立体专一性交叉偶联反应提供具有抗白血病活性的构象偏向性芳基烷烃。
Stereospecific Cross-Coupling Reactions Provide Conformationally-Biased Arylalkanes with Anti-Leukemia Activity.
作者信息
Sanford Amberly B, Tollefson Emily J, Jarvo Elizabeth R
机构信息
Department of Chemistry, University of California, Irvine, Natural Sciences II, Irvine, CA, 92697.
出版信息
Isr J Chem. 2020 Mar;60:402-405. doi: 10.1002/ijch.201900071. Epub 2019 Sep 6.
Abstract
A focused small library of carbamates and alcohols was prepared employing stereospecific Kumada-ring opening reactions of tetrahydropyrans. The core framework of the library members is acyclic and incorporates 1,3-substituents, to provide a conformational bias in avoiding syn-pentane interactions. A new compound with micromolar activity against MOLT-4, CCRF-CEM, and HL-60(TB) leukemia cell lines was identified from this series.
摘要
利用四氢吡喃的立体定向 Kumada 开环反应制备了一个聚焦的氨基甲酸酯和醇类小型文库。文库成员的核心骨架是无环的，并含有 1,3 - 取代基，以在避免顺式戊烷相互作用方面提供构象偏向。从该系列中鉴定出一种对 MOLT - 4、CCRF - CEM 和 HL - 60(TB)白血病细胞系具有微摩尔活性的新化合物。
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本文引用的文献
1
Molecular Complexity as a Driver for Chemical Process Innovation in the Pharmaceutical Industry.
J Org Chem. 2019 Apr 19;84(8):4583-4603. doi: 10.1021/acs.joc.9b00735. Epub 2019 Apr 10.
2
The many roles of molecular complexity in drug discovery.
Drug Discov Today. 2017 Jan;22(1):120-126. doi: 10.1016/j.drudis.2016.08.009. Epub 2016 Aug 26.
3
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Org Process Res Dev. 2015 Oct 16;19(10):1356-1359. doi: 10.1021/acs.oprd.5b00148. Epub 2015 Sep 11.
4
Siladifluoromethylation and Difluoromethylation onto C(sp(3)), C(sp(2)), and C(sp) Centers Using Ruppert-Prakash Reagent and Fluoroform.
Org Lett. 2016 Jul 15;18(14):3354-7. doi: 10.1021/acs.orglett.6b01476. Epub 2016 Jun 24.
5
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Acc Chem Res. 2015 Aug 18;48(8):2344-53. doi: 10.1021/acs.accounts.5b00223. Epub 2015 Jul 21.
6
Selective synthesis of either enantiomer of an anti-breast cancer agent via a common enantioenriched intermediate.
Tetrahedron Lett. 2015 Jun 3;56(23):3486-3488. doi: 10.1016/j.tetlet.2015.02.121.
7
Conformation-activity relationships of polyketide natural products.
Nat Prod Rep. 2015 Aug;32(8):1183-206. doi: 10.1039/c5np00014a.
8
Organic carbamates in drug design and medicinal chemistry.
J Med Chem. 2015 Apr 9;58(7):2895-940. doi: 10.1021/jm501371s. Epub 2015 Jan 7.
9
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10
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J Med Chem. 2014 Dec 26;57(24):10257-74. doi: 10.1021/jm501100b. Epub 2014 Oct 7.
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