SavedAdd your journal

Journals / Hittite Journal of Science and Engineering / 2026 / Volume: 9 Issue: 3

Synthesis of New Methoxy Actived Mono and Bis-indole Compounds

Hakan Kandemir(TEKIRDAG NAMIK KEMAL UNIVERSITY)0000-0002-7347-2223
Pages
—
Publication Date
2022-09-28
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Also, bromination of bis-indole with N-bromo succinimide was produced corresponding bromo bis-indol derivative.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:An indole hydrazone has successfully been synthesized employing Schiff base reaction conditions starting from 4,6-dimethoxy-2,3-diphenylindole-7-carbaldehyde with hydrazine hydrate.
📊
Key Findings & Data:The reaction of this compound with acetone yielded indole based imine compound.
💡
Conclusion & Impact:Also, bromination of bis-indole with N-bromo succinimide was produced corresponding bromo bis-indol derivative.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:indole · bis-indole · hydrazone

Abstract

An indole hydrazone has successfully been synthesized employing Schiff base reaction conditions starting from 4,6-dimethoxy-2,3-diphenylindole-7-carbaldehyde with hydrazine hydrate. The reaction of this compound with acetone yielded indole based imine compound. The structure of targeted compound was identified by mass and 1H spectroscopy along with single crystal X-ray diffraction technique. Also, bromination of bis-indole with N-bromo succinimide was produced corresponding bromo bis-indol derivative.

🔖

Cite This Article

Kandemir, H. (2022). Synthesis of New Methoxy Actived Mono and Bis-indole Compounds. Hittite Journal of Science and Engineering, Volume: 9 Issue: 3. https://doi.org/10.17350/HJSE19030000276

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (39)

  1. Saglam MF, Bingul M, Şenkuytu E, Boga M, Zorlu Y, Kandemir H, Sengul IF. Synthesis, Characterization, UV-Vis Absorption and Cholinesterase Inhibition Properties of Bis-Indolyl Imine Ligand Systems. Journal of Molecular Structure 1215 (2020) 128-308.
  2. Joshi KC, Chand P. Biologically Active Indole Derivatives. Pharmazie 37(1) (1982) 1-12.
  3. Bingul M, Saglam MF, Kandemir H, Boga M, Sengul IF. Synthesis of Indole-2-Carbohydrazides and 2-(Indol-2-yl)-1,3,4-Oxadiazoles as Antioxidants and Their Acetylcholinesterase Inhibition Properties. Monatshefte für Chemie - Chemical Monthly 150 (2019) 1553-1560.
  4. Berger M, Gray JA, Roth BL. The Expanded Biology of Serotonin. Annual Review of Medicine 60(1) (2009) 355-366.
  5. Duarte RRR, Copertino Jr DC, Iñiguez LP, Marston JL, Nixon DF, Powell TR. Repurposing FDA-Approved Drugs for COVID-19 Using a Data-Driven Approach. ChemRxiv. Preprint. https://chemrxiv.org/engage/chemrxiv/article-details/60c74a1f469df4a04 0f43cb6 (2020) Erişim tarihi: 09.09.2021, https://doi.org/10.26434/chemrxiv.12148764.v1
  6. Mehta RG, Liu J, Constantinou A, Thomas CF, Hawthorne M, You M, Gerhüser C, Pezzuto JM, Moon RC, Moriarty RM. Cancer Chemopreventive Activity of Brassinin, a Phytoalexin from Cabbage. Carcinogenesis 16(2) (1995) 399-404.
  7. Pedras MSC, Montaut S, Suchy M. Phytoalexins from the Crucifer Rutabaga: Structures, Syntheses, Biosyntheses, and Antifungal Activity. The Journal of Organic Chemistry 69(13) (2004) 4471-4476.
  8. Lal S, Snape TJ. 2-Arylindoles: A Privileged Molecular Scaffold with Potent, Broadranging Pharmacological Activity. Current Medicinal Chemistry 19(28) (2012) 4828-4837.
  9. Sravanthi TV, Manju SL. Indoles - a Promising Scaffold for Drug Development. European Journal of Pharmaceutical Sciences 91 (2016) 1-10.
  10. Feniuk W, Humphrey PPA. The Development of a Highly Selective 5-HT1 Receptor Agonist, Sumatriptan, for the Treatment of Migraine. Drug Development Research 26 (1992) 235.
  11. Sinha D, Tiwari AK, Singh S, Shukla G, Mishra P, Chandra H, Mishra AK. Synthesis, Characterization and Biological Activity of Schiff Base Analogues of Indole-3-Carboxaldehyde, European Journal of Medicinal Chemistry 43 (2008) 160-165.
  12. Karthikeyan MS, Prasad DJ, Poojary B, Bhat KS, Holla BS, Kumari NS. Synthesis and Biological Activity of Schiff and Mannich Bases Bearing 2,4-Dichloro-5-Fluorophenyl Moiety. Bioorganic Medicinal Chemistry 14 (2006) 7482-7489.
  13. 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.
  14. Abu-Hussen AAA. Synthesis and Spectroscopic Studies on Ternary Bis-Schiff-Base Complexes Having Oxygen and/or Nitrogen Donors. Journal of Coordination Chemistry 59 (2006) 157-176.
  15. Campbell MJM. Transition Metal Complexes of Thiosemicarbazide and Thiosemicarbazones. Coordination Chemistry Reviews 15 (1975) 279-319.
  16. Gupta KC, Sutar AK. Catalytic Activities of Schiff Base Transition Metal Complexes. Coordination Chemistry Reviews 252 (2008) 1420-1450.
  17. Özbek N, Katırcıoğlu H, Karacan N, Baykal T. Synthesis, Characterization and Antimicrobial Activity of New Aliphatic Sulfonamide. Bioorganic & Medicinal Chemistry 15(23) (2007) 5105-5109.
  18. Avais M, Rashid G, Ijaz M, Khan MA, Nasir A, Jahanzaib MS, Khan JA, Hameed S, Reichel MP. Evaluation of Furazolidone, Sulfadimidine and Amprolium to Treat Coccidiosis in Beetal Goats Under Field Conditions. Pakistan Journal of Pharmaceutical Sciences 29(2) (2016) 485-487.
  19. Main RJ. The Nitrofurans a New Type of Antibacterial Agent. Journal of the American Pharmacists Association 36(10) (1947) 317-320.
  20. Gibbs TJK, Tomkinson NCO. Aminocatalytic Preparation of Bisindolylalkanes. Organic and Biomolecular Chemistry 3 (2005) 4043-4045.
  21. Oh KB, Mar W, Kim S, Kim JY, Lee TH, Kim JG, Shin D, Sim CJ, Shin J. Antimicrobial Activity and Cytotoxicity of Bis(indole) Alkaloids from the Sponge Spongosorites sp. Biological and Pharmaceutical Bulletin 29 (2006) 570-573.
  22. Bergman J, Janosik T, Wahlström N. Indolocarhazoles. Advances in Heterocyclic Chemistry 80 (2001) 1-71.
  23. Knölker HJ, Reddy KR. Isolation and Synthesis of Biologically Active Carbazole Alkaloids. Chemical Reviews 102 (2002) 4303-4427.
  24. Sánchez C, Méndez C, Salas JA. Indolocarbazole Natural Products: Occurrence, Biosynthesis, and Biological Activity. Natural Product Reports 23 (2006) 1007-1045.
  25. Sakemi S, Sun HH. Nortopsentins A, B, and C. Cytotoxic and Antifungal Imidazolediylbis[indoles] from the Sponge Spongosorites Ruetzleri. The Journal of Organic Chemistry 56 (1991) 4304-4307.
  26. Alvarez-Builla, J, Vaquero JJ, Barluenga, J. Five-Membered Heterocycles: Indole and Related Systems. Modern Heterocyclic Chemistry 1 (2011) 377-513.
  27. Beyer RL, Kandemir H, Bhadbhadea M, Sengul IF, Leu C-W, Wenholz D, Kumar N, Black DStC. Synthesis of Dipyrrolo[2,3-a:1',2',3'-fg]Acridin-12(1H)-Ones. Tetrahedron Letters 59 (2018) 4483-4486.
  28. Black DStC, Bowyer MC, Kumar N, Mitchell PSR. Calix[3] indoles, New Macrocyclic Tris(indolylmethylene) Compounds with 2,7-Linkages. Journal of the Chemical Society, Chemical Communications (1993) 819-821.
  29. Black DStC, Keller PA, Kumar N. Palladium-Catalysed Intramolecular Cyclisation of 7-Halo-N-Allyl-Indoles. Tetrahedron 48 (1992) 7601-7608.
  30. Wahyuningsih TD, Kumar N, Nugent SJ, Black DStC. Effective Synthesis of Some Indole Nitriles from the Related Carbaldoximes. Tetrahedron 61 (2005) 10501-10506.
  31. Deodhar M, Black DStC, Chan DS-H, Kumar N. Synthesis of Some New Biheterocycles by a One-Pot Suzuki-Miyaura Coupling Reaction. Chem Inform 80 (2010) 1267-1274.
  32. Vilsmeier A, Haack A. Über die Einwirkung von Halogenphosphor auf Alkyl Formanilide. Eine Neue Methode zur Darstellung Sekundärer und Tertiärerp-Alkylamino-Benzaldehyde. Berichte der Deutschen Chemischen Gesellschaft, 60 (1927) 119-122.
  33. 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, Urbino, pp. 162-212, 2021.
  34. Black D StC, Kumar N, Wong L C H, Investigation of the Bischler Indole Synthesis from 3,5-Dimethoxyaniline. Australian Journal of Chemistry 39 (1986) 15-20.
  35. Kandemir H, İzgi, S, Cınar, I, Cebeci, F, Dirican, E, Saglam, MF, Sengul IF. Methoxy-activated indole-7-carbohydrazides; synthesis, antioxidant, and anticancer properties. Journal of Heterocyclic Chemistry Erişim tarihi: 19 August 2022, https:// doi.org/10.1002/jhet.4562
  36. Black D StC, Bowyer MC, Catalano MM, Ivory AJ, Keller PA, Kumar N, Nugent SJ. Substitution, Oxidation and Addition Reactions at C-7 of Activated Indoles. Tetrahedron 50 (1994) 10497-10508.
  37. Purwono B, Kumar N, Black DStC. Mannich Reactions of Activated 4,6-Dimethoxyindoles. Arkivoc 4 (2022) 58-69.
  38. Duarte RRR, Copertino Jr DC, Iñiguez LP, Marston JL, Nixon DF, Powell TR. Repurposing FDA-Approved Drugs for COVID-19 Using a Data-Driven Approach. ChemRxiv. Preprint. https://chemrxiv.org/engage/chemrxiv/article-details/60c74a1f469df4a04 0f43cb6 (2020) Erişim tarihi: 09.09.2021, https://doi.org/10.26434/chemrxiv.12148764.v1
  39. Kandemir H, İzgi, S, Cınar, I, Cebeci, F, Dirican, E, Saglam, MF, Sengul IF. Methoxy-activated indole-7-carbohydrazides; synthesis, antioxidant, and anticancer properties. Journal of Heterocyclic Chemistry Erişim tarihi: 19 August 2022, https:// doi.org/10.1002/jhet.4562