Research Article
PDF EndNote BibTex RIS Cite

Synthesis of New Methoxy Actived Mono and Bis-indole Compounds

Year 2022, Volume 9, Issue 3, 235 - 239, 28.09.2022
https://doi.org/10.17350/HJSE19030000276

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.

References

  • 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.
  • Joshi KC, Chand P. Biologically Active Indole Derivatives. Pharmazie 37(1) (1982) 1-12.
  • 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.
  • Berger M, Gray JA, Roth BL. The Expanded Biology of Serotonin. Annual Review of Medicine 60(1) (2009) 355-366.
  • 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
  • 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.
  • 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.
  • Lal S, Snape TJ. 2-Arylindoles: A Privileged Molecular Scaffold with Potent, Broadranging Pharmacological Activity. Current Medicinal Chemistry 19(28) (2012) 4828-4837.
  • Sravanthi TV, Manju SL. Indoles - a Promising Scaffold for Drug Development. European Journal of Pharmaceutical Sciences 91 (2016) 1-10.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Campbell MJM. Transition Metal Complexes of Thiosemicarbazide and Thiosemicarbazones. Coordination Chemistry Reviews 15 (1975) 279-319.
  • Gupta KC, Sutar AK. Catalytic Activities of Schiff Base Transition Metal Complexes. Coordination Chemistry Reviews 252 (2008) 1420-1450.
  • 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.
  • 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.
  • Main RJ. The Nitrofurans a New Type of Antibacterial Agent. Journal of the American Pharmacists Association 36(10) (1947) 317-320.
  • Gibbs TJK, Tomkinson NCO. Aminocatalytic Preparation of Bisindolylalkanes. Organic and Biomolecular Chemistry 3 (2005) 4043-4045.
  • 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.
  • Bergman J, Janosik T, Wahlström N. Indolocarhazoles. Advances in Heterocyclic Chemistry 80 (2001) 1-71.
  • Knölker HJ, Reddy KR. Isolation and Synthesis of Biologically Active Carbazole Alkaloids. Chemical Reviews 102 (2002) 4303-4427.
  • Sánchez C, Méndez C, Salas JA. Indolocarbazole Natural Products: Occurrence, Biosynthesis, and Biological Activity. Natural Product Reports 23 (2006) 1007-1045.
  • 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.
  • Alvarez-Builla, J, Vaquero JJ, Barluenga, J. Five-Membered Heterocycles: Indole and Related Systems. Modern Heterocyclic Chemistry 1 (2011) 377-513.
  • 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.
  • 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.
  • Black DStC, Keller PA, Kumar N. Palladium-Catalysed Intramolecular Cyclisation of 7-Halo-N-Allyl-Indoles. Tetrahedron 48 (1992) 7601-7608.
  • Wahyuningsih TD, Kumar N, Nugent SJ, Black DStC. Effective Synthesis of Some Indole Nitriles from the Related Carbaldoximes. Tetrahedron 61 (2005) 10501-10506.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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
  • 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.
  • Purwono B, Kumar N, Black DStC. Mannich Reactions of Activated 4,6-Dimethoxyindoles. Arkivoc 4 (2022) 58-69.

Year 2022, Volume 9, Issue 3, 235 - 239, 28.09.2022
https://doi.org/10.17350/HJSE19030000276

Abstract

References

  • 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.
  • Joshi KC, Chand P. Biologically Active Indole Derivatives. Pharmazie 37(1) (1982) 1-12.
  • 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.
  • Berger M, Gray JA, Roth BL. The Expanded Biology of Serotonin. Annual Review of Medicine 60(1) (2009) 355-366.
  • 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
  • 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.
  • 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.
  • Lal S, Snape TJ. 2-Arylindoles: A Privileged Molecular Scaffold with Potent, Broadranging Pharmacological Activity. Current Medicinal Chemistry 19(28) (2012) 4828-4837.
  • Sravanthi TV, Manju SL. Indoles - a Promising Scaffold for Drug Development. European Journal of Pharmaceutical Sciences 91 (2016) 1-10.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Campbell MJM. Transition Metal Complexes of Thiosemicarbazide and Thiosemicarbazones. Coordination Chemistry Reviews 15 (1975) 279-319.
  • Gupta KC, Sutar AK. Catalytic Activities of Schiff Base Transition Metal Complexes. Coordination Chemistry Reviews 252 (2008) 1420-1450.
  • 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.
  • 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.
  • Main RJ. The Nitrofurans a New Type of Antibacterial Agent. Journal of the American Pharmacists Association 36(10) (1947) 317-320.
  • Gibbs TJK, Tomkinson NCO. Aminocatalytic Preparation of Bisindolylalkanes. Organic and Biomolecular Chemistry 3 (2005) 4043-4045.
  • 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.
  • Bergman J, Janosik T, Wahlström N. Indolocarhazoles. Advances in Heterocyclic Chemistry 80 (2001) 1-71.
  • Knölker HJ, Reddy KR. Isolation and Synthesis of Biologically Active Carbazole Alkaloids. Chemical Reviews 102 (2002) 4303-4427.
  • Sánchez C, Méndez C, Salas JA. Indolocarbazole Natural Products: Occurrence, Biosynthesis, and Biological Activity. Natural Product Reports 23 (2006) 1007-1045.
  • 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.
  • Alvarez-Builla, J, Vaquero JJ, Barluenga, J. Five-Membered Heterocycles: Indole and Related Systems. Modern Heterocyclic Chemistry 1 (2011) 377-513.
  • 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.
  • 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.
  • Black DStC, Keller PA, Kumar N. Palladium-Catalysed Intramolecular Cyclisation of 7-Halo-N-Allyl-Indoles. Tetrahedron 48 (1992) 7601-7608.
  • Wahyuningsih TD, Kumar N, Nugent SJ, Black DStC. Effective Synthesis of Some Indole Nitriles from the Related Carbaldoximes. Tetrahedron 61 (2005) 10501-10506.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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
  • 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.
  • Purwono B, Kumar N, Black DStC. Mannich Reactions of Activated 4,6-Dimethoxyindoles. Arkivoc 4 (2022) 58-69.

Details

Primary Language English
Subjects Basic Sciences
Journal Section Research Articles
Authors

Hakan KANDEMİR> (Primary Author)
TEKIRDAG NAMIK KEMAL UNIVERSITY
0000-0002-7347-2223
Türkiye

Thanks I would like to thank Ibrahim Fazil Sengul and Tugce Nur USLU for their support to this study
Publication Date September 28, 2022
Application Date August 11, 2022
Acceptance Date September 23, 2022
Published in Issue Year 2022, Volume 9, Issue 3

Cite

Bibtex @research article { hjse1160718, journal = {Hittite Journal of Science and Engineering}, eissn = {2148-4171}, address = {Hitit Üniversitesi Mühendislik Fakültesi Kuzey Kampüsü Çevre Yolu Bulvarı 19030 Çorum / TÜRKİYE}, publisher = {Hitit University}, year = {2022}, volume = {9}, number = {3}, pages = {235 - 239}, doi = {10.17350/HJSE19030000276}, title = {Synthesis of New Methoxy Actived Mono and Bis-indole Compounds}, key = {cite}, author = {Kandemir, Hakan} }
APA Kandemir, H. (2022). Synthesis of New Methoxy Actived Mono and Bis-indole Compounds . Hittite Journal of Science and Engineering , 9 (3) , 235-239 . DOI: 10.17350/HJSE19030000276
MLA Kandemir, H. "Synthesis of New Methoxy Actived Mono and Bis-indole Compounds" . Hittite Journal of Science and Engineering 9 (2022 ): 235-239 <https://dergipark.org.tr/en/pub/hjse/issue/72726/1160718>
Chicago Kandemir, H. "Synthesis of New Methoxy Actived Mono and Bis-indole Compounds". Hittite Journal of Science and Engineering 9 (2022 ): 235-239
RIS TY - JOUR T1 - Synthesis of New Methoxy Actived Mono and Bis-indole Compounds AU - HakanKandemir Y1 - 2022 PY - 2022 N1 - doi: 10.17350/HJSE19030000276 DO - 10.17350/HJSE19030000276 T2 - Hittite Journal of Science and Engineering JF - Journal JO - JOR SP - 235 EP - 239 VL - 9 IS - 3 SN - -2148-4171 M3 - doi: 10.17350/HJSE19030000276 UR - https://doi.org/10.17350/HJSE19030000276 Y2 - 2022 ER -
EndNote %0 Hittite Journal of Science and Engineering Synthesis of New Methoxy Actived Mono and Bis-indole Compounds %A Hakan Kandemir %T Synthesis of New Methoxy Actived Mono and Bis-indole Compounds %D 2022 %J Hittite Journal of Science and Engineering %P -2148-4171 %V 9 %N 3 %R doi: 10.17350/HJSE19030000276 %U 10.17350/HJSE19030000276
ISNAD Kandemir, Hakan . "Synthesis of New Methoxy Actived Mono and Bis-indole Compounds". Hittite Journal of Science and Engineering 9 / 3 (September 2022): 235-239 . https://doi.org/10.17350/HJSE19030000276
AMA Kandemir H. Synthesis of New Methoxy Actived Mono and Bis-indole Compounds. Hittite J Sci Eng. 2022; 9(3): 235-239.
Vancouver Kandemir H. Synthesis of New Methoxy Actived Mono and Bis-indole Compounds. Hittite Journal of Science and Engineering. 2022; 9(3): 235-239.
IEEE H. Kandemir , "Synthesis of New Methoxy Actived Mono and Bis-indole Compounds", Hittite Journal of Science and Engineering, vol. 9, no. 3, pp. 235-239, Sep. 2022, doi:10.17350/HJSE19030000276