3-芳基香豆素类化合物抗肿瘤活性研究进展
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摘要
综述了3-芳基香豆素在抗人肺癌细胞株A549活性、抗人鼻咽癌细胞株KB活性、抗人乳腺癌细胞株MCF-7活性、抗人气道平滑肌细胞株KV和抗其它肿瘤活性方面的研究进展;通过Perkin反应、Knoevenagel反应、Suzuki偶联反应及其它反应总结了3-芳基香豆素合成方面的研究进展,以期为该类化合物抗肿瘤活性深入研究和开发提供参考。
The research progress of 3-aryl coumarins in anti-human lung cancer cell line A549, anti-human nasopharyngeal carcinoma cell line KB, anti-human breast cancer cell line MCF-7, anti-human duct smooth muscle cell line KV and other tumor activities were reviewed. The progress in the synthesis of 3-aryl coumarins were summarized by Perkin reaction, Knoevenagel reaction, Suzuki coupling reaction and other reactions, in order to provide a reference for the further study and development of anti-tumor activities of these compounds.
The research progress of 3-aryl coumarins in anti-human lung cancer cell line A549, anti-human nasopharyngeal carcinoma cell line KB, anti-human breast cancer cell line MCF-7, anti-human duct smooth muscle cell line KV and other tumor activities were reviewed. The progress in the synthesis of 3-aryl coumarins were summarized by Perkin reaction, Knoevenagel reaction, Suzuki coupling reaction and other reactions, in order to provide a reference for the further study and development of anti-tumor activities of these compounds.
引文
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[18] Kiran T, Borse D S, Pradeep L. Facile metal-free synthesis of 3-aryl-4-substituted coumarins from o-hydroxycarbonyl compounds[J]. Synthetic Communications, 2010,40(15):2284-2290.
[19] Matos M J,Saleta V R, Fernanda B, et al. Synthesis of 3-ary lcoumarins via Suzuki-cross-coupling reactions of3-chlorocoumarin[J]. Tetrahedron Letters, 2011, 52(11):1225-1227.
[20] Mosrin M, Gabriel M, Tomke B, et al. High temperature zincation of functionalized aromatics and heteroaromatics using TMPZnCl.LiCl and microwave irradistion[J]. Chemical Communications, 2009, 37(8):5615-5617.
[21] Donald C D,Qun L,Dimitry V A, Synthesis of coumarins, 4-Hydroxycoumarins, and 4-hydroxyquinolinones by tellurium-triggered cyclizations[J]. J Org Chem, 2005, 70(12):4682-4686.
[2] Billard C, Menasria F, Quiney C, et al. 4-Arylcoumarin analogues of combretastatins stimulate apoptosis of leukemic cells from chronic lymphocytic leukemia patients[J]. Exp Hematol, 36(12):1625-1633.
[3] Matos M J, Hogger V, Gaspar A, et al. Synthesis and adenosine receptors bingding affinities of a series of 3-arylcoumarins[J]. J Pharm Pharmacol, 2013, 65(11):1590-1597.
[4] Limper C, Wang Y, Ruhl S, et al. Compounds isolated from Paoralea corylifolia seeds inhibit protein kinase activity and induce apoptotic cell death in mammalian cells[J]. J Pharm Pharmacol, 2013, 65(9):1393-1408.
[5] Matos M J, Vilar S, Garcia M V, et al. Insight into the functional and structural properties of 3-arylcoumarin as an interesting scaffold in monoamine oxidase B inhibition[J]. Chem Med Chem, 2014, 9(7):1488-1500.
[6] Ferino G, Cadoni E, Matos M J, et al. MAO inhibition activity of 2-arylbenzofurans versus 3-arylcoumarin:Synthesis, in vitro study, and docking calculations[J]. Chem Med Chem, 2013, 8(6):956-966.
[7] Musa M A, Badisa V L, Latinwo L M, et al. In vitro cytotoxicity of benzopyranone derivatives with basic side chain against human lung cell lines[J]. Anticancer Res, 2010, 30(11):4613-4617.
[8] Musa M A, Badisa V L, Latinwo L M, et al. Cytotoxic activity of new acetoxycoumarin derivatives in cancer cell lines[J].Anticancer Res, 2011, 31(6):2017-2022.
[9] Musa M A, Badisa V L, Latinwo L M, et al. Coumarin-based benzopyranone derivatives induced apoptosis in human lung(A549)cancer cells[J]. Anticancer Res, 2012, 32(10):4271-4276.
[10] Musa M A, Latinwo L M, Virgile C, et al. Synthesis and in vitro evaluation of 3-(4-nitrophenyl)coumarin derivatives in tumor cell lines[J]. Bioorg Chem, 2015, 58(2):96-103.
[11] Musa M A, Joseph M Y, Latinwo L M, et al. In vitro evaluation of 3-arylcoumarin derivatives in A549 cell line[J]. Anticancer Res, 2015, 35(2):653-659.
[12]肖春芬,陈辉芳,何笑薇,等.新型3-芳基香豆素类化合物的合成及其抗肿瘤活性[J].合成化学,2015, 23(5):376-381.
[13] Xiao C F, Tao L Y, Sun H Y, et al. Design, synthesis and antitumor activity of a series of novel coumarin-stilbnes hybrids, the3-arylcoumarins[J]. Chinese Chemical Letters, 2010(21):1295-1298.
[14] Musa M A, Latinwo LM, Joseph M Y, et al. Identification of 7,8-diacetoxy-3-arylcoumarin derivative as a selective cytotoxic and apoptosis-inducing agent in a human prostate cancer cell line[J]. Anticancer Research, 2017, 37(11):6005-6014.
[15] Ranjith C, Nidhin P, Vijayan K K. One-pot greener protocol for the synthesis of substituted coumarins[J]. Asian Journal of Chemistry, 2011, 23(1):235-238.
[16] Matos M J, Dolores V, Elias Q, et al. A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors[J].Bioorganic&Medicinal Chemistry Letters, 2009, 19(12):3268-3270.
[17] Luciana M K, Anderson A M, Alexandre K, et al. Inhibitition of horseradish peroxidase catalytic activity by new3-phenylcoumarin derivatives:Synthesis and structure-activity relationships[J]. Bioorganic&Medicinal Chemistry, 2007,15(3):1516-1524.
[18] Kiran T, Borse D S, Pradeep L. Facile metal-free synthesis of 3-aryl-4-substituted coumarins from o-hydroxycarbonyl compounds[J]. Synthetic Communications, 2010,40(15):2284-2290.
[19] Matos M J,Saleta V R, Fernanda B, et al. Synthesis of 3-ary lcoumarins via Suzuki-cross-coupling reactions of3-chlorocoumarin[J]. Tetrahedron Letters, 2011, 52(11):1225-1227.
[20] Mosrin M, Gabriel M, Tomke B, et al. High temperature zincation of functionalized aromatics and heteroaromatics using TMPZnCl.LiCl and microwave irradistion[J]. Chemical Communications, 2009, 37(8):5615-5617.
[21] Donald C D,Qun L,Dimitry V A, Synthesis of coumarins, 4-Hydroxycoumarins, and 4-hydroxyquinolinones by tellurium-triggered cyclizations[J]. J Org Chem, 2005, 70(12):4682-4686.