含1,2,11,11a-四氢环丙并[c]萘并[2,3-e]吲哚-4-酮（CNI）和1,2,11,11a-四氢环丙并[c]萘并[1,2-e]吲哚-4-酮（异-CNI）烷基化亚基的多卡霉素类似物的合成与初步评价
Synthesis and Preliminary Evaluation of Duocarmycin Analogues Incorporating the 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[2,3-e]indol-4-one (CNI) and 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[1,2-e]indol-4-one (iso-CNI) Alkylation Subunits.
作者信息
Gauss Carla M, Hamasaki Akiyuki, Parrish Jay P, Macmillan Karen S, Rayl Thomas J, Hwang Inkyu, Boger Dale L
机构信息
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
出版信息
Tetrahedron. 2009 Aug 15;65(33):6591-6599. doi: 10.1016/j.tet.2009.02.065.
Abstract
Efficient syntheses and a preliminary evaluation of 1,2,11,11a-tetrahydrocyclopropa[c]-naphtho[2,3-e]indole (CNI) and 1,2,11,11a-tetrahydrocyclopropa[c]naphtho[1,2-e]indole (iso-CNI), and their derivatives containing an anthracene and phenanthrene variant of the CC-1065 or duocarmycin alkylation subunit are detailed.
摘要
详细介绍了1,2,11,11a-四氢环丙[c]-萘并[2,3-e]吲哚（CNI）和1,2,11,11a-四氢环丙[c]萘并[1,2-e]吲哚（异-CNI）及其含有CC-1065或双吲哚霉素烷基化亚基的蒽和菲变体的衍生物的高效合成及初步评估。
相似文献
1
Synthesis and Preliminary Evaluation of Duocarmycin Analogues Incorporating the 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[2,3-e]indol-4-one (CNI) and 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[1,2-e]indol-4-one (iso-CNI) Alkylation Subunits.含1,2,11,11a-四氢环丙并[c]萘并[2,3-e]吲哚-4-酮（CNI）和1,2,11,11a-四氢环丙并[c]萘并[1,2-e]吲哚-4-酮（异-CNI）烷基化亚基的多卡霉素类似物的合成与初步评价
Tetrahedron. 2009 Aug 15;65(33):6591-6599. doi: 10.1016/j.tet.2009.02.065.
2
Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]imidazolo[4,5-e]indol-4-one-6-carboxylate (CImI) alkylation subunit.包含甲基1,2,8,8a-四氢环丙基[c]咪唑并[4,5-e]吲哚-4-酮-6-羧酸酯（CImI）烷基化亚基的多卡霉素SA类似物的合成与评价。
Bioorg Med Chem. 2016 Oct 15;24(20):4779-4786. doi: 10.1016/j.bmc.2016.04.050. Epub 2016 Apr 26.
3
Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indol-4-one-6-carboxylate (COI) alkylation subunit.含有甲基 1,2,8,8a-四氢环丙[a]氧杂卓[2,3-e]吲哚-4-酮-6-羧酸酯（COI）烷基化亚单位的 duocarmycin SA 类似物的合成与评价。
Bioorg Med Chem Lett. 2010 Mar 15;20(6):1854-7. doi: 10.1016/j.bmcl.2010.01.145. Epub 2010 Feb 2.
4
Synthesis and evaluation of 1,2,8, 8a-Tetrahydrocyclopropa[c]pyrrolo[3,2-e]indol-4(5H)-one, the parent alkylation subunit of CC-1065 and the duocarmycins: impact of the alkylation subunit substituents and its implications for DNA alkylation catalysis.CC-1065和双环霉素的母体烷基化亚基1,2,8,8a-四氢环丙并[c]吡咯并[3,2-e]吲哚-4(5H)-酮的合成与评估：烷基化亚基取代基的影响及其对DNA烷基化催化的意义
J Org Chem. 2000 Jun 30;65(13):4101-11. doi: 10.1021/jo000297j.
5
Synthesis and evaluation of duocarmycin and CC-1065 analogues incorporating the 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]-3-azaindol-4-one (CBA) alkylation subunit.包含1,2,9,9a-四氢环丙并[c]苯并[e]-3-氮杂吲哚-4-酮（CBA）烷基化亚基的多卡霉素和CC-1065类似物的合成与评价
J Org Chem. 2003 Nov 14;68(23):8984-90. doi: 10.1021/jo035119f.
6
1,2,9,9a-Tetrahydrocyclopropa[c]benz[e]indol-4-one (CBI) analogs of CC-1065 and the duocarmycins: synthesis and evaluation.CC-1065和双环霉素的1,2,9,9a-四氢环丙[c]苯[e]吲哚-4-酮（CBI）类似物：合成与评价
Bioorg Med Chem. 1995 Nov;3(11):1429-53. doi: 10.1016/0968-0896(95)00130-9.
7
Rational design, synthesis, and evaluation of key analogues of CC-1065 and the duocarmycins.CC-1065和双环霉素关键类似物的合理设计、合成与评估
J Am Chem Soc. 2007 Nov 14;129(45):14092-9. doi: 10.1021/ja073989z. Epub 2007 Oct 19.
8
Selective metal cation activation of a DNA alkylating agent: synthesis and evaluation of methyl 1,2,9, 9a-Tetrahydrocyclopropa[c]pyrido[3,2-e]indol-4-one-7-carboxylate (CPyI).一种DNA烷基化剂的选择性金属阳离子活化：1,2,9,9a-四氢环丙基[c]吡啶并[3,2-e]吲哚-4-酮-7-羧酸甲酯（CPyI）的合成与评价
J Org Chem. 2000 Jun 30;65(13):4088-100. doi: 10.1021/jo000177b.
9
Evaluation of functional analogs of CC-1065 and the duocarmycins incorporating the cross-linking 9a-chloromethyl-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-on e (C2BI) alkylation subunit.CC-1065和双环霉素功能类似物的评估，其中包含交联的9a-氯甲基-1,2,9,9a-四氢环丙[c]苯并[e]吲哚-4-酮（C2BI）烷基化亚基。
Bioorg Med Chem. 1993 Jul;1(1):27-38. doi: 10.1016/s0968-0896(00)82100-8.
10
Effective asymmetric synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI).1,2,9,9a-四氢环丙并[c]苯并[e]吲哚-4-酮（CBI）的有效不对称合成
J Org Chem. 2004 Apr 2;69(7):2284-9. doi: 10.1021/jo035465x.
引用本文的文献
1
Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles.基底促进的乙烯基环丙烷甲酰胺的分子内加成反应，用于构建具有受限构象的氮杂[3.1.0]双环。
Molecules. 2023 Apr 25;28(9):3691. doi: 10.3390/molecules28093691.
2
The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface.单原子的差异：化学-生物学界面的合成与设计。
J Org Chem. 2017 Dec 1;82(23):11961-11980. doi: 10.1021/acs.joc.7b02088. Epub 2017 Oct 13.
3
Synthesis and evaluation of a series of C5'-substituted duocarmycin SA analogs.合成与评价一系列 C5′-取代双氰胺 SA 类似物。
Bioorg Med Chem Lett. 2010 May 1;20(9):2722-5. doi: 10.1016/j.bmcl.2010.03.078. Epub 2010 Mar 25.
4
Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indol-4-one-6-carboxylate (COI) alkylation subunit.含有甲基 1,2,8,8a-四氢环丙[a]氧杂卓[2,3-e]吲哚-4-酮-6-羧酸酯（COI）烷基化亚单位的 duocarmycin SA 类似物的合成与评价。
Bioorg Med Chem Lett. 2010 Mar 15;20(6):1854-7. doi: 10.1016/j.bmcl.2010.01.145. Epub 2010 Feb 2.
本文引用的文献
2
An additional spirocyclization for duocarmycin SA.多卡霉素SA的额外螺环化反应。
J Am Chem Soc. 2008 Dec 10;130(49):16521-3. doi: 10.1021/ja806593w.
3
Yatakemycin: total synthesis, DNA alkylation, and biological properties.抑念霉素：全合成、DNA烷基化及生物学特性
Nat Prod Rep. 2008 Apr;25(2):220-6. doi: 10.1039/b705665f. Epub 2007 Nov 6.
4
Rational design, synthesis, and evaluation of key analogues of CC-1065 and the duocarmycins.CC-1065和双环霉素关键类似物的合理设计、合成与评估
J Am Chem Soc. 2007 Nov 14;129(45):14092-9. doi: 10.1021/ja073989z. Epub 2007 Oct 19.
5
Systematic exploration of the structural features of yatakemycin impacting DNA alkylation and biological activity.对影响DNA烷基化和生物活性的谷田霉素结构特征的系统探索。
J Am Chem Soc. 2007 Sep 5;129(35):10858-69. doi: 10.1021/ja072777z. Epub 2007 Aug 11.
6
Asymmetric total synthesis of (+)- and ent-(-)-yatakemycin and duocarmycin SA: evaluation of yatakemycin key partial structures and its unnatural enantiomer.（+）-和对映体-（-）-Yatakemycin及多卡霉素SA的不对称全合成：Yatakemycin关键部分结构及其非天然对映体的评估
J Am Chem Soc. 2006 Dec 13;128(49):15683-96. doi: 10.1021/ja064228j.
7
Alkylation of duplex DNA in nucleosome core particles by duocarmycin SA and yatakemycin.双吲哚霉素SA和矢车菊霉素对核小体核心颗粒中双链DNA的烷基化作用。
Nat Chem Biol. 2006 Feb;2(2):79-82. doi: 10.1038/nchembio761. Epub 2006 Jan 15.
8
Sequence-selective DNA recognition: natural products and nature's lessons.序列选择性DNA识别：天然产物与自然的启示
Chem Biol. 2004 Dec;11(12):1607-17. doi: 10.1016/j.chembiol.2003.08.012.
9
Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin.（+）-矢车菊霉素的全合成、结构修正及绝对构型
J Am Chem Soc. 2004 Jul 14;126(27):8396-8. doi: 10.1021/ja0472735.
10
Effective asymmetric synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI).1,2,9,9a-四氢环丙并[c]苯并[e]吲哚-4-酮（CBI）的有效不对称合成
J Org Chem. 2004 Apr 2;69(7):2284-9. doi: 10.1021/jo035465x.
Zotero 插件