Synthesis, Characterization and Thermal Analysis of Novel Methylene Bridged Bis-carbazole Based Bisbenzimidazoles

Year 2022, , 281 - 286, 31.12.2022

Mehmet Fatih Saglam

https://doi.org/10.17350/HJSE19030000281

Abstract

The synthesis of novel bis(3-carbazoly1)methane linked bis-benzimidazoles is described. Construction of symmetrical bis-benzimidazoles on the bis-carbazolylmethane scaffold was succeeded by condensation reaction of benzene-1,2-diamine derivatives with bis(9-ethyl-9H-carbazole-3-carbaldehyde). The structural analysis of the targeted compounds 4-7 were confirmed by NMR, FT-IR spectroscopy and mass spectrometry. The thermal stability of final products 4-7 was also studied by thermogravimetric analysis (TGA).

Keywords

Bis-benzimidazole, Bis-carbazole, Formylation, Thermal stability

References

• 1. Eftekhari-Sis B, Zirak M, Akbari A. Arylglyoxals in synthesis of heterocyclic compounds. Chemical Reviews 113 (2013) 2958–3043.
• 2. Ju Y.Varma RS. Aqueous N-heterocyclization of primary amines and hydrazines with dihalides: microwave-assisted syntheses of N-azacycloalkanes, isoindole, pyrazole, pyrazolidine, and phthalazinederivatives. Journal of Organic Chemistry 71 (2006) 135–141.
• 3. Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. A review on recent advances in nitrogen-containing molecules and their biological applications. Molecules 25 (2020) 1909-1951.
• 4. Bingul M, Şenkuytu E, Saglam MF, Boga M, Kandemir H, Sengul IF. Synthesis, photophysical and antioxidant properties of carbazole based bis thiosemicarbazones. Research on Chemical Intermediates 45 (2019) 4487-4499.
• 5. Saglam MF, Gündogdu A, Hora M, Kandemir H, Sengul IF.Synthesis of Pyrrolo[3,2-c]carbazole-2-carbohydrazide and Pyrrolo[3,2-c]carbazol-2-yl-1,3,4-oxadiazole and Their in vitro Antibacterial Evaluation. Synthetic Communications 51 (2021) 3164-3174.
• 6. Sengul IF, Bingul M, Kandemir H, Kumar N, Black DStC. Synthesis, Reactivity and Biological Properties of Methoxy-Activated Indoles. in: Attanasi OA, Gabriele B, Merino P, Spinelli D (Eds.). Targets in Heterocyclic Systems. Società Chimica Italiana, Italy, pp. 162-212, 2021.
• 7. Pathare B, Bansode T. Review- biological active benzimidazole derivatives. Results in Chemistry 3 (2021) 100200.
• 8. Negi DS, Kumar G, SinghM, Singh N. Antibacterial Activity of Benzimidazole Derivatives: A Mini Review. Research & Reviews: Journal of Chemistry 6 ( 2017) 18-28.
• 9. Bashir M, Bano A, Ijaz AS, Chaudhary BA. Recent Developments and Biological Activities of N-Substituted Carbazole Derivatives: A Review. Molecules 20 (2015)13496-13517.
• 10. Knölker HJ, Reddy KR. Isolation and Synthesis of Biologically Active Carbazole Alkaloids. Chemical Reviews 102 (2002) 4303−4427.
• 11. Son DS, Lee ES, Adunyah SA. The Antitumor Potentials of Benzimidazole Anthelmintics as Repurposing Drugs. Immune Network 20 (2020) 1−20.
• 12. Satija G, Sharma B, Madan A, Iqubal A, Shaquiquzzaman M, Akhter M, Parvez S, Khan MA, Alam MM. Benzimidazole based derivatives as anticancer agents: Structure activity relationship analysis for various targets. Journal of Heterocyclic Chemistry 59 (2022) 22−66.
• 13. Dokla EME, Abutaleb NS, Milik SN, Li D, El-Baz K, Shalaby MAW, Al-Karaki R, Nasr M, Klein CD, Abouzid KAM, Seleem MN. Development of benzimidazole-based derivatives as antimicrobial agents and their synergistic effect with colistin against gram-negative bacteria. European Journal of Medicinal Chemistry 186 (2020) 111850.
• 14. Porcari AR, Devivar RV, Kucera LS, Drach JC, Townsend LB. Design, Synthesis, and Antiviral Evaluations of 1-(Substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as Nonnucleoside Analogues of 2,5,6-Trichloro-1-(β-d-ribofuranosyl)benzimidazole. Journal of Medicinal Chemistry 41 (1998) 1252-1262.
• 15. Migawa MT, Girardet JL, Walker JA, Koszalka GW, Chamberlain SD, Drach JC, Townsend LB. Design, Synthesis, and Antiviral Activity of α-Nucleosides:  d- and l-Isomers of Lyxofuranosyl- and (5-Deoxylyxofuranosyl)benzimidazoles. Journal of Medicinal Chemistry 41 (1998) 1242-1251.
• 16. Tamm I, Folkers K, Shunk CH, Horsfall FL, Jr MD. Inhibition of Influenza Virus Multiplication by N-Glycosides of Benzimidazoles. Journal of Experimental Medicine 99 (1954) 227-250.
• 17. Alpan AS, Zencir S, Zupkó I, Coban G, Réthy B, Gunes HS, Topcu Z. Biological activity of bis-benzimidazole derivatives on DNA topoisomerase I and HeLa, MCF7 and A431 cells. Journal of Enzyme Inhibition and Medicinal Chemistry 24 (2009) 844-849.
• 18. Maji B, Kumar K, Kaulage M, Muniyappa K, Bhattacharya S. Design and Synthesis of New Benzimidazole–Carbazole Conjugates for the Stabilization of Human Telomeric DNA, Telomerase Inhibition, and Their Selective Action on Cancer Cells. Journal of Medicinal Chemistry 57 (2014) 6973-6988.
• 19. Neidle S, Mann J, Rayner EL, Baron A, Opoku-Boahen Y, Simpson IJ, Smith NJ, Fox KR, Hartleyd JA, Kellande LR. Symmetric bis-benzimidazoles: new sequence-selective DNA-binding molecules. Chemical Communications (1999) 929–930.
• 20. Chaudhuri P, Ganguly B, Bhattacharya S. An Experimental and Computational Analysis on the Differential Role of the Positional Isomers of Symmetric Bis-2-(pyridyl)-1H-benzimidazoles as DNA Binding Agents. Journal of Organic Chemistry 72 (2007) 1912-1923.
• 21. Bhattacharya S, Chaudhuri P, Jain AK, Paul A. Symmetrical Bisbenzimidazoles with Benzenediyl Spacer: The Role of the Shape of the Ligand on the Stabilization and Structural Alterations in Telomeric G-Quadruplex DNA and Telomerase Inhibition. Bioconjugate Chemistry 21 (2010) 1148-1159.
• 22. Soderlind KJ, Gorodetsky B, Singh AK, Bachur NR, Miller GG, Lown JW. Bis-benzimidazole anticancer agents: targeting human tumour helicases. Anti-Cancer Drug Design 14(1999) 19-36.
• 23. Huang ST, Hseib IJ, Chen C. Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles. Bioorganic & Medicinal Chemistry 14 (2006) 6106–6119.
• 24. Hebishy AMS, Abdelfattah MS, Elmorsy A, Elwahy AHM. Synthesis of novel bis- and poly(benzimidazoles) as well as bis- and poly(benzothiazoles) as anticancer agents. Journal of Heterocyclic Chemistry 57 (2020) 2256– 2270.
• 25. Küçükbay H, Yılmaz Ü, Şireci N, Güvenç AN. Synthesis and antimicrobial activities of some bridged bis-benzimidazole derivatives. Turkish Journal of Chemistry 35 (2011) 561 – 571.
• 26. Moreira JB, Mann J, Neidle S, McHugh TD, Taylor PW. Antibacterial activity of head-to-head bis-benzimidazoles. International Journal of Antimicrobial Agents 42 (2013) 361-366.
• 27. Smaili, A. Jebbari, S. Rifai, L.A, Faize L, Koussa T, Sir HA, Makroum K, Belfaiza M, Kihel A, Ahbala M, Venisse JS, Faize M. Synthesis and in planta antibacterial activity of head-to-head bis-benzimidazole and bis-benzoxazole derivatives. Phytoparasitica 47 (2019) 733–741.
• 28. Rahman, M. M. and Gray A. I. A benzoisofuranone derivative and carbazole alkaloids from Murraya koenigii and their antimicrobial activity. Phytochemistry 66 (2005) 1601-1606.
• 29. David CI, Prabakaran G, Karuppasamy A, Veetil JC, Kumar RS, Almansour AI, Perumal, Ramalingan KC, Nandhakumar R. A single carbazole based chemosensor for multiple targets: Sensing of Fe3+ and arginine by fluorimetry and its applications, Journal of Photochemistry and Photobiology A: Chemistry 425 (2022) 113693.
• 30. Feng XJ, Tian PZ, Xu Z, Chen SF, Wong MS. Fluorescence-Enhanced Chemosensor for Metal Cation Detection Based on Pyridine and Carbazole. The Journal of Organic Chemistry 78 (2013) 11318-11325.
• 31. Sathiyan G, Sivakumar EKT, Ganesamoorthy R, Thangamuthu R, P Sakthivel P. Review of carbazole based conjugated molecules for highly efficient organic solar cell application. Tetrahedron Letters 57 (2016) 243-252.
• 32. Ledwon P. Recent advances of donor-acceptor type carbazole-based molecules for light emitting applications. Organic Electronics 75 (2019) 105422.
• 33. Xue YJ, Li MY, Jin XJ, Zheng CJ, Piao HR. Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents. Journal of Enzyme Inhibition and Medicinal Chemistry 36 (2021) 296-307.
• 34. Caruso A, Ceramella J, Iacopetta D, Saturnino C, Mauro MV, Bruno R, Aquaro S, Sinicropi MS. Carbazole Derivatives as Antiviral Agents: An Overview. Molecules. 24 (2019) 1912.
• 35. Liu LX, Wang XQ, Zhou B, Yang LJ, Li Y, Zhang HB, Yang XD. Synthesis and antitumor activity of novel N-substituted carbazole imidazolium salt derivatives. Scientific Reports 5(2015) 13101.
• 36. Bringmann G. Tasler S. Synthesis of methylene-bridged binary carbazole alkaloids and a related tricarbazole. Tetrahedron 57 (2001) 2337-2343.
• 37. Börger C, Schmid WA, Knölker H. First total syntheses of chrestifoline-B and (±)-chrestifoline-C, and improved synthetic routes to bismurrayafoline-A, bismurrayafolinol and chrestifoline-D. Journal of Organic and Biomolecular Chemistry 12 (2014) 3831-3835.
• 38. Horton DA, Bourne GT, Smythe ML. The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures. Chemical Reviews 103 (2003) 893-930.
• 39. Gil C, Brase S. Solid-Phase Synthesis of Biologically Active Benzoannelated Nitrogen Heterocycles: An Update. Journal of Combinatorial Chemistry 11 (2009) 175-97.
• 40. Armarego WLF, Chai CLL. Purification of Laboratory Chemicals, seventh ed. Elsevier, Oxford, 2013.
• 41. Sengul IF, Wood K, Bowyer PK, Bhadbhade, Chen R, Kumar N, Black DStC. Synthesis of new di-(3-indolyl)arenes. Tetrahedron 68 (2012) 7429-7434.
• 42. Kandemir H, Sengul IF, Kumar N, Black, DStC. Synthesis of Imine and Amine-Linked Macrocycles Containing Tris-Indoles. Australian Journal Chemistry 70 (2017) 1196-1201.
• 43. Kandemir H, Saglam MF, Sengul IF. Synthesis of Methylene Bridged Bis-pyrrolo[3,2-c] Carbazoles via an Unusual Vilsmeier-Haack Product of N-ethylcarbazole. Polycyclic Aromatic Compounds 40 (2020) 516-523.
• 44. Sengul IF, Astarci E, Kandemir H. Synthesis of novel pyrrolo[3,2-c]carbazole and dipyrrolo[3,2-c:2',3'-g]carbazole derivatives. Synlett 27 (2016) 1277-1281.
• 45. Wright JB. The Chemistry of the Benzimidazoles. Chemical Reviews 48 (1951) 397-541.
• 46. Faheem M, Rathaur A, Pandey A, Singh VK, Tiwari AK. A Review on the Modern Synthetic Approach of Benzimidazole Candidate. Chemistry Select 5 (2020) 3981-3994.
• 47. Alaqeel SI. Synthetic approaches to benzimidazoles from o-phenylenediamine: A literature review. Journal of Saudi Chemical Society 21 (2017) 229-237.