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Chemical reactivity of ethyl 4-(1-ethyl-1,2-dihydro-4-hydroxy-2-oxoquinolin-3-yl)-2,4-dioxobutanoate towards some nucleophilic reagents

Year 2016, Volume: 3 Issue: 2, 75 - 88, 08.02.2016
https://doi.org/10.18596/jotcsa.11975

Abstract

Abstract

A novel series of heterocyclic systems linked with quinolin-2-one was efficiently synthesized from reaction of ethyl 4-(1-ethyl-1,2-dihydro-4-hydroxy-2-oxoquinolin-3-yl) -2,4-dioxobutanoate (1) with a variety of nitrogen and/or carbon nucleophiles. A variety of heterocyclic systems such as pyrazoles, pyrimidines, pyrazines, oxazines and triazines containing quinoline moiety were synthesized. Structures of the new synthesized products were deduced on basis of their analytical and spectral data.

References

  • Ibrahim MA, Hassanin HM, Gabr YA, Alnamer YA. Studies on the chemical behavior of 3-(nitroacetyl)-1-ethyl-4-hydroxyquinolin-2(1H)-one towards some electrophilic and nucleophilic reagents. Journal of the Brazilian Chemical Society. 2012 May;23(5):905–12. DOI: 10.1590/S0103-50532012000500016.
  • Moradi Rufchahi EO, Pouramir H, Yazdanbakhsh MR, Yousefi H, Bagheri M, Rassa M. Novel azo dyes derived from 8-methyl-4-hydroxyl-2-quinolone: Synthesis, UV–vis studies and biological activity. Chinese Chemical Letters. 2013 May;24(5):425–8. DOI: 10.1016/j.cclet.2013.03.002.
  • De Melo EB. Multivariate SAR/QSAR of 3-aryl-4-hydroxyquinolin-2(1H)-one derivatives as type I fatty acid synthase (FAS) inhibitors. European Journal of Medicinal Chemistry. 2010 Dec;45(12):5817–26. DOI: 10.1016/j.ejmech.2010.09.044.
  • Abass M, Mostafa BB. Synthesis and evaluation of molluscicidal and larvicidal activities of some novel enaminones derived from 4-hydroxyquinolinones: Part IX. Bioorganic & Medicinal Chemistry. 2005 Nov;13(22):6133–44. DOI: 10.1016/j.bmc.2005.06.038.
  • Chen Y-L, Fang K-C, Sheu J-Y, Hsu S-L, Tzeng C-C. Synthesis and Antibacterial Evaluation of Certain Quinolone Derivatives. Journal of Medicinal Chemistry. 2001 Jul;44(14):2374–7. DOI: 10.1021/jm0100335.
  • Detsi A, Bouloumbasi D, Prousis KC, Koufaki M, Athanasellis G, Melagraki G, et al. Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents. Journal of Medicinal Chemistry. 2007 May;50(10):2450–8. DOI: 10.1021/jm061173n.
  • Kaur K, Jain M, Kaur T, Jain R. Antimalarials from nature. Bioorganic & Medicinal Chemistry. 2009 May;17(9):3229–56. DOI: 10.1016/j.bmc.2009.02.050.
  • Behforouz M, Cai W, Mohammadi F, Stocksdale MG, Gu Z, Ahmadian M, et al. Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones. Bioorganic & Medicinal Chemistry. 2007 Jan 1;15(1):495–510. DOI: 10.1016/j.bmc.2006.09.039.
  • Abas F, Lajis NH, Israf DA, Khozirah S, Umi Kalsom Y. Antioxidant and nitric oxide inhibition activities of selected Malay traditional vegetables. Food Chemistry. 2006 Apr;95(4):566–73. DOI: 10.1016/j.foodchem.2005.01.034.
  • Rocha LG, Almeida JRGS, Macêdo RO, Barbosa-Filho JM. A review of natural products with antileishmanial activity. Phytomedicine. 2005 Jun;12(6-7):514–35. DOI: 10.1016/j.phymed.2003.10.006.
  • Kuo R-Y, Chang F-R, Chen C-Y, Teng C-M, Yen H-F, Wu Y-C. Antiplatelet activity of N-methoxycarbonyl aporphines from Rollinia mucosa. Phytochemistry. 2001 Jun;57(3):421–5. DOI: 10.1016/S0031-9422(01)00076-0.
  • Chen Y-L, Chen I-L, Tzeng C-C, Wang T-C. Synthesis and Cytotoxicity Evaluation of Certain α-Methylidene-γ-butyrolactones Bearing Coumarin, Flavone, Xanthone, Carbazole, and Dibenzofuran Moieties. Helvetica Chimica Acta. 2000 May 10;83(5):989–94. DOI: 10.1002/(SICI)1522-2675(20000510)83:5<989::AID-HLCA989>3.0.CO;2-E.
  • Rivkin A, Kim YR, Goulet MT, Bays N, Hill AD, Kariv I, et al. 3-Aryl-4-hydroxyquinolin-2(1H)-one derivatives as type I fatty acid synthase inhibitors. Bioorganic & Medicinal Chemistry Letters. 2006 Sep;16(17):4620–3. DOI: 10.1016/j.bmcl.2006.06.014.
  • Roussaki M, Hall B, Lima SC, da Silva AC, Wilkinson S, Detsi A. Synthesis and anti-parasitic activity of a novel quinolinone–chalcone series. Bioorganic & Medicinal Chemistry Letters. 2013 Dec;23(23):6436–41. DOI: 10.1016/j.bmcl.2013.09.047.
  • Ismail M, Mohamed H. Synthesis and cyclization reactions with quinolinyl keto esters II. Synthesis of novel 3-diazolylquunolinones and their enzymic activity. Chemical Papers. 2005;59(2):127–38. URL: http://www.chempap.org/file_access.php?file=592a127.pdf.13.09.047.
Year 2016, Volume: 3 Issue: 2, 75 - 88, 08.02.2016
https://doi.org/10.18596/jotcsa.11975

Abstract

References

  • Ibrahim MA, Hassanin HM, Gabr YA, Alnamer YA. Studies on the chemical behavior of 3-(nitroacetyl)-1-ethyl-4-hydroxyquinolin-2(1H)-one towards some electrophilic and nucleophilic reagents. Journal of the Brazilian Chemical Society. 2012 May;23(5):905–12. DOI: 10.1590/S0103-50532012000500016.
  • Moradi Rufchahi EO, Pouramir H, Yazdanbakhsh MR, Yousefi H, Bagheri M, Rassa M. Novel azo dyes derived from 8-methyl-4-hydroxyl-2-quinolone: Synthesis, UV–vis studies and biological activity. Chinese Chemical Letters. 2013 May;24(5):425–8. DOI: 10.1016/j.cclet.2013.03.002.
  • De Melo EB. Multivariate SAR/QSAR of 3-aryl-4-hydroxyquinolin-2(1H)-one derivatives as type I fatty acid synthase (FAS) inhibitors. European Journal of Medicinal Chemistry. 2010 Dec;45(12):5817–26. DOI: 10.1016/j.ejmech.2010.09.044.
  • Abass M, Mostafa BB. Synthesis and evaluation of molluscicidal and larvicidal activities of some novel enaminones derived from 4-hydroxyquinolinones: Part IX. Bioorganic & Medicinal Chemistry. 2005 Nov;13(22):6133–44. DOI: 10.1016/j.bmc.2005.06.038.
  • Chen Y-L, Fang K-C, Sheu J-Y, Hsu S-L, Tzeng C-C. Synthesis and Antibacterial Evaluation of Certain Quinolone Derivatives. Journal of Medicinal Chemistry. 2001 Jul;44(14):2374–7. DOI: 10.1021/jm0100335.
  • Detsi A, Bouloumbasi D, Prousis KC, Koufaki M, Athanasellis G, Melagraki G, et al. Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents. Journal of Medicinal Chemistry. 2007 May;50(10):2450–8. DOI: 10.1021/jm061173n.
  • Kaur K, Jain M, Kaur T, Jain R. Antimalarials from nature. Bioorganic & Medicinal Chemistry. 2009 May;17(9):3229–56. DOI: 10.1016/j.bmc.2009.02.050.
  • Behforouz M, Cai W, Mohammadi F, Stocksdale MG, Gu Z, Ahmadian M, et al. Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones. Bioorganic & Medicinal Chemistry. 2007 Jan 1;15(1):495–510. DOI: 10.1016/j.bmc.2006.09.039.
  • Abas F, Lajis NH, Israf DA, Khozirah S, Umi Kalsom Y. Antioxidant and nitric oxide inhibition activities of selected Malay traditional vegetables. Food Chemistry. 2006 Apr;95(4):566–73. DOI: 10.1016/j.foodchem.2005.01.034.
  • Rocha LG, Almeida JRGS, Macêdo RO, Barbosa-Filho JM. A review of natural products with antileishmanial activity. Phytomedicine. 2005 Jun;12(6-7):514–35. DOI: 10.1016/j.phymed.2003.10.006.
  • Kuo R-Y, Chang F-R, Chen C-Y, Teng C-M, Yen H-F, Wu Y-C. Antiplatelet activity of N-methoxycarbonyl aporphines from Rollinia mucosa. Phytochemistry. 2001 Jun;57(3):421–5. DOI: 10.1016/S0031-9422(01)00076-0.
  • Chen Y-L, Chen I-L, Tzeng C-C, Wang T-C. Synthesis and Cytotoxicity Evaluation of Certain α-Methylidene-γ-butyrolactones Bearing Coumarin, Flavone, Xanthone, Carbazole, and Dibenzofuran Moieties. Helvetica Chimica Acta. 2000 May 10;83(5):989–94. DOI: 10.1002/(SICI)1522-2675(20000510)83:5<989::AID-HLCA989>3.0.CO;2-E.
  • Rivkin A, Kim YR, Goulet MT, Bays N, Hill AD, Kariv I, et al. 3-Aryl-4-hydroxyquinolin-2(1H)-one derivatives as type I fatty acid synthase inhibitors. Bioorganic & Medicinal Chemistry Letters. 2006 Sep;16(17):4620–3. DOI: 10.1016/j.bmcl.2006.06.014.
  • Roussaki M, Hall B, Lima SC, da Silva AC, Wilkinson S, Detsi A. Synthesis and anti-parasitic activity of a novel quinolinone–chalcone series. Bioorganic & Medicinal Chemistry Letters. 2013 Dec;23(23):6436–41. DOI: 10.1016/j.bmcl.2013.09.047.
  • Ismail M, Mohamed H. Synthesis and cyclization reactions with quinolinyl keto esters II. Synthesis of novel 3-diazolylquunolinones and their enzymic activity. Chemical Papers. 2005;59(2):127–38. URL: http://www.chempap.org/file_access.php?file=592a127.pdf.13.09.047.
There are 15 citations in total.

Details

Journal Section Articles
Authors

Hany Hassanin

Magdi A. Ibrahim

Shimaa Badran This is me

Publication Date February 8, 2016
Submission Date December 10, 2015
Published in Issue Year 2016 Volume: 3 Issue: 2

Cite

Vancouver Hassanin H, Ibrahim MA, Badran S. Chemical reactivity of ethyl 4-(1-ethyl-1,2-dihydro-4-hydroxy-2-oxoquinolin-3-yl)-2,4-dioxobutanoate towards some nucleophilic reagents. JOTCSA. 2016;3(2):75-88.