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Synthesis, antimycobacterial activity, and acid dissociation constants of polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives

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Abstract

This study reports on synthesis and determination of antimycobacterial activity and acid dissociation constants of polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives, containing thiazole, coumarin, and pyrrolidine octahydropyrrolo[3,4-c]pyrrole moieties. The products were synthesized by a cyclization reaction of 5,5-diphenylpyrrolidine N-aroylthioureas or methyl 5-substituted 4,6-dioxo-3,3-diphenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate N-aroylthioureas and 3-(bromoacetyl)coumarin with good to excellent yield (81–97%). The compounds exhibited antimycobacterial activity against the M. tuberculosis H37Rv strain with minimum inhibitory concentration values in the range of 31.25–125 μg/cm3. Acid dissociation constants of the compounds were determined using data which were obtained using a potentiometric titration method in 50% (v/v) dimethyl sulfoxide–water hydroorganic solvent at 25 ± 0.1 °C, at an ionic background of 0.1 mol/dm3 of NaCl. Acid dissociation constants were calculated using the HYPERQUAD computer program. The acid dissociation constants obtained might be associated with SH, OH, and two NH groups, which were formed by the protonation of thiazole and pyrrolidine rings.

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References

  1. Arora P, Narang R, Nayak SK, Singh SK, Judge V (2016) Med Chem Res 25:1717

    Article  CAS  Google Scholar 

  2. Kashyap SJ, Garg VK, Sharma PK, Kumar N, Dudhe R, Gupta JK (2012) Med Chem Res 21:2123

    Article  CAS  Google Scholar 

  3. Nural Y, Gemili M, Ulger M, Sari H, De Coen LM, Sahin E (2018) Bioorg Med Chem Lett 28:942

    Article  CAS  PubMed  Google Scholar 

  4. Bhalerao MB, Dhumal ST, Deshmukh AR, Nawale LU, Khedkar V, Sarkar D, Mane RA (2017) Bioorg Med Chem Lett 27:288

    Article  CAS  PubMed  Google Scholar 

  5. Mjambili F, Njoroge M, Naran K, De Kock C, Smith PJ, Mizrahi V, Warner D, Chibale K (2014) Bioorg Med Chem Lett 24:560

    Article  CAS  PubMed  Google Scholar 

  6. Rekha T, Durgamma S, Padmaja A, Padmavathi V (2017) Monatsh Chem 148:1781

    Article  CAS  Google Scholar 

  7. Shankar B, Jalapathi P, Nagamani M, Gandu B, Kudle KR (2017) Monatsh Chem 148:999

    Article  CAS  Google Scholar 

  8. Khan M-ul-H, Hameed S, Akhtar T, Al-Masoudi NA, Al-Masoudi WA, Jones PG, Pannecouque C (2016) Med Chem Res 25:2399

    Article  CAS  Google Scholar 

  9. Sahin O, Ozdemir UO, Seferoglu N, Genc ZK, Kaya K, Aydiner B, Tekin S, Seferoglu Z (2018) J Photochem Photobiol B 178:428

    Article  CAS  PubMed  Google Scholar 

  10. Gomha SM, Salah TA, Abdelhamid AO (2015) Monatsh Chem 146:149

    Article  CAS  Google Scholar 

  11. Kim H, Cho SJ, Yoo M, Kang SK, Kim KR, Lee HH, Song JS, Rhee SD, Jung WH, Ahn JH, Jung J-K, Jung K-Y (2017) Bioorg Med Chem Lett 27:5213

    Article  CAS  PubMed  Google Scholar 

  12. Narayan R, Potowski M, Jia ZJ, Antonchick AP, Waldmann H (2014) Acc Chem Res 47:1296

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Mayol-Llinàs J, Nelson A, Farnaby W, Ayscough A (2017) Drug Discov Today 22:965

    Article  CAS  PubMed  Google Scholar 

  14. Dandia A, Khan S, Soni P, Indora A, Mahawar DK, Pandya P, Chauhan CS (2017) Bioorg Med Chem Lett 27:2873

    Article  CAS  PubMed  Google Scholar 

  15. Nural Y, Gemili M, Seferoglu N, Sahin E, Ulger M, Sari H (2018) J Mol Struct 1160:375

    Article  CAS  Google Scholar 

  16. Huang J, Wang M, Wang B, Wu Z, Liu M, Feng L, Zhang J, Li X, Yang Y, Lu Y (2016) Bioorg Med Chem Lett 26:2262

    Article  CAS  PubMed  Google Scholar 

  17. Huang J, Liu H, Liu M, Zhang R, Li L, Wang B, Wang M, Wang C, Lu Y (2015) Bioorg Med Chem Lett 25:5058

    Article  CAS  PubMed  Google Scholar 

  18. Matviiuk T, Madacki J, Mori G, Orena BS, Menendez C, Kysil A, Andre-Barres C, Rodriguez F, Kordulakova J, Mallet-Ladeira S, Voitenko Z, Pasca MR, Lherbet C, Baltas M (2016) Eur J Med Chem 123:462

    Article  CAS  PubMed  Google Scholar 

  19. Zhang T, Shen W, Liu M, Zhang R, Wang M, Li L, Wang B, Guo H, Lu Y (2015) Eur J Med Chem 104:73

    Article  CAS  PubMed  Google Scholar 

  20. Ersen D, Ulger M, Mangelinckx S, Gemili M, Sahin E, Nural Y (2017) Med Chem Res 26:2152

    Article  CAS  Google Scholar 

  21. Gemili M, Sari H, Ulger M, Sahin E, Nural Y (2017) Inorg Chim Acta 463:88

    Article  CAS  Google Scholar 

  22. Aguilar A, Lu J, Liu L, Du D, Bernard D, McEachern D, Przybranowski S, Li X, Luo R, Wen B, Sun D, Wang H, Wen J, Wang G, Zhai Y, Guo M, Yang D, Wang S (2017) J Med Chem 60:2819

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Cox JM, Chu HD, Kuethe JT, Gao YD, Scapin G, Eiermann G, He H, Li X, Lyons KA, Metzger J, Petrov A, Wu JK, Xu S, Sinha-Roy R, Weber AE, Biftu T (2016) Bioorg Med Chem Lett 26:2622

    Article  CAS  PubMed  Google Scholar 

  24. Liang J, Labadie S, Zhang B, Ortwine DF, Patel S, Vinogradova M, Kiefer JR, Mauer T, Gehling VS, Harmange JC, Cummings R, Lai T, Liao J, Zheng X, Liu Y, Gustafson A, Van der Porten E, Mao W, Liederer BM, Deshmukh G, An L, Ran Y, Classon M, Trojer P, Dragovich PS, Murray L (2017) Bioorg Med Chem Lett 27:2974

    Article  CAS  PubMed  Google Scholar 

  25. Hu YQ, Xu Z, Zhang S, Wu X, Ding JW, Lv ZS, Feng LS (2017) Eur J Med Chem 136:122

    Article  CAS  PubMed  Google Scholar 

  26. Jameel E, Umar T, Kumar J, Hoda N (2016) Chem Biol Drug Des 87:21

    Article  CAS  PubMed  Google Scholar 

  27. Barot KP, Jain SV, Kremer L, Singh S, Ghate MD (2015) Med Chem Res 24:2771

    Article  CAS  Google Scholar 

  28. Angelova VT, Valcheva V, Vassilev NG, Buyukliev R, Momekov G, Dimitrov I, Saso L, Djukic M, Shivachev B (2017) Bioorg Med Chem Lett 27:223

    Article  CAS  PubMed  Google Scholar 

  29. Reddy DS, Hosamani KM, Devarajegowda HC, Kurjogi MM (2015) RSC Adv 5:64566

    Article  CAS  Google Scholar 

  30. Aragade P, Palkar M, Ronad P, Satyanarayana D (2013) Med Chem Res 22:2279

    Article  CAS  Google Scholar 

  31. Aksungur T, Aydiner B, Seferoglu N, Ozkutuk M, Arslan L, Reis Y, Acik L, Seferoglu Z (2017) J Mol Struct 1147:364

    Article  CAS  Google Scholar 

  32. Ostrowska K, Grzeszczuk D, Maciejewska D, Młynarczuk-Biały I, Czajkowska A, Sztokfisz A, Dobrzycki L, Kruszewska H (2016) Monatsh Chem 147:1615

    Article  CAS  Google Scholar 

  33. Hassan MZ, Osman H, Ali MA, Ahsan MJ (2016) Eur J Med Chem 123:236

    Article  CAS  PubMed  Google Scholar 

  34. Ostrowska K, Hejchman E, Maciejewska D, Włodarczyk A, Wojnicki K, Matosiuk D, Czajkowska A, Młynarczuk-Biały I, Dobrzycki Ł (2015) Monatsh Chem 146:89

    Article  CAS  PubMed  Google Scholar 

  35. Matiadis D, Stefanou V, Athanasellis G, Hamilakis S, McKee V, Igglessi-Markopoulou O, Markopoulos J (2013) Monatsh Chem 144:1063

    Article  CAS  Google Scholar 

  36. Zhao H, Blagg BSJ (2013) Bioorg Med Chem Lett 23:552

    Article  CAS  PubMed  Google Scholar 

  37. Hassan HE, Myers AL, Coop A, Eddington ND (2009) J Pharm Sci 98:4928

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. Pramanik C, Bapat K, Chaudhari A, Tripathy NK, Gurjar MK (2012) Org Process Res Dev 16:1591

    Article  CAS  Google Scholar 

  39. Soman SS, Soni JN, Patel TB (2014) Med Chem Res 23:3803

    Article  CAS  Google Scholar 

  40. Krasikovs A (2015) Chem Heterocycl Compd 51:385

    Article  CAS  Google Scholar 

  41. Manallack DT (2009) SAR QSAR Environ Res 20:611

    Article  CAS  PubMed  Google Scholar 

  42. Xiao JJ, Chen JS, Lum BL, Graham RA (2017) Anticancer Drugs 28:677

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  43. Farajtabar A, Gharib F (2010) Monatsh Chem 141:381

    Article  CAS  Google Scholar 

  44. Ersen D, Gemili M, Sari H, Nural Y (2017) CBU J Sci 13:125  

    CAS  Google Scholar 

  45. Narin I, Sarioglan S, Anilanmert B, Sari H (2010) J Solut Chem 39:1582

    Article  CAS  Google Scholar 

  46. Hakli O, Ertekin K, Ozer MS, Aycan S (2008) J Anal Chem 63:1051

    Article  CAS  Google Scholar 

  47. Atabey H, Sari H (2014) Turk J Chem 38:806

    Article  CAS  Google Scholar 

  48. Furia E, Sindona G, Tagarelli A (2016) Monatsh Chem 147:1009

    Article  CAS  Google Scholar 

  49. Nural Y (2017) J Turk Chem Soc Sect A Chem 4:841

    Article  CAS  Google Scholar 

  50. Nurchi VM, Crisponi G, Lachowicz JI, Sanna G, Peana M, Zoroddu MA (2016) Monatsh Chem 147:719

    Article  CAS  Google Scholar 

  51. Zayed EM, Ismail EH, Mohamed GG, Khalil MMH, Kamel AB (2014) Monatsh Chem 145:755

    Article  CAS  Google Scholar 

  52. Sanli S, Sanli N, Lunte C (2017) Curr Pharm Anal 13:31

    Article  CAS  Google Scholar 

  53. Thomas KK, Reshmy R, Ushadevi KS (2007) J Indian Chem Soc 84:1016

    CAS  Google Scholar 

  54. De Brabandere S, Mangelinckx S, Kadam ST, Nural Y, Augustyns K, Van der Veken P, Tornroos KW, De Kimpe N (2014) Eur J Org Chem 2014:1220

    Article  CAS  Google Scholar 

  55. Khlebnikov AF, Novikov MS, Khlebnikov VA, Kostikov RR (2001) Russ J Org Chem 37:507

    Article  CAS  Google Scholar 

  56. Gumus I, Solmaz U, Binzet G, Keskin E, Arslan B, Arslan H (2018) J Mol Struct 1157:78

    Article  CAS  Google Scholar 

  57. Binzet G, Gumus I, Dogen A, Florke U, Kulcu N, Arslan H (2018) J Mol Struct 1161:519

    Article  CAS  Google Scholar 

  58. Golcu A, Tumer M, Demirelli H, Wheatley RA (2005) Inorg Chim Acta 358:1785

    Article  CAS  Google Scholar 

  59. Ruzanov DO, Samoilov DV, Gensh KV, Zevatskii YE, Novoselov NP (2011) Russ J Gen Chem 81:1153

    Article  CAS  Google Scholar 

  60. El-Sherif AA, Shoukry MM, Abd-Elgawad MMA (2013) J Solut Chem 42:412

    Article  CAS  Google Scholar 

  61. Ogretir C, Demirayak S, Duran M (2010) J Chem Eng Data 55:1137

    Article  CAS  Google Scholar 

  62. Ugur I, Marion A, Parant S, Jensen JH, Monard G (2014) J ChemInf Model 54:2200

    Article  CAS  Google Scholar 

  63. Stewart R, Linden RVD (1960) Can J Chem 38:399

    Article  CAS  Google Scholar 

  64. Gans P, Sabatini A, Vacca A (1996) Talanta 43:1739

    Article  CAS  PubMed  Google Scholar 

  65. Atabey H, Sari H, Al-Obaidi FN (2012) J Solut Chem 41:793

    Article  CAS  Google Scholar 

  66. Nateche F, Martin A, Baraka S, Palomino JC, Khaled S, Portaels F (2006) J Med Microbiol 55:857

    Article  PubMed  Google Scholar 

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Acknowledgements

This work was funded by Mersin University Research Fund (Project No: BAP 2016-2-AP3-1800). The authors grateful to Prof. Dr. Hayati Sari (University of Gaziosmanpaşa, Turkey) for his contribution on discussions of the acid dissociation constants and to Dr. Mahmut Ulger (University of Mersin, Turkey) for his contribution on determination of antimycobacterial results.

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  1. Department of Analytical Chemistry, Faculty of Pharmacy, Mersin University, Mersin, TR-33169, Turkey

    Yahya Nural

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Correspondence to Yahya Nural.

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Nural, Y. Synthesis, antimycobacterial activity, and acid dissociation constants of polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives. Monatsh Chem 149, 1905–1918 (2018). https://doi.org/10.1007/s00706-018-2250-7

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