Core-Scaffold-Inspired Asymmetric Synthesis of Polysubstituted Chiral Hexahydropyridazines that Potently Inhibit Breast Cancer Cell Proliferation by Inducing Apoptosis

Leng Hai-Jun; Peng Fu; Zingales Sarah; Huang Wei; Wang Biao; Zhao Qian; Zhou Rui; He Gu; Peng Cheng; Han Bo

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Core-Scaffold-Inspired Asymmetric Synthesis of Polysubstituted Chiral Hexahydropyridazines that Potently Inhibit Breast Cancer Cell Proliferation by Inducing Apoptosis

机译：核心脚手架启发的不对称合成的多取代手性六氢哒嗪，可通过诱导凋亡有效抑制乳腺癌细胞的增殖。

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The highly enantioselective preparation of pharmacologically interesting hexahydropyridazine derivatives based on a multicomponent cascade reaction is described. This one-pot approach utilizes an organocatalytic Michael reaction followed by intermolecular alpha-amination and intramolecular hemiaminalization to yield a chiral pyridazine backbone with contiguous stereogenic centers and multiple functional groups in good yield and with high stereoselectivity. Compounds synthesized by this method potently inhibited proliferation of MCF-7 breast cancer cells. Mechanistic studies suggest that compound 5c exerts these anticancer effects by inducing apoptosis through extracellular signal related kinase (ERK)- and poly(adenosine diphosphate ribose) polymerase (PARP)-regulated pathways, as well as mitochondrial pathways.

机译：描述了基于多组分级联反应的药理学上令人感兴趣的六氢哒嗪衍生物的高度对映选择性制备。这种一锅法利用有机催化迈克尔反应，随后进行分子间α胺化和分子内半缩醛化，以高收率和高立体选择性产生具有连续立体中心和多个官能团的手性哒嗪骨架。通过这种方法合成的化合物有效抑制MCF-7乳腺癌细胞的增殖。机理研究表明，化合物5c通过细胞外信号相关激酶（ERK）和多聚腺苷二磷酸核糖）聚合酶（PARP）调控的途径以及线粒体途径诱导凋亡，从而发挥这些抗癌作用。

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来源
《Chemistry: A European journal》 |2015年第50期|共9页
作者
Leng Hai-Jun; Peng Fu; Zingales Sarah; Huang Wei; Wang Biao; Zhao Qian; Zhou Rui; He Gu; Peng Cheng; Han Bo;
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正文语种 eng
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antitumor agents; asymmetric catalysis; heterocycles; medicinal chemistry; organocatalysis;

机译：抗肿瘤药;不对称催化;杂环;药物化学;有机催化;

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1. Core-Scaffold-Inspired Asymmetric Synthesis of Polysubstituted Chiral Hexahydropyridazines that Potently Inhibit Breast Cancer Cell Proliferation by Inducing Apoptosis [J] . Leng Hai-Jun, Peng Fu, Zingales Sarah, Chemistry: A European journal . 2015,第50期

机译：核心脚手架启发的不对称合成的多取代手性六氢哒嗪，可通过诱导凋亡有效抑制乳腺癌细胞的增殖。
2. Novel C-4 Heteroaryl 13-cis-Retinamide Mnk/AR Degrading Agents Inhibit Cell Proliferation and Migration and Induce Apoptosis in Human Breast and Prostate Cancer Cells and Suppress Growth of MDA-MB-231 Human Breast and CWR22Rv1 Human Prostate Tumor Xenografts in Mice [J] . Mbatia Hannah W., Ramalingam Senthilmurugan, Ramamurthy Vidya P., Journal of Medicinal Chemistry . 2015,第4期

机译：新型C-4杂芳基13-顺式视黄酰胺Mnk / AR降解剂抑制人乳腺癌和前列腺癌细胞的增殖和迁移并诱导其凋亡，并抑制MDA-MB-231人乳腺癌和CWR22Rv1人前列腺肿瘤异种移植物的生长。
3. Panduratin A Inhibits Cell Proliferation by Inducing G0/G1 Phase Cell Cycle Arrest and Induces Apoptosis in Breast Cancer Cells [J] . Liu Qiuming, Cao Yali, Zhou Ping, Biomolecules & therapeutics . 2018,第3期

机译：Panduratin A通过诱导G0 / G1期细胞周期骤停抑制细胞增殖，并在乳腺癌细胞中诱导细胞凋亡
4. Alternol Inhibits Proliferation and Induces Apoptosis in Human Leukemia HL-60 Cells [C] . Chen Ji, Li Defang, Zhang Bo, 5th International Conference on Bioinformatics and Biomedical Engineering . 2011

机译：交替烷抑制人白血病HL-60细胞的增殖并诱导其凋亡。
5. Cannabinol Inhibits Proliferation and Induces Cell Cycle Arrest and Apoptosis in Glioblastoma, Hepatocellular Carcinoma and Breast Cancer Cells [D] . Zhong, Nuanying. 2020

机译：大麻素抑制胶质母细胞瘤，肝细胞癌和乳腺癌细胞中的增殖和诱导细胞周期停滞和凋亡
6. MART-10 a New Generation of Vitamin D Analog Is More Potent than 1α25-Dihydroxyvitamin D3 in Inhibiting Cell Proliferation and Inducing Apoptosis in ER+ MCF-7 Breast Cancer Cells [O] . Kun-Chun Chiang, Chun-Nan Yeh, Shin-Cheh Chen, 2012

机译：新一代的维生素D类似物MART-10在抑制ER + MCF-7乳腺癌细胞的增殖和诱导细胞凋亡方面比1α25-二羟基维生素D3更有效
7. Novel C-4 Heteroaryl 13-cis-Retinamide Mnk/AR Degrading Agents Inhibit Cell Proliferation and Migration and Induce Apoptosis in Human Breast and Prostate Cancer Cells and Suppress Growth of MDA-MB-231 Human Breast and CWR22Rv1 Human Prostate Tumor Xenografts in Mice [O] . Hannah W. Mbatia, Senthilmurugan Ramalingam, Vidya P. Ramamurthy, 2015

机译：新型C-4杂芳基13-CIS-视黄酰胺MNK / AR降解剂抑制细胞增殖和迁移，诱导人乳腺癌和前列腺癌细胞中的凋亡，抑制MDA-MB-231人乳腺癌和CWR222RV1人前列腺肿瘤异种移植物的凋亡
8. Role of GADD34 (Growth Arrest and DNA Damage-Inducible Protein) in Regulating Apoptosis, Proliferation, and Protein Synthesis in Human Breast Cancer Cells [R] . Welser, D. C. 2005

机译：GaDD34（生长抑制和DNa损伤诱导蛋白）在调节人乳腺癌细胞凋亡，增殖和蛋白质合成中的作用

Core-Scaffold-Inspired Asymmetric Synthesis of Polysubstituted Chiral Hexahydropyridazines that Potently Inhibit Breast Cancer Cell Proliferation by Inducing Apoptosis

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