Several lipases were used for the kinetic resolution in different pH values and different solvent systems of racemic 4,5,6,7-tetrahydro-6-phenyl-4-oxo-benzofuranone-5-yl acetate (rac-3) in which the lipases from HPL, PPL, RNL and PCL displayed high enentioselectivity towards 4,5,6,7-tetrahydro-6- phenyl-4-oxo-benzofuranone-5-yl hydroxy derivative (4) at pH=7.
📌 3 Maddede Bu Makale
🎯
Amaç & Hipotez:Benzofuranone derivatives are important structural units in many biologically active compounds thus, synthesis of these types of compounds in optically pure form found increased interest in pharmaceutical chemistry.
📊
Temel Bulgular & Veri:In this study, the enantioselective synthesis of 4,5,6,7-tetrahydro-6-phenyl-4-oxo-benzofuranone-5-yl acetate (3) and 4,5,6,7-tetrahydro-6- phenyl-4-oxo-benzofuranone-5-yl hydroxy derivative (4) was carried out for the first time, by enzyme-mediated hydrolysis reactions with high enantiomeric excesses.
💡
Sonuç & Katkı:Several lipases were used for the kinetic resolution in different pH values and different solvent systems of racemic 4,5,6,7-tetrahydro-6-phenyl-4-oxo-benzofuranone-5-yl acetate (rac-3) in which the lipases from HPL, PPL, RNL and PCL displayed high enentioselectivity towards 4,5,6,7-tetrahydro-6- phenyl-4-oxo-benzofuranone-5-yl hydroxy derivative (4) at pH=7.
Benzofuranone derivatives are important structural units in many biologically active compounds thus, synthesis of these types of compounds in optically pure form found increased interest in pharmaceutical chemistry. In this study, the enantioselective synthesis of 4,5,6,7-tetrahydro-6-phenyl-4-oxo-benzofuranone-5-yl acetate (3) and 4,5,6,7-tetrahydro-6- phenyl-4-oxo-benzofuranone-5-yl hydroxy derivative (4) was carried out for the first time, by enzyme-mediated hydrolysis reactions with high enantiomeric excesses. Several lipases were used for the kinetic resolution in different pH values and different solvent systems of racemic 4,5,6,7-tetrahydro-6-phenyl-4-oxo-benzofuranone-5-yl acetate (rac-3) in which the lipases from HPL, PPL, RNL and PCL displayed high enentioselectivity towards 4,5,6,7-tetrahydro-6- phenyl-4-oxo-benzofuranone-5-yl hydroxy derivative (4) at pH=7.
Çalışkan, Z. Z., Ay, E. N. (2018). Synthesis of Dihydrobenzofuranone Derivatives with Biotechnological Methods. Journal of the Turkish Chemical Society Section A: Chemistry, Cilt: 5 - Sayı: 3, 1221–1232. https://ajindex.com/articles/781335
Keay BA, Hopkins JM, Dibble PW. Furans and their benzo derivatives: Applications. Comprehensive Heterocyclic Chemistry III. 2008:571-623
Mishra RC. Second Generation Benzofuranone Ring Substituted Noscapine Analogs: Synthesis and Biological Evaluation. Biochemical Pharmacology. 2011; 82:110-21
Tan YX, Wang HQ, Chen RY. Anti-inflammatory and cytotoxic 2-arylbenzofurans from Morus wittiorum. Fitoterapia. 2012; 83:750-3
Tan YX, Yang Y, Zhang T, Chen RY, Yu DQ. Bioactive 2-arylbenzofuran derivatives from Morus wittiorum. Fitoterapia. 2010; 81:742-6
Kim YJ, Sohn MJ, Kim WG. Chalcomoracin and moracin C, new inhibitors of Staphylococcus aureus enoyl-acyl carrier protein reductase from Morus alba. Biol Pharm Bull. 2012; 35: 791-5
Romagnoli R, Baraldi PG, Sarkar T, et al. Synthesis and biological evaluation of 2-aroyl-4-phenyl-5-hydroxybenzofurans as a new class of antitubulin agents. Med Chem. 2008; 4:558-64
Flynn BL, Gill GS, Grobelny DW, et al. Discovery of 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzofuran (BNC105), a tubulin polymerization inhibitor with potent antiproliferative and tumor vascular disrupting properties. J Med Chem. 2011; 54:6014-27
Shi W, Lowary TL. Structure-activity relationships in glycosylated 2-phenyl-indoles, 2-phenyl-benzo[b]thiophenes and 2-phenylbenzo[b]furans as DNA binding and potential antitumor agents. Bioorg. Med. Chem. 2011; 19:1779-89
Kossakowski J, Ostrowska K, Hejchman E, Wolska I. Synthesis and structural characterization of derivatives of 2- and 3-benzo[b]furan carboxylic acids with potential cytotoxic activity. II Farmaco. 2005; 60:519-27
George JH, Baldwin JE, Adlington RM. Enantiospecific, biosynthetically inspired formal total synthesis of (+)-liphagal. Org Lett. 2010; 12:2394-7
Caner H, Groner E, Levy L, Agranat I. Trends in the development of chiral drugs. Drug Discovery Today. 2004; 9(3):105-10
Carey JS, Laffan D, Thomson C, Williams MT. Analysis of the reactions used for the preparation of drug candidate molecules. Org. Biomol. Chem. 2006; 4:2337–47
Gotor V, Alfonso I, García-Urdiales E. Asymmetric Organic Synthesis with Enzymes. Weinheim, Germany: Wiley-VCH; 2008
Patel RN. Synthesis of chiral pharmaceutical intermediates by biocatalysis. Coord. Chem. Rev. 2008; 252:659–701
Hudlicky T, Reed JW. Applications of biotransformations and biocatalysis to complexity generation in organic synthesis. Chem. Soc. Rev. 2009; 38(11):3117–32