超分子化学中的胆汁酸支架：设计与合成的相互作用
Bile acid scaffolds in supramolecular chemistry: the interplay of design and synthesis.
作者信息
Davis Anthony P
机构信息
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
出版信息
Molecules. 2007 Aug 29;12(9):2106-22. doi: 10.3390/12082106.
Abstract
Since early work in the 1980s, the bile acids have become well established as building blocks for supramolecular chemistry. The author's laboratory has specialised in converting cholic acid, the archetypal bile acid, into macrocyclic and acyclic receptors for anions and carbohydrates. This review highlights the synthetic aspects of this work, especially the use of modern synthetic methodology to perform less obvious structural transformations.
摘要
自20世纪80年代早期开展相关工作以来，胆汁酸已成为超分子化学的重要构建单元。作者所在的实验室专门致力于将典型的胆汁酸——胆酸转化为用于阴离子和碳水化合物的大环及非环受体。本综述着重介绍了这项工作的合成方面，特别是利用现代合成方法进行不太明显的结构转变。
相似文献
1
Bile acid scaffolds in supramolecular chemistry: the interplay of design and synthesis.
Molecules. 2007 Aug 29;12(9):2106-22. doi: 10.3390/12082106.
2
Chemical and metabolic transformations of selected bile acids.
Eur J Drug Metab Pharmacokinet. 2006 Jul-Sep;31(3):179-235. doi: 10.1007/BF03190713.
3
Cholic acid in guinea pig bile.
Proc Soc Exp Biol Med. 1960 Nov;105:337-9. doi: 10.3181/00379727-105-26103.
4
Synthesis, aggregation behavior and cholesterol solubilization studies of 16-epi-pythocholic acid (3 alpha,12 alpha,16 beta-trihydroxy-5 beta-cholan-24-oic acid).
Steroids. 2010 Jul;75(7):506-12. doi: 10.1016/j.steroids.2010.03.007. Epub 2010 Mar 30.
5
Recent methods for diversification of bile acids and related steroids towards supramolecular.
Steroids. 2019 Nov;151:108442. doi: 10.1016/j.steroids.2019.108442. Epub 2019 Jul 19.
6
Design and synthesis of novel chiral dendritic species derived from bile acids.
J Org Chem. 2001 May 4;66(9):3035-40. doi: 10.1021/jo0013305.
7
Twisted nanoribbons from a RGD-bearing cholic acid derivative.
Colloids Surf B Biointerfaces. 2017 Nov 1;159:183-190. doi: 10.1016/j.colsurfb.2017.07.084. Epub 2017 Jul 31.
8
A combinatorial biocatalysis approach to an array of cholic acid derivatives.
Biotechnol Bioeng. 2003 Feb 20;81(4):391-6. doi: 10.1002/bit.10486.
9
Shortcut access to peptidosteroid conjugates: building blocks for solid-phase bile acid scaffold decoration by convergent ligation.
Molecules. 2011 Dec 7;16(12):10168-86. doi: 10.3390/molecules161210168.
10
Novel bile acid-based cyclic bisimidazolium receptors for anion recognition.
Org Lett. 2006 Apr 27;8(9):1755-8. doi: 10.1021/ol060168a.
引用本文的文献
1
Regiochemical Effects on the Carbohydrate Binding and Selectivity of Flexible Synthetic Carbohydrate Receptors with Indole and Quinoline Heterocyclic Groups.
European J Org Chem. 2021 Oct 7;2021(37):5262-5274. doi: 10.1002/ejoc.202100763. Epub 2021 Sep 12.
2
Bile Acids Transporters of Enterohepatic Circulation for Targeted Drug Delivery.
Molecules. 2022 May 5;27(9):2961. doi: 10.3390/molecules27092961.
3
Novel Semisynthetic Derivatives of Bile Acids as Effective Tyrosyl-DNA Phosphodiesterase 1 Inhibitors.
Molecules. 2018 Mar 17;23(3):679. doi: 10.3390/molecules23030679.
4
Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands.
Beilstein J Org Chem. 2017 Mar 20;13:564-570. doi: 10.3762/bjoc.13.55. eCollection 2017.
5
Shortcut access to peptidosteroid conjugates: building blocks for solid-phase bile acid scaffold decoration by convergent ligation.
Molecules. 2011 Dec 7;16(12):10168-86. doi: 10.3390/molecules161210168.
6
Stigmasterol-based novel low molecular weight/mass organic gelators.
Molecules. 2011 Nov 8;16(11):9357-67. doi: 10.3390/molecules16119357.
7
Bis[3α,7α,12α-tris-(4-nitro-benzo-yloxy)-5β-cholan-24-yl] disulfide-ethyl acetate-n-hexane (4/4/1).
Acta Crystallogr Sect E Struct Rep Online. 2010 Dec 11;67(Pt 1):o74-5. doi: 10.1107/S1600536810050385.
8
Role of the intestinal bile acid transporters in bile acid and drug disposition.
Handb Exp Pharmacol. 2011(201):169-203. doi: 10.1007/978-3-642-14541-4_4.
9
Bile acids: chemistry, physiology, and pathophysiology.
World J Gastroenterol. 2009 Feb 21;15(7):804-16. doi: 10.3748/wjg.15.804.
本文引用的文献
1
Development of synthetic membrane transporters for anions.
Chem Soc Rev. 2007 Feb;36(2):348-57. doi: 10.1039/b512651g. Epub 2006 Oct 23.
2
The "triamino-analogue" of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry.
Chem Commun (Camb). 2006 Jun 14(22):2335-7. doi: 10.1039/b602415g. Epub 2006 May 15.
3
Substrate discrimination by cholapod anion receptors: geometric effects and the "affinity-selectivity principle".
J Am Chem Soc. 2005 Aug 3;127(30):10739-46. doi: 10.1021/ja0524144.
4
A fluorescent assay for chloride transport; identification of a synthetic anionophore with improved activity.
Chem Commun (Camb). 2005 Feb 28(8):1087-9. doi: 10.1039/b414589e. Epub 2005 Jan 12.
5
Differentially-protected steroidal triamines; scaffolds with potential for medicinal, supramolecular, and combinatorial chemistry.
Org Biomol Chem. 2004 Nov 21;2(22):3320-8. doi: 10.1039/B412298D. Epub 2004 Oct 15.
6
Chloride transport across vesicle and cell membranes by steroid-based receptors.
Angew Chem Int Ed Engl. 2003 Oct 20;42(40):4931-3. doi: 10.1002/anie.200351957.
7
Steroidal ureas as enantioselective receptors for an N-acetyl alpha-amino carboxylate.
Org Lett. 2002 Dec 26;4(26):4639-42. doi: 10.1021/ol027009l.
8
Enantioselective transport by a steroidal guanidinium receptor.
Chemistry. 2002 Jul 2;8(13):2931-6. doi: 10.1002/1521-3765(20020703)8:13<2931::AID-CHEM2931>3.0.CO;2-H.
9
An extraction-based assay for neutral anionophores: the measurement of high binding constants to steroidal receptors in a nonpolar solvent.
Chemistry. 2002 May 3;8(9):2197-203. doi: 10.1002/1521-3765(20020503)8:9<2197::AID-CHEM2197>3.0.CO;2-J.
10
Dimeric and Oligomeric Steroids.
Chem Rev. 1997 Feb 5;97(1):283-304. doi: 10.1021/cr9600565.
Zotero 插件