Potansiyel Biyolojik Aktif Metil-4,5-dimetoksi-2-(2-(4-metoksifenil)-2-oksoetil)benzoat’ın Sentezi

Year 2021, Volume: 11 Issue: 3, 2152 - 2159, 01.09.2021

Kadir Aksu

https://doi.org/10.21597/jist.875097

Cited By: 1

Abstract

Benzoik asit, metil benzoat bileşikleri ve bunların türevleri oldukça geniş bir alanda aktivite gösteren, sentezi organik kimyacılar için önemli olan kıymetli bileşiklerdir. Bu çalışmada 3,4- dimetoksisinamik asitten başlanarak bir seri reaksiyon sonucunda benzoik asitin metil ester türevi olan metil-4,5-dimetoksi-2-(2-(4-metoksifenil)-2-oksoetil)benzoat’ın sentezi etkin bir şekilde gerçekleştirildi. Sentezlenen bileşiğin yapısı 1H NMR ve 13C NMR spektrumları ile karakterize edildi.

Keywords

Benzoik asit, Sinamik asit, Poli sübstitüe metil benzoat

Supporting Institution

Ordu Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi

Project Number

AP-1714

Thanks

Bu çalışma, Ordu Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi tarafından “AP-1714” kodlu proje ile desteklenmiş olup, Ordu Üniversitesi Fen Edebiyat Fakültesi Kimya Bölümünde gerçekleştirilmiştir.

Synthesis of Potentially Biologically Active Methyl-4,5-dimethoxy-2-(2-(4-methoxyphenyl)-2- oxoethyl)benzoate

Abstract

Benzoic acid, methyl benzoate compounds and their derivatives are valuable compounds that have a wide range of activities and synthesis of these is important for organic chemists. In this study, the synthesis of methyl-4,5-dimethoxy-2-(2-(4-methoxyphenyl)-2-oxoethyl) benzoate, methyl ester derivative of benzoic acid, was carried out effectively as a result of a series of reactions starting from 3,4-dimethoxycinnamic acid. The structure of synthesized compound was characterized by 1H NMR and 13C NMR spectra.

Keywords

Benzoic acid, Cinnamic acid, Poly substituted methyl benzoate

Project Number

AP-1714

References

• Ahmed HBUD, Rama NH, Malana MA, Qadeer G, 2006. A Convenient Synthesis of Xyridin A Metabolite from Xyris Indica L. Indian Journal of Chemistry. 45B: 820-822.
• Chakrabarti, PM, 1968. Brazilin and Haematoxylin. Part IV. Synthesis of π-Trimethylbrazilone. Tetrahedron Letters, 9 (37): 3999-4002.
• Choi SZ, Choi SU, Bae S Y, neung Pyo S, Lee KR, 2005. Immunobioloical Activity of A New Benzyl Benzoate from the Aerial Parts of Solidago virga-aurea var. gigantea. Archives of Pharmacal Research, 28 (1): 49-54.
• Fillion E, Fishlock D, Wilsily A, Goll JM, 2005. Meldrum's Acids as Acylating Agents in the Catalytic Intramolecular Friedel−Crafts Reaction. The Journal of Organic Chemistry. 70 (4): 1316-1317.
• Geneste H, Ochse, M, Drescher K, Turner S, Behl B, Laplanche L, et al., 2013. Novel Inhibitor Compounds of Phosphodiesterase Type 10a. U.S. Patent Application, No. 13/660,524.
• Li Q, Lu F, Tian Y, Feng S, Shen Y, Wang B, 2013. Solubility of Veratric Acid in Eight Monosolvents and Ethanol + 1-Butanol at Various Temperatures. Journal of Chemical & Engineering Data, 58 (4): 1020-1028.
• Mostafiz MM, Shim JK, Hwang HS, Bunch H, Lee KY, 2020. Acaricidal Effects of Methyl Benzoate Against Tetranychus Urticae Koch (Acari: Tetranychidae) on Common Crop Plants. Pest Management Science, 76 (7): 2347-2354.
• Narasimhan B, Ohlan S, Ohlan R, Judge V, Narang R, 2009. Hansch Analysis of Veratric Acid Derivatives as Antimicrobial Agents. European Journal of Medicinal Chemistry, 44 (2): 689-700.
• Pirinç B, Türkoğlu Ş, 2016. Etil Paraben ve Metil Parabenin Caenorhabditis Elegans’ ta Yumurta Verimi, Yaşama Yüzdesi ve Fiziksel Büyüme Üzerine Olan Etkilerinin Araştırılması. Cumhuriyet Üniversitesi Fen Bilimleri Dergisi, 37 (4): 371-390.
• Qualley AV, Widhalm JR, Adebesin F, Kish CM, Dudareva, N, 2012. Completion of the Core β-oxidative Pathway of Benzoic Acid Biosynthesis in Plants. Proceedings of the National Academy of Sciences, 109 (40): 16383-16388.
• Saravanakumar M, Raja B, 2011. Veratric Acid, A Phenolic Acid Attenuates Blood Pressure and Oxidative Stress in L-NAME İnduced Hypertensive Rats. European Journal of Pharmacology, 671 (1-3): 87-94.
• Saravanakumar M, Raja B, 2012. Effect of Veratric Acid on the Cardiovascular Risk of L-NAME–İnduced Hypertensive Rats. Journal of Cardiovascular Pharmacology, 59 (6): 553-562.
• Soni MG, Taylor SL, Greenberg NA, Burdock GA, 2002. Evaluation of the Health Aspects of Methyl Paraben: A Review of the Published Literature. Food and Chemical Toxicology, 40 (10): 1335-1373.
• Stubba D, Lahm G, Geffe M, Runyon JW, Arduengo AJ, Opatz T. 2015. Xylochemistry—Making Natural Products Entirely from Wood. Angewandte Chemie International Edition. 54 (47): 14187-14189.
• Unelius CR, Nordlander G, Nordenhem H, Hellqvist C, Legrand S, Borg-Karlson AK, 2006. Structure–Activity Relationships of Benzoic Acid Derivatives as Antifeedants for the Pine Weevil, Hylobius Abietis. Journal of Chemical Ecology, 32 (10): 2191-2203.
• Wang JH, Chen KQ, Jiang JX, Li HY, Pan JP, Su JY, et al., 2020. Excretion, Metabolism and Cytochrome P450 Inhibition of Methyl 3, 4-Dihydroxybenzoate (MDHB): A Potential Candidate to Treat Neurodegenerative Diseases. European Journal of Drug Metabolism and Pharmacokinetics, 45 (1): 51-69.