Synthesis of some novel 4-benzothiazol-2-yl-benzoyl-1H-pyrazoles, and evaluation as antiangiogenic agents

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• 作者：Eman Ali Abd El-Meguid ; Mamdouh Moawad Ali
• 关键词：4 ; Benzothiazol ; 2 ; yl ; benzoyl ; Pyrazole ; MCF ; 7 ; VEGFR
• 刊名：Research on Chemical Intermediates
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：42
• 期：2
• 页码：1521-1536
• 全文大小：521 KB
• 参考文献：1.J. Folkman, Nat. Med. 1, 27 (1995)CrossRef
  2.R.S. Kerbel, Carcinogenesis 21, 505 (2005)CrossRef
  3.A.F. Karamysheva, Biochemistry 73, 751 (2008)
  4.P. Carmeliet, Oncology 69, 4 (2005)CrossRef
  5.N. Ferrara, Oncology 69, 11 (2005)CrossRef
  6.M.R. Raspollini, G. Amunni, A. Villanucci, G. Baroni et al., Int. J. Gynecol. Cancer 14, 815 (2004)CrossRef
  7.R.D.R. Reis, E.C. Azevedo et al., Eur. J. Med. Chem. 46, 1448 (2011)CrossRef
  8.I. Caleta, M. Kralj, M. Marjanovic, B. Bertosa, S. Tomic, G. Pavlovic, K. Pavelic, G.K. Zamola, J. Med. Chem. 52(6), 1744 (2009)CrossRef
  9.J. Shukla, K. Hazra, P. Rashmi, L.V.G. Nargund, Der Chem. Sinici 2(3), 4 (2011)
  10.C. Jimenez, Bioactive Nat. Prod. 25, 811 (2001)
  11.G. Turan-Zitouni, S. Demirayak, A. Ozdemir, Z.A. Kaplancikli, M.T. Yildiz, Eur. J. Med. Chem. 39(3), 267 (2003)CrossRef
  12.Y.J. Cao, J.C. Dreixler, J.J. Couey, K.M. Houamed, Eur. J. Pharmacol. 449, 47 (2002)CrossRef
  13.A.D. Ramirez, S.K.F. Wong, F.S. Menniti, Eur. J. Pharmacol. 475, 29 (2003)CrossRef
  14.S.W. Gangadhar, B.C. Anil, N.B. Vijay, R.S. Giridhar, V.K. Sharad, J. Pharm. Res. 7, 823 (2013)
  15.S. Sohail, R. Naghmana, G.J. Peter, A. Muhammad, H. Rizwan, Eur. J. Med. Chem. 45(4), 1323 (2010)CrossRef
  16.I. Hutchinson, S.A. Jennings, B.R. Vishnuvajjala, A.D. Westwell, M.F.G. Stevenes, J. Med. Chem. 45(3), 744 (2002)CrossRef
  17.C.O. Leong, M. Gaskell, E.A. Martin, R.T. Heydon, P.B. Farmer, M.C. Bibby, P.A. Cooper, J.A. Double, T.D. Bradshaw, M.F.G. Stevens, Br. J. Cancer 88, 470 (2003)CrossRef
  18.B.L. Eric, A.d-B. Monique, R.A.V. Thatyana, O.d-M. Manuel, C.M. Raquel, D.Y. Jwliane, Z.L. Kátia, Eur. J. Med. Chem. 86, 12 (2014)CrossRef
  19.D.F. Shi, T.D. Bradshaw, M.S. Chua, A.D. Westwell, M.F.G. Stevens, Bioorg. Med. Chem. Lett. 11, 1093 (2001)CrossRef
  20.R. Lin, G. Chiu, Y. Yu, P.J. Connolly et al., Bioorg. Med. Chem. Lett. 17(16), 4557 (2007)CrossRef
  21.G. Daidone, B. Maggio, D. Raffa, S. Plescia et al., IL Farmaco 59, 413 (2004)CrossRef
  22.A.A. Bekhit, T.A. El-Azim, Bioorg. Med. Chem. 12(8), 1935 (2004)CrossRef
  23.G. Menozzi, L. Merello, P. Fossa, L. Mosti et al., IL Farmaco 58(9), 795 (2003)CrossRef
  24.J.G. Varnes, D.A. Wacker, I.C. Jacobson, M.L. Quan et al., Bioorg. Med. Chem. Lett. 17, 6481 (2007)CrossRef
  25.T. Tanitame, Y. Oyamada, K. Ofuji, H. Terauchi et al., Bioorg. Med. Chem. Lett. 15(19), 4299 (2005)CrossRef
  26.E.Y. Song, N. Kaur, M.Y. Park, Y. Jin, K. Lee, G. Kim, K.Y. Lee, J.S. Yang, J.H. Shin, K.Y. Nam, K.T. No, G. Han, Eur. J. Med. Chem. 43, 1519 (2008)CrossRef
  27.R.M. Kumbhare, T. Dadmal, U. Kosurkar, V. Sridhar, J.V. Rao, Bioorg. Med. Chem. Lett. 22, 453 (2012)CrossRef
  28.K.M. Amin, M. El-Zahar, M.M. Anwar, M.M. Kamel, M.H. Mohamed, Acta Poloniae Pharm. Drug Res. 66(3), 279 (2009)
  29.S. Shubhanjali, S. Radhey, K.S. Sushant, S. Ajit, K. Pankaj, Asian Pac. J. Trop. Biomed. 2(2), S1040 (2012)CrossRef
  30.I. Perkovic, I. Butula, M. Kralj, I. Martin-Kleiner, J. Balzarini, D. Hadjipavlou-Litina, A.-M. Katson, B. Zorc, Eur. J. Med. Chem. 51, 227 (2012)CrossRef
  31.I.F. Nassar, S.A. El-Assaly, Der Pharm. Chem. 3(1), 229 (2011)
  32.A. Kumar, I. Ahmad, B.S. Chhikara, R. Tiwari, D. Mandal, K. Parang, Bioorg. Med. Chem. Lett. 21, 1342 (2011)CrossRef
  33.B.S. Holla, B. Veerendra, M.K. Shivananda, B. Poojary, Eur. J. Med. Chem. 38, 759 (2003)CrossRef
  34.S. Pautus, S.W. Yee, M. Jayne, M.P. Coogan, C. Simons, Bioorg. Med. Chem. 14, 3643 (2006)CrossRef
  35.P. Stoppie, M. Borgers, P. Borghgraef, L. Dillen et al., J. Pharmacol. Exp. Ther. 293(1), 304 (2000)
  36.S.E.H. Wageeh, M.A. Kamelia, A.E.A. Samy, A.A.M. Eman, Der Pharma Chemica 3(6), 282 (2011)
  37.P. Skehan, R. Storeng, D. Scudiero, A. Monks et al., J. Natl Cancer Inst. 82, 1107 (1990)CrossRef
  38.H.M. Verheul, E.E. Voest, R.O. Schlingemann, J. Pathol. 202, 5 (2004)CrossRef
  39.N. Ferrara, Nat. Rev. Cancer 2, 795 (2002)CrossRef
  40.J. Folkman, Nat. Rev. Drug Discov. 6, 273 (2007)CrossRef
  41.K.J. Gotink, H.M.W. Verheul, Angiogenesis 13, 1 (2010)CrossRef
  
• 作者单位：Eman Ali Abd El-Meguid (1)
  Mamdouh Moawad Ali (2)
  
  1. Division of Pharmaceutical Industries Research, Department of Chemistry of Natural and Microbial Products, National Research Center, Cairo, Egypt
  2. Division of Genetic Engineering and Biotechnology, Department of Biochemistry, National Research Center, Cairo, Egypt
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1568-5675

文摘

Some 4-(1,3-benzothiazol-2-yl)-benzoyl-1H-pyrazole derivatives have been synthesized by reaction of o-aminothiophenol (1) with different electrophilic and nucleophilic reagents. All of the newly synthesized compounds were evaluated for cytotoxicity against breast cancer cell line MCF-7. Two of the compounds were more potent than tamoxifen and three were as potent as tamoxifen. These results were consistent with percentage inhibition of human VEGF compared with control untreated cells.