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Synthesis of {4-[1-(2-Fluorophenyl)-1H-thieno[3,2-c]pyrazol-3-yl]piperazin-1-yl}(1-methyl-1H-imidazol-4-yl)methanone

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Abstract

An efficient synthesis of {4-[1-(2-fluorophenyl)-1H-thieno[3,2-c]pyrazol-3-yl]piperazin-1-yl}(1-methyl-1H-imidazol-4-yl)methanone starting from 3-bromothiophene-2-carboxylic acid and 2-fluoro­phenylhydrazine is described. The structures of the final and intermediate products have been determined by spectral analysis.

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REFERENCES

  1. Singh, K., Siddiqui, H.H., Shakya, P., Bagga, P., Kumar, A., Khalid, M., Arif, M., and Alok, S., Int. J. Pharm. Sci. Res., 2015, vol. 6, p. 4145. https://doi.org/10.13040/IJPSR.0975-8232.6(10).4145-58

    Article  CAS  Google Scholar 

  2. Kossakowski, J., Krawiecka, M., and Kuran, B., Molecules, 2006, vol. 11, p. 615. https://doi.org/10.3390/11080615

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Malviya, M., Sunil Kumar, Y.C., Mythri, R.B., Venkateshappa, C., Subhash, M.N., and Rangappa, K.S., Bioorg. Med. Chem., 2009, vol. 17, p. 5526. https://doi.org/10.1016/j.bmc.2009.06.032

    Article  CAS  PubMed  Google Scholar 

  4. Ryckebusch, A., Debreu-Fontaine, M.-A., Mouray, E., Grellier, P., Sergheraert, C., and Melnyk, P., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 297. https://doi.org/10.1016/j.bmcl.2004.10.080

    Article  CAS  PubMed  Google Scholar 

  5. Kimura, M., Masuda, T., Yamada, K., Kawakatsu, N., Kubota, N., Mitani, M., Kishii, K., Inazu, M., Kiuchi, Y., Oguchi, K., Namiki, T., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 4287. https://doi.org/10.1016/j.bmcl.2004.05.091

    Article  CAS  PubMed  Google Scholar 

  6. Acri, J.B., Siedleck, B.K., and Witkin, J.M., J. Pharma­col. Exp. Ther., 1996, vol. 277, p. 198. PMID: 8613919

    CAS  PubMed  Google Scholar 

  7. Cecchetti, V., Schiaffella, F., Tabarrini, O., and Fravo­lini, A., Bioorg. Med. Chem. Lett., 2000, vol. 10, p. 465. https://doi.org/10.1016/S0960-894X(00)00016-0

    Article  CAS  PubMed  Google Scholar 

  8. Rondu, F., Bihan, G.L., Wang, X., Lamouri, A., Touboul, E., Dive, G., Bellahsene, T., Pfeiffer, B., Renard, P., Lemaitre, B.G., Manechez, D., Penicaud, L., Ktorza, A., and Godfroid, J.J., J. Med. Chem., 1997, vol. 40, p. 3793. https://doi.org/10.1021/jm9608624

    Article  CAS  PubMed  Google Scholar 

  9. Dauzonne, D., Gillardin, J.M., Lepage, F., Pointet, R., Risse, S., Lamotte, G., and Demerseman, P., Eur. J. Med. Chem., 1995, vol. 30, p. 53. https://doi.org/10.1016/0223-5234(96)88209-2

    Article  CAS  Google Scholar 

  10. Sasse, B.C., Mach, U.R., Leppaenen, J., Calmels, T., and Stark, H., Bioorg. Med. Chem., 2007, vol. 15, p. 7258. https://doi.org/10.1016/j.bmc.2007.08.034

    Article  CAS  PubMed  Google Scholar 

  11. Ananda Kumar, C.S., Benaka Prasad, S.B., Vinaya, K., Chandrappa, S., Thimmegowda, N.R., Sunil Kumar, Y.C., Swarup, S., and Rangappa, K.S., Eur. J. Med. Chem., 2009, vol. 44, p. 1223. https://doi.org/10.1016/j.ejmech.2008.09.025

    Article  CAS  PubMed  Google Scholar 

  12. Youssef, K.M., Al-Omar, M.A., El-Subbagh, H.I., Abou-zeid, L.A., Abdel-Gader, A.-G.M., Haress, N.G., and Al-Tuwaijri, A.S., Med. Chem. Res., 2011, vol. 20, p. 898. https://doi.org/10.1007/s00044-010-9411-5

    Article  CAS  Google Scholar 

  13. Gan, L.L., Fang, B., and Zhou, C.H., Bull. Korean Chem. Soc., 2010, vol. 31, p. 3684. https://doi.org/10.5012/bkcs.2010.31.12.3684

    Article  CAS  Google Scholar 

  14. Bali, A., Sharma, K., Bhalla, A., Bala, S., Reddy, D., Singh, A., and Kumar, A., Eur. J. Chem., 2010, vol. 45, p. 2656. https://doi.org/10.1016/j.ejmech.2010.02.008

    Article  CAS  Google Scholar 

  15. Sapa, J., Filipek, B., and Nowiński, L., Pharmacol. Rep., 2011, vol. 63, p. 455. https://doi.org/10.1016/S1734-1140(11)70512-6

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Jawaharlal Nehru Technological University Hyderabad, Kukatpally, 500085, Hyderabad, India

    R. D. Thoomuganti, T. C. Maringanti & K. K. Ananthoju

  2. Sreenidhi Institute of Science and Technology (Autonomous), Ghatkesar, 501301, Hyderabad, India

    L. Eppakayala

Authors
  1. R. D. Thoomuganti
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  2. T. C. Maringanti
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  3. K. K. Ananthoju
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  4. L. Eppakayala
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Correspondence to L. Eppakayala.

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Thoomuganti, R.D., Maringanti, T.C., Ananthoju, K.K. et al. Synthesis of {4-[1-(2-Fluorophenyl)-1H-thieno[3,2-c]pyrazol-3-yl]piperazin-1-yl}(1-methyl-1H-imidazol-4-yl)methanone. Russ J Org Chem 59, 548–551 (2023). https://doi.org/10.1134/S1070428023030259

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