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The synthesis and photoactivated cytotoxicity of novel 5-phenyl-3- (2, 2':5', 2''-terthien-5-yl)-4, 5-dihydro-1H-pyrazolines

Zhi-Gang Luo ,  Zheng-Yong Liu ,  Zhuo-Hong Yang

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Citation:  Zhi-Gang Luo, Zheng-Yong Liu, Zhuo-Hong Yang. The synthesis and photoactivated cytotoxicity of novel 5-phenyl-3- (2, 2':5', 2''-terthien-5-yl)-4, 5-dihydro-1H-pyrazolines[J]. Chinese Chemical Letters, 2014, 25(2): 333-336. shu

The synthesis and photoactivated cytotoxicity of novel 5-phenyl-3- (2, 2':5', 2''-terthien-5-yl)-4, 5-dihydro-1H-pyrazolines

    • 通讯作者: Zhuo-Hong Yang,
  • 基金项目:

    The authors are thankful for partial financial support by Guangdong Natural Science Foundation (No. 7006672)  (No. 7006672)

    South China Agricultural University Foundation (Nos. 2009B010100001, 2009C020604002). (Nos. 2009B010100001, 2009C020604002)

摘要: A series of novel 5-phenyl-3-(2,2':5',2''-terthien-5-yl)-4,5-dihydro-1H-pyrazolines were synthesized in this report. Their photoactivated cytotoxicities on the Spodoptera litura (SL) cell line were evaluated using the MTT method. It was noticed that the inhibitory activities of all the conjugates was enhanced when irradiated with UV-A light. Compounds 4, 6 and 8 were found to be most effective with inhibition rates of 88.1%, 88.0%, and 90.5%, respectively. For compound 5, the inhibition rate value was only slightly enhanced under the irradiation treatment (78.3%) compared to the dark treatment (74.8%). The relationship analysis between structure and activity showed that the middle thiophene ring played an important role on the inhibitory activities. It was shown that these compounds could be the potential candidates for new photoactivated pesticides.

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    1. [1] R.S. Joshi, P.G. Mandhane, S.D. Diwakar, S.K. Dabhade, C.H. Gill, Synthesis, analgesic and anti-inflammatory activities of some novel pyrazolines derivatives, Bioorg. Med. Chem. Lett. 20 (2010) 3721-3725.[1] R.S. Joshi, P.G. Mandhane, S.D. Diwakar, S.K. Dabhade, C.H. Gill, Synthesis, analgesic and anti-inflammatory activities of some novel pyrazolines derivatives, Bioorg. Med. Chem. Lett. 20 (2010) 3721-3725.

    2. [2] R. Bashir, S. Ovais, S. Yaseen, et al., Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents, Bioorg. Med. Chem. Lett. 21 (2011) 4301-4305.[2] R. Bashir, S. Ovais, S. Yaseen, et al., Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents, Bioorg. Med. Chem. Lett. 21 (2011) 4301-4305.

    3. [3] S.L. Zhu, Y. Wu, C.J. Liu, et al., Design and stereoselective synthesis of novel isosteviol-fused pyrazolines and pyrazoles as potential anticancer agents, Eur. J. Med. Chem. 65 (2013) 70-82.[3] S.L. Zhu, Y. Wu, C.J. Liu, et al., Design and stereoselective synthesis of novel isosteviol-fused pyrazolines and pyrazoles as potential anticancer agents, Eur. J. Med. Chem. 65 (2013) 70-82.

    4. [4] D.Q. Zhang, G.F. Gao, Z.J. Fan, et al., Synthesis and anti-TMV activity of novel N-(3- alkyl-1H-pyrazol-4-yl)-3-alkyl-4-substituted-1H-pyrazole-5-carboxamides, Chin. Chem. Lett. 23 (2012) 669-672.[4] D.Q. Zhang, G.F. Gao, Z.J. Fan, et al., Synthesis and anti-TMV activity of novel N-(3- alkyl-1H-pyrazol-4-yl)-3-alkyl-4-substituted-1H-pyrazole-5-carboxamides, Chin. Chem. Lett. 23 (2012) 669-672.

    5. [5] P. Singh, J.S. Negi, K. Singh, et al., Synthesis and structure dependent photophysical properties of novel 2-pyrazolines, Synth. Metals 162 (2012) 1977-1980.[5] P. Singh, J.S. Negi, K. Singh, et al., Synthesis and structure dependent photophysical properties of novel 2-pyrazolines, Synth. Metals 162 (2012) 1977-1980.

    6. [6] S. Khode, V. Maddi, P. Aragade, et al., Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents, Eur. J. Med. Chem. 44 (2009) 1682- 1688.[6] S. Khode, V. Maddi, P. Aragade, et al., Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents, Eur. J. Med. Chem. 44 (2009) 1682- 1688.

    7. [7] A.M.A. Hameed, Synthesis of new 1,2,4-oxadiazolidin-5-ylthiophenes and thienopyrimidine derivatives by aza-Wittig reaction using a thienyl carbodiimide, Chin. Chem. Lett. 23 (2012) 411-414.[7] A.M.A. Hameed, Synthesis of new 1,2,4-oxadiazolidin-5-ylthiophenes and thienopyrimidine derivatives by aza-Wittig reaction using a thienyl carbodiimide, Chin. Chem. Lett. 23 (2012) 411-414.

    8. [8] I. Opsenica, V. Filipovic, J.E. Nuss, et al., The synthesis of 2,5-bis(4-amidinophenyl) thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease, Eur. J. Med. Chem. 53 (2012) 374-379.[8] I. Opsenica, V. Filipovic, J.E. Nuss, et al., The synthesis of 2,5-bis(4-amidinophenyl) thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease, Eur. J. Med. Chem. 53 (2012) 374-379.

    9. [9] A.M. Isloor, B. Kalluraya, K.S. Pai, Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives, Eur. J. Med. Chem. 45 (2010) 825-830.[9] A.M. Isloor, B. Kalluraya, K.S. Pai, Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives, Eur. J. Med. Chem. 45 (2010) 825-830.

    10. [10] D.J. Ye, Y. Zhang, F. Wang, et al., Novel thiophene derivatives as PTP1B inhibitors with selectivity and cellular activity, Bioorg. Med. Chem. 18 (2010) 1773-1782.[10] D.J. Ye, Y. Zhang, F. Wang, et al., Novel thiophene derivatives as PTP1B inhibitors with selectivity and cellular activity, Bioorg. Med. Chem. 18 (2010) 1773-1782.

    11. [11] M. Nivsarkar, B. Cherian, H. Padh, Alpha-terthienyl: a plant-derived new generation insecticide, Curr. Sci. 81 (2001) 667-672.[11] M. Nivsarkar, B. Cherian, H. Padh, Alpha-terthienyl: a plant-derived new generation insecticide, Curr. Sci. 81 (2001) 667-672.

    12. [12] C.V. Pham, A. Burkhardt, R. Shabanas, A convent synthesis of 2,5-thienylene oligomers: some of their spectroscopic and electrochemical properties, Phosphorus Sulfur Silicon Relat. Elem. 46 (1989) 153-168.[12] C.V. Pham, A. Burkhardt, R. Shabanas, A convent synthesis of 2,5-thienylene oligomers: some of their spectroscopic and electrochemical properties, Phosphorus Sulfur Silicon Relat. Elem. 46 (1989) 153-168.

    13. [13] Y. Wei, Y. Yang, J.M. Ye, Synthesis and electronic properties of aldehyde endcapped thiophene oligomers and other a,v-substituted sexithiophenes, Chem. Mater. 8 (1996) 2659-2666.[13] Y. Wei, Y. Yang, J.M. Ye, Synthesis and electronic properties of aldehyde endcapped thiophene oligomers and other a,v-substituted sexithiophenes, Chem. Mater. 8 (1996) 2659-2666.

    14. [14] J. Rojas, J.N. Dominguez, J.E. Charris, Synthesis and inhibitory activity of dimethylamine- chalcone derivatives on the induction of nitric oxide synthase, Eur. J. Med. Chem. 37 (2002) 699-705.[14] J. Rojas, J.N. Dominguez, J.E. Charris, Synthesis and inhibitory activity of dimethylamine- chalcone derivatives on the induction of nitric oxide synthase, Eur. J. Med. Chem. 37 (2002) 699-705.

    15. [15] M.A. Ali, M.S. Yar, Antitubercular activity of novel substituted 4,5-dihydro-1H-1- pyrazolylmethanethiones, J. Enzyme Inhib. Med. Chem. 22 (2007) 183-189.[15] M.A. Ali, M.S. Yar, Antitubercular activity of novel substituted 4,5-dihydro-1H-1- pyrazolylmethanethiones, J. Enzyme Inhib. Med. Chem. 22 (2007) 183-189.

    16. [16] P.L. Zhao, F. Wang, M.Z. Zhang, et al., Synthesis, fungicidal, and insecticidal activities of β-methoxyacrylate-containing N-acetyl pyrazoline derivatives, J. Agric. Food Chem. 56 (2008) 10767-10773.[16] P.L. Zhao, F. Wang, M.Z. Zhang, et al., Synthesis, fungicidal, and insecticidal activities of β-methoxyacrylate-containing N-acetyl pyrazoline derivatives, J. Agric. Food Chem. 56 (2008) 10767-10773.

    17. [17] T.Mosmann, Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J. Immunol. Methods 65 (1983) 55-63.c[17] T.Mosmann, Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J. Immunol. Methods 65 (1983) 55-63.c

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  • 收稿日期:  2013-07-16
  • 网络出版日期:  2013-10-23
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