A shortened, protecting group free, synthesis of the anti-wrinkle venom analogue Syn-Ake® exploiting an optimized Hofmann-type rearrangement

被引:11
作者
Balaev, A. N. [1 ]
Okhmanovich, K. A. [1 ]
Osipov, V. N. [1 ]
机构
[1] Pharm Sintez, Moscow 115419, Russia
关键词
Peptides; Tripeptide; Syn-Ake (R); Hofmann-type rearrangement; mnAChR antagonist;
D O I
10.1016/j.tetlet.2014.08.117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unusual five-step synthesis of H-beta-Ala-Pro-DabNHBz diacetate (a muscular nicotinic acetylcholine receptor antagonist) has been delineated through Hofmann-type rearrangement as a final step to build the target skeleton. The synthesis has been carried out using a protecting group free strategy and employed readily available reagents as the starting materials. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5745 / 5747
页数:3
相关论文
共 7 条
[1]  
Chhipa N. M. R., 2012, J CURR PHARM RES, V9, P11
[2]   Bioactive peptides: signaling the future [J].
Fields, K. ;
Falla, T. J. ;
Rodan, K. ;
Bush, L. .
JOURNAL OF COSMETIC DERMATOLOGY, 2009, 8 (01) :8-13
[3]  
Kozma J., 2006, KOZMETIKA, V55, P16
[4]   Skin peptides: Biological activity and therapeutic opportunities [J].
Namioshi, Sarika ;
Caccetta, Rima ;
Benson, Heather A. E. .
JOURNAL OF PHARMACEUTICAL SCIENCES, 2008, 97 (07) :2524-2542
[5]  
Pentapharm A.-G., 2006, [No title captured], Patent No. [WO 20,060,447,900, 20060447900]
[6]   Cyclic dipeptides as building blocks for combinatorial libraries. Part 2: Synthesis of bifunctional diketopiperazines [J].
Rodionov, IL ;
Rodionova, LN ;
Baidakova, LK ;
Romashko, AM ;
Balashova, TA ;
Ivanov, VT .
TETRAHEDRON, 2002, 58 (42) :8515-8523
[7]  
Ziegler H., 2006, FRAGR J, V34, P93