Yıl: 2021 Cilt: 45 Sayı: 6 Sayfa Aralığı: 1841 - 1853 Metin Dili: İngilizce DOI: 10.3906/kim-2104-54 İndeks Tarihi: 01-07-2022

Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles

Öz:
Heterocyclic compounds with diaryl substituents have been a milestone approach for selective cyclooxygenase 2 (COX 2) inhibition by bioisosteric replacements and modifications. It is also known that thiazole derivatives have different pharmacological activities. In this study, nine novel 2-[(1,5-diphenyl-1H-imidazole-2-yl)thio]-N-(thiazole-2-yl)acetamide derivatives (Compound 1-9) were synthesized via the reaction of 1,5-disubstitued phenyl-imidazole-2-thiole and N-thiazole acetamide. The inhibitory effects of COX-1 and COX-2 enzymes were tested for the synthesized compounds. Enzyme-ligand interactions of the most active compound on COX subtypes were elucidated by molecular modeling studies. The percent inhibitory effect for compound 1, which is the naked derivative among all the compounds, was found to be the most active on COX-2 at 10 μM concentration $(C1_{COX-2}: 88%, SC-560_{COX-2}: 98.2%, C1_{COX-1}: 60.9%)$; whereas compound 9 showed the highest inhibitory effect and was found to be the most selective derivative on COX-1 isoenzyme $(C9_{COX-1}: 85%, DuP-697_{COX-1}: 97.2%, C9_{COX-2}: 57.9%)$.
Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
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  • 1. Kwon J, Kim MJ, Kim DC, Kwon H, Ryu SM et al. Anti-inflammatory spiroditerpenoids from Penicillium bialowiezense. Bioorganic Chemistry 2021; 113:105012. doi: 10.1016/j.bioorg.2021.105012
  • 2. Yarla NS, Pathuri G, Gali H, Terzyan S, Panneer S et al. Discovery and Development of a Novel mPGES-1/5-LOX Dual Inhibitor LFA-9 for Prevention and Treatment of Chronic Inflammatory Diseases. Journal of Inflammation Research 2020; 31 (13): 1261-1278. doi: 10.2147/ JIR.S286110
  • 3. Murphy RC, Hammarström S, Samuelsson B, Leukotriene C. A slow-reacting substance from murine mastocytoma cells. Proceedings of the National Academy of Sciences of the United States of America 1979; 76 (9): 4275-4279. doi: 10.1073/pnas.76.9.4275
  • 4. Allaj V, Guo C, Nie D. Non-steroid anti-inflammatory drugs, prostaglandins, and cancer. Cell Bioscience 2013; 3: (8). doi: 10.1186/2045- 3701-3-8
  • 5. Kawamori T, Rao CV, Seibert K, Reddy BS. Chemopreventive activity of celecoxib, a specific cyclooxygenase-2 inhibitor, against colon carcinogenesis. Cancer Research 1998; 58 (3): 409-412.
  • 6. Katori M, Majima M. Cyclooxygenase-2: Its rich diversity of roles and possible application of its selective inhibitors. Inflammation Research 2000; 49 (8): 367-392.
  • 7. Vane JR, Botting RM. Anti-inflammatory drugs and their mechanism of action. Inflammation Research 1998; 47: 78-87. doi: 10.1007/ s000110050605
  • 8. Patrono C. Cardiovascular effects of cyclooxygenase-2 inhibitors: a mechanistic and clinical perspective. British Journal of Clinical Pharmacology 2016; 82 (4): 957–964. doi: 10.1111/bcp.13048
  • 9. Chen CS, Tan CM, Huang CH, Chang LC, Wang JP. Discovery of 3-(4-bromophenyl)-6-nitrobenzo[1.3.2] dithiazoliumylide 1,1-dioxide as a novel dual cyclooxygenase/5-lipoxygenase inhibitor that also inhibits tumor necrosis factor-α production. Bioorganic & Medicinal Chemistry 2010; 18 (2): 597-604. doi: 10.1016/j.bmc.2009.12.008
  • 10. Saberi MR, Hadizadeh F, Imenshahidi M, Shakeri H, Toktam S et al. Synthesis and Effects of 4,5-Diaryl-2-(2-alkylthio-5-imidazolyl) Imidazoles as Selective Cyclooxygenase Inhibitors. Science 2010; 13 (4): 225-231. doi: 10.22038/IJBMS.2010.5121
  • 11. Dinges J, Harris CM, Wallace GA, Argiriadi MA, Queeney KL et al. Hit-to-lead evaluation of a novel class of sphingosine 1-phosphate lyase inhibitors. Bioorganic & Medicinal Chemistry Letters 2016; 26 (9): 2297–2302. doi: 10.1016/j.bmcl.2016.03.043
  • 12. Pandeya SN, Bipin B, Aparna M, Ashish B. Synthesis and analgesic activity of 2-S-benzyl-1,5-diphenyl-1H imidazoles. Journal of Scientific Research in Pharmacy 2012; 1 (3): 19-22.
  • 13. Demirayak S, Kayagil I, Yurttas L, Aslan R. Synthesis of some imidazolyl-thioacetyl-pyrazolinone derivatives and their antinociceptive and anticancer activities. Journal of Enzyme Inhibition and Medicinal Chemistry 2009; 25 (1): 74-79. doi: 10.3109/14756360903016751
  • 14. Papadopoulou C, Geronikaki A, Hadjipavlou-Litina D. Synthesis and biological evaluation of new thiazolyl/benzothiazolyl-amides, derivatives of 4-phenyl-piperazine. Farmaco 2005; 60 (11–12): 969-973. doi: 10.1016/j.farmac.2005.06.014
  • 15. Kaur A, Wakode S, Pathak DP, Sharma V, Shakya AK. Synthesis, cyclooxygenase-2 inhibition, anti-inflammatory evaluation and docking study of substituted-N-(3,4,5-trimethoxyphenyl)-benzo[d]oxazole derivatives. Medicinal Chemistry 2018; 14 (7): 660-673. doi: 10.2174/ 1573406414666180322091832
  • 16. Chegaev K, Lazzarato L, Tosco P, Cena C, Marini E et al. NO-donor COX-2 inhibitors. New nitrooxy-substituted 1,5-diarylimidazoles endowed with COX-2 inhibitory and vasodilator properties. Journal of Medicinal Chemistry 2007; 50 (7): 1449-1457. doi: 10.1021/ jm0607247
  • 17. Assadieskandar A, Amirhamzeh A, Salehi M, Ozadali K, Ostad S et al. Synthesis, cyclooxygenase inhibitory effects, and molecular modeling study of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and -2-alkylsulfonyl-1H- imidazole derivatives. Bioorganic & Medicinal Chemistry 2013; 21 (8): 2355-2362. doi: 10.1016/j.bmc.2013.01.058
  • 18. Chavatte P, Yous S, Marot C, Baurin N, Lesieur D. Three-dimensional quantitative structure-activity relationships of cyclo-oxygenase-2 (COX-2) inhibitors: A comparative molecular field analysis. Journal of Medicinal Chemistry 2001; 44 (20): 3223-3230. doi: 10.1021/ jm0101343
  • 19. Chen H, Li Q, Yao X, Fan BT, Yuan S et al. CoMFA/CoMSIA/HQSAR and Docking study of the binding mode of selective cyclooxygenase (COX-2) inhibitors. QSAR Combinatorial Science 2004; 23 (1): 36-55. doi: 10.1002/qsar.200330844
  • 20. Zarghi A, Arfaei S, Ghodsi R. Design and synthesis of new 2,4,5-triarylimidazole derivatives as selective cyclooxygenase (COX-2) inhibitors. Medicinal Chemistry Research 2012; 21 (8): 1803-1810. doi: 10.1007/s00044-011-9710-5
  • 21. Santosa H, Yuniarta TA, Kesuma D, Putra GS (2019). 2-Hydroxy-N′-(4-Fluorobenzoyl)Benzohydrazide. Molbank, 2020 (1): M1103. doi:10.3390/m1103.
  • 22. Abdel-Sayed MA, Bayomi SM, El-Sherbeny MA, Abdel-Aziz NI, ElTahir KEH et al. Synthesis, anti-inflammatory, analgesic, COX-1/2 inhibition activities and molecular docking study of pyrazoline derivatives. Bioorganic & Medicinal Chemistry 2016; 24 (9): 2032-2042. doi: 10.1016/j.bmc.2016.03.032
  • 23. Qandeel NA, El-Damasy AK, Sharawy MH, Bayomi SM, El-Gohary NS. Synthesis, in vivo anti-inflammatory, COX-1/COX-2 and 5-LOX inhibitory activities of new 2,3,4-trisubstituted thiophenes. Bioorganic Chemistry 2020; 103890. doi: 10.1016/j.bioorg.2020.103890
  • 24. Abdellatif KRA, Fadaly WAA, Elshaier YAM, Ali WAM, Kamel GM. Non-acidic 1,3,4-trisubstituted-pyrazole derivatives as lonazolac analogs with promising COX-2 selectivity, anti-inflammatory activity and gastric safety profile. Bioorganic Chemistry 2018; 77: 568-578. doi:10.1016/j.bioorg.2018.02.018
  • 25. Abdel-Sayed MA, Bayomi SM, El-Sherbeny MA, Abdel-Aziz NI, ElTahir KEH et al. Synthesis, anti-inflammatory, analgesic, COX-1/2 inhibition activities and molecular docking study of pyrazoline derivatives. Bioorganic & Medicinal Chemistry 2016; 24 (9): 2032-2042. doi:10.1016/j.bmc.2016.03.032
APA ŞAHİN Z, Kalkan M, Berk B, Yurttaş L, BENDER C, BILTEKIN S, Demirayak Ş (2021). Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. , 1841 - 1853. 10.3906/kim-2104-54
Chicago ŞAHİN ZAFER,Kalkan Melike,Berk Barkin,Yurttaş Leyla,BENDER Ceysu,BILTEKIN SEVDE NUR,Demirayak Şeref Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. (2021): 1841 - 1853. 10.3906/kim-2104-54
MLA ŞAHİN ZAFER,Kalkan Melike,Berk Barkin,Yurttaş Leyla,BENDER Ceysu,BILTEKIN SEVDE NUR,Demirayak Şeref Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. , 2021, ss.1841 - 1853. 10.3906/kim-2104-54
AMA ŞAHİN Z,Kalkan M,Berk B,Yurttaş L,BENDER C,BILTEKIN S,Demirayak Ş Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. . 2021; 1841 - 1853. 10.3906/kim-2104-54
Vancouver ŞAHİN Z,Kalkan M,Berk B,Yurttaş L,BENDER C,BILTEKIN S,Demirayak Ş Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. . 2021; 1841 - 1853. 10.3906/kim-2104-54
IEEE ŞAHİN Z,Kalkan M,Berk B,Yurttaş L,BENDER C,BILTEKIN S,Demirayak Ş "Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles." , ss.1841 - 1853, 2021. 10.3906/kim-2104-54
ISNAD ŞAHİN, ZAFER vd. "Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles". (2021), 1841-1853. https://doi.org/10.3906/kim-2104-54
APA ŞAHİN Z, Kalkan M, Berk B, Yurttaş L, BENDER C, BILTEKIN S, Demirayak Ş (2021). Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. Turkish Journal of Chemistry, 45(6), 1841 - 1853. 10.3906/kim-2104-54
Chicago ŞAHİN ZAFER,Kalkan Melike,Berk Barkin,Yurttaş Leyla,BENDER Ceysu,BILTEKIN SEVDE NUR,Demirayak Şeref Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. Turkish Journal of Chemistry 45, no.6 (2021): 1841 - 1853. 10.3906/kim-2104-54
MLA ŞAHİN ZAFER,Kalkan Melike,Berk Barkin,Yurttaş Leyla,BENDER Ceysu,BILTEKIN SEVDE NUR,Demirayak Şeref Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. Turkish Journal of Chemistry, vol.45, no.6, 2021, ss.1841 - 1853. 10.3906/kim-2104-54
AMA ŞAHİN Z,Kalkan M,Berk B,Yurttaş L,BENDER C,BILTEKIN S,Demirayak Ş Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. Turkish Journal of Chemistry. 2021; 45(6): 1841 - 1853. 10.3906/kim-2104-54
Vancouver ŞAHİN Z,Kalkan M,Berk B,Yurttaş L,BENDER C,BILTEKIN S,Demirayak Ş Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. Turkish Journal of Chemistry. 2021; 45(6): 1841 - 1853. 10.3906/kim-2104-54
IEEE ŞAHİN Z,Kalkan M,Berk B,Yurttaş L,BENDER C,BILTEKIN S,Demirayak Ş "Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles." Turkish Journal of Chemistry, 45, ss.1841 - 1853, 2021. 10.3906/kim-2104-54
ISNAD ŞAHİN, ZAFER vd. "Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles". Turkish Journal of Chemistry 45/6 (2021), 1841-1853. https://doi.org/10.3906/kim-2104-54