Stereoselective ring contraction of 2,5-diketopiperazines: An innovative approach to the synthesis of promising bioactive 5-membered scaffolds

被引：25

作者：

Coursindel, Thibault ^{[1
]}

Restouin, Audrey ^{[2
,3
,4
]}

Dewynter, Georges ^{[1
]}

Martinez, Jean ^{[1
]}

Collette, Yves ^{[2
,3
,4
]}

Parrot, Isabelle ^{[1
]}

机构：

[1] Univ Montpellier 2, IBMM, CNRS, Univ Montpellier 1,UMR 5247, F-34095 Montpellier 5, France

[2] Ctr Rech Cancerol Marseille, INSERM, U891, F-13009 Marseille, France

[3] Inst J Paoli I Calmettes, F-13009 Marseille, France

[4] Univ Aix Marseille 2, F-13007 Marseille, France

来源：

BIOORGANIC CHEMISTRY | 2010年 / 38卷 / 4-6期

关键词：

Ring contraction; Diketopiperazines; Stereoselective rearrangement; Spiroheterocycle; Anti-proliferative activity; SCHOLLKOPF CHIRAL AUXILIARIES; MICROWAVE-ASSISTED SYNTHESIS; BIOLOGICAL-ACTIVITY; TRANSANNULAR REARRANGEMENT; ASYMMETRIC-SYNTHESIS; CYCLIC DIPEPTIDES; DIKETOPIPERAZINES; DERIVATIVES; POTENT; ROUTE;

D O I：

10.1016/j.bioorg.2010.05.002

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Ring contraction of 2,5-diketopiperazines by TRAL-alkylation led us to the stereoselective synthesis of original pyrrolidine-2,4-diones, a novel series of promising molecules with moderate anti-proliferative activity on breast cancer cells. (C) 2010 Elsevier Inc. All rights reserved.

引用

页码：210 / 217

页数：8

共 5 条

[1] Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry
Bruttomesso, Andrea C.
Eiras, Javier
Ramirez, Javier A.
Galagovsky, Lydia R.
TETRAHEDRON LETTERS, 2009, 50 (28) : 4022 - 4024
[2] Cyclodipeptide synthases: a promising biotechnological tool for the synthesis of diverse 2,5-diketopiperazines
Canu, Nicolas
Moutiez, Mireille
Belin, Pascal
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NATURAL PRODUCT REPORTS, 2020, 37 (03) : 312 - 321
[3] Stereoselective Nucleophilc Substitution of α-Bromo Tertiary Amides for Asymmetric Synthesis of Highly Substituted 2,5-Diketopiperazines
Lee, Myung-su
Kim, Yongtae
Youk, Eunjee
Park, Yong Sun
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (06) : 981 - 984
[4] Microwave-Assisted Stereoselective One-Pot Synthesis of Symmetrical and Unsymmetrical 2,5-Diketopiperazines from Unprotected Amino Acids
Jainta, Manuet
Nieger, Martin
Braese, Stefan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (32) : 5418 - 5424
[5] Cyclohepta[b]indole Synthesis through [5+2] Cycloaddition: Bifunctional Indium(III)-Catalyzed Stereoselective Construction of 7-Membered Ring Fused Indoles
Takeda, Takuya
Harada, Shinji
Okabe, Akito
Nishida, Atsushi
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19) : 11541 - 11551

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