Novel C-4 heteroaromatic kainoid analogues: A parallel synthesis approach

被引：23

作者：

Baldwin, JE ^{[1
]}

Fryer, AM ^{[1
]}

Pritchard, GJ ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2000年 / 10卷 / 03期

关键词：

alkaloids; amino acids and derivatives; natural products; neurologically active compounds;

D O I：

10.1016/S0960-894X(99)00690-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

New C-4 thiazole 4, 5 and aminothiazole 6, 7 kainoid analogues were efficiently synthesised in five steps from commercially available (-)-alpha-kainic acid 1 and exhibited strong binding to the kainate receptors. A reactive alpha-bromoketone 10 was generated and reacted with thioamides and thioureas to form thiazole and aminothiazole heterocycles 11-14. Deprotection gave the new kainoid amino acids 4-7 in excellent yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：309 / 311

页数：3

共 15 条

[1] Towards a versatile synthesis of kainoids .1. Introduction of the C-3 and C-4 substituents [J].

Baldwin, JE ;

Bamford, SJ ;

Fryer, AM ;

Rudolph, MPW ;

Wood, ME .

TETRAHEDRON, 1997, 53 (14) :5233-5254

[2] Towards a versatile synthesis of kainoids .3. Efficient methods for control of C-4 stereochemistry [J].

Baldwin, JE ;

Fryer, AM ;

Spyvee, MR ;

Whitehead, RC ;

Wood, ME .

TETRAHEDRON, 1997, 53 (14) :5273-5290

[3] A biomimetic approach to the pyridone rings of the acromelic acids: A concise synthesis of acromelic acid A and an approach to acromelic acid B. [J].

Baldwin, JE ;

Fryer, AM ;

Pritchard, GJ ;

Spyvee, MR ;

Whitehead, RC ;

Wood, ME .

TETRAHEDRON, 1998, 54 (26) :7465-7484

[4] Concise syntheses of acromelic acid A and allo-acromelic acid A [J].

Baldwin, JE ;

Fryer, AM ;

Pritchard, GJ ;

Spyvee, MR ;

Whitehead, RC ;

Wood, ME .

TETRAHEDRON LETTERS, 1998, 39 (07) :707-710

[5] Synthesis of a series of aryl kainic acid analogs and evaluation in cells stably expressing the kainate receptor humGluR6 [J].

Cantrell, BE ;

Zimmerman, DM ;

Monn, JA ;

Kamboj, RK ;

Hoo, KH ;

Tizzano, JP ;

Pullar, IA ;

Farrell, LN ;

Bleakman, D .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) :3617-3624

[6] A hippocampal GluR5 kainate receptor regulating inhibitory synaptic transmission [J].

Clarke, VRJ ;

Ballyk, BA ;

Hoo, KH ;

Mandelzys, A ;

Pellizzari, A ;

Bath, CP ;

Thomas, J ;

Sharpe, EF ;

Davies, CH ;

Ornstein, PL ;

Schoepp, DD ;

Kamboj, RK ;

Collingridge, GL ;

Lodge, D ;

Bleakman, D .

NATURE, 1997, 389 (6651) :599-603

[7] HIGHLY SELECTIVE, KINETICALLY CONTROLLED ENOLATE FORMATION USING LITHIUM DIALKYLAMIDES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].

COREY, EJ ;

GROSS, AW .

TETRAHEDRON LETTERS, 1984, 25 (05) :495-498

[8]

FUSHIYA S, 1992, HETEROCYCLES, V34, P1277

[9] ACROMELIC ACID-C - A NEW TOXIC CONSTITUENT OF CLITOCYBE-ACROMELALGA - AN EFFICIENT ISOLATION OF ACROMELIC ACIDS [J].

FUSHIYA, S ;

SATO, S ;

KANAZAWA, T ;

KUSANO, G ;

NOZOE, S .

TETRAHEDRON LETTERS, 1990, 31 (27) :3901-3904

[10] SIMPLE ANALOGS OF ACROMELIC ACID, WHICH ARE HIGHLY-ACTIVE AGONISTS OF KAINATE TYPE NEUROEXCITANT [J].

HASHIMOTO, K ;

HORIKAWA, M ;

SHIRAHAMA, H .

TETRAHEDRON LETTERS, 1990, 31 (48) :7047-7050

← 1 2 →