Yıl: 2018 Cilt: 5 Sayı: 2 Sayfa Aralığı: 551 - 568 Metin Dili: İngilizce DOI: 10.18596/jotcsa.390928 İndeks Tarihi: 22-02-2020

Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides

Öz:
In this work, 15 different coumarin hydrazides were successfully synthesized andscreened for their antioxidant and antilipase activities. To do this, firstly, salicylaldehydederivatives and Meldrum's Acid were reacted in absolute ethanol with catalytic amount ofpyridine to obtain coumarin-3-carboxylic acid derivatives (1a-e). Then, these compounds weretreated with 1H-benzotriazole in dichloromethane by using thionyl chloride to synthesizebenzotriazole derivatives (2a-e). Then, compounds 2a-e were reacted with three commercialhydrazides (nicotinic hydrazide, benzhydrazide,and phenyl acetichydrazide) in ethanol by usingmicrowave irradiation and conventional heating procedures to obtain final products (3-5a-e).Finally, these compounds were tested for their anti-oxidant and anti-lipase activities. Thestructure of newly synthesized compounds was identified by IR, 1H NMR, 13C NMR, and elementalanalysis data.
Anahtar Kelime:

Konular: Kimya, Analitik Termodinamik Spektroskopi Kimya, Uygulamalı Kimya, Organik Kimya, Tıbbi Fizikokimya Kimya, İnorganik ve Nükleer
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • 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. 2. 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.
  • 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.
  • Kappe CO, Dallinger D. Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature. Mol Divers. 2009;13(2):71-193.
  • 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.
  • de Souza SM, Delle Monache F, Smania A. Antibacterial activity of coumarins. Z Naturforsch C. 2005;60(9-10):693-700.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Kamiyama H, Kubo Y, Sato H, Yamamoto N, Fukuda T, Ishibashi F, et al. Synthesis, structureactivity relationships, and mechanism of action of anti-HIV-1 lamellarin alpha 20-sulfate analogues. Bioorgan Med Chem. 2011;19(24):7541-50.
  • Carocho M, Morales P, Ferreira ICFR. Natural food additives: Quo vadis? Trends Food Sci Tech. 2015;45(2):284-95.
  • 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.
  • 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.
  • 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.
  • Karatas MO, Uslu H, Sari S, Alagoz MA, Karakurt A, Alici B, et al. Coumarin or benzoxazinone based novel carbonic anhydrase inhibitors: synthesis, molecular docking and anticonvulsant studies. J Enzym Inhib Med Ch. 2016;31(5):760-72.
  • Maresca A, Temperini C, Vu H, Pham NB, Poulsen SA, Scozzafava A, et al. Non-Zinc Mediated Inhibition of Carbonic Anhydrases: Coumarins Are a New Class of Suicide Inhibitors. J Am Chem Soc. 2009;131(8):3057-62.
  • Anand P, Singh B, Singh N. A review on coumarins as acetylcholinesterase inhibitors for Alzheimer's disease. Bioorgan Med Chem. 2012;20(3):1175-80.
  • Aziz-ur-Rehman, Magsi S, Abbasi MA, Rasool S, Malik A, Hussain G, et al. Synthesis, characterization and enzyme inhibition study of O-substituted derivatives of chlorinated coumarin. Pak J Pharm Sci. 2014;27(2):271-8.
  • Ali MY, Jannat S, Jung HA, Choi RJ, Roy A, Choi JS. Anti-Alzheimer's disease potential of coumarins from Angelica decursiva and Artemisia capillaris and structure-activity analysis. Asian Pac J Trop Med. 2016;9(2):101-8.
  • Mentese E, Yilmaz F, Emirik M, Ulker S, Kahveci B. Synthesis, molecular docking and biological evaluation of some benzimidazole derivatives as potent pancreatic lipase inhibitors. Bioorg Chem. 2018;76:478-86.
  • Mentese E, Bektas H, Sokmen BB, Emirik M, Cakir D, Kahveci B. Synthesis and molecular docking study of some 5,6-dichloro-2cyclopropyl-1H-benzimidazole derivatives bearing triazole, oxadiazole, and imine functionalities as potent inhibitors of urease. Bioorg Med Chem Lett. 2017;27(13):3014-8.
  • 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).
  • Mentese E, Karaali N, Akyuz G, Yilmaz F, Ulker S, Kahveci B. Synthesis and evaluation of alphaglucosidase and pancreatic lipase inhibition by quinazolinone-coumarin hybrids. Chem Heterocycl Com+. 2016;52(12):1017-24.
  • 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.
  • 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.
  • 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.
  • 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.
  • Tang J, Huang X. An efficient solid-phase synthesis of 3-carboxycoumarins based on a scaffoldpolymer- bound cyclic malonic ester. J Chem Res-S. 2003(6):354-5.
  • 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.
  • 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.
  • 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. 36. Katritzky AR, Cusido J, Narindoshvili T. Monosaccharide-based water-soluble fluorescent tags. Bioconjugate Chem. 2008;19(7):1471-5.
  • Katritzky AR, Abdelmajeid A, Tala SR, Amine MS, Steel PJ. Novel Fluorescent Aminoxy Acids and Aminoxy Hybrid Peptides. Synthesis-Stuttgart. 2011(1):83-90.
  • Badran MM, El-Gendy AA, Soliman LN, El-Assi HR. Synthesis of certain novel 3-substituted coumarins. Bulletin of the Faculty of Pharmacy (Cairo University). 1990;28(2):39-42.
  • 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.
  • 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.
  • 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.
  • Badran MM, Elansari AK, Elmeligie S. Novel Substituted-Aminocoumarins as Potential Antimicrobial Agents. Rev Roum Chim. 1990;35(6):777-83.
  • Mohareb RM, Ho JZ, Alfarouk FO. Synthesis of thiophenes, azoles and azines with potential biological activity by employing the versatile heterocyclic precursor Nbenzoycyanoacetylhydrazine. J Chin Chem Soc-Taip. 2007;54(4):1053-66.
  • Ma L, Xu YX, Wang KN, Zhou CJ, Cao DX, Shan YY, et al. Synthesis and recognition properties for copper ions and cyanide anions of two coumarin hydrazide compounds. Inorg Chem Commun. 2015;58:24-6.
  • Long LL, Zhang DD, Li XF, Zhang JF, Zhang C, Zhou LP. A fluorescence ratiometric sensor for hypochlorite based on a novel dual-fluorophore response approach. Anal Chim Acta. 2013;775:100-5.
  • Heck AM, Yanovski JA, Calis KA. Orlistat, a new lipase inhibitor for the management of obesity. Pharmacotherapy. 2000;20(3):270-9.
APA Yılmaz F, Faiz Ö (2018). Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. , 551 - 568. 10.18596/jotcsa.390928
Chicago Yılmaz Fatih,Faiz Özlem Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. (2018): 551 - 568. 10.18596/jotcsa.390928
MLA Yılmaz Fatih,Faiz Özlem Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. , 2018, ss.551 - 568. 10.18596/jotcsa.390928
AMA Yılmaz F,Faiz Ö Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. . 2018; 551 - 568. 10.18596/jotcsa.390928
Vancouver Yılmaz F,Faiz Ö Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. . 2018; 551 - 568. 10.18596/jotcsa.390928
IEEE Yılmaz F,Faiz Ö "Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides." , ss.551 - 568, 2018. 10.18596/jotcsa.390928
ISNAD Yılmaz, Fatih - Faiz, Özlem. "Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides". (2018), 551-568. https://doi.org/10.18596/jotcsa.390928
APA Yılmaz F, Faiz Ö (2018). Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. Journal of the Turkish Chemical Society, Section A: Chemistry, 5(2), 551 - 568. 10.18596/jotcsa.390928
Chicago Yılmaz Fatih,Faiz Özlem Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. Journal of the Turkish Chemical Society, Section A: Chemistry 5, no.2 (2018): 551 - 568. 10.18596/jotcsa.390928
MLA Yılmaz Fatih,Faiz Özlem Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. Journal of the Turkish Chemical Society, Section A: Chemistry, vol.5, no.2, 2018, ss.551 - 568. 10.18596/jotcsa.390928
AMA Yılmaz F,Faiz Ö Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. Journal of the Turkish Chemical Society, Section A: Chemistry. 2018; 5(2): 551 - 568. 10.18596/jotcsa.390928
Vancouver Yılmaz F,Faiz Ö Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides. Journal of the Turkish Chemical Society, Section A: Chemistry. 2018; 5(2): 551 - 568. 10.18596/jotcsa.390928
IEEE Yılmaz F,Faiz Ö "Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides." Journal of the Turkish Chemical Society, Section A: Chemistry, 5, ss.551 - 568, 2018. 10.18596/jotcsa.390928
ISNAD Yılmaz, Fatih - Faiz, Özlem. "Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides". Journal of the Turkish Chemical Society, Section A: Chemistry 5/2 (2018), 551-568. https://doi.org/10.18596/jotcsa.390928