β-Lactams as promising anticancer agents: Molecular hybrids, structure activity relationships and potential targets

被引:38
作者
Fu, Dong-Jun [1 ]
Zhang, Yun-Feng [1 ]
Chang, An-Qi [1 ]
Li, Jun [1 ]
机构
[1] Beijing Univ Chinese Med, Modern Res Ctr Tradit Chinese Med, Sch Chinese Mat Med, Beijing 100029, Peoples R China
关键词
beta-Lactam; Molecular hybridization approach; Structure activity relationship; Anticancer mechanisms; NF-KAPPA-B; ANAPLASTIC LYMPHOMA KINASE; C-H INSERTION; BIOLOGICAL EVALUATION; STEREOSELECTIVE-SYNTHESIS; BREAST-CANCER; PROTEASOME INHIBITOR; REFORMATSKY REACTION; ANTITUMOR-ACTIVITY; BUILDING-BLOCKS;
D O I
10.1016/j.ejmech.2020.112510
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
beta-Lactam, commonly referred as azetidin-2-one, is a multifunctional building block for synthesizing beta-amino ketones, gamma-amino alcohols, and other compounds. Besides its well known antibiotic activity, this ring system exhibits a wide range of activities, attracting the attention of researchers. However, the structurally diverse beta-lactam analogues as anticancer agents and their different molecular targets are poorly discussed. The purpose of this review is 3-fold: (1) to explore the molecular hybridization approach to design beta-lactams hybrids as anticancer agents; (2) the structure activity relationship of the most active anticancer beta-lactams and (3) to summarize their antitumor mechanisms. (C) 2020 Elsevier Masson SAS. All rights reserved.
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页数:21
相关论文
共 215 条
[1]   Synthesis of optically pure highly functionalized γ-lactams via 2-azetidinone-tethered iminophosphoranes [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) :993-996
[2]   β-lactams:: Versatile building blocks for the stereoselective synthesis of non-β-lactam products [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina .
CHEMICAL REVIEWS, 2007, 107 (11) :4437-4492
[3]   Carbonyl allenylation/free radical cyclization sequence as a new regio- and stereocontrolled access to bi- and tricyclic β-lactams [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina ;
Redondo, Maria C. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (05) :1604-1608
[4]   Domino metal-free allene-β-lactam-based access to functionalized pyrroles [J].
Alcaide, Benito ;
Almendros, Pedro ;
Redondo, Maria C. .
CHEMICAL COMMUNICATIONS, 2006, (24) :2616-2618
[5]   Endocrine-responsive breast cancer and strategies for combating resistance [J].
Ali, S ;
Coombes, RC .
NATURE REVIEWS CANCER, 2002, 2 (02) :101-+
[6]   Highly enantioselective construction of the key azetidin-2-ones for the synthesis of carbapenem antibiotics via intramolecular C-H insertion reactions of α-methoxycarbonyl-α-diazoacetamides catalysed by chiral dirhodium(II) carboxylates [J].
Anada, M ;
Watanabe, N ;
Hashimoto, S .
CHEMICAL COMMUNICATIONS, 1998, (15) :1517-1518
[7]   A regio and diastereoselective transformation of 3-dienyl-2-azetidinones to novel pyrroloxazine [J].
Anand, Amit ;
Bhargava, Gaurav ;
Kumar, Vipan ;
Mahajan, Mohinder P. .
TETRAHEDRON LETTERS, 2010, 51 (17) :2312-2315
[8]   Direct Access to α,α-Difluoroacylated Arenes by Palladium-Catalyzed Carbonylation of (Hetero)Aryl Boronic Acid Derivatives [J].
Andersen, Thomas L. ;
Frederiksen, Mette W. ;
Domino, Katrine ;
Skrydstrup, Troels .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (35) :10396-10400
[9]  
Arul K., 2014, INT J PHARM PHARM SC, V6, P506
[10]   The chemistry and biological potential of azetidin-2-ones [J].
Arya, Nikhilesh ;
Jagdale, Archana Y. ;
Patil, Tushar A. ;
Yeramwar, Shradha S. ;
Holikatti, Sidharam S. ;
Dwivedi, Jaya ;
Shishoo, Chamanlal J. ;
Jain, Kishor S. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 74 :619-656