用六氯乙烷、三苯基膦和5-氨基吡唑衍生物一锅法合成关键中间体膦亚胺.再利用串联aza-Wittig反应,加入对氯苯基异氰酸酯,进一步和烷基胺或取代酚反应合成了11个未见文献报道的6-烷氨(氧)基-3-甲硫基-1H-吡唑并[3,4-d]嘧啶4(5H)-酮衍生物.通过1 H NMR、EI-MS、IR和元素分析等方法对所合成的化合物进行了结构表征,并测试了它们的杀菌和除草活性.测试结果表明,部分化合物对稗草(barnyard grass)和油菜(Rape)均表现出了较好的抑制活性.
参考文献
| [1] | Hassan G S,Kadry H H,Abou-Seri S M,et al.Synthesis and in vitro Cytotoxic Activity of Novel Pyrazolo【3,4-d】pyrimidines and Related Pyrazole Hydrazones toward Breast Adenocarcinoma MCF-7 Cell Line[J].Bioorg Med Chem,2011,19:6808-6817.,2011. |
| [2] | Gilbert A M,Nowak P,Brooijmans N,et al.Novel Purine and Pyrazolo【3,4-d】pyrimidine Inhibitors of PI3 Kinase-αt:Hit to Lead Studies[J].Bioorg Med Chem Lett,2010,20:636-639.,2010. |
| [3] | Baraldi P G,Cacciari B,Spalluto G,et al.Design,Synthesis,and Biological Evaluation of a Second Generation of Pyrazolo【4,3-e】-1,2,4-triazolo【1,5-c】pyrimidines as Potent and Selective A2A Adenosine Antagonists[J].J Med Chem,1998,41(12):2126-2133.,1998. |
| [4] | Baraldi P G,Cacciari B,Spalluto G,et al.Pyrazolo【4,3-e】-1,2,4-triazolo【1,5-c】pyrimidine Derivatives:Potent and Selective A2A Adenosine Antagonists[J].J Med Chem,1996,39 (5):1164-1171.,1996. |
| [5] | Chiara B V,Giuseppe F,Maurizio M,et al.Development of New Fungicides Against Magnaporthe Grisea:Synthesis and Biological Activity of Pyrazolo【3,4-d】【1,3】thiazine,Pyrazolo【1,5-c】【1,3,5】thiadiazine,and Pyrazolo【3,4-d】pyrimidine Derivatives[J].J Agric Food Chem,2002,50:4839-4845.,2002. |
| [6] | Gatta F,Giudice M R,Borioni A,et al.Synthesis of Imidazo【1,2-c】pyrasolo【4,3-e】pyrimidines,Pyrazolo【4,3-e】1,2,4-triazolo【1,5-c】pyrimidines and 1,2,4-Triazolo【5,1-i】purines:New Potent Adenosine Receptor Antagonists[J].Eur J Med Chem,1993,28(7/8):569-576.,1993. |
| [7] | Gillespie R J,Cliffe I A,Dawson C E,et al.Antagonists of the Adenosine A2A Receptor.Part 3:Design and Synthesis of Pyrazolo【3,4-d】pyrimidines,Pyrrolo【2,3-d】pyrimidines and 6-Arylpurines[J].Bioorg Meal Chem Lett,2008,18:2924-2929.,2008. |
| [8] | Omar M,Mohamed L T,Hassan B L,et al.A New Approach for Preparing a Controlled Release Ketoprofen Tablets by Using Beeswax[J].Il Farmaco,2005,57:27-32.,2005. |
| [9] | Quintela J M,Peinador C,Moreira M J,et al.Pyrazolopyrimidines:Synthesis,Effect on Histamine Release from Rat Peritoneal Mast Cells and Cytotoxic Activity[J].Eur J Med Chem,2001,36:321-332.,2001. |
| [10] | Chauhan M,Kumar R.Medicinal Attributes of Pyrazolo【3,4-d】pyrimidines:A Reviews[J].Bioorg Med Chem,2013,21:5657-5668.,2013. |
| [11] | Wang H Q,Liu Z J,Yang L M,et al.A New Regioselective Synthesis and Bioactivity of 1 H-pyrazolo【3,4-d】pyrimidin-4 (5H)-one Derivatives[J].J Heterocycl Chem,2004,41:393-397.,2004. |
| [12] | Wang H Q,Ding M W,Liu Z J.Synthesis of Properties of Novel Pyrazolopyrimidine Derivatives Containing Sulfur Atom[J].Heteroatom Chem,2004,15:333-338.,2004. |
| [13] | 刘惠,王宏青,刘钊杰.吡唑并嘧啶-4-酮衍生物的合成与除草活性[J].应用化学,2005(03):286-290. |
| [14] | 刘惠,王宏青,刘钊杰.吡唑并嘧啶-4-酮衍生物的合成与除草活性[J].应用化学,2005(03):286-290. |
| [15] | WANG Hongqing.Studies on Synthesis and Properties of Novel Biological Activity Pyrazole and Pyrazolopyrimidine Derivatives[D].Wuhan:Huazhong Normal University,2004(in Chinese).,2004. |
| [16] | 王宏清.具有生物活性的吡唑及吡唑并嘧啶衍生物的合成与生物活性[D].武汉:华中师范大学,2004.,2004. |
| [17] | Ding M W,Chen Y F,Huang L Y.Synthesis and Fungicidal of Derivatives of 2-Alkylthio-3-amino-4H-imidazol-4-one[J].Phosphorus,Sulfur Silicon,2004,179:2287-2296.,2004. |
| [18] | Chen T,Shen P,Li Y J,et al.Synthesis and Herbicidal Activity of O,O-Dialkyl Phenoxyacetoxyalkylphosphonates Containing Fluorine[J].J Fluorine Chem,2006,127:291-295.,2006. |
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%