Research Article
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Year 2017, Volume: 4 Issue: 3, 709 - 720, 05.07.2017
https://doi.org/10.18596/jotcsa.311736

Abstract

References

  • 1. Walsh CT, Wencewicz TA. Prospects for new antibiotics: a molecule-centered perspective. J. Antibiot. 2014; 67(1): 7-22.
  • 2. Simard F, Gauthier C, Chiasson E, Lavoie S, Mshvildadze V, Legault J, Pichette A. Antibacterial Balsacones J-M, Hydroxycinnamoylated Dihydrochalcones from Populus balsamifera Buds. J. Nat. Prod. 2015; 78: 1147-1153.
  • 3. Taylor PW. Alternative natural sources for a new generation of antibacterial agents. J. Antimicrob. Agents 2013; 42(3): 195-201.
  • 4. Uprety Y, Asselin H, Dhakal A, Julien N. Traditional use of medicinal plants in the boreal forest of Canada: review and perspectives. J. Ethnobiol. Ethnomed. 2012; 8(7): 1-14.
  • 5. Koné WM, Atindehou KK, Terreaux C, Hostettmann K, Traoré D, Dosso M. Traditional medicine in North Côte-d’Ivoire: screening of 50 medicinal plants for antibacterial activity. J. Ethnopharmacol. 2004; 93(1): 43-49.
  • 6. Bonjar S. Evaluation of antibacterial properties of some medicinal plants used in Iran. J. Ethnopharmacol. 2004; 94(2-3): 301-305.
  • 7. Omar S, Lemonnier B, Jones N, Ficker C, Smith ML, Neema C, Towers GHN, Goel K, Arnason JT. Antimicrobial activity of extracts of eastern North American hardwood trees and relation to traditional medicine. J. Ethnopharmacol. 2000; 73(1-2): 161-170.
  • 8. Lavoie S, Legault J, Simard F, Chiasson E, Pichette A. New antibacterial dihydrochalcone derivatives from buds of Populus balsamifera. Tetrahedron Lett. 2013; 54(13): 1631-1633.
  • 9. Isidorov VA, Vinogorova VT. GC-MS analysis of compounds extracted from buds of Populus balsamifera and Populus nigra. Z. Naturforsch C: Biosci. 2003; 58(5-6): 355-360.
  • 10. Polyakov VV, Orlov VK, Shukenova RZ, Mullaeva NI. Carboxylic acids of Populus balsamifera. Chem. Nat. Comp. 1985; 21(6): 795.
  • 11. Mattes BR, Clausen TP, Reichardt PB. Volatile constituents of balsam poplar - the phenol glycoside connection. Phytochemistry 1987; 26(5): 1361-1366.
  • 12. Greenaway W, May J, Whatley FR. Flavonoid aglycones identified by gas-chromatography mass-spectrometry in bud exudate of populus-balsamifera. J. Chromatogr. 1989; 472(2): 393-400.
  • 13. Levin ED, Isaeva EV, Cherepanova VE. Arachidonic-acid and prostaglandins in buds of populus-balsamifera. Phytochemistry 1990; 7: 2325-2326.
  • 14. Merghachea D, Boucherit-Otmania Z, Hacib IE, Merghachec FS, Chikhid I, Boucherita K. Antioxidant and antimicrobial activities of algerian populus nigra l. buds extracts. Bioscience & Engineering: An International Journal (BIOEJ) 2016; 3(1-2): 1-8.
  • 15. Khupse RS, Erhardt PW. Total Synthesis of Xanthohumol. J. Nat. Prod. 2007; 70: 1507-1509.
  • 16. Jun N, Hong G, Jun K. Synthesis and evaluation of 2’,4’,6’-trihydroxychalcones as a new class of tyrosinase inhibitors. Bioorg. Med. Chem. 2007; 15: 2396-2402.
  • 17. Zhao LM, Jin HS, Sun LP, Piao HR, Quan ZS. Synthesis and evaluation of antiplatelet activity of trihydroxychalcone derivatives. Bioorg. Med. Chem. Lett. 2005; 15: 5027-5029.
  • 18. Mustafa KA, Kjaergaard HG, Perry NB, Weavers RT. Hydrogen-bonded rotamers of 2',4',6'-trihydroxy-3'-formyldihydrochalcone, an intermediate in the synthesis of a dihydrochalcone from Leptospermum recurvum. Tetrahedron 2003; 59(32): 6113−6120.
  • 19. Jesus AR, Vila-Vicosa D, Machuqueiro M, Marques AP, Dore TM, Rauter AP. Targeting Type 2 Diabetes with C-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation. J. Med. Chem. 2017; 60(2): 568-579.
  • 20. Huang WJ, Chen CC, Chao SW, Lee SS, Hsu FL, Lu YL, Hung MF, Chang CI. Synthesis of N-Hydroxycinnamides Capped with a Naturally Occurring Moiety as Inhibitors of Histone Deacetylase. ChemMedChem. 2010; 5(4): 598-607.
  • 21. Kim E, Koh M, Lim BJ, Park SB. Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one. JACS 2011; 133(17): 6642-6649. DOI: 10.1021/ja110766a
  • 22. Young SD, Payne LS, Thompson WJ, Gaffin N, Lyle TA, Britcher SF, Graham SL, Schultz TH, Deana A A, Darke PL, Zugay J, Schleif WA, Quintero JC, Emini EA, Anderson PS, Huff JR. HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres - an investigation into the role of the p1' side-chain on structure activity. J. Med. Chem. 1992; 35(10): 1702–1709.

Total Syntheses of Balsacone B and Balsacone C

Year 2017, Volume: 4 Issue: 3, 709 - 720, 05.07.2017
https://doi.org/10.18596/jotcsa.311736

Abstract

The first total
syntheses of Balsacone C (16) and
Balsacone B (17), mainly based on a
convergent strategy, were described. The crucial step of this strategy was the
alkylation of trihydroxydihydrochalcone derivatives 7 and 8 with cinnamylbromide
derivative 13. For this, compounds 7 and 8 were prepared starting from trihydroxyacetophenone (1) in four steps. Then compound 13 was prepared starting from coumaric
acid (9) in four steps.      

References

  • 1. Walsh CT, Wencewicz TA. Prospects for new antibiotics: a molecule-centered perspective. J. Antibiot. 2014; 67(1): 7-22.
  • 2. Simard F, Gauthier C, Chiasson E, Lavoie S, Mshvildadze V, Legault J, Pichette A. Antibacterial Balsacones J-M, Hydroxycinnamoylated Dihydrochalcones from Populus balsamifera Buds. J. Nat. Prod. 2015; 78: 1147-1153.
  • 3. Taylor PW. Alternative natural sources for a new generation of antibacterial agents. J. Antimicrob. Agents 2013; 42(3): 195-201.
  • 4. Uprety Y, Asselin H, Dhakal A, Julien N. Traditional use of medicinal plants in the boreal forest of Canada: review and perspectives. J. Ethnobiol. Ethnomed. 2012; 8(7): 1-14.
  • 5. Koné WM, Atindehou KK, Terreaux C, Hostettmann K, Traoré D, Dosso M. Traditional medicine in North Côte-d’Ivoire: screening of 50 medicinal plants for antibacterial activity. J. Ethnopharmacol. 2004; 93(1): 43-49.
  • 6. Bonjar S. Evaluation of antibacterial properties of some medicinal plants used in Iran. J. Ethnopharmacol. 2004; 94(2-3): 301-305.
  • 7. Omar S, Lemonnier B, Jones N, Ficker C, Smith ML, Neema C, Towers GHN, Goel K, Arnason JT. Antimicrobial activity of extracts of eastern North American hardwood trees and relation to traditional medicine. J. Ethnopharmacol. 2000; 73(1-2): 161-170.
  • 8. Lavoie S, Legault J, Simard F, Chiasson E, Pichette A. New antibacterial dihydrochalcone derivatives from buds of Populus balsamifera. Tetrahedron Lett. 2013; 54(13): 1631-1633.
  • 9. Isidorov VA, Vinogorova VT. GC-MS analysis of compounds extracted from buds of Populus balsamifera and Populus nigra. Z. Naturforsch C: Biosci. 2003; 58(5-6): 355-360.
  • 10. Polyakov VV, Orlov VK, Shukenova RZ, Mullaeva NI. Carboxylic acids of Populus balsamifera. Chem. Nat. Comp. 1985; 21(6): 795.
  • 11. Mattes BR, Clausen TP, Reichardt PB. Volatile constituents of balsam poplar - the phenol glycoside connection. Phytochemistry 1987; 26(5): 1361-1366.
  • 12. Greenaway W, May J, Whatley FR. Flavonoid aglycones identified by gas-chromatography mass-spectrometry in bud exudate of populus-balsamifera. J. Chromatogr. 1989; 472(2): 393-400.
  • 13. Levin ED, Isaeva EV, Cherepanova VE. Arachidonic-acid and prostaglandins in buds of populus-balsamifera. Phytochemistry 1990; 7: 2325-2326.
  • 14. Merghachea D, Boucherit-Otmania Z, Hacib IE, Merghachec FS, Chikhid I, Boucherita K. Antioxidant and antimicrobial activities of algerian populus nigra l. buds extracts. Bioscience & Engineering: An International Journal (BIOEJ) 2016; 3(1-2): 1-8.
  • 15. Khupse RS, Erhardt PW. Total Synthesis of Xanthohumol. J. Nat. Prod. 2007; 70: 1507-1509.
  • 16. Jun N, Hong G, Jun K. Synthesis and evaluation of 2’,4’,6’-trihydroxychalcones as a new class of tyrosinase inhibitors. Bioorg. Med. Chem. 2007; 15: 2396-2402.
  • 17. Zhao LM, Jin HS, Sun LP, Piao HR, Quan ZS. Synthesis and evaluation of antiplatelet activity of trihydroxychalcone derivatives. Bioorg. Med. Chem. Lett. 2005; 15: 5027-5029.
  • 18. Mustafa KA, Kjaergaard HG, Perry NB, Weavers RT. Hydrogen-bonded rotamers of 2',4',6'-trihydroxy-3'-formyldihydrochalcone, an intermediate in the synthesis of a dihydrochalcone from Leptospermum recurvum. Tetrahedron 2003; 59(32): 6113−6120.
  • 19. Jesus AR, Vila-Vicosa D, Machuqueiro M, Marques AP, Dore TM, Rauter AP. Targeting Type 2 Diabetes with C-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation. J. Med. Chem. 2017; 60(2): 568-579.
  • 20. Huang WJ, Chen CC, Chao SW, Lee SS, Hsu FL, Lu YL, Hung MF, Chang CI. Synthesis of N-Hydroxycinnamides Capped with a Naturally Occurring Moiety as Inhibitors of Histone Deacetylase. ChemMedChem. 2010; 5(4): 598-607.
  • 21. Kim E, Koh M, Lim BJ, Park SB. Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one. JACS 2011; 133(17): 6642-6649. DOI: 10.1021/ja110766a
  • 22. Young SD, Payne LS, Thompson WJ, Gaffin N, Lyle TA, Britcher SF, Graham SL, Schultz TH, Deana A A, Darke PL, Zugay J, Schleif WA, Quintero JC, Emini EA, Anderson PS, Huff JR. HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres - an investigation into the role of the p1' side-chain on structure activity. J. Med. Chem. 1992; 35(10): 1702–1709.
There are 22 citations in total.

Details

Primary Language English
Subjects Engineering, Chemical Engineering
Journal Section Articles
Authors

Serdar Burmaoğlu

Publication Date July 5, 2017
Submission Date May 10, 2017
Acceptance Date July 1, 2017
Published in Issue Year 2017 Volume: 4 Issue: 3

Cite

Vancouver Burmaoğlu S. Total Syntheses of Balsacone B and Balsacone C. JOTCSA. 2017;4(3):709-20.