将2-巯基-5-取代基-1,3,4-噻二唑经与β-氯苯丙酮取代、盐酸羟胺肟化和氯甲基(口恶)二唑醚化,合成了6种3-(5-取代基-1,3,4-噻二唑-2-硫代基)-1-苯基丙酮-O-(5-苯基-1,3,4-(口恶)二唑-2-甲基)肟醚化合物(4a~4f),用1 H NMR、IR、MS和元素分析表征了其结构.用MTT法测试了6种目标化合物对人黑色素瘤细胞株B16、人白血病细胞株HL60和人肝癌细胞株SMMC-7721的体外细胞毒活性.测试结果表明,部分化合物对3种癌细胞具有潜在的体外生长抑制活性.
参考文献
[1] | HU Guoqiang,YAO Sumei,LI Sheng,et al.Synthesis and Antibacterial Activity of s-Triazole Salicylidene-amino Schiffbases Containing Oxadiazole-Substituted Oxime-ether[J].Chinese J Org Chem,2007,27 (5):636-639 (in Chinese).胡国强,姚素梅,李省,等.含(口恶)二唑肟醚取代的均三唑水杨醛席夫碱的合成及抗菌活性[J].有机化学,2007,27 (5):636-639. |
[2] | Ijichi K,Fujiwara M,Nagano H,et al.Anti-HIV-1.Activity of Thiadiazole Derivatives:Structure-activity Relationship,Reverse Transcriptase Inhibition,and Lipophilicity[J].Antiviral Res,1996,31 (1):87-89. |
[3] | Noolvia M N,Patela H M,Singha N,et al.Synthesis and Anticancer Evaluation of Novel 2-Cyclopropylimidazo[2,1-b][1,3,4]-thiadiazole Derivative[J].Eur J Med Chem,2011,46(9):4411-4418. |
[4] | Elson P J,Kvols L K,Vogl S E,et al.Phase Ⅱ Trials of 5-Day Vinblastine Infusion (NSC 49842),L-Alanosine (NSC 153353),Acivicin(NSC 163501),and Aminothiadiazole(NSC 4728) in Patients with Recurrent or Metastatic Renal Cell Carcinoma[J].Invest New Drugs,1988,6(2):97-103. |
[5] | Locker G Y,Kilton L,Khandekar J D,et al.High-dose Aminothiadiazole in Advanced Colorectal Cancer.An Illinois Cancer Center Phase Ⅱ Trial[J].Invest New Drugs,1994,12(4):299-301. |
[6] | Asbury R F,Wilson J,Blessing J A,et al.Aminothiadiazole (NSC #4728) in Patients with Advanced Ovarian Carcinoma.A Phase Ⅱ Study of the Gynecologic Oncology Group[J].Am J Clin Oncol,1986,9(4):334-336. |
[7] | Locker G Y,Khandekar J,Krauss S,et al.Phase Ⅱ Trial of Aminothiadiazole in Previously Treated and Untreated Patients with Advanced Colorectal Carcinoma:an Illinois Cancer Council Trial[J].Cancer Treat Rep,1987,71(6):649-650. |
[8] | SONG Baoan,CHEN Caijun,YANG Song,et al.Synthesis,Structure and Antitumor Activity of 2-Alkylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole Compounds[J].Acta Chim Sin,2005,63 (18):1720-1726 (in Chinese).宋宝安,陈才俊,杨松,等.2-取代硫醚-5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑类化合物的合成、结构与体外抗癌活性[J].化学学报,2005,63(18):1720-1726. |
[9] | LI Sheng,HU Guoqiang,XIE Songqiang,et al.Syntheses and Antibacterial Activities of s-Triazole Salicylaldimine Schiffbases Containing Oxadiazole Oxime-ether Subunits[J].Chinese J Appl Chem,2007,24(3):310-313 (in Chinese).李省,胡国强,谢松强,等.(口恶)二唑肟醚取代的均三唑水杨醛席夫碱衍生物的合成及抗菌活性[J].应用化学,2007,24(3):310-313. |
[10] | QIU Zaozao,ZHANG Huanhuan,HUI Xinping,et al.Synthesis of 3-Thioheterocycloyl-1,3,4,5-tetrahydro-2-oxo-1H-benazepine[J].Chinese J Org Chem,2007,27 (5):607-618 (in Chinese).邱早早,张欢欢,惠新平,等.3-杂环基硫取代-1,3,4,5-四氢-2-氧代-苯并氮杂衍生物的合成[J].有机化学,2007,27(5):607-618. |
[11] | Elwahy A H,Abbas A A.Synthesis of New Benzo-substituted Macrocyclic Ligands Containing Pyridine or Triazole as Subcyclic Units[J].Tetrahedron,2000,56 (6):885-895. |
[12] | HU Guoqiang,YAN Dalian,HOU Lili,et al.An Improved Synthetic Method for 2-Aryl-5-chloromethyl-1,3,4-oxadiazoles[J].Chem Reag,2004,26(2):99-100(in Chinese).胡国强,闫大连,侯莉莉,等.2-芳基-5-氯甲基-1,3,4-(口恶)二唑的改进合成方法[J].化学试剂,2004,26(2):99-100. |
[13] | Karakurt A,Dalkara S,Ozalp M,et al.Synthesis of Some 1-(2-Naphthyl)-2-(imidazole-1-yl) ethanone Oxime and Oxime Ether Derivatives and Their Anticonvulsant and Antimicrobial Activities[J].Eur J Med Chem,2001,36 (5):421-433. |
[14] | LIN Xianjie,XU Weiren,WANG Jianwu,et al.Experimental and Theoretical Studies on the Structures,IR Spectrum and Inter-molecular Interaction of p-Methoxybenzaldoxime[J].Chem J Chinese Univ,2006,27 (5):897-900 (in Chinese).林宪杰,徐为人,王建武,等.对甲氧基苯甲醛肟晶体结构、红外光谱及分子间相互作用的实验与理论研究[J].高等学校化学学报,2006,27 (5):897-900. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%