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硅酸钡纳米颗粒,一种用于一锅法绿色合成α-苄基氨基香豆素衍生物的高效催化剂,该衍生物为潜在的化疗药物。

Barium silicate nanoparticles, an efficient catalyst for one-pot green synthesis of α-benzyl amino coumarin derivatives as potential chemotherapeutic agents.

作者信息

Taghrir Hadi, Faghih Zeinab, Ghashang Majid, Emami Leila, Dalili Shadi, Khabnadideh Soghra

机构信息

Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences Shiraz Islamic Republic of Iran

Department of Chemistry, Najafabad Branch, Islamic Azad University Najafabad Iran

出版信息

RSC Adv. 2023 Jul 12;13(31):21127-21137. doi: 10.1039/d3ra00796k.

DOI:10.1039/d3ra00796k
PMID:37449028
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10337722/
Abstract

A new, simple, and efficient method for synthesis of α-benzyl amino coumarin and its derivatives (1-24) is described a one-pot, three-component condensation of aromatic aldehydes, amine, and 4-hydroxycoumarin under green chemistry conditions: water as a solvent and BaSiO nanoparticles as catalyst. BaSiO nanoparticles and all synthesized derivatives were characterized by multiple methods including; XRD, NMR, and FE-SEM. This method which gives higher yields, is also less expensive, and more environmentally friendly compared with other methods in the literature. physicochemical and pharmacokinetics analyses were done on all synthesized compounds and indicated that these α-benzyl amino coumarins would be effective scaffolds for the future development of chemotherapeutic agents.

摘要

描述了一种合成α-苄基氨基香豆素及其衍生物(1-24)的新颖、简单且高效的方法:在绿色化学条件下,即水作为溶剂、BaSiO纳米颗粒作为催化剂,使芳香醛、胺和4-羟基香豆素进行一锅三组分缩合反应。通过多种方法对BaSiO纳米颗粒和所有合成的衍生物进行了表征,包括X射线衍射(XRD)、核磁共振(NMR)和场发射扫描电子显微镜(FE-SEM)。与文献中的其他方法相比,该方法产率更高、成本更低且更环保。对所有合成的化合物进行了物理化学和药代动力学分析,结果表明这些α-苄基氨基香豆素将成为未来化疗药物开发的有效骨架。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/af087e8afe1b/d3ra00796k-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/b2b56516ddfe/d3ra00796k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/1deb6d19ec72/d3ra00796k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/f7db551656e6/d3ra00796k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/18fbfd3cfda9/d3ra00796k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/2557e84428eb/d3ra00796k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/965190a041ed/d3ra00796k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/af087e8afe1b/d3ra00796k-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/b2b56516ddfe/d3ra00796k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/1deb6d19ec72/d3ra00796k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/f7db551656e6/d3ra00796k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/18fbfd3cfda9/d3ra00796k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/2557e84428eb/d3ra00796k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/965190a041ed/d3ra00796k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f173/10337722/af087e8afe1b/d3ra00796k-f4.jpg

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本文引用的文献

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2
Nanocrystalline and reusable ZnO catalyst for the assembly of densely functionalized 4H-chromenes in aqueous medium via one-pot three component reactions: a greener "NOSE" approach.纳米晶且可重复使用的 ZnO 催化剂用于在水相中通过一锅法三组分反应组装稠合多功能化 4H-色烯:更绿色的“NOSE”方法。
J Org Chem. 2013 Jun 21;78(12):6170-81. doi: 10.1021/jo400763z. Epub 2013 Jun 6.
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Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives.
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Bioorg Med Chem. 2010 May 15;18(10):3371-8. doi: 10.1016/j.bmc.2010.04.009. Epub 2010 Apr 8.
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Coumarins: old compounds with novel promising therapeutic perspectives.香豆素:具有新颖治疗前景的老化合物。
Curr Med Chem. 2010;17(13):1325-38. doi: 10.2174/092986710790936284.
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Synthesis and HIV-1 integrase inhibition of novel bis- or tetra-coumarin analogues.新型双香豆素或四香豆素类似物的合成及其对HIV-1整合酶的抑制作用
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