Construction of Difluorinated Cycloheptadienones via Substrate-Controlled Regioselective Conjugate Addition of Difluoroenoxysilanes to Tropones and Their Anticancer Activity

被引：0

作者：

Wang, Xi-Yu ^{[1
]}

Guo, Yan-Zhi ^{[2
]}

Shi, Shanshan ^{[3
]}

Li, Shiliang ^{[4
]}

Yu, Jin-Sheng ^{[2
]}

Dong, Su-Zhen ^{[2
]}

Hao, Yong-Jia ^{[1
]}

Zhou, Jian ^{[1
,2
,5
]}

机构：

[1] Guizhou Univ Tradit Chinese Med, Sch Pharm, Guiyang 550025, Peoples R China

[2] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug Dev, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

[3] East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China

[4] East China Normal Univ, Innovat Ctr AI & Drug Discovery, Shanghai 200062, Peoples R China

[5] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 17期

关键词：

Regioselective conjugate addition; difluoroenoxysilanes; tropones; difluorinated cycloheptadienones; anticancer activity; AZOMETHINE YLIDES; 6+3 CYCLOADDITION; ENOL ETHERS; REAGENTS; ACCESS;

D O I：

10.1002/adsc.202400176

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The substrate-controlled regioselective conjugate addition (1,8- and 1,4-addition) of tropones with difluoroenoxysilanes is reported, which offered an approach for the selective synthesis of multifunctional seven-membered 3,5-cycloheptadien-1-ones and 1,3-cycloheptadien-1-ones featuring a gem-difluoroketone moiety. Moreover, these fluorinated cyclo-heptadienones exhibit effective anti-proliferative activities (IC50<1 mu M) for human colon carcinoma HCT116 cells in vitro, thus providing potential lead compounds for developing new anticancer agents. image

引用

页码：3585 / 3590

页数：6

共 4 条

[1] Transition-Metal-Free Reactions of Boronic Acids: 1,3-Stereochemical Induction in the Substrate-Controlled Conjugate Addition
Roscales, Silvia
Ortega, Victor
Csaky, Aurelio G.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (24): : 12825 - 12830
[2] The Quinary Catalyst-Substrate Complex Induced Construction of Spiro-Bridged or Cagelike Polyheterocyclic Compounds via a Substrate-Controlled Cascade Process
Wang, Chen
Chen, Ying-Han
Wu, Hui-Chun
Wang, Cong
Liu, Yan-Kai
ORGANIC LETTERS, 2019, 21 (17) : 6750 - 6755
[3] Stereoselective Protection-Free Asymmetric Total Synthesis of (+)-Chamuvarinin, a Potent Anticancer and Antitrypanosomal Agent: Substrate-Controlled Construction of the Adjacently Linked Oxatricyclic Core by Internal Alkylation
Sarnala, Mallesham
Thien Nhan Lu
Mandava, Suresh
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Bogonda, Ganganna
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Park, Haeil
Kim, Deukjoon
Lee, Jongkook
ORGANIC LETTERS, 2018, 20 (20) : 6398 - 6402
[4] A stereoselective construction of a cis-1,2-oxazadecaline skeleton using a substrate-controlled intramolecular oxy-Michael addition of tyrosine-derived hydroxylamines
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Saito, Hayato
Yamaguchi, Ayuta
Arai, Masayoshi
TETRAHEDRON LETTERS, 2020, 61 (04)

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