Synthesis of cyclic prodrugs of Aggrastat and its analogue with a modified phenylpropionic acid linker

被引：12

作者：

Song, XP ^{[1
]}

He, HT ^{[1
]}

Siahaan, TJ ^{[1
]}

机构：

[1] Univ Kansas, Dept Pharmaceut Chem, Lawrence, KS 66047 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 04期

关键词：

D O I：

10.1021/ol010282n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The objective of this work was to synthesize cyclic prodrugs 1a and 1b from Aggrastat 2a and its analogue 2b, respectively, to improve their membrane permeation. Cyclic prodrugs is and 1b were formed using an ester bond between the -COON group of Aggrastat or its analogue and the phenylpropionic acid linker 3 and an amide bond between the piperidinylamine and the -COOH group of the linker 3, respectively, as outlined in Scheme 4.

引用

页码：549 / 552

页数：4

共 18 条

[1] Synthesis and evaluation of the physicochemical properties of esterase-sensitive cyclic prodrugs of opioid peptides using an (acyloxy)alkoxy linker [J].

Bak, A ;

Siahaan, TJ ;

Gudmundsson, OS ;

Gangwar, S ;

Friis, GJ ;

Borchardt, RT .

JOURNAL OF PEPTIDE RESEARCH, 1999, 53 (04) :393-402

[2]

Bazzino O, 1998, NEW ENGL J MED, V338, P1498

[3] REDUCTIVE LACTONIZATION OF STRATEGICALLY METHYLATED QUINONE PROPIONIC-ACID ESTERS AND AMIDES [J].

CARPINO, LA ;

TRIOLO, SA ;

BERGLUND, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) :3303-3310

[4] NONPEPTIDE FIBRINOGEN RECEPTOR ANTAGONISTS .2. OPTIMIZATION OF A TYROSINE TEMPLATE AS A MIMIC FOR ARG-GLY-ASP [J].

EGBERTSON, MS ;

CHANG, CTC ;

DUGGAN, ME ;

GOULD, RJ ;

HALCZENKO, W ;

HARTMAN, GD ;

LASWELL, WL ;

LYNCH, JJ ;

LYNCH, RJ ;

MANNO, PD ;

NAYLOR, AM ;

PRUGH, JD ;

RAMJIT, DR ;

SITKO, GR ;

SMITH, RS ;

TURCHI, LM ;

ZHANG, GX .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (16) :2537-2551

[5] Synthesis of a novel esterase-sensitive cyclic prodrug of a hexapeptide using an (acyloxy)alkoxy promoiety [J].

Gangwar, S ;

Pauletti, GM ;

Siahaan, TJ ;

Stella, VJ ;

Borchardt, RT .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1356-1362

[6] Phenylpropionic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeation [J].

Gudmundsson, OS ;

Nimkar, K ;

Gangwar, S ;

Siahaan, T ;

Borchardt, RT .

PHARMACEUTICAL RESEARCH, 1999, 16 (01) :16-23

[7] The effect of conformation on the membrane permeation of coumarinic acid- and phenylpropionic acid-based cyclic prodrugs of opioid peptides [J].

Gudmundsson, OS ;

Jois, SDS ;

Vander Velde, DG ;

Siahaan, TJ ;

Wang, B ;

Borchardt, RT .

JOURNAL OF PEPTIDE RESEARCH, 1999, 53 (04) :383-392

[8]

Hanrath P, 1997, CIRCULATION, V96, P1445

[9] NONPEPTIDE FIBRINOGEN RECEPTOR ANTAGONISTS .1. DISCOVERY AND DESIGN OF EXOSITE INHIBITORS [J].

HARTMAN, GD ;

EGBERTSON, MS ;

HALCZENKO, W ;

LASWELL, WL ;

DUGGAN, ME ;

SMITH, RL ;

NAYLOR, AM ;

MANNO, PD ;

LYNCH, RJ ;

ZHANG, GX ;

CHANG, CTC ;

GOULD, RJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (24) :4640-4642

[10]

Kereiakes DJ, 1996, J AM COLL CARDIOL, V27, P536

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