Efficient one-pot synthesis of 5-perfluoroalkylpyrazoles by cyclization of hydrazone dianions
作者： Thang Ngoc Ngo , Syeda Abida Ejaz , Tran Quang Hung , Tuan Thanh Dang , Jamshed Iqbal
DOI: 10.1039/C5OB01151E
关键词:
摘要: A highly selective and efficient method for the synthesis of 5-trifluoromethylated 5-perfluoroalkylated pyrazoles has been developed which relies on cyclization hydrazine dianions with ethyl perfluorocarboxylates. The prepared were evaluated as potential inhibitors alkaline phosphatases, namely human tissue non-specific phosphatase (h-TNAP) specific intestinal (IAP). Most pyrazole derivatives inhibited h-IAP more markedly than h-TNAP had minor effects nucleotide pyrophosphatase/phosphodiesterases. Therefore, compounds appear h-IAP.
rsc.org
sci-hub.se 参考文章(56)
José Luis Millán, Mammalian Alkaline Phosphatases: From Biology to Applications in Medicine and Biotechnology ,(2006)
Petra Vollmayer, Timothy Clair, James W. Goding, Kimihiko Sano, J��rg Servos, Herbert Zimmermann, Hydrolysis of diadenosine polyphosphates by nucleotide pyrophosphatases/phosphodiesterases FEBS Journal. ,vol. 270, pp. 2971- 2978 ,(2003) , 10.1046/J.1432-1033.2003.03674.X
Robert S. Foote, Charles F. Beam, Charles R. Hauser, A new synthesis of substituted pyrazoles from 1,4-dianions of phenylhydrazones having an α-hydrogen Journal of Heterocyclic Chemistry. ,vol. 7, pp. 589- 592 ,(1970) , 10.1002/JHET.5570070318
Guojing Ji, Xi Wang, Songnan Zhang, Yan Xu, Yuxuan Ye, Ming Li, Yan Zhang, Jianbo Wang, Synthesis of 3-trifluoromethylpyrazoles via trifluoromethylation/cyclization of α,β-alkynic hydrazones using a hypervalent iodine reagent. Chemical Communications. ,vol. 50, pp. 4361- 4363 ,(2014) , 10.1039/C4CC01280A
Yoshihisa Nakada, Thomas D. Aicher, Yvan Le Huerou, Timothy Turner, Scott A. Pratt, Stephen S. Gonzales, Steve A. Boyd, Hiroshi Miki, Toshihiro Yamamoto, Hiroshi Yamaguchi, Koki Kato, Shuji Kitamura, Novel acyl coenzyme A (CoA): diacylglycerol acyltransferase-1 inhibitors: synthesis and biological activities of diacylethylenediamine derivatives. Bioorganic & Medicinal Chemistry. ,vol. 18, pp. 2785- 2795 ,(2010) , 10.1016/J.BMC.2010.01.067
Gisele A. Nishiguchi, Alice L. Rodriguez, John A. Katzenellenbogen, Diaryl-dialkyl-substituted pyrazoles: regioselective synthesis and binding affinity for the estrogen receptor Bioorganic & Medicinal Chemistry Letters. ,vol. 12, pp. 947- 950 ,(2002) , 10.1016/S0960-894X(02)00057-4
K. Muller, C. Faeh, F. Diederich, Fluorine in Pharmaceuticals: Looking Beyond Intuition. Science. ,vol. 317, pp. 1881- 1886 ,(2007) , 10.1126/SCIENCE.1131943
Eduard A Sergienko, José Luis Millán, High-throughput screening of tissue-nonspecific alkaline phosphatase for identification of effectors with diverse modes of action Nature Protocols. ,vol. 5, pp. 1431- 1439 ,(2010) , 10.1038/NPROT.2010.86
Takeru Furuya, Adam S. Kamlet, Tobias Ritter, Catalysis for fluorination and trifluoromethylation Nature. ,vol. 473, pp. 470- 477 ,(2011) , 10.1038/NATURE10108
Noboru Matsumura, Akira Kunugihara, Shigeo Yoneda, 1,4-Dianion of acetophenone n-ethoxycarbonylhydrazone as a synthetic intermediate Tetrahedron Letters. ,vol. 24, pp. 3239- 3242 ,(1983) , 10.1016/S0040-4039(00)88145-9