44) :7901-7904

← 1 2 →