Research Article
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Year 2018, Volume: 5 Issue: 2, 551 - 568, 01.01.2018
https://doi.org/10.18596/jotcsa.390928

Abstract

References

  • Hu YQ, Xu Z, Zhang S, Wu X, Ding JW, Lv ZS, et al. Recent developments of coumarin-containing derivatives and their anti-tubercular activity. Eur J Med Chem. 2017;136:122-30. DOI: 10.1016/j.ejmech.2017.05.004.
  • Liu MM, Chen XY, Huang YQ, Feng P, Guo YL, Yang G, et al. Hybrids of Phenylsulfonylfuroxan and Coumarin as Potent Antitumor Agents. J Med Chem. 2014;57(22):9343-56. DOI: 10.1021/jm500613m.
  • Kumbhare RM, Kosurkar UB, Ramaiah MJ, Dadmal TL, Pushpavalli SNCVL, Pal-Bhadra M. Synthesis and biological evaluation of novel triazoles and isoxazoles linked 2-phenyl benzothiazole as potential anticancer agents. Bioorg Med Chem Lett. 2012;22(17):5424-7. DOI: 10.1016/j.bmcl.2012.07.041.
  • Musad EA, Mohamed R, Saeed BA, Vishwanath BS, Rai KML. Synthesis and evaluation of antioxidant and antibacterial activities of new substituted bis(1,3,4-oxadiazoles), 3,5-bis(substituted) pyrazoles and isoxazoles. Bioorg Med Chem Lett. 2011;21(12):3536-40. DOI: 10.1016/j.bmcl.2011.04.142.
  • Kahveci B, Yilmaz F, Mentese E, Ulker S. Design, Synthesis, and Biological Evaluation of Coumarin-Triazole Hybrid Molecules as Potential Antitumor and Pancreatic Lipase Agents. Arch Pharm. 2017;350(8). DOI: ARTN e1600369.10.1002/ardp.201600369.
  • Mentese E, Karaali N, Akyuz G, Yilmaz F, Ulker S, Kahveci B. Synthesis and evaluation of alpha-glucosidase and pancreatic lipase inhibition by quinazolinone-coumarin hybrids. Chem Heterocycl Com. 2016;52(12):1017-24. DOI: 10.1007/s10593-017-2002-3.
  • Kamiyama H, Kubo Y, Sato H, Yamamoto N, Fukuda T, Ishibashi F, et al. Synthesis, structure-activity relationships, and mechanism of action of anti-HIV-1 lamellarin alpha 20-sulfate analogues. Bioorgan Med Chem. 2011;19(24):7541-50. DOI: 10.1016/j.bmc.2011.10.030.
  • Carocho M, Morales P, Ferreira ICFR. Natural food additives: Quo vadis? Trends Food Sci Tech. 2015;45(2):284-95. DOI: 10.1016/j.tifs.2015.06.007. Karaoglu K, Yilmaz F, Mentese E. A New Fluorescent "Turn-Off" Coumarin-Based Chemosensor: Synthesis, Structure and Cu-Selective Fluorescent Sensing in Water Samples. J Fluoresc. 2017;27(4):1293-8. DOI: 10.1007/s10895-017-2062-x.
  • Acar M, Bozkurt E, Meral K, Ank M, Onganer Y. The fluorescence quenching mechanism of coumarin 120 with CdS nanoparticles in aqueous suspension. J Lumin. 2015;157:10-5. DOI: 10.1016/j.jlumin.2014.08.027.
  • Raghav SK, Gupta B, Shrivastava A, Das HR. Inhibition of lipopolysaccharide-inducible nitric oxide synthase and IL-1 beta through suppression of NF-kappa B activation by 3-(1 '-1 '-dimethyl-allyl)-6-hydroxy-7-methoxy-coumarin isolated from Ruta graveolens L. Eur J Pharmacol. 2007;560(1):69-80. DOI: 10.1016/j.ejphar.2007.01.002.
  • Kahveci B, Yilmaz F, Mentese E, Beris FS. Effect of microwave irradiation on the synthesis of 1,2,4-triazol-3-one derivatives and their antimicrobial activities. J Chem Res. 2012(8):484-8. DOI: 10.3184/174751912X13400138806685.
  • Nagamallu R, Srinivasan B, Ningappa MB, Kariyappa AK. Synthesis of novel coumarin appended bis(formylpyrazole) derivatives: Studies on their antimicrobial and antioxidant activities. Bioorg Med Chem Lett. 2016;26(2):690-4. DOI: 10.1016/j.bmcl.2015.11.038.
  • Wen F, Jin H, Tao K, Hou TP. Design, synthesis and antifungal activity of novel furancarboxamide derivatives. Eur J Med Chem. 2016;120:244-51. DOI: 10.1016/j.ejmech.2016.04.060.
  • Kahveci B, Yilmaz F, Mentese E, Ulker S. Microwave-assisted synthesis of some new coumarin derivatives including 1,2,4-triazol-3-one and investigation of their biological activities. Chem Heterocycl Com. 2015;51(5):447-56. DOI: 10.1007/s10593-015-1714-5.
  • Garino C, Tomita T, Pietrancosta N, Laras Y, Rosas R, Herbette G, et al. Naphthyl and coumarinyl biarylpiperazine derivatives as highly potent human beta-secretase inhibitors. Design, synthesis, and enzymatic BACE-1 and cell assays. J Med Chem. 2006;49(14):4275-85. DOI: 10.1021/jm0602864.
  • Tang J, Huang X. An efficient solid-phase synthesis of 3-carboxycoumarins based on a scaffold-polymer-bound cyclic malonic ester. J Chem Res-S. 2003(6):354-5. DOI: https://doi.org/10.3184/030823403103174092
  • Hekmatshoar R, Rezaei A, Beheshtiha SYS. Silica Sulfuric Acid: A Versatile and Reusable Catalyst for Synthesis of Coumarin-3-carboxylic Acids in a Solventless System. Phosphorus Sulfur. 2009;184(9):2491-6. DOI: 10.1080/10426500802505580.
  • Creaven BS, Egan DA, Kavanagh K, McCann M, Noble A, Thati B, et al. Synthesis, characterization and antimicrobial activity of a series of substituted coumarin-3-carboxylatosilver(I) complexes. Inorg Chim Acta. 2006;359(12):3976-84. DOI: 10.1016/j.ica.2006.04.006.
  • Bardajee GR, Jafarpour F, Afsari HS. ZrOCl2 center dot 8H(2)O: An efficient catalyst for rapid one-pot synthesis of 3-carboxycoumarins under ultrasound irradiation in water. Cent Eur J Chem. 2010;8(2):370-4. DOI: 10.2478/s11532-009-0141-9.
  • Katritzky AR, Cusido J, Narindoshvili T. Monosaccharide-based water-soluble fluorescent tags. Bioconjugate Chem. 2008;19(7):1471-5. DOI: 10.1021/bc8001369.
  • Katritzky AR, Abdelmajeid A, Tala SR, Amine MS, Steel PJ. Novel Fluorescent Aminoxy Acids and Aminoxy Hybrid Peptides. Synthesis-Stuttgart. 2011(1):83-90. DOI: 10.1055/s-0030-1258345.
  • Kahveci B, Mentese E. Microwave-Assisted Synthesis of Benzimidazoles and Their Derivatives From 1994 to 2016-A Review. Curr Microwav Chem. 2017;4(1):73-101. DOI: 10.2174/2213335603666160517154048.
  • Winkler UK, Stuckmann M. Glycogen, hyaluronate, and some other polysaccharides greatly enhance the formation of exolipase by Serratia marcescens. Journal of Bacteriology. 1979;138(3):663-70. URLs: http://jb.asm.org/content/138/3/663
  • Kantar GK, Faiz O, Sahin O, Sasmaz S. Phthalocyanine and azaphthalocyanines containing eugenol: synthesis, DNA interaction and comparison of lipase inhibition properties. J Chem Sci. 2017;129(8):1247-56. DOI: 10.1007/s12039-017-1320-4.
  • Apak R, Guclu K, Ozyurek M, Celik SE. Mechanism of antioxidant capacity assays and the CUPRAC (cupric ion reducing antioxidant capacity) assay. Microchim Acta. 2008;160(4):413-9. DOI: 10.1007/s00604-007-0777-0.
  • Heck AM, Yanovski JA, Calis KA. Orlistat, a new lipase inhibitor for the management of obesity. Pharmacotherapy. 2000;20(3):270-9. DOI: 10.1592/phco.20.4.270.34882.
  • Frecentese F, Saccone I, Caliendo G, Corvino A, Fiorino F, Magli E, et al. Microwave Assisted Organic Synthesis of Heterocycles in Aqueous Media: Recent Advances in Medicinal Chemistry. Med Chem. 2016;12(8):720-32. DOI: 10.2174/1573406412666160502153553.
  • Kappe CO, Dallinger D. Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature. Mol Divers. 2009;13(2):71-193. DOI: 10.1007/s11030-009-9138-8.
  • Kappe CO, Stadler A, Dallinger D, Strohmeier G, Perez R, Zbruyev OI, et al. Adventures in microwave-assisted organic synthesis: Contributions from the Kappe laboratory 2000-2005. Nato Sci Ser Ii-Math. 2008;246:225-51. DOI: 10.1007/978-1-4020-6793-8_11.
  • de Souza SM, Delle Monache F, Smania A. Antibacterial activity of coumarins. Z Naturforsch C. 2005;60(9-10):693-700. DOI: 10.1515/znc-2005-9-1006.
  • Srinivas B, Suryachandram J, Devi YK, Rao KP. Synthesis and Antibacterial Activity Studies of 8,9-Dihydro [7h] Benzo 1,2,4-Oxadiazoles and its Coumarin Derivatives. J Heterocyclic Chem. 2017;54(6):3730-4. DOI: 10.1002/jhet.2960.
  • Zhang RR, Liu J, Zhang Y, Hou MQ, Zhang MZ, Zhou FE, et al. Microwave-assisted synthesis and antifungal activity of novel coumarin derivatives: Pyrano[3,2-c]chromene-2,5-diones. Eur J Med Chem. 2016;116:76-83. DOI: 10.1016/j.ejmech.2016.03.069.
  • Khan KM, Saify ZS, Khan MZ, Zia-Ullah, Choudhary MI, Atta-ur-Rahman, et al. Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activity. J Enzym Inhib Med Ch. 2004;19(4):373-9. DOI: 10.1080/1475636042000206428.

Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides

Year 2018, Volume: 5 Issue: 2, 551 - 568, 01.01.2018
https://doi.org/10.18596/jotcsa.390928

Abstract

In this work, 15 different coumarin hydrazides were successfully synthesized
and screened for their antioxidant and antilipase activities. To do this,
firstly, salicylaldehyde derivatives and 2,2-dimethyl-1,3-dioxane-4,6-dione
(Meldrum's Acid) were reacted in ethanol in the presence  of catalytic amount of pyridine to obtain
coumarin-3-carboxylic acid derivatives (1a-e). Then, these compounds
were treated with benzotriazole in dichloromethane by using thionyl chloride to
synthesized benzotriazole derivatives (2a-e).
Then, compounds 2a-e were reacted
with three commercial hydrazides (nicotinic hydrazide, benzhydrazide and
phenylacetichydrazide) in ethanol by using microwave irradiation and
conventional heating procedures to obtain final products (3-5a-e). Finally, these compounds were tested for their anti-oxidant
and anti-pancreatic lipase activities. The structure of newly synthesized
compounds was identified by 1H NMR, 13C NMR and elemental
analysis data.

References

  • Hu YQ, Xu Z, Zhang S, Wu X, Ding JW, Lv ZS, et al. Recent developments of coumarin-containing derivatives and their anti-tubercular activity. Eur J Med Chem. 2017;136:122-30. DOI: 10.1016/j.ejmech.2017.05.004.
  • Liu MM, Chen XY, Huang YQ, Feng P, Guo YL, Yang G, et al. Hybrids of Phenylsulfonylfuroxan and Coumarin as Potent Antitumor Agents. J Med Chem. 2014;57(22):9343-56. DOI: 10.1021/jm500613m.
  • Kumbhare RM, Kosurkar UB, Ramaiah MJ, Dadmal TL, Pushpavalli SNCVL, Pal-Bhadra M. Synthesis and biological evaluation of novel triazoles and isoxazoles linked 2-phenyl benzothiazole as potential anticancer agents. Bioorg Med Chem Lett. 2012;22(17):5424-7. DOI: 10.1016/j.bmcl.2012.07.041.
  • Musad EA, Mohamed R, Saeed BA, Vishwanath BS, Rai KML. Synthesis and evaluation of antioxidant and antibacterial activities of new substituted bis(1,3,4-oxadiazoles), 3,5-bis(substituted) pyrazoles and isoxazoles. Bioorg Med Chem Lett. 2011;21(12):3536-40. DOI: 10.1016/j.bmcl.2011.04.142.
  • Kahveci B, Yilmaz F, Mentese E, Ulker S. Design, Synthesis, and Biological Evaluation of Coumarin-Triazole Hybrid Molecules as Potential Antitumor and Pancreatic Lipase Agents. Arch Pharm. 2017;350(8). DOI: ARTN e1600369.10.1002/ardp.201600369.
  • Mentese E, Karaali N, Akyuz G, Yilmaz F, Ulker S, Kahveci B. Synthesis and evaluation of alpha-glucosidase and pancreatic lipase inhibition by quinazolinone-coumarin hybrids. Chem Heterocycl Com. 2016;52(12):1017-24. DOI: 10.1007/s10593-017-2002-3.
  • Kamiyama H, Kubo Y, Sato H, Yamamoto N, Fukuda T, Ishibashi F, et al. Synthesis, structure-activity relationships, and mechanism of action of anti-HIV-1 lamellarin alpha 20-sulfate analogues. Bioorgan Med Chem. 2011;19(24):7541-50. DOI: 10.1016/j.bmc.2011.10.030.
  • Carocho M, Morales P, Ferreira ICFR. Natural food additives: Quo vadis? Trends Food Sci Tech. 2015;45(2):284-95. DOI: 10.1016/j.tifs.2015.06.007. Karaoglu K, Yilmaz F, Mentese E. A New Fluorescent "Turn-Off" Coumarin-Based Chemosensor: Synthesis, Structure and Cu-Selective Fluorescent Sensing in Water Samples. J Fluoresc. 2017;27(4):1293-8. DOI: 10.1007/s10895-017-2062-x.
  • Acar M, Bozkurt E, Meral K, Ank M, Onganer Y. The fluorescence quenching mechanism of coumarin 120 with CdS nanoparticles in aqueous suspension. J Lumin. 2015;157:10-5. DOI: 10.1016/j.jlumin.2014.08.027.
  • Raghav SK, Gupta B, Shrivastava A, Das HR. Inhibition of lipopolysaccharide-inducible nitric oxide synthase and IL-1 beta through suppression of NF-kappa B activation by 3-(1 '-1 '-dimethyl-allyl)-6-hydroxy-7-methoxy-coumarin isolated from Ruta graveolens L. Eur J Pharmacol. 2007;560(1):69-80. DOI: 10.1016/j.ejphar.2007.01.002.
  • Kahveci B, Yilmaz F, Mentese E, Beris FS. Effect of microwave irradiation on the synthesis of 1,2,4-triazol-3-one derivatives and their antimicrobial activities. J Chem Res. 2012(8):484-8. DOI: 10.3184/174751912X13400138806685.
  • Nagamallu R, Srinivasan B, Ningappa MB, Kariyappa AK. Synthesis of novel coumarin appended bis(formylpyrazole) derivatives: Studies on their antimicrobial and antioxidant activities. Bioorg Med Chem Lett. 2016;26(2):690-4. DOI: 10.1016/j.bmcl.2015.11.038.
  • Wen F, Jin H, Tao K, Hou TP. Design, synthesis and antifungal activity of novel furancarboxamide derivatives. Eur J Med Chem. 2016;120:244-51. DOI: 10.1016/j.ejmech.2016.04.060.
  • Kahveci B, Yilmaz F, Mentese E, Ulker S. Microwave-assisted synthesis of some new coumarin derivatives including 1,2,4-triazol-3-one and investigation of their biological activities. Chem Heterocycl Com. 2015;51(5):447-56. DOI: 10.1007/s10593-015-1714-5.
  • Garino C, Tomita T, Pietrancosta N, Laras Y, Rosas R, Herbette G, et al. Naphthyl and coumarinyl biarylpiperazine derivatives as highly potent human beta-secretase inhibitors. Design, synthesis, and enzymatic BACE-1 and cell assays. J Med Chem. 2006;49(14):4275-85. DOI: 10.1021/jm0602864.
  • Tang J, Huang X. An efficient solid-phase synthesis of 3-carboxycoumarins based on a scaffold-polymer-bound cyclic malonic ester. J Chem Res-S. 2003(6):354-5. DOI: https://doi.org/10.3184/030823403103174092
  • Hekmatshoar R, Rezaei A, Beheshtiha SYS. Silica Sulfuric Acid: A Versatile and Reusable Catalyst for Synthesis of Coumarin-3-carboxylic Acids in a Solventless System. Phosphorus Sulfur. 2009;184(9):2491-6. DOI: 10.1080/10426500802505580.
  • Creaven BS, Egan DA, Kavanagh K, McCann M, Noble A, Thati B, et al. Synthesis, characterization and antimicrobial activity of a series of substituted coumarin-3-carboxylatosilver(I) complexes. Inorg Chim Acta. 2006;359(12):3976-84. DOI: 10.1016/j.ica.2006.04.006.
  • Bardajee GR, Jafarpour F, Afsari HS. ZrOCl2 center dot 8H(2)O: An efficient catalyst for rapid one-pot synthesis of 3-carboxycoumarins under ultrasound irradiation in water. Cent Eur J Chem. 2010;8(2):370-4. DOI: 10.2478/s11532-009-0141-9.
  • Katritzky AR, Cusido J, Narindoshvili T. Monosaccharide-based water-soluble fluorescent tags. Bioconjugate Chem. 2008;19(7):1471-5. DOI: 10.1021/bc8001369.
  • Katritzky AR, Abdelmajeid A, Tala SR, Amine MS, Steel PJ. Novel Fluorescent Aminoxy Acids and Aminoxy Hybrid Peptides. Synthesis-Stuttgart. 2011(1):83-90. DOI: 10.1055/s-0030-1258345.
  • Kahveci B, Mentese E. Microwave-Assisted Synthesis of Benzimidazoles and Their Derivatives From 1994 to 2016-A Review. Curr Microwav Chem. 2017;4(1):73-101. DOI: 10.2174/2213335603666160517154048.
  • Winkler UK, Stuckmann M. Glycogen, hyaluronate, and some other polysaccharides greatly enhance the formation of exolipase by Serratia marcescens. Journal of Bacteriology. 1979;138(3):663-70. URLs: http://jb.asm.org/content/138/3/663
  • Kantar GK, Faiz O, Sahin O, Sasmaz S. Phthalocyanine and azaphthalocyanines containing eugenol: synthesis, DNA interaction and comparison of lipase inhibition properties. J Chem Sci. 2017;129(8):1247-56. DOI: 10.1007/s12039-017-1320-4.
  • Apak R, Guclu K, Ozyurek M, Celik SE. Mechanism of antioxidant capacity assays and the CUPRAC (cupric ion reducing antioxidant capacity) assay. Microchim Acta. 2008;160(4):413-9. DOI: 10.1007/s00604-007-0777-0.
  • Heck AM, Yanovski JA, Calis KA. Orlistat, a new lipase inhibitor for the management of obesity. Pharmacotherapy. 2000;20(3):270-9. DOI: 10.1592/phco.20.4.270.34882.
  • Frecentese F, Saccone I, Caliendo G, Corvino A, Fiorino F, Magli E, et al. Microwave Assisted Organic Synthesis of Heterocycles in Aqueous Media: Recent Advances in Medicinal Chemistry. Med Chem. 2016;12(8):720-32. DOI: 10.2174/1573406412666160502153553.
  • Kappe CO, Dallinger D. Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature. Mol Divers. 2009;13(2):71-193. DOI: 10.1007/s11030-009-9138-8.
  • Kappe CO, Stadler A, Dallinger D, Strohmeier G, Perez R, Zbruyev OI, et al. Adventures in microwave-assisted organic synthesis: Contributions from the Kappe laboratory 2000-2005. Nato Sci Ser Ii-Math. 2008;246:225-51. DOI: 10.1007/978-1-4020-6793-8_11.
  • de Souza SM, Delle Monache F, Smania A. Antibacterial activity of coumarins. Z Naturforsch C. 2005;60(9-10):693-700. DOI: 10.1515/znc-2005-9-1006.
  • Srinivas B, Suryachandram J, Devi YK, Rao KP. Synthesis and Antibacterial Activity Studies of 8,9-Dihydro [7h] Benzo 1,2,4-Oxadiazoles and its Coumarin Derivatives. J Heterocyclic Chem. 2017;54(6):3730-4. DOI: 10.1002/jhet.2960.
  • Zhang RR, Liu J, Zhang Y, Hou MQ, Zhang MZ, Zhou FE, et al. Microwave-assisted synthesis and antifungal activity of novel coumarin derivatives: Pyrano[3,2-c]chromene-2,5-diones. Eur J Med Chem. 2016;116:76-83. DOI: 10.1016/j.ejmech.2016.03.069.
  • Khan KM, Saify ZS, Khan MZ, Zia-Ullah, Choudhary MI, Atta-ur-Rahman, et al. Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activity. J Enzym Inhib Med Ch. 2004;19(4):373-9. DOI: 10.1080/1475636042000206428.
There are 33 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Articles
Authors

Fatih Yılmaz

Özlem Faiz This is me 0000-0003-2447-0763

Publication Date January 1, 2018
Submission Date February 6, 2018
Acceptance Date March 16, 2018
Published in Issue Year 2018 Volume: 5 Issue: 2

Cite

Vancouver Yılmaz F, Faiz Ö. Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. JOTCSA. 2018;5(2):551-68.