Skip to content
2000
image of Innovative Synthesis of 3,5-Disubstituted Pyrazoline with Heterocyclic System for Hybrid Development

Abstract

The synthesis of 3,5-disubstituted pyrazolines, integrated with heterocyclic systems, represents a crucial area of chemical research due to their pharmacological and biological significance. This article reviews various synthetic methods used to prepare 3,5-disubstituted pyrazolines with different heterocyclic groups. The methodology employed in this study entails a multi-step synthesis, where readily available starting materials are transformed into complex pyrazoline derivatives through strategic reaction sequences. Incorporating heterocyclic systems not only enhances the structural diversity but also imparts unique chemical and biological properties to these compounds. Various heterocyclic groups, such as furans, thiophenes, and pyridines, are introduced at the 3,5-positions of the pyrazoline ring, yielding a versatile library of compounds. This study highlights the potential applications of these novel compounds in medicinal chemistry and drug discovery, emphasizing their bioactivity against specific targets. Preliminary data suggests that certain derivatives possess promising pharmacological activities, making them potential candidates for further development as therapeutic agents. In summary, this review provides a valuable contribution to the field of organic synthesis, offering a novel and efficient route to synthesize 3,5-disubstituted pyrazolines with heterocyclic systems. Furthermore, the structural activity relationship of the compounds is also discussed. The structural diversity and potential pharmacological properties of these compounds make them valuable candidates for further exploration and development in drug discovery and related areas.

Loading

Article metrics loading...

/content/journals/loc/10.2174/0115701786329318240925115206
2024-10-09
2024-11-23
Loading full text...

Full text loading...

References

  1. Upadhyay S. Tripathi A.C. Paliwal S. Saraf S.K. Pharm. Chem. J. 2017 51 7 564 575 10.1007/s11094‑017‑1655‑7
    [Google Scholar]
  2. Karabacak M. Altıntop M. İbrahim Çiftçi H. Koga R. Otsuka M. Fujita M. Özdemir A. Molecules 2015 20 10 19066 19084 10.3390/molecules201019066 26492233
    [Google Scholar]
  3. Sahu S.K. Banerjee M. Samantray A. Behera C. Azam M.A. Trop. J. Pharm. Res. 2008 7 2 961 968 10.4314/tjpr.v7i2.14664
    [Google Scholar]
  4. Soni N. Pande K. Kalsi R. Gupta T.K. Parmar S.S. Barthwal J.P. Res. Commun. Chem. Pathol. Pharmacol. 1987 56 1 129 132 3589148
    [Google Scholar]
  5. Gok S. Murat Demet M. Özdemir A. Turan-Zitouni G. Med. Chem. Res. 2010 19 1 94 101 10.1007/s00044‑009‑9176‑x
    [Google Scholar]
  6. Manna F. Chimenti F. Bolasco A. Cenicola M.L. D’Amico M. Parrillo C. Rossi F. Marmo E. Eur. J. Med. Chem. 1992 27 6 633 639 10.1016/0223‑5234(92)90142‑N
    [Google Scholar]
  7. Nugent R.A. Murphy M. Schlachter S.T. Dunn C.J. Smith R.J. Staite N.D. Galinet L.A. Shields S.K. Aspar D.G. Richard K.A. Rohloff N.A. J. Med. Chem. 1993 36 1 134 139 10.1021/jm00053a017 8421279
    [Google Scholar]
  8. Siddiqui A.A. Rahman M.A. Chem. Sci. J. 2010 1 1 1 10 10.4172/2150‑3494.1000006
    [Google Scholar]
  9. Parmar S.S. Pandey B.R. Dwivedi C. Harbison R.D. J. Pharm. Sci. 1974 63 7 1152 1155 10.1002/jps.2600630730 4850598
    [Google Scholar]
  10. Berghot M.A. Moawad E.B. Eur. J. Pharm. Sci. 2003 20 2 173 179 10.1016/S0928‑0987(03)00162‑3 14550883
    [Google Scholar]
  11. Govindaraju M. IOSR J. Pharm. Biol. Sci. 2012 2 6 30 32 10.9790/3008‑0263032
    [Google Scholar]
  12. Nayal S.S. Singh C.P. Asian J. Chem. 1999 11 1 207
    [Google Scholar]
  13. Kumar S. Bawa S. Drabu S. Kumar R. Gupta H. Recent Pat. Anti-Infect. Drug Discov. 2009 4 3 154 163 10.2174/157489109789318569 19545230
    [Google Scholar]
  14. Amir M. Kumar S. Indian J. Chem. Sect. [B] 2005 44 12 2532 2537
    [Google Scholar]
  15. Gowramma B. Jubie S. Kalirajan R. Gomathy S. Elango K. Int. J. Pharm. Tech. Res. 2009 1 2 347 352
    [Google Scholar]
  16. Lu Z.H. Gu X.J. Shi K.Z. Li X. Chen D.D. Chen L. Arab. J. Chem. 2017 10 5 624 630 10.1016/j.arabjc.2014.11.002
    [Google Scholar]
  17. Murugan V. Revathi S. Sumathi K. Geetha K.M. Divekar K. Asian J. Res. Chem. 2010 3 2 496 499
    [Google Scholar]
  18. Gilani S.J. Khan S.A. Alam O. Kumar H. Orient. J. Chem. 2008 24 2 607
    [Google Scholar]
  19. Tripathi A.C. Upadhyay S. Paliwal S. Saraf S.K. Med. Chem. Res. 2016 25 3 390 406 10.1007/s00044‑015‑1489‑3
    [Google Scholar]
  20. Singh N. Gupta M. Curr. Bioact. Compd. 2020 16 9 1260 1272 10.2174/1573407216666200128155640
    [Google Scholar]
  21. Nehra B. Rulhania S. Jaswal S. Kumar B. Singh G. Monga V. Eur. J. Med. Chem. 2020 205 112666 10.1016/j.ejmech.2020.112666 32795767
    [Google Scholar]
  22. Secrieru A. O’Neill P.M. Cristiano M.L.S. Molecules 2019 25 1 42 10.3390/molecules25010042 31877672
    [Google Scholar]
  23. Kitawat B.S. Singh M. New J. Chem. 2014 38 9 4290 10.1039/C4NJ00594E
    [Google Scholar]
  24. Desai N.C. Vaja D.V. Jadeja K.A. Joshi S.B. Khedkar V.M. Anti-Infect. Agents 2020 18 3 306 314
    [Google Scholar]
  25. Tanitame A. Oyamada Y. Ofuji K. Fujimoto M. Suzuki K. Ueda T. Terauchi H. Kawasaki M. Nagai K. Wachi M. Yamagishi J. Bioorg. Med. Chem. 2004 12 21 5515 5524 10.1016/j.bmc.2004.08.010 15465328
    [Google Scholar]
  26. Liu J.J. Sun J. Fang Y.B. Yang Y.A. Jiao R.H. Zhu H.L. Org. Biomol. Chem. 2014 12 6 998 1008 10.1039/c3ob41953c 24382549
    [Google Scholar]
  27. D’Atanasio N. Capezzone de Joannon A. Di Sante L. Mangano G. Ombrato R. Vitiello M. Bartella C. Magarò G. Prati F. Milanese C. Vignaroli C. Di Giorgio F.P. Tongiani S. PLoS One 2020 15 2 e0228509 10.1371/journal.pone.0228509 32074119
    [Google Scholar]
  28. Elkanzi N.A.A. Hrichi H. Bakr R.B. Hendawy O. Alruwaili M.M. Alruwaili E.D. Almamtrfi R.W. Alsharary H.K. J. Indian Chem. Soc. 2021 18 4 977 991 10.1007/s13738‑020‑02086‑8
    [Google Scholar]
  29. Jomova K. Raptova R. Alomar S.Y. Alwasel S.H. Nepovimova E. Kuca K. Valko M. Arch. Toxicol. 2023 97 10 2499 2574 10.1007/s00204‑023‑03562‑9 37597078
    [Google Scholar]
  30. Hanukoglu I. Drug Metab. Rev. 2006 38 1-2 171 196 10.1080/03602530600570040 16684656
    [Google Scholar]
  31. Kang M.Y. Tsuchiya M. Packer L. Manabe M. Acta Anaesthesiol. Scand. 1998 42 1 4 12 10.1111/j.1399‑6576.1998.tb05073.x
    [Google Scholar]
  32. Kumar A. Varadaraj B.G. Singla R.K. Bull. Fac. Pharm. Cairo Univ. 2013 51 2 167 173 10.1016/j.bfopcu.2013.04.002
    [Google Scholar]
  33. He J. Qiao W. An Q. Yang T. Luo Y. Eur. J. Med. Chem. 2020 195 112268 10.1016/j.ejmech.2020.112268
    [Google Scholar]
  34. Kuyper L.F. Baccanari D.P. Jones M.L. Hunter R.N. Tansik R.L. Joyner S.S. Boytos C.M. Rudolph S.K. Knick V. Wilson H.R. Caddell J.M. Friedman H.S. Comley J.C.W. Stables J.N. J. Med. Chem. 1996 39 4 892 903 10.1021/jm9505122 8632413
    [Google Scholar]
  35. Chawla P. Teli G. Gill R.K. Narang R.K. ChemistrySelect 2021 6 43 12101 12145 10.1002/slct.202102555
    [Google Scholar]
  36. Singh P. Kaur M. Sachdeva S. J. Med. Chem. 2012 55 14 6381 6390 10.1021/jm300644g 22734697
    [Google Scholar]
  37. Bayazeed A. Alenazi N.A. Alsaedi A.M.R. Ibrahim M.H. Al-Qurashi N.T. Farghaly T.A. J. Mol. Struct. 2022 1258 132653 10.1016/j.molstruc.2022.132653
    [Google Scholar]
  38. Othman I.M.M. Gad-Elkareem M.A.M. Amr A.E.G.E. Al-Omar M.A. Nossier E.S. Elsayed E.A. J. Enzyme Inhib. Med. Chem. 2020 35 1 1491 1502 10.1080/14756366.2020.1791842 32668994
    [Google Scholar]
  39. Yuthavong Y. Yuvaniyama J. Chitnumsub P. Vanichtanankul J. Chusacultanachai S. Tarnchompoo B. Vilaivan T. Kamchonwongpaisan S. Parasitology 2005 130 3 249 259 10.1017/S003118200400664X 15796007
    [Google Scholar]
  40. Bekhit A.A. Lodebo E.T. Hymete A. Ragab H.M. Bekhit S.A. Amagase K. Batubara A. Abourehab M.A.S. Bekhit A.E.D.A. Ibrahim T.M. J. Enzyme Inhib. Med. Chem. 2022 37 1 2320 2333 10.1080/14756366.2022.2117316 36036155
    [Google Scholar]
  41. Linda Ekawati L.E. Beta Achromi Nurohmah B.A.N. Jufrizal Syahri J.S. Bambang Purwono B.P. Sains Malays. 2022 51 10 3215 3236 10.17576/jsm‑2022‑5110‑09
    [Google Scholar]
  42. Dhameliya TM Kathuria D. Patel T.M. Dave B.P. Chaudhari A.Z. Vekariya D.D. Curr. Top Med. Chem. 2023 23 9 753 790 10.2174/1568026623666230427115241
    [Google Scholar]
  43. Blanco F.J. Guitian R. Moreno J. de Toro F.J. Galdo F. J. Rheumatol. 1999 26 6 1366 1373 10381057
    [Google Scholar]
  44. Fioravanti R. Bolasco A. Manna F. Rossi F. Orallo F. Ortuso F. Alcaro S. Cirilli R. Eur. J. Med. Chem. 2010 45 12 6135 6138 10.1016/j.ejmech.2010.10.005 20974503
    [Google Scholar]
  45. Sharma P.K. Kumar S. Kumar P. Kaushik P. Sharma C. Kaushik D. Aneja K.R. Med. Chem. Res. 2012 21 10 2945 2954 10.1007/s00044‑011‑9823‑x
    [Google Scholar]
  46. Mantzanidou M. Pontiki E. Hadjipavlou-Litina D. Molecules 2021 26 11 3439 10.3390/molecules26113439 34198914
    [Google Scholar]
  47. Schneider I. Bucar F. Phytother. Res. 2005 19 2 81 102 10.1002/ptr.1603 15852496
    [Google Scholar]
  48. Kostopoulou I. Diassakou A. Kavetsou E. Kritsi E. Zoumpoulakis P. Pontiki E. Hadjipavlou-Litina D. Detsi A. Mol. Divers. 2021 25 2 723 740 10.1007/s11030‑020‑10045‑x 32065346
    [Google Scholar]
  49. Frigola J. Colombo A. Pares J. Martinez L. Sagarra R. Roser R. Eur. J. Med. Chem. 1989 24 4 435 445 10.1016/0223‑5234(89)90089‑5
    [Google Scholar]
  50. Ali S.A. Awad S.M. Said A.M. Mahgoub S. Taha H. Ahmed N.M. J. Enzyme Inhib. Med. Chem. 2020 35 1 847 863 10.1080/14756366.2020.1742116 32216479
    [Google Scholar]
  51. Reddy M.V.R. Billa V.K. Pallela V.R. Mallireddigari M.R. Boominathan R. Gabriel J.L. Reddy E.P. Bioorg. Med. Chem. 2008 16 7 3907 3916 10.1016/j.bmc.2008.01.047 18272371
    [Google Scholar]
  52. van Hoorebeke C. Yang K. Mussetter S.J. Koch G. Rutz N. Lokey R.S. Crews P. Holman T.R. ACS Omega 2022 7 47 43169 43179 10.1021/acsomega.2c05877 36467910
    [Google Scholar]
  53. Lee C.K. Davies L. Wu Y.L. Mitsudomi T. Inoue A. Rosell R. Zhou C. Nakagawa K. Thongprasert S. Fukuoka M. Lord S. Marschner I. Tu Y.K. Gralla R.J. Gebski V. Mok T. Yang J.C.H. J. Natl. Cancer Inst. 2017 109 6 279 10.1093/jnci/djw279 28376144
    [Google Scholar]
  54. Normanno N. Maiello M.R. De Luca A. J. Cell. Physiol. 2003 194 1 13 19 10.1002/jcp.10194 12447985
    [Google Scholar]
  55. Sharma B. Singh V.J. Chawla P.A. Bioorg. Chem. 2021 116 105393 10.1016/j.bioorg.2021.105393 34628226
    [Google Scholar]
  56. Nagarajan R. Antimicrob. Agents Chemother. 1991 35 4 605 609 10.1128/AAC.35.4.605 2069366
    [Google Scholar]
  57. Taylor S.D. Palmer M. Bioorg. Med. Chem. 2016 24 24 6253 6268 10.1016/j.bmc.2016.05.052 27288182
    [Google Scholar]
  58. Otarigho B. Falade M.O. Bioinformation 2018 14 3 113 122 10.6026/97320630014113 29785070
    [Google Scholar]
  59. Verma R. Verma S.K. Rakesh K.P. Girish Y.R. Ashrafizadeh M. Sharath Kumar K.S. Rangappa K.S. Eur. J. Med. Chem. 2021 212 113134 10.1016/j.ejmech.2020.113134 33395624
    [Google Scholar]
  60. Fišar Z. Hroudová J. Raboch J. Neuroendocrinol. Lett. 2010 31 5 645 656 21200377
    [Google Scholar]
  61. Bijo M. Githa E.M Jerad S. Gülberk U. Gülberk S. Sockalingam A. Jobin V.K. Venkatesan J. Curr. Enzym. Inhib. 2016 12 2 115 122 10.2174/1573408012666160402001715
    [Google Scholar]
  62. Singh K. Pal R. Khan S.A. Kumar B. Akhtar M.J. J. Mol. Struct. 2021 1237 130369 10.1016/j.molstruc.2021.130369
    [Google Scholar]
  63. Ghabbour H.A. Kadi A.A. ElTahir K.E.H. Angawi R.F. El-Subbagh H.I. Med. Chem. Res. 2015 24 8 3194 3211 10.1007/s00044‑015‑1371‑3
    [Google Scholar]
  64. Shaaban M.R. Mayhoub A.S. Farag A.M. Expert Opin. Ther. Pat. 2012 22 3 253 291 10.1517/13543776.2012.667403 22397588
    [Google Scholar]
  65. Tripathi A.C. Upadhyay S. Paliwal S. Saraf S.K. Med. Chem. Res. 2018 27 5 1485 1503 10.1007/s00044‑018‑2167‑z
    [Google Scholar]
  66. Stephanie F Tambunan US Siahaan TJ Life 2022 12 11 1774 10.3390/life12111774
    [Google Scholar]
  67. Pedelac J.D. Nguyen M.C. Terwilliger T.C. Mourey L. J. Struct. Biol. 2020 545 566
    [Google Scholar]
  68. Roberto Chiarelli L. Mori G. Esposito M. Silvia Orena B. Rosalia Pasca M. Curr. Med. Chem. 2016 23 33 3813 3846 10.2174/1389557516666160831164925 27666933
    [Google Scholar]
  69. Kooner A. Thesis, The University of Auckland 2021
    [Google Scholar]
  70. Dixit S.R. Joshi S.D. Kulkarni V.H. Jalalpure S.S. Kumbar V.M. Mudaraddi T.Y. Nadagouda M.N. Aminabhavi T.M. Open Med. Chem. J. 2017 11 1 92 108 10.2174/1874104501711010092 29151986
    [Google Scholar]
  71. Ustuner Z. Saip P. Yasasever V. Vural B. Yazar A. Bal C. Ozturk B. Ozbek U. Topuz E. Med. Oncol. 2008 25 4 394 399 10.1007/s12032‑008‑9052‑4 18317954
    [Google Scholar]
  72. Tanno S. Ohsaki Y. Nakanishi K. Toyoshima E. Kikuchi K. Lung Cancer 2004 46 1 11 19 10.1016/j.lungcan.2004.03.006 15364128
    [Google Scholar]
  73. Dimova I. Popivanov G. Djonov V. J. BUON 2014 19 1 15 21 24659637
    [Google Scholar]
  74. Roskoski R. Jr Pharmacol. Res. 2017 120 116 132 10.1016/j.phrs.2017.03.010 28330784
    [Google Scholar]
  75. Upadhyay N. Tilekar K. Safuan S. Kumar A.P. Schweipert M. Meyer-Almes F.J. Ramaa C.S. Future Med. Chem. 2021 13 22 1963 1986 10.4155/fmc‑2021‑0139 34581188
    [Google Scholar]
  76. Ferenz N.P. Gable A. Wadsworth P. Semin. Cell Dev. Biol. 2010 21 3 255 259 10.1016/j.semcdb.2010.01.019 20109572
    [Google Scholar]
  77. Huszar D. Theoclitou M.E. Skolnik J. Herbst R. Cancer Metastasis Rev. 2009 28 1-2 197 208 10.1007/s10555‑009‑9185‑8 19156502
    [Google Scholar]
  78. Myers S.M. Collins I. Future Med. Chem. 2016 8 4 463 489 10.4155/fmc.16.5 26976726
    [Google Scholar]
  79. Roecker A.J. Coleman P.J. Mercer S.P. Schreier J.D. Buser C.A. Walsh E.S. Hamilton K. Lobell R.B. Tao W. Diehl R.E. South V.J. Davide J.P. Kohl N.E. Yan Y. Kuo L.C. Li C. Fernandez-Metzler C. Mahan E.A. Prueksaritanont T. Hartman G.D. Bioorg. Med. Chem. Lett. 2007 17 20 5677 5682 10.1016/j.bmcl.2007.07.074
    [Google Scholar]
  80. Mahale S. Bharate S.B. Manda S. Joshi P. Jenkins P.R. Vishwakarma R.A. Chaudhuri B. Cell Death Dis. 2015 6 5 e1743 10.1038/cddis.2015.96 25950473
    [Google Scholar]
  81. Sliva D. Curr. Cancer Drug Targets 2004 4 4 327 336 10.2174/1568009043332961 15180498
    [Google Scholar]
  82. Dabydeen D.A. Florence G.J. Paterson I. Hamel E. Cancer Chemother. Pharmacol. 2004 53 5 397 403 10.1007/s00280‑003‑0755‑0 15060743
    [Google Scholar]
  83. Li Q. Sham H.L. Expert Opin. Ther. Pat. 2002 12 11 1663 1702 10.1517/13543776.12.11.1663
    [Google Scholar]
  84. Rajak H. Kumar Dewangan P. Patel V. Kumar Jain D. Singh A. Veerasamy R. Chander Sharma P. Dixit A. Curr. Pharm. Des. 2013 19 10 1923 1955 10.2174/1381612811319100013 23237054
    [Google Scholar]
  85. Fertig B. Baillie G. J. Cardiovasc. Dev. Dis. 2018 5 1 8 10.3390/jcdd5010008 29385021
    [Google Scholar]
  86. Dastidar S.G. Rajagopal D. Ray A. Curr. Opin. Investig. Drugs 2007 8 5 364 372 17520865
    [Google Scholar]
  87. Abusnina A. Keravis T. Zhou Q. Justiniano H. Lobstein A. Lugnier C. Thromb. Haemost. 2015 113 2 319 328 10.1160/TH14‑05‑0454 25230992
    [Google Scholar]
  88. Schafer P.H. Parton A. Capone L. Cedzik D. Brady H. Evans J.F. Man H.W. Muller G.W. Stirling D.I. Chopra R. Cell. Signal. 2014 26 9 2016 2029 10.1016/j.cellsig.2014.05.014 24882690
    [Google Scholar]
  89. Giembycz M.A. Monaldi Arch. Chest Dis. 2002 57 1 48 64 12174704
    [Google Scholar]
  90. Crespo M.I. Gràcia J. Puig C. Vega A. Bou J. Beleta J. Doménech T. Ryder H. Segarra V. Palacios J.M. Bioorg. Med. Chem. Lett. 2000 10 23 2661 2664 10.1016/S0960‑894X(00)00548‑5
    [Google Scholar]
  91. Vahedpour T. Hamzeh-Mivehroud M. Hemmati S. Dastmalchi S. ChemistrySelect 2021 6 25 6483 6506 10.1002/slct.202101467
    [Google Scholar]
  92. Mahé O. Frath D. Dez I. Marsais F. Levacher V. Brière J.F. Org. Biomol. Chem. 2009 7 18 3648 3651 10.1039/b911577c 19707665
    [Google Scholar]
  93. Hu F. Zhang H. Chu Y. Hui X.P. Org. Chem. Front. 2022 9 10 2734 2738 10.1039/D2QO00147K
    [Google Scholar]
  94. Scinto S.L. Bilodeau D.A. Hincapie R. Lee W. Nguyen S.S. Xu M. am Ende C.W. Finn M.G. Lang K. Lin Q. Pezacki J.P. Prescher J.A. Robillard M.S. Fox J.M. Nat. Rev. Methods Primers. 2021 1 1 30 10.1038/s43586‑021‑00028‑z 34585143
    [Google Scholar]
  95. Manna K. Agrawal Y.K. Bioorg. Med. Chem. Lett. 2009 19 10 2688 2692 10.1016/j.bmcl.2009.03.161 19395261
    [Google Scholar]
  96. Martins M.A.P. Beck P. Machado P. Brondani S. Moura S. Zanatta N. Bonacorso H.G. Flores A.F.C. J. Braz. Chem. Soc. 2006 17 2 408 411 10.1590/S0103‑50532006000200027
    [Google Scholar]
  97. Majumder A. Gupta R. Jain A. Green Chem. Lett. Rev. 2013 6 2 151 182 10.1080/17518253.2012.733032
    [Google Scholar]
  98. Waldman A.J. Ng T.L. Wang P. Balskus E.P. Chem. Rev. 2017 117 8 5784 5863 10.1021/acs.chemrev.6b00621 28375000
    [Google Scholar]
  99. Yavari I. Fadakar Y. Mol. Divers. 2022 26 2 1141 1150 10.1007/s11030‑021‑10240‑4 34129183
    [Google Scholar]
  100. Lohidakshan K. Rajan M. Ganesh A. Paul M. Jerin J. Bangladesh J. Pharmacol. 2018 13 1 23 29 10.3329/bjp.v13i1.33625
    [Google Scholar]
  101. Ismail A.H. Abdula A.M. Tomi I.H. Al-Daraji A.H.R. Baqi Y. J. Med. Chem. 2020 16 1 2
    [Google Scholar]
  102. Bandgar B.P. Adsul L.K. Chavan H.V. Jalde S.S. Shringare S.N. Shaikh R. Meshram R.J. Gacche R.N. Masand V. Bioorg. Med. Chem. Lett. 2012 22 18 5839 5844 10.1016/j.bmcl.2012.07.080 22901385
    [Google Scholar]
  103. Rana M. Hungyo H. Parashar P. Ahmad S. Mehandi R. Tandon V. Raza K. Assiri M.A. Ali T.E. El-Bahy Z.M. Rahisuddin RSC Advances 2023 13 38 26766 26779 10.1039/D3RA04873J 37681049
    [Google Scholar]
  104. Mansour B. El-Sherbeny M.A. Al-Omary F.A.M. Saber S. Ramadan H.A. El-Baz A.M. Mourad A.A.E. Abdel-Aziz N.I. ACS Omega 2023 8 46 44250 44264 10.1021/acsomega.3c06936 38027391
    [Google Scholar]
  105. Dawane B.S. Konda S.G. Mandawad G.G. Shaikh B.M. Eur. J. Med. Chem. 2010 45 1 387 392 10.1016/j.ejmech.2009.10.015 19896247
    [Google Scholar]
  106. Deshpande S.R. Nagrale S.N. Patil M.V. Chavan S.S. Indian J. Pharm. Sci. 2015 77 1 24 33 10.4103/0250‑474X.151588 25767315
    [Google Scholar]
  107. Lévai A. Jekő J. Monatsh. Chem. 2006 137 3 339 345 10.1007/s00706‑006‑0437‑9
    [Google Scholar]
  108. Yar M.S. Siddiqui A.A. Ali M.A. Murugan V. Chandrashekhar R. J. Chin. Chem. Soc. (Taipei) 2007 54 1 81 86 10.1002/jccs.200700014
    [Google Scholar]
  109. Bondock S. Naser T. Ammar Y.A. Eur. J. Med. Chem. 2013 62 270 279 10.1016/j.ejmech.2012.12.050 23357308
    [Google Scholar]
  110. Sebest F. Lachhani K. Pimpasri C. Casarrubios L. White A.J.P. Rzepa H.S. Díez-González S. Adv. Synth. Catal. 2020 362 9 1877 1886 10.1002/adsc.201901614
    [Google Scholar]
  111. Sharma P. Singh M. Mathew B. ChemistrySelect 2021 6 7 1404 1429 10.1002/slct.202004188
    [Google Scholar]
  112. Passedouet A.H. Roussos M.G. Pigeot J. Paillole N. US Patent 3652584A 1972
  113. Pearson I. Harlow E. US Patent 3883549A 1975
  114. Verge J.P. Neville M.C. Friedman H. US Patent 3947467 1976
  115. Fahmy M.A.H. Harrison C.R. Lahm G.P. Stevenson T.M. EP Patent 0365155B1 1995
  116. Fuchs R. Fischer R. Erdelen C. Stendel W. US Patent 5502070A 1996
  117. Donald J.P. US Patent 6630468B2 2003
  118. Brohm D. Diedrichs N. Hubsch W. FRÖHLEN B.N. Gerdes C. Gnoth M.J. Perzborn E. Vöhringer V. WO Patent 2006072349A1 2006
  119. Brohm D. Diedrichs N. Hubsch W. FRÖHLEN B.N. Gerdes C. Gnoth M.J. Perzborn E. Vöhringer V. WO Patent 2006072351A1 2006
  120. Allerheiligen S. Brohm D. Diedrichs N. Hubsch W. Fröhlen B.N. Gerdes C. Gnoth M.J. Perzborn E. Vöhringer V. WO Patent 2006072350A1 2006
  121. McElroy J.F. Chorvat R.J. 2012 US Patent 8236821B2
  122. McElroy J.F. Chorvat R.J. US Patent 8648072B2 2014
  123. Debrabander J. Liang Q. Levine B. Chiang W.C. CA Patent 3102828A1 2019
  124. Valery N. US Patent 10800966B2 2020
/content/journals/loc/10.2174/0115701786329318240925115206
Loading
/content/journals/loc/10.2174/0115701786329318240925115206
Loading

Data & Media loading...

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test