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Efficient synthesis, structure elucidation, and anti-parasitic activities of novel quinolinyl β–enaminones

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Abstract

In the present study, a novel series of side chain-modified quinoline β-enaminones were synthesized in good-to-excellent yields. The structures of all the synthesized compounds have been established with the help of spectral and analytical data and also by X-ray crystallography. All the compounds were screened for their potential in vitro anti-malarial activity against chloroquine resistant strain K1 and chloroquine sensitive strain 3D7. The compounds were also evaluated for their in vitro microfilaricidal and adulticidal effect against B. malayi microfilariae and adult worms using ivermectin as positive control. The cytotoxicity of the compounds was checked against Vero cell line and all the compounds were found to be non-toxic. The compounds showed low antimalarial activities against both the plasmodial strains compared to the standard drug chloroquine. However, four of the evaluated compounds have shown significant in vitro adulticidal activity and their percentage inhibition were found to be 68, 55, 64, and 66, respectively. Two of these were selected for further preliminary in vivo activity studies.

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References

  1. Kaping S, Kalita U, Sunn M, Singha LI, Vishwakarma JN (2016) Monatsh Chem 147:1257

    Article  CAS  Google Scholar 

  2. Kalita U, Kaping S, Nongkynrih R, Singha LI, Vishwakarma JN (2015) Med Chem Res 24:2742

    Article  CAS  Google Scholar 

  3. Devi AS, Kaping S, Vishwakarma JN (2015) Mol Divers 19:759

    Article  CAS  Google Scholar 

  4. Pérez BC, Teixeira C, Albuquerque IS, Gut J, Rosenthal PJ, Gomes JR, Prudêncio M, Gomes P (2013) J Med Chem 56:556

    Article  Google Scholar 

  5. Mukherjee S, Joardar N, Mondal S, Schiefer A, Hoerauf A, Pfarr K, Babu SP (2018) Sci Rep 8:1

    Google Scholar 

  6. Upadhyay A, Kushwaha P, Gupta S, Dodda RP, Ramalingam K, Kant R, Goyal N, Sashidhara KV (2018) Eur J Med Chem 154:172

    Article  CAS  Google Scholar 

  7. Gryzło B, Kulig K (2014) Mini Rev Med Chem 14:332

    Article  Google Scholar 

  8. Svete J (2004) Monatsh Chem 135:629

    Article  CAS  Google Scholar 

  9. Puebla P, Honores Z, Medarde M, Morina L, Caballero E, Feliciano AS (1999) Tetrahedron 55:7915

    Article  CAS  Google Scholar 

  10. Mosto L, Menozzi G, Schenone P (1983) J Heterocycl Chem 20:649

    Article  Google Scholar 

  11. Abdelkhalika MM, Eltoukhya AF, Agamya SM, Elnagdi MH (2004) J Heterocycl Chem 41:431

    Article  Google Scholar 

  12. Al-Omran F, El-Khair A (2005) J Heterocycl Chem 42:307

    Article  CAS  Google Scholar 

  13. Chanda K, Dutta MC, Karim E, Vishwakarma JN (2004) J Heterocycl Chem 41:627

    Article  CAS  Google Scholar 

  14. Kalita U, Kaping S, Vishwakarma JN (2016) Mol Divers 20:581

    Article  CAS  Google Scholar 

  15. Kalita U, Kaping S, Nongkynrih R, Boiss I, Singha LI, Vishwakarma JN (2017) Monatsh Chem 148:2155

    Article  CAS  Google Scholar 

  16. Dutta MC, Chanda K, Vishwakarma JN (2005) J Heterocycl Chem 42:121

    Article  CAS  Google Scholar 

  17. Vishwakarma JN, Dutta MC, Chanda K, Das B, Laskar MA, Nongkhlaw RL (2009) ARKIVOC xiii:131

    Article  Google Scholar 

  18. Foster JE, Nicholson JM, Butcher R, Stables JP, Edafiogho IO, Goodwin AM, Henson MC, Smith CA, Scott KR (1999) Bioorg Med Chem 7:2415

    Article  CAS  Google Scholar 

  19. Michael JP, de Koning CB, Hosken GD, Stanbury TV (2001) Tetrahedron 57:9635

    Article  CAS  Google Scholar 

  20. Boger DL, Ishizaki T, Wysocki RJ Jr, Munk SA, Kitos PA, Suntornwat O (1989) J Am Chem Soc 111:6461

    Article  CAS  Google Scholar 

  21. Ferraz H, Goncalo ER (2007) Quin Nova 30:957

    Article  CAS  Google Scholar 

  22. Elassar AZ, El-Khair AA (2003) Tetrahedron 59:8463

    Article  CAS  Google Scholar 

  23. Kalita U, Kaping S, Nongkynrih R, Sunn M, Boiss I, Singha LI, Vishwakarma JN (2015) Med Chem Res 24:32

    Article  CAS  Google Scholar 

  24. World Health Organization (2019) WHO World Malaria Report 2019. https://www.who.int/publications/i/item/9789241565721

  25. Kremsner PG, Krishna S (2004) Lancet 364:285

    Article  CAS  Google Scholar 

  26. Klein EY (2013) Int J Antimicrob Agents 41:311

    Article  CAS  Google Scholar 

  27. Rosenthal PJ (2013) Mol Microbiol 89:1025

    Article  CAS  Google Scholar 

  28. Wongsrichanalai C, Sibley CH (2013) Clin Microbiol Infect 19:908

    Article  CAS  Google Scholar 

  29. Duru V, Witkowski B, Ménard D (2016) Am J Trop Med Hyg 95:1228

    Article  CAS  Google Scholar 

  30. World Health Organization (2017) Validation of elimination of lymphatic filariasis as a public health problem: WHO Geneva. https://www.who.int/lymphatic_filariasis/resources/9789241511957/en/

  31. Lustigman S, McCarter JP (2007) PLoS Negl Trop Dis 1:e76

    Article  Google Scholar 

  32. Schwab AE, Boakye DA, Kyelem D, Prichard RK (2005) Am J Trop Med Hyg 73:234

    Article  CAS  Google Scholar 

  33. Kalyanasundaram A, Bastille MO, Lukashow-Moore SP, Kendall RJ (2020) J Parasitol 106:623

    Article  Google Scholar 

  34. Turner HC, Bettis AA, Chu BK, McFarland DA, Hooper PJ, Mante SD, Fitzpatrick C, Bradley MH (2017) Clin Infect Dis 64:728

    PubMed  Google Scholar 

  35. Sheldrick GM (2015) Acta Cryst 71:3

    Google Scholar 

  36. Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JA, Puschmann H (2009) J Appl Cryst 42:339

    Article  CAS  Google Scholar 

  37. Trager W, Jensen JB (1976) Science 193:673

    Article  CAS  Google Scholar 

  38. Lambros C, Vanderberg JP (1979) J Parasitol 418

  39. Johnson JD, Dennull RA, Gerena L, Lopez-Sanchez M, Roncal NE, Waters NC (2007) Antimicrob Agents Chemother 51:1926

    Article  CAS  Google Scholar 

  40. O’Brien J, Wilson I, Orton T, Pognan F (2000) Eur J Biochem 267:5421

    Article  CAS  Google Scholar 

  41. Gupta J, Misra S, Mishra SK, Srivastava S, Srivastava MN, Lakshmi V, Misra-Bhattacharya S (2012) Exp Parasitol 130:449

    Article  Google Scholar 

  42. Sashidhara KV, Avula SR, Doharey PK, Singh LR, Balaramnavar VM, Gupta J, Misra-Bhattacharya S, Rathaur S, Saxena AK, Saxena JK (2015) Eur J Med Chem 103:418

    Article  CAS  Google Scholar 

  43. Misra S, Singh LK, Priyanka, Gupta J, Misra-Bhattacharya S, Katiyar D (2015) Eur J Med Chem 94:211

    Article  CAS  Google Scholar 

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Acknowledgements

We express our thanks to Rev. Fr. Dr. Stephen Mavely, Vice Chancellor, Assam Don Bosco University for providing infrastructure for the execution of this work. We also wish to express our gratitude to Tezpur University, Tezpur and SAIF-CDRI, Lucknow for providing spectral and analytical data. The work reported herein was supported by a fund granted by the Department of Biotechnology (DBT), Government of India for a Twinning Research Grant. (BT/PR16679/NER/95/247/2015 dated 13/10/2016) and SK expresses her gratitude to DBT for a research fellowship.

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Authors and Affiliations

  1. Organic Research Lab, Department of Chemical Science, Assam Don Bosco University, Tapesia Gardens, Kamarkuchi, Sonapur, 782 402, Assam, India

    Shilpika Khanikar, Shunan Kaping & Jai N. Vishwakarma

  2. Laboratoire de Chimie Therapeutique, UMR CNRS No 8638, Université Paris Descartes, Faculte Des Sciences Pharmaceutiques, 75270 Cedex 06, Paris, France

    Philippe Helissey

  3. Molecular Parasitology and Immunology Division, CSIR-Central Drug Research Institute, Lucknow, UP, 226031, India

    Prince Joshi, Salique Hassan Shaham, Shikha Mishra, Mrigank Srivastava & Renu Tripathi

  4. Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

    Prince Joshi, Salique Hassan Shaham & Renu Tripathi

Authors
  1. Shilpika Khanikar
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  2. Shunan Kaping
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  3. Philippe Helissey
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  4. Prince Joshi
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  5. Salique Hassan Shaham
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  9. Jai N. Vishwakarma
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Correspondence to Jai N. Vishwakarma.

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Dedicated to Rev. Fr. Dr. Stephen Mavely on the occasion of his 70th Birth Anniversary.

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Khanikar, S., Kaping, S., Helissey, P. et al. Efficient synthesis, structure elucidation, and anti-parasitic activities of novel quinolinyl β–enaminones. Monatsh Chem 152, 665–678 (2021). https://doi.org/10.1007/s00706-021-02776-w

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  • DOI: https://doi.org/10.1007/s00706-021-02776-w

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