Synthesis of a reported calpain inhibitor isolated from Streptomyces griseus

被引：20

作者：

Donkor, IO ^{[1
]}

Sanders, ML ^{[1
]}

机构：

[1] Univ Tennessee, Ctr Hlth Sci, Dept Pharmaceut Sci, Memphis, TN 38163 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2001年 / 11卷 / 19期

关键词：

D O I：

10.1016/S0960-894X(01)00524-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The reported diketopiperazine calpain inhibitor, cis-L-L-3.6-bis-(4-hydroxybenzyl)-1,4-dimethylpiperazine-2,5-dione 1, and its analogues 3 and 4 were synthesized from the corresponding amino acids. The previously assigned structure of 1 is confirmed but neither synthetic 1 nor its N-methylphenylalanine analogues 3 and 4 inhibit porcine erythrocyte calpain I. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2647 / 2649

页数：3

共 15 条

[1] ISOLATION AND STRUCTURE ELUCIDATION OF 2 NEW CALPAIN INHIBITORS FROM STREPTOMYCES-GRISEUS [J].

ALVAREZ, ME ;

HOUCK, DR ;

WHITE, CB ;

BROWNELL, JE ;

BOBKO, MA ;

RODGER, CA ;

STAWICKI, MB ;

SUN, HH ;

GILLUM, AM ;

COOPER, R .

JOURNAL OF ANTIBIOTICS, 1994, 47 (11) :1195-1201

[2] PHEVALIN, A NEW CALPAIN INHIBITOR, FROM A STREPTOMYCES SP [J].

ALVAREZ, ME ;

WHITE, CB ;

GREGORY, J ;

KYDD, GC ;

HARRIS, A ;

SUN, HH ;

GILLUM, AM ;

COOPER, R .

JOURNAL OF ANTIBIOTICS, 1995, 48 (10) :1165-1167

[3] The calpain hypothesis of neurodegeneration: Evidence for a common cytotoxic pathway [J].

Bartus, RT .

NEUROSCIENTIST, 1997, 3 (05) :314-327

[4] Synthesis and calpain inhibitory activity of α-ketoamides with 2,3-methanoleucine stereoisomers at the P2 position [J].

Donkor, IO ;

Zheng, XZ ;

Miller, DD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (22) :2497-2500

[5] Significance of hydrogen bonding at the S1′ subsite of calpain I [J].

Donkor, IO ;

Zheng, XZ ;

Han, J ;

Lacy, C ;

Miller, DD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (13) :1753-1755

[6] A survey of calpain inhibitors [J].

Donkor, IO .

CURRENT MEDICINAL CHEMISTRY, 2000, 7 (12) :1171-1188

[7] Crystal structure of calcium bound domain VI of calpain at 1.9 angstrom resolution and its role in enzyme assembly, regulation, and inhibitor binding [J].

Lin, GD ;

Chattopadhyay, D ;

Maki, M ;

Wang, KKW ;

Carson, M ;

Jin, L ;

Yuen, P ;

Takano, E ;

Hatanaka, M ;

DeLucas, LJ ;

Narayana, SVL .

NATURE STRUCTURAL BIOLOGY, 1997, 4 (07) :539-547

[8] PYRAZINE CHEMISTRY .3. SYNTHESIS AND STEREOCHEMISTRY OF 1,4-DIMETHYL AND 1,4-DIACETYL DERIVATIVES OF 3,6-DIBENZYLPIPERAZINE-2,5-DIONE [J].

MARCUCCIO, SM ;

ELIX, JA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (11) :2397-2402

[9] A SIMPLE ROUTE TO STERICALLY PURE DIKETOPIPERAZINES [J].

NITECKI, DE ;

HALPERN, B ;

WESTLEY, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (02) :864-&

[10] Cysteine proteases and their inhibitors [J].

Otto, HH ;

Schirmeister, T .

CHEMICAL REVIEWS, 1997, 97 (01) :133-171

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