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Synthesis and in vitro evaluation of tetrahydropyridines as potential CDK2 and DprE1 inhibitors

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Abstract

The present work describes the unrevealed potential of tetrahydropyridines as anticancer and anti-tubercular agents along with DFT, ADMET, drug-likeliness and molecular docking studies synthesized by using Bronsted acidic ionic liquid viz. 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium chloride [MSbIM-Cl]. The synthesized derivatives have been screened for their anticancer and anti-tubercular evaluation against MCF-7 cell lines and Mycobacterium tuberculosis respectively. The compound 4e showed the highest anticancer activity while the compound 4h showed the highest anti-tubercular activity. The in vitro evaluation has been supported by computational methods such as molecular docking, density functional study and in silico ADMET and drug-likeliness prediction.

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Scheme 1
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References

  1. R. Kaur, S. Chaudhary, K. Kumar, M.K. Gupta, R.K. Rawal, Eur. J. Med. Chem. 132, 108 (2017)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. L.E. Rodriguez, C.H. House, K.E. Smith, M.R. Roberts, M.P. Callahan, Sci. Rep. 9, 9281 (2019)

    Article  PubMed  PubMed Central  Google Scholar 

  3. N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu, S.B. Jonnalagadda, Molecules 25, 1909 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. D. Zárate-Zárate, R. Aguilar, R.I. Hernández-Benitez, E.M. Labarrios, F. Delgado, J. Tamariz, Tetrahedron 71, 6961 (2015)

    Article  Google Scholar 

  5. E.K. Davison, J. Sperry, J. Nat. Prod. 80, 3060 (2017)

    Article  CAS  PubMed  Google Scholar 

  6. W.Y. Fang, L. Ravindar, K.P. Rakesh, H.M. Manukumar, C.S. Shantharam, N.S. Alharbi, H.L. Qin, Eur. J. Med. Chem. 173, 117 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. B. Eftekhari-Sis, M. Zirak, A. Akbari, Chem. Rev. 113, 2958 (2013)

    Article  CAS  PubMed  Google Scholar 

  8. Y. Ju, R.S. Varma, J. Org. Chem. 71, 135 (2006)

    Article  CAS  PubMed  Google Scholar 

  9. P.D. Leeson, B. Springthorpe, Nat. Rev. Drug Discov. 6, 881 (2007)

    Article  CAS  PubMed  Google Scholar 

  10. C. Lamberth, Pest Manag. Sci. 69, 1106 (2013)

    Article  CAS  PubMed  Google Scholar 

  11. B.R. Smith, C.M. Eastman, J.T. Njardarson, J. Med. Chem. 57, 9764 (2014)

    Article  CAS  PubMed  Google Scholar 

  12. J. Liu, J. Jiang, L. Zheng, Z.Q. Liu, Adv. Synth. Catal. 362, 4876 (2020)

    Article  CAS  Google Scholar 

  13. K. Paruch, Ł Popiołek, A. Biernasiuk, A. Hordyjewska, A. Malm, M. Wujec, Molecules 25, 5844 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. S.B. Bakare, Bull. Chem. Soc. Ethiop. 35, 449 (2021)

    Article  CAS  Google Scholar 

  15. V. Alagarsamy, R. Giridhar, M.R. Yadav, J. Pharm. Pharmacol. 58, 1249 (2010)

    Article  Google Scholar 

  16. S. Nabil, S.N. Abd El-Rahman, S.S. Al-Jameel, A.M. Elsharif, Biol. Pharm. Bull. 41, 1071 (2018)

    Article  CAS  PubMed  Google Scholar 

  17. M. Marinescu, Antibiotics 10, 1002 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. R. Bouley, M. Kumarasiri, Z. Peng, L.H. Otero, W. Song, M.A. Suckow, V.A. Schroeder, W.R. Wolter, E. Lastochkin, N.T. Antunes, H. Pi, S. Vakulenko, J.A. Hermoso, M. Chang, S. Mobashery, J. Am. Chem. Soc. 137, 1738 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. J. Jampilek, Molecules 24, 3839 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. W. Wang, L. Lei, Z. Liu, H. Wang, Q. Meng, Molecules 24, 877 (2019)

    Article  PubMed  PubMed Central  Google Scholar 

  21. S.H. Sharma, J.L. Pablo, M.S. Montesinos, A. Greka, C.R. Hopkins, Bioorg. Med. Chem. Lett. 29, 155 (2019)

    Article  CAS  PubMed  Google Scholar 

  22. J. Liu, C. Wu, H. Jin, K. Du, H. Zheng, J. Heterocycl. Chem. 56, 3088 (2019)

    Article  CAS  Google Scholar 

  23. P. Herdewijn, Antisense Nucleic Acid Drug Dev. 10, 297 (2000)

    Article  CAS  PubMed  Google Scholar 

  24. S.S. Gupta, S. Kumari, I. Kumar, U. Sharma, Chem. Heterocycl. Compd. (New York) 56, 433 (2020)

    Article  CAS  Google Scholar 

  25. K.P. Srivastava, I. Singh, A. Kumari, Der Pharma Chem. 6, 119 (2014)

    Google Scholar 

  26. N.C. Desai, A.M. Dodiya, Arab. J. Chem. 9, S379 (2016)

    Article  CAS  Google Scholar 

  27. M.S. Praceka, S. Megantara, R. Maharani, M. Muchtaridi, J. Adv. Pharm. Technol. Res. 12, 321 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. R. Kakuchi, R. Ito, S. Nomura, H. Abroshan, K. Ninomiya, T. Ikai, K. Maeda, H.J. Kim, K. Takahashi, RSC Adv. 7, 9423 (2017)

    Article  CAS  Google Scholar 

  29. J.D. Patil, S.N. Korade, D.M. Pore, RSC Adv. 4, 50449 (2014)

    Article  CAS  Google Scholar 

  30. H.R. Safaei, M. Shekouhy, V. Shafiee, M. Davoodi, J. Mol. Liq. 180, 139 (2013)

    Article  CAS  Google Scholar 

  31. H. Zang, Q. Su, Y. Mo, B.W. Cheng, S. Jun, Ultrason. Sonochem. 17, 749 (2010)

    Article  CAS  PubMed  Google Scholar 

  32. S.N. Korade, J.D. Patil, D.M. Pore, Monatsh. Chem. 147, 2143 (2016)

    Article  CAS  Google Scholar 

  33. J.D. Patil, S.A. Patil, D.M. Pore, RSC Adv. 5, 21396 (2015)

    Article  CAS  Google Scholar 

  34. V.I. Pârvulescu, C. Hardacre, Chem. Rev. 107, 2615 (2007)

    Article  PubMed  Google Scholar 

  35. G. Bhasin, R. Srivastava, R. Singh, Org. Prep. Proc. Int. 49, 370 (2017)

    Article  CAS  Google Scholar 

  36. C. Maton, N. De Vos, C.V. Stevens, Chem. Soc. Rev. 42, 5963 (2013)

    Article  CAS  PubMed  Google Scholar 

  37. R. Sheldon, ChemComm 1, 2399 (2001)

    Google Scholar 

  38. B.J. Butler, J.B. Harper, New J. Chem. 39, 213 (2015)

    Article  CAS  Google Scholar 

  39. R.L. Vekariya, J. Mol. Liq. 227, 44 (2017)

    Article  CAS  Google Scholar 

  40. W.L. Wong, K.Y. Wong, Can. J. Chem. 90, 1 (2012)

    Article  CAS  Google Scholar 

  41. R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16, 2958 (2014)

    Article  CAS  Google Scholar 

  42. B.H. Rotstein, S. Zaretsky, V. Rai, A.K. Yudin, Chem. Rev. 114, 8323 (2014)

    Article  CAS  PubMed  Google Scholar 

  43. A. Rahmati, N. Pashmforoush, Iran. Chem. Soc. 12, 993 (2015)

    Article  CAS  Google Scholar 

  44. J.D. Sunderhaus, S.F. Martin, Chem. Eur. J. 15, 1300 (2009)

    Article  CAS  PubMed  Google Scholar 

  45. J.R. Resting, I.L. Tolderlund, A.F. Pedersen, M. Witt, J.W. Jaroszewski, D. Staerk, J. Nat. Prod. 72, 312 (2009)

    Article  Google Scholar 

  46. G.L. Lozano, H.B. Park, J.I. Bravo, E.A. Armstrong, J.M. Denu, E.V. Stabb, N.A. Broderick, J.M. Crawford, J. Handelsman, Appl. Environ. Microbiol. 85, e03058 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  47. M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi, R.P. Tripathi, Bioorg. Med. Chem. 17, 625 (2009)

    Article  CAS  PubMed  Google Scholar 

  48. M. Gangapuram, K. Redda, J. Heterocycl. Chem. 43, 709 (2006)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  49. K. Rao, K. Redda, F. Onayemi, H. Melles, J. Choi, J. Heterocycl. Chem. 32, 307 (1995)

    Article  CAS  Google Scholar 

  50. S. Petit, J. Nallet, M. Guillard, J. Dreux, R. Chermat, M. Poncelet, C. Bulach, P. Simon, C. Fontaine, M. Barthelmebs, J. Imbs, Eur. J. Med. Chem. 26, 19 (1991)

    Article  CAS  Google Scholar 

  51. Y. Zhou, V.E. Gregor, B.K. Ayida, G.C. Winters, Z. Sun, D. Murphy, G. Haley, D. Bailey, J.M. Froelich, S. Fish, S.E. Webber, T. Hermann, D. Wall, Bioorg. Med. Chem. Lett. 15, 1206 (2007)

    Article  Google Scholar 

  52. B. Ho, A.M. Crider, J.P. Stables, Eur. J. Med. Chem. 36, 265 (2001)

    Article  CAS  PubMed  Google Scholar 

  53. S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.J. Shams-Najafi, Monatsh. Chem. 143, 939 (2012)

    Article  CAS  Google Scholar 

  54. L. Wu, S. Yan, W. Wang, Y. Li, Res. Chem. Intermed. 46, 4311 (2020)

    Article  CAS  Google Scholar 

  55. S. Mohammadi, M. Abbasi, J. Chem. Res. 39, 123 (2015)

    Article  CAS  Google Scholar 

  56. M. Lashkari, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.S. Sajadikhah, R. Doostmohamadi, Synth. Commun. 43, 635 (2013)

    Article  CAS  Google Scholar 

  57. J. Aboonajmi, M.T. Maghsoodlou, N. Hazeri, M. Lashkari, M. Kangani, Res. Chem. Intermed. 41, 8057 (2015)

    Article  CAS  Google Scholar 

  58. D. Dogra, R. Bharti, R. Sharma, Orbital 12, 232 (2020)

    CAS  Google Scholar 

  59. S. Geetha, A. Thangamani, R. Valliappan, S. Vedanayaki, A. Ganapathi, Chem. Data Collect. 30, 100565 (2020)

    Article  CAS  Google Scholar 

  60. A.T. Khan, M. Lal, M.M. Khan, Tetrahedron Lett. 51, 4419 (2010)

    Article  CAS  Google Scholar 

  61. A. Mulik, P. Hegade, D. Patil, G. Mulik, S. Salunkhe, M. Deshmukh, Res. Chem. Intermed. 43, 729 (2016)

    Article  Google Scholar 

  62. S. Sardar, C.D. Wilfred, L.J. Marc, AIP Conf. Proc. 1787, 030010 (2016)

    Article  Google Scholar 

  63. S.A. Hattarki, C. Bogar, K. Bhat, Int. J. Pharm. Res. Health Sci. 8, 3220 (2020)

    Article  CAS  Google Scholar 

  64. P. Mandroli, A. Prabhakar, K. Bhat, S. Krishnamurthy, C. Bogar, Ayu 40, 192 (2019)

    Article  PubMed  Google Scholar 

  65. S. Cho, H.S. Lee, S. Franzblau, Methods Mol. Biol. 1285, 281 (2015)

    Article  CAS  PubMed  Google Scholar 

  66. M.C.S. Lourenço, M.V.N. de Souza, A.C. Pinheiro, M.L. de Ferreira, R.S.B. Gonçalves, T.M. Cristina Nogueira, M.A. Peralta, ARKIVOC 15, 181 (2007)

    Article  Google Scholar 

  67. E.J. Walsh, J. Chem. Educ. 74, 3 (1997)

    Google Scholar 

  68. Dassault Systèmes, (2020).

  69. N.M. O’boyle, M. Banck, C.A. James, C. Morley, T. Vandermeersch, G.R. Hutchison, J. Cheminform. 3, 1 (2011)

    Article  Google Scholar 

  70. V.K. Bagal, S.S. Rathod, M.M. Mulla, S.C. Pawar, P.B. Choudhari, V.T. Pawar, D.V. Mahuli, Nat. Prod. Res. 37, 1 (2023)

    Article  Google Scholar 

  71. A. Daina, O. Michielin, V. Zoete, Sci. Rep. 7, 42717 (2017)

    Article  PubMed  PubMed Central  Google Scholar 

  72. D.E.V. Pires, T.L. Blundell, D.B. Ascher, J. Med. Chem. 58, 4066 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  73. S. Rochlani, M. Bhatia, S. Rathod, P. Choudhari, and R. Dhavale, Nat. Prod. Res. 1 (2023).

  74. J. T. Kilbile, Y. Tamboli, S. A. Ansari, S. S. Rathod, P. B. Choudhari, H. Alkahtani, and S. B. Sapkal, Polycycl. Aromat. Compd. 1 (2023).

  75. S. Rathod, S. Dey, S. Pawar, R. Dhavale, P. Choudhari, E. Rajakumara, D. Mahuli, D. Bhagwat, Y. Tamboli, P. Sankpal, S. Mali, and H. More, J. Biomol. Struct. Dyn. 1 (2023).

  76. F. Neese, Wiley Interdiscip. Rev. Comput. Mol. Sci. 2, 73 (2012)

    Article  CAS  Google Scholar 

  77. H.D. Snyder, T.G. Kucukkal, J. Chem. Educ. 98, 1335 (2021)

    Article  CAS  Google Scholar 

  78. V. Puthanveedu, K. Muraleedharan, Struct. Chem. 33, 1423 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  79. S. Choudhari, S. K. Patil, and S. Rathod, J Biomol Struct Dyn 1 (2023).

  80. S. Rathod, D. Bhande, S. Pawar, K. Gumphalwad, P. Choudhari, and H. More, Chem. Afr. (2023).

  81. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, P.E. Bourne, Nucleic Acids Res. 28, 235 (2000)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  82. R. D. Bakale, P. S. Phatak, S. S. Rathod, P. B. Choudhari, E. M. Rekha, D. Sriram, R. S. Kulkarni, and K. P. Haval, J Biomol Struct Dyn 1 (2023).

  83. J. Eberhardt, D. Santos-Martins, A.F. Tillack, S. Forli, J. Chem. Inf. Model. 61, 3891 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  84. S. Rathod, P. Chavan, D. Mahuli, S. Rochlani, S. Shinde, S. Pawar, P. Choudhari, R. Dhavale, P. Mudalkar, F. Tamboli, J. Mol. Model. 29, 1 (2023)

    Article  Google Scholar 

  85. S.Y. Salunkhe, R.P. Gurav, S.S. Rathod, P.B. Choudhari, T.P. Yadav, S.B. Wakshe, P.V. Anbhule, G.B. Kolekar, J. Mol. Struct. 1301, 137288 (2024)

    Article  CAS  Google Scholar 

  86. S. Rathod, K. Shinde, J. Porlekar, P. Choudhari, R. Dhavale, D. Mahuli, Y. Tamboli, M. Bhatia, K.P. Haval, A.G. Al-Sehemi, M. Pannipara, ACS Omega 8, 391 (2022)

    Article  PubMed  PubMed Central  Google Scholar 

  87. P. Swami, S. Rathod, P. Choudhari, D. Patil, A. Patravale, Y. Nalwar, S. Sankpal, S. Hangirgekar, J. Mol. Struct. 1292, 136079 (2023)

    Article  CAS  Google Scholar 

  88. S. Dey, S. Rathod, K. Gumphalwad, N. Yadav, P. Choudhari, E. Rajakumara, R. Dhavale, and D. Mahuli, J Biomol Struct Dyn 1 (2023).

  89. H. Eshghi, A. Khojastehnezhad, F. Moeinpour, M. Bakavoli, S.M. Seyedi, M. Abbasi, RSC Adv. 4, 39782 (2014)

    Article  CAS  Google Scholar 

  90. M. Abbasi, RSC Adv. 5, 67405 (2015)

    Article  CAS  Google Scholar 

  91. R. Jahanshahi, B. Akhlaghinia, New J. Chem. 41, 7203 (2017)

    Article  CAS  Google Scholar 

  92. N.R. Agrawal, S.P. Bahekar, P.B. Sarode, S.S. Zade, H.S. Chandak, RSC Adv. 5, 47053 (2015)

    Article  CAS  Google Scholar 

  93. R. Ramachandran, S. Jayanthi, Y.T. Jeong, Tetrahedron 68, 363 (2012)

    Article  CAS  Google Scholar 

  94. G.V. Ramin, S. Hajar, C. R. Chim. 16, 1047 (2013)

    Article  CAS  Google Scholar 

  95. S.S. Sajadikhah, N. Hazeri, M. Taher Maghsoodlou, M. Habibi-Khorassani, A. Beigbabaei, M. Lashkari, J. Chem. Res. 36, 463 (2012)

    Article  CAS  Google Scholar 

  96. M. Zarei, S.S. Sajadikhah, Res. Chem. Intermed. 42, 7005 (2016)

    Article  CAS  Google Scholar 

  97. D.D. Gadge, P.S. Kulkarni, J. Heterocycl. Chem. 59, 1320 (2022)

    Article  CAS  Google Scholar 

  98. C.A. Lipinski, Drug Discov. Today Technol. 1, 337 (2004)

    Article  CAS  PubMed  Google Scholar 

  99. C.A. Lipinski, B.W. Dominy, P.J. Feeney, Adv. Drug Deliv. Rev. 23, 3 (1997)

    Article  CAS  Google Scholar 

  100. C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Adv. Drug Deliv. Rev. 23, (2001)

  101. D.F. Veber, S.R. Johnson, H.Y. Cheng, B.R. Smith, K.W. Ward, K.D. Kopple, J. Med. Chem. 45, 2615 (2002)

    Article  CAS  PubMed  Google Scholar 

  102. J.X. Mu, Y.X. Shi, M.Y. Yang, Z.H. Sun, X.H. Liu, B.J. Li, N.B. Sun, Molecules 21, 68 (2016)

    Article  PubMed  PubMed Central  Google Scholar 

  103. P. Patil, P. Patil, P. Dandge, P. Bansode, B. Kumbhar, W. Chandane, S. Rathod, P. Choudhari, S. Khot, N. Valekar, D. Pore, G. Rashinkar, J. Mol. Struct. 1301, 137202 (2024)

    Article  CAS  Google Scholar 

  104. E.B. Elkaeed, R.G. Yousef, H. Elkady, I.M.M. Gobaara, B.A. Alsfouk, D.Z. Husein, I.M. Ibrahim, A.M. Metwaly, I.H. Eissa, Molecules 27, 4606 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  105. P.K. Patial, D.S. Cannoo, Nat. Prod. Res. 35, 4611 (2021)

    Article  CAS  PubMed  Google Scholar 

  106. M.A. Mumit, T.K. Pal, M.A. Alam, M.A.A.A.A. Islam, S. Paul, M.C. Sheikh, J. Mol. Struct. 1220, 128715 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  107. R.D. Bakale, S.M. Sulakhe, S.L. Kasare, B.P. Sathe, S.S. Rathod, P.B. Choudhari, E. Madhu Rekha, D. Sriram, K.P. Haval, Bioorg. Med. Chem. Lett. 97, 129551 (2023)

    Article  CAS  PubMed  Google Scholar 

  108. A. Das, A. Das, B.K. Banik, J. Indian Chem. Soc. 98, 100005 (2021)

    Article  CAS  Google Scholar 

  109. A. Das, B.K. Banik, Green Approaches in Medicinal Chemistry for Sustainable Drug Design (Elsevier, Amsterdam, 2020), pp.921–964

    Book  Google Scholar 

  110. D.M. Kara, I.J. Smallman, J.J. Hudson, B.E. Sauer, M.R. Tarbutt, E.A. Hinds, New J. Phys. 14, 103051 (2012)

    Article  Google Scholar 

  111. M.N. Tahir, M. Khalid, A. Islam, S.M. Ali Mashhadi, A.A.C. Braga, J. Mol. Struct. 1127, 766 (2017)

    Article  CAS  Google Scholar 

  112. A.R. Pasha, M. Khalid, Z. Shafiq, M.U. Khan, M.M. Naseer, M.N. Tahir, R. Hussain, A.A.C. Braga, R. Jawaria, J. Mol. Struct. 1230, 129852 (2021)

    Article  CAS  Google Scholar 

  113. G. Mustafa, I. Shafiq, Q.U.A. Shaikh, A. Mustafa, R. Zahid, F. Rasool, M.A. Asghar, R. Baby, S.M. Alshehri, M. Haroon, ACS Omega 8, 22673 (2023)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  114. A. Ali, M. Khalid, K.P. Marrugo, G.M. Kamal, M. Saleem, M.U. Khan, O. Concepción, A.F. de la Torre, J. Mol. Struct. 1207, 127838 (2020)

    Article  CAS  Google Scholar 

  115. M. Khalid, H.M. Lodhi, M.U. Khan, M. Imran, RSC Adv. 11, 14237 (2021)

    Article  CAS  Google Scholar 

  116. M. Riaz, F. Jan, A. Khan, A. Ullah, H. Haq, A.F. AlAsmari, M. Alharbi, F. Alasmari, MominKhan, Arab. J. Chem. 16, 105259 (2023)

    Article  CAS  Google Scholar 

  117. C. Weetman, S. Inoue, ChemCatChem 10, 4213 (2018)

    Article  CAS  Google Scholar 

  118. P. Wu, P. Du, H. Zhang, C. Cai, J. Phys. Chem. C 116, 20472 (2012)

    Article  CAS  Google Scholar 

  119. S.K. Seth, G.C. Maity, T. Kar, J. Mol. Struct. 1000, 120 (2011)

    Article  CAS  Google Scholar 

  120. S.K. Seth, N.C. Saha, S. Ghosh, T. Kar, Chem. Phys. Lett. 506, 309 (2011)

    Article  CAS  Google Scholar 

  121. S.K. Seth, S. Banerjee, T. Kar, J. Mol. Struct. 965, 45 (2010)

    Article  CAS  Google Scholar 

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Acknowledgements

We are thankful to Instrumentation Centre, Punyashlok Ahilyadevi Holkar Solapur University, Solapur, Council for Scientific and Industrial Research-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad and Sophisticated Analytical Instrumental Facility-Common Facility Center (SAIF-CFC), Shivaji University, Kolhapur for spectral analysis. The authors are thankful to Maratha Mandal’s Central Research Laboratory, Belgaum for providing biological activities.

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This research work has not received any funds.

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Authors and Affiliations

  1. Department of Chemistry, Karmaveer Hire Arts, Science, Commerce and Education College, Gargoti, Maharashtra, 416209, India

    Pravin R. Kharade & Uttam B. Chougale

  2. Department of Chemistry, Vivekanand College (Autonomous), Kolhapur, Maharashtra, 416003, India

    Dipak S. Gaikwad & Satish S. Kadam

  3. Department of Chemistry, Dr. Ghali College, Gadhinglaj, Maharashtra, 416502, India

    Kiran N. Patil

  4. Department of Pharmaceutical Chemistry, Bharati Vidyapeeth College of Pharmacy, Kolhapur, Maharashtra, 416013, India

    Sanket S. Rathod & Prafulla B. Choudhari

  5. Research Laboratory in Heterocyclic Chemistry, Devchand College, Arjunnagar, Maharashtra, 416216, India

    Pravin R. Kharade, Uttam B. Chougale & Savita S. Desai

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  1. Pravin R. Kharade
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Contributions

PRK and SSR analyzed the data and wrote the main manuscript, SSR worked on software, SSD supervised the work, All authors reviewed the manuscript.

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Correspondence to Pravin R. Kharade or Savita S. Desai.

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Kharade, P.R., Chougale, U.B., Gaikwad, D.S. et al. Synthesis and in vitro evaluation of tetrahydropyridines as potential CDK2 and DprE1 inhibitors. Res Chem Intermed 50, 1777–1808 (2024). https://doi.org/10.1007/s11164-024-05228-2

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