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On the absolute configuration in 1,4-dihydrothiazepine covalent complexes derived from inhibition of class A and C beta-lactamases with 6-methylidene penems.

作者信息

Mansour Tarek S, Agarwal Atul, Venkatesan Aranapakam, Abe Takao, Mihira Ado, Takasaki Tsuyoshi, Sato Koichi, Ushirogochi Hideki, Yamamura Itsuki, Isoda Takeshi, Li Zhong, Yang Youjun, Kumagai Toshio

机构信息

Chemical and Screening Sciences and Infectious Diseases Wyeth Research, 401 North Middeltown Road, Pearl River, NY 10965, USA.

出版信息

ChemMedChem. 2007 Dec;2(12):1713-6. doi: 10.1002/cmdc.200700144.

DOI:10.1002/cmdc.200700144
PMID:17868160
Abstract
摘要

相似文献

1
On the absolute configuration in 1,4-dihydrothiazepine covalent complexes derived from inhibition of class A and C beta-lactamases with 6-methylidene penems.关于由6-亚甲基青霉烯抑制A类和C类β-内酰胺酶所衍生的1,4-二氢噻氮杂䓬共价复合物的绝对构型
ChemMedChem. 2007 Dec;2(12):1713-6. doi: 10.1002/cmdc.200700144.
2
Inhibition of class A and class C beta-lactamases by penems: crystallographic structures of a novel 1,4-thiazepine intermediate.青霉烯类对A类和C类β-内酰胺酶的抑制作用：一种新型1,4-噻氮杂环庚烷中间体的晶体结构
Biochemistry. 2003 Nov 18;42(45):13152-9. doi: 10.1021/bi034986b.
3
Structure-activity relationship of 6-methylidene penems bearing tricyclic heterocycles as broad-spectrum beta-lactamase inhibitors: crystallographic structures show unexpected binding of 1,4-thiazepine intermediates.作为广谱β-内酰胺酶抑制剂的含三环杂环的6-亚甲基青霉烯类化合物的构效关系：晶体结构显示1,4-噻氮杂环中间体的意外结合
J Med Chem. 2004 Dec 16;47(26):6556-68. doi: 10.1021/jm049680x.
4
Structure-activity relationship of 6-methylidene penems bearing 6,5 bicyclic heterocycles as broad-spectrum beta-lactamase inhibitors: evidence for 1,4-thiazepine intermediates with C7 R stereochemistry by computational methods.作为广谱β-内酰胺酶抑制剂的含6,5-双环杂环的6-亚甲基青霉烯类化合物的构效关系：通过计算方法证明具有C7 R立体化学的1,4-硫氮杂环庚烷中间体
J Med Chem. 2006 Jul 27;49(15):4623-37. doi: 10.1021/jm060021p.
5
5,5,6-Fused tricycles bearing imidazole and pyrazole 6-methylidene penems as broad-spectrum inhibitors of beta-lactamases.作为β-内酰胺酶广谱抑制剂的含咪唑和吡唑6-亚甲基青霉烯的5,5,6-稠合三环化合物。
Bioorg Med Chem. 2008 Feb 15;16(4):1890-902. doi: 10.1016/j.bmc.2007.11.006. Epub 2007 Nov 5.
6
Mechanism of inactivation of beta-lactamases by novel 6-methylidene penems elucidated using electrospray ionization mass spectrometry.利用电喷雾电离质谱法阐明新型6-亚甲基青霉烯类对β-内酰胺酶的失活机制。
J Med Chem. 2004 Jul 1;47(14):3674-88. doi: 10.1021/jm049903j.
7
Understanding the longevity of the beta-lactam antibiotics and of antibiotic/beta-lactamase inhibitor combinations.了解β-内酰胺类抗生素以及抗生素/β-内酰胺酶抑制剂组合的使用寿命。
Biochem Pharmacol. 2006 Mar 30;71(7):930-40. doi: 10.1016/j.bcp.2005.11.012. Epub 2005 Dec 13.
8
Synthesis and evaluation of thiazepines as interleukin-1beta converting enzyme (ICE) inhibitors.作为白细胞介素-1β转化酶（ICE）抑制剂的硫氮杂䓬类化合物的合成与评价
Bioorg Med Chem Lett. 2006 Sep 15;16(18):4728-32. doi: 10.1016/j.bmcl.2006.07.016. Epub 2006 Jul 25.
9
3-Methylidene-beta-lactams as potential inhibitors of beta-lactamases. Part 1: Synthesis of alpha-substituted derivatives from imines by Reformatzky reaction with chlorotrimethylsilane, silylation and Peterson olefination.
Pharmazie. 1996 Nov;51(11):811-5.
10
Targeting Val 216 in class A beta-lactamases with tricyclic 6-methylidene penems.用三环6-亚甲基青霉烯靶向A类β-内酰胺酶中的缬氨酸216。
ChemMedChem. 2008 Nov;3(11):1658-61. doi: 10.1002/cmdc.200800167.

引用本文的文献

1
Exploring Additional Dimensions of Complexity in Inhibitor Design for Serine β-Lactamases: Mechanistic and Intra- and Inter-molecular Chemistry Approaches.探索丝氨酸β-内酰胺酶抑制剂设计中复杂性的其他维度：机理及分子内和分子间化学方法
Front Microbiol. 2018 Apr 5;9:622. doi: 10.3389/fmicb.2018.00622. eCollection 2018.
2
Structures of SHV-1 β-lactamase with penem and penam sulfone inhibitors that form cyclic intermediates stabilized by carbonyl conjugation.与碳基共轭稳定的环中间体形成的碳青霉烯和青霉烯砜抑制剂与 SHV-1 β-内酰胺酶的结构。
PLoS One. 2012;7(11):e49035. doi: 10.1371/journal.pone.0049035. Epub 2012 Nov 8.
3
Substitutions at position 105 in SHV family β-lactamases decrease catalytic efficiency and cause inhibitor resistance.
在 SHV 家族β-内酰胺酶的位置 105 发生取代会降低催化效率并导致抑制剂耐药性。
Antimicrob Agents Chemother. 2012 Nov;56(11):5678-86. doi: 10.1128/AAC.00711-12. Epub 2012 Aug 20.
4
Inhibition of OXA-1 beta-lactamase by penems.青霉烯类对OXA-1β-内酰胺酶的抑制作用。
Antimicrob Agents Chemother. 2008 Sep;52(9):3135-43. doi: 10.1128/AAC.01677-07. Epub 2008 Jun 16.