微波辅助合成有机金属铼（I）碳酸戊酯配合物：用于羧基、磺酸基和氯配合物的新型合成子
Microwave-Assisted Synthesis of Organometallic Rhenium (I) Pentylcarbonato Complexes: New Synthon for Carboxylato, Sulfonato and Chlorido Complexes.
作者信息
Winstead Angela J, Alabrash Khayra, Powell Brent V, Parnell Sabreea J, Hinton Tiara V, Odebode Tijesunimi, Peng Jiangnan, Krause Jeanette A, Zavalij Peter Y, Mandal Santosh K
机构信息
Morgan State University, Department of Chemistry, Baltimore, MD 21251.
University of Cincinnati, Department of Chemistry, Cincinnati, OH 45221.
出版信息
J Organomet Chem. 2021 Mar 15;936. doi: 10.1016/j.jorganchem.2021.121718. Epub 2021 Jan 27.
Abstract
Tricarbonylrhenium(I)(α-diimine) complexes are of importance because of their strong cytotoxic and fluorescence properties. Syntheses of such complexes were achieved through a two-step process. First, the pentylcarbonato complexes, -(CO)(α-diimine)ReOC(O)OCH were synthesized through a microwave-assisted reaction of Re(CO), α-diimine, 1-pentanol and CO in a few hours. Second, the pentylcarbonato complexes are treated with carboxylic, sulfonic and halo acids to obtain the corresponding carboxylato, sulfonato and halido complexes. This is the first example of conversion of Re(CO) into a rhenium carbonyl complex through microwave-assisted reaction.
摘要
三羰基铼（I）（α-二亚胺）配合物因其强大的细胞毒性和荧光特性而备受关注。此类配合物通过两步法合成。首先，通过在数小时内将铼（CO）、α-二亚胺、1-戊醇和一氧化碳进行微波辅助反应，合成戊基碳酸酯配合物-（CO）（α-二亚胺）ReOC（O）OCH。其次，将戊基碳酸酯配合物用羧酸、磺酸和卤代酸处理，以获得相应的羧基、磺基和卤化物配合物。这是通过微波辅助反应将铼（CO）转化为铼羰基配合物的首个实例。
相似文献
1
Microwave-Assisted Synthesis of Organometallic Rhenium (I) Pentylcarbonato Complexes: New Synthon for Carboxylato, Sulfonato and Chlorido Complexes.微波辅助合成有机金属铼（I）碳酸戊酯配合物：用于羧基、磺酸基和氯配合物的新型合成子
J Organomet Chem. 2021 Mar 15;936. doi: 10.1016/j.jorganchem.2021.121718. Epub 2021 Jan 27.
2
Chemical and biological characterization of technetium(I) and Rhenium(I) tricarbonyl complexes with dithioether ligands serving as linkers for coupling the Tc(CO)(3) and Re(CO)(3) moieties to biologically active molecules.锝（I）和铼（I）三羰基配合物与二硫醚配体的化学和生物学特性，二硫醚配体作为将Tc(CO)₃和Re(CO)₃部分与生物活性分子偶联的连接体。
Bioconjug Chem. 2000 May-Jun;11(3):414-24. doi: 10.1021/bc990162o.
3
Unprecedented anticancer activities of organorhenium sulfonato and carboxylato complexes against hormone-dependent MCF-7 and hormone-independent triple-negative MDA-MB-231 breast cancer cells.有机铼磺酸盐和羧酸盐配合物对激素依赖性 MCF-7 和激素非依赖性三阴性 MDA-MB-231 乳腺癌细胞的前所未有的抗癌活性。
Mol Cell Biochem. 2018 Apr;441(1-2):151-163. doi: 10.1007/s11010-017-3181-z. Epub 2017 Sep 14.
4
Mono-, di- and tetrarhenium Fischer carbene complexes with thienothiophene substituents.带有噻吩并噻吩取代基的单铼、二铼和四铼费舍尔卡宾配合物。
Dalton Trans. 2017 Oct 17;46(40):13983-13993. doi: 10.1039/c7dt02969a.
5
Anticancer Properties of Novel Rhenium Pentylcarbanato Compounds against MDA-MB-468(HTB-132) Triple Node Negative Human Breast Cancer Cell Lines.新型戊基碳酸铼化合物对MDA-MB-468(HTB-132)三阴性人乳腺癌细胞系的抗癌特性
Br J Pharm Res. 2015 Feb 1;4(3):362-367. doi: 10.9734/BJPR/2014/4697.
6
Reactivity of electrochemically generated rhenium (II) Tricarbonyl alpha-diimine complexes: a reinvestigation of the oxidation of luminescent Re(CO)3(alpha-Diimine)Cl and related compounds.电化学生成的铼（II）三羰基α-二亚胺配合物的反应活性：对发光的Re(CO)3(α-二亚胺)Cl及相关化合物氧化反应的重新研究
Inorg Chem. 2008 Sep 1;47(17):7880-7. doi: 10.1021/ic800530n. Epub 2008 Aug 6.
7
Microwave-assisted synthesis of organometallic complexes of ⁹⁹mTc(CO)₃ and Re(CO)₃: its application to radiopharmaceuticals.⁹⁹mTc(CO)₃和Re(CO)₃有机金属配合物的微波辅助合成：其在放射性药物中的应用。
Chem Pharm Bull (Tokyo). 2012;60(1):79-85. doi: 10.1248/cpb.60.79.
8
Synthesis, structure, and reactivity of ruthenium carboxylato and 2-oxocarboxylato complexes bearing the bis(3,5-dimethylpyrazol-1-yl)acetato ligand.含双（3,5-二甲基吡唑-1-基）乙酸根配体的钌羧基和2-氧代羧基配合物的合成、结构及反应活性
Inorg Chem. 2008 Oct 20;47(20):9624-41. doi: 10.1021/ic8000224. Epub 2008 Sep 19.
9
Synthesis and assessment of CO-release capacity of manganese carbonyl complexes derived from rigid α-diimine ligands of varied complexity.源自不同复杂程度刚性α-二亚胺配体的羰基锰配合物的一氧化碳释放能力的合成与评估。
Eur J Inorg Chem. 2015 Oct;2015(30):5021-5026. doi: 10.1002/ejic.201500816. Epub 2015 Sep 30.
10
Synthesis of Re tricarbonyl complexes with various sulfur- and oxygen-donating ligands: crystal structures of two Re dinuclear structures bridged by S atoms.
Acta Crystallogr C Struct Chem. 2018 Oct 1;74(Pt 10):1116-1122. doi: 10.1107/S205322961801207X. Epub 2018 Sep 13.
引用本文的文献
1
Microwave-Assisted Synthesis: Can Transition Metal Complexes Take Advantage of This "Green" Method?微波辅助合成：过渡金属配合物能利用这种“绿色”方法吗？
Molecules. 2022 Jun 30;27(13):4249. doi: 10.3390/molecules27134249.
本文引用的文献
1
Unprecedented anticancer activities of organorhenium sulfonato and carboxylato complexes against hormone-dependent MCF-7 and hormone-independent triple-negative MDA-MB-231 breast cancer cells.有机铼磺酸盐和羧酸盐配合物对激素依赖性 MCF-7 和激素非依赖性三阴性 MDA-MB-231 乳腺癌细胞的前所未有的抗癌活性。
Mol Cell Biochem. 2018 Apr;441(1-2):151-163. doi: 10.1007/s11010-017-3181-z. Epub 2017 Sep 14.
2
Carbonic acid monoethyl ester as a pure solid and its conformational isomerism in the gas-phase.纯固态单乙基碳酸酯及其在气相中的构象异构现象。
RSC Adv. 2017 Apr 21;7(36):22222-22233. doi: 10.1039/c7ra02792c.
3
Microwave-assisted synthesis of organometallic complexes of ⁹⁹mTc(CO)₃ and Re(CO)₃: its application to radiopharmaceuticals.⁹⁹mTc(CO)₃和Re(CO)₃有机金属配合物的微波辅助合成：其在放射性药物中的应用。
Chem Pharm Bull (Tokyo). 2012;60(1):79-85. doi: 10.1248/cpb.60.79.
4
Chloro-fac-tricarbonylrhenium(I) complexes of asymmetric azines derived from 6-acetyl-1,3,7-trimethylpteridine-2,4(1H,3H)-dione with hydrazine and aromatic aldehydes: preparation, structural characterization and biological activity against several human tumor cell lines.6-乙酰基-1,3,7-三甲基蝶啶-2,4(1H,3H)-二酮与肼及芳香醛形成的不对称吖嗪的氯代三羰基铼(I)配合物：制备、结构表征及对几种人类肿瘤细胞系的生物活性
J Inorg Biochem. 2009 Jan;103(1):94-100. doi: 10.1016/j.jinorgbio.2008.09.014. Epub 2008 Oct 10.
5
Expedient multi-step synthesis of organometallic complexes of Tc and Re in high effective specific activity. A new platform for the production of molecular imaging and therapy agents.高效比活度下锝和铼有机金属配合物的便捷多步合成。分子成像与治疗剂生产的新平台。
Inorg Chem. 2008 Sep 15;47(18):8213-21. doi: 10.1021/ic800775w. Epub 2008 Aug 19.
6
Microwave-assisted synthesis of tricarbonyl rhenacarboranes: steric and electronic effects on the 1,2 --> 1,7 carborane cage isomerization.
Inorg Chem. 2007 Mar 19;46(6):2148-58. doi: 10.1021/ic0617543. Epub 2007 Feb 16.
7
DNA binding and cytotoxicity of ruthenium(II) and rhenium(I) complexes of 2-amino-4-phenylamino-6-(2-pyridyl)-1,3,5-triazine.2-氨基-4-苯基氨基-6-(2-吡啶基)-1,3,5-三嗪的钌(II)和铼(I)配合物的DNA结合及细胞毒性
Inorg Chem. 2007 Feb 5;46(3):740-9. doi: 10.1021/ic061518s.
8
Microwave-assisted synthesis of 3,1,2- and 2,1,8-Re(I) and 99mTc(I)-metallocarborane complexes.微波辅助合成3,1,2-和2,1,8-铼（I）以及99m锝（I）-金属碳硼烷配合物。
Inorg Chem. 2006 Jul 24;45(15):5727-9. doi: 10.1021/ic0605928.
Zotero 插件