Reviews on flavanone compounds synthesis research

LIANG Hai; XIANG Zhuo; ZHANG Xuehui; WU Jiuhong

doi:10.3969/j.issn.1006-0111.2015.02.001

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Volume 33 Issue 2

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2015 > 33(2): 97-101,130

LIANG Hai, XIANG Zhuo, ZHANG Xuehui, WU Jiuhong. Reviews on flavanone compounds synthesis research[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(2): 97-101,130. doi: 10.3969/j.issn.1006-0111.2015.02.001

Citation:

LIANG Hai, XIANG Zhuo, ZHANG Xuehui, WU Jiuhong. Reviews on flavanone compounds synthesis research[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(2): 97-101,130. doi: 10.3969/j.issn.1006-0111.2015.02.001

Reviews on flavanone compounds synthesis research

doi: 10.3969/j.issn.1006-0111.2015.02.001

1.
School of Pharmacy, Anhui Medical University, Hefei 230032, China;Department of Pharmacy, No.306 Hospital of PLA, Beijing 100101, China
2.
Department of Pharmacy, No.306 Hospital of PLA, Beijing 100101, China

Received Date: 2013-11-28
Rev Recd Date: 2014-04-21

Abstract

Research progress of flavanone compounds synthesis was reviewed, various types of synthesis methods of flavanone compounds were summarized, and methodological support for flavanone compounds in new drug research and development was provided. Research progress in synthesis of flavanone compounds includes chalcone cyclization, Friedel-Crafts reaction, Knoevenagel condensation, Hoesch single acetoxylation, and asymmetric synthesis of flavanone compounds. Solvent-free synthesis of flavanone compounds and other green chemistry methods were also introduced.
- flavanone compounds,
- chalcone,
- cyclization,
- synthesis

References

[1]	Noushin A, Alireza N, Christophe W. Anti-bacterial, antioxidant activity and phytochemical study of Uvaria grandiflora: a rare species of Annonaceae[J]. J Pharm Res, 2011, 4(4): 944-955.
[2]	Chavan PN. Comparative study of flavonoids from chyavanprash for anti-inflammatory activity[J]. J Pharm Res, 2011, 4(5): 1338-1339.
[3]	Szliszka E, Kostrzewa SE, Bronikowska J, et al. Synthetic flavanones augment the anticancer effect of tumor necrosis factor-related apoptosis-inducing ligand (trail)[J]. Molecules, 2012, 17(10): 11693-11711.
[4]	Wang B, Ge L, Huang WL, et al. Synthesis and preliminary anti-HIV activities of andrographolide derivatives[J]. J Med Chem, 2010, 6(4): 252-258.
[5]	Resende FA, Vilegas W, Dos Santos LC, et al. Mutagenicity of flavonoids assayed by bacterial reverse mutation (Ames) test[J]. Molecules, 2012, 17(5): 5255-5268.
[6]	Zhou ZL, Fu CY. A new flavanone and other constituents from the rhizomes of Cyperus rotundus and their antioxidant activities[J]. Chem Nat Compd, 2013, 48(6): 963-965.
[7]	Bhattachaqryya A, Chaudhuri A. Synthesis of didymocarpin-A, a new flavanone isolated from didymocarpus pedicellata[J]. Indian J Chem, 1980, 19B: 428-429.
[8]	Anguly A, Bhattacharyya P, Bhattacharyya A, et al. A synthesis of candidone—a new flavanone isolated from Tephrosia candida[J]. Indian J Chem, 1988, 27(5): 462-463.
[9]	郭冬冬, 杨金会, 梁西周, 等. 两种天然异戊烯基黄烷酮的全合成[J]. 合成化学, 2013, 21(5): 550-553.
[10]	Deshpande VH. Synthesis of 5,3'-dihydroxy-4'-methoxy-flavanone[J]. Indian J Chem, 1981, 20(10): 917-918.
[11]	何文香, 郑旭煦, 殷钟意, 等. 基于吡啶-水体系的2'-羟基查尔酮的环化反应研究[J]. 化学研究与应用, 2010, 22(9): 1142-1146.
[12]	Namrata A, Priyanka S, Anindra S, et al. Synthesis and evaluation of small libraries of triazolylmethoxy chalcones, flavanones and 2-aminopyrimidines as inhibitors of mycobacterial FAS-II and PknG[J]. J Med Chem, 2012, 20(17): 5150-5163.
[13]	Sangwan MK, Verma BS. Association and path-coefficients in Plantago ovata Forsk[J]. Indian J Chem, 1984: 54(12) 1090-1091.
[14]	Bagade MB, Thool AW, Lokhande PD, et al. Simple technics for isomerization of 2'-hydroxychalcones to flavanones—use of silicagel, ethylenediamine and hydroxylamine hydrochloride[J]. Ind J Chem, 1991, 30B: 973-975.
[15]	Naseem A, Ansare WH. An improved procedure for the isomerisation of 2'-hydroxy substituted chalcones to flavaones using silica supported-BiCl3 under dry conditions[J]. J Chem Res, 2004,35(17):572-573.
[16]	Naseem A, Johan EVL. Silica gel supported TaBr5: new catalyst for the facile and rapid cyclization of 2'-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent-free conditions[J]. Tetrahedron Lett, 2006, 47(16): 2725-2729.
[17]	Beena N, Sharad F, Abdul R, et al. Efficient synthesis of 3-methyl-flavanones and evaluation of their anti-bacterial activity[J]. Chin J Chem, 2012, 30(8): 1695-1698.
[18]	Michele TD, Michael DA. Kinetic investigation of the heterogeneous synthesis of flavanone over MgO[J]. Catal Lett, 2002, 79(1-4): 175-181.
[19]	Liu Z, Cortés-Concepción JA, Mustian M, et al. Effect of basic properties of MgO on the heterogeneous synthesis of flavanone[J]. Appl Catal A-Gen, 2006, 302(2): 232-236.
[20]	Choudary BM, Ranganath KVS, Yadav J, et al. Synthesis of flavanones using nanocrystalline MgO[J]. Tetrahedron Lett, 2005, 46(8): 1369-1371.
[21]	Saravanamurugan S, Palanichamy M, Arabmdoo B, et al. Solvent free synthesis of chalcone and flavanone over zinc oxide supported metal oxide catalysts[J]. Catal Commun, 2005, 6(6): 399-403.
[22]	Makrandi JK,Shasi B.Potassium ferricyanide mediated cyclisation of 2'-hydroxychalcones to flavanones using phase transfer catalysis [J].Synth Commun,2000,30(19):3555-3558.
[23]	Hemanth KK, Perumal TP. A simple and facile solventless procedure for the cyclization of 2'-amino-and-2'-hydroxychalcones sodium hydrogen sulphate as heterogenous catalyst[J]. Can J Chem, 2006, 84(8): 1079-1083.
[24]	Raghavendra S, Marzieh Y, Noorsaadah AR. Synthesis of flavanones, azaflavanones, and thioflavanones catalyzed by PMA-SiO₂ as a mild, efficient, and reusable catalyst[J]. Monatsh Chem, 2012, 143(5): 797-800.
[25]	Koichi T, Teize S. Efficient conversion of 2'-hydroxychalcones into flavanones and flavanols[J]. Green Chem, 2001, 3(3): 133-134.
[26]	Jiang HY, Zheng XX, Yin ZY, et al. An efficient catalytic synthesis of flavanones under green conditions[J]. J Chem Res, 2011, 35(4): 220-221.
[27]	Chandrasekhar S, Vijeender K, Venkatram RK. New synthesis of flavanone catalyzed by L-proline[J]. Tetrahedron Lett, 2005, 46(41): 6991-6993.
[28]	Wang X, Cheng S. Solvent-free synthesis of flavanones over aminopropyl-functionalized SBA-15[J]. Catal Commun, 2006, 7(9): 689-695.
[29]	Shunmugavel S, Sujandia, Prasetyantoa EA, et al. Liquid-phase reaction of 2'-hydroxyacetophenone and benzaldehyde over SO₃H-SBA-15 catalysts: influence of microwave and thermal effects[J]. Micropor Mesopor Mat, 2008, 112(1): 97-107.
[30]	Wang H, Nu XD, Zhao M, et al. Solvent-free synthesis of flavanone over new hybrid mesoporous base- catalysts[J]. Chem Res Chin U, 2011, 27(4): 664-668.
[31]	Tibor T.A novel synthesis of precocenes. Efficient synthesis and regioselective o-alkylation of dihydroxy-2,2-dimethyl-4-chromanones[J].J Heterocycl Chem,1988,25(3):871-877.
[32]	覃章兰, 李文新, 黄天宝, 等. 5,7-二羟基-4'-苄氧基黄烷酮的合成及生物活性[J]. 武汉大学学报(自然科学版), 2000, 46(6): 706-708.
[33]	陈俊杰, 李裕林. 黄酮类化合物的合成方法[J]. 厦门大学学报(自然科学版), 1992, 31(6): 651-655.
[34]	Zhang WH, Chan WL, Lin YH,et al. Synthesis of hydroxyflavanones from substituted acetophenones and benzaldehydes in the presence of silica gel, boric acid and piperidine[J]. Heterocycles, 1997, 45(1): 71-75.
[35]	Takashi Y, Kodai N, Kanji S, et al. Synthesis of chalcone and flavanone derivatives from condensation of 2'-hydroxyacetophenones and benzaldehyde over basic β-zeolites[J]. J Jpn Petrol Inst, 2010, 53(6): 351-354.
[36]	Solladie G, Gehrold N, Maignan J. Synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methyl-flavanone[J]. Tetrahedron Asymmetr, 1999, 10(14): 2739-2747.
[37]	Biddle MM, Lin M, Scheidt KA. Enantioselective synthesis of flavanones and chromanones[J]. J Am Chem Soc, 2007, 129(13): 3830-3831.
[38]	Wang LJ, Liu XH, Dong ZH, et al. Asymmetric intramolecular Oxa-Michael addition of activated a,b-unsaturated ketones catalyzed by a chiral N,N'-dioxide nickel(II) complex: highly enantioselective synthesis of flavanoneses[J]. Angew Chem Int Ed, 2008, 47(45): 8670-8673.
[39]	Nibbs AE, Scheidt KA. Asymmetric methods for the synthesis of flavanones, chromanones and azaflavanones[J]. Eur J Org Chem, 2012, 2012(3): 449-462.

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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Reviews on flavanone compounds synthesis research

1. School of Pharmacy, Anhui Medical University, Hefei 230032, China;Department of Pharmacy, No.306 Hospital of PLA, Beijing 100101, China

2. Department of Pharmacy, No.306 Hospital of PLA, Beijing 100101, China

Received Date: 2013-11-28

Rev Recd Date: 2014-04-21

Key words:

Abstract: Research progress of flavanone compounds synthesis was reviewed, various types of synthesis methods of flavanone compounds were summarized, and methodological support for flavanone compounds in new drug research and development was provided. Research progress in synthesis of flavanone compounds includes chalcone cyclization, Friedel-Crafts reaction, Knoevenagel condensation, Hoesch single acetoxylation, and asymmetric synthesis of flavanone compounds. Solvent-free synthesis of flavanone compounds and other green chemistry methods were also introduced.

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Reference (39)

[1]	Noushin A, Alireza N, Christophe W. Anti-bacterial, antioxidant activity and phytochemical study of Uvaria grandiflora: a rare species of Annonaceae[J]. J Pharm Res, 2011, 4(4): 944-955.
[2]	Chavan PN. Comparative study of flavonoids from chyavanprash for anti-inflammatory activity[J]. J Pharm Res, 2011, 4(5): 1338-1339.
[3]	Szliszka E, Kostrzewa SE, Bronikowska J, et al. Synthetic flavanones augment the anticancer effect of tumor necrosis factor-related apoptosis-inducing ligand (trail)[J]. Molecules, 2012, 17(10): 11693-11711.
[4]	Wang B, Ge L, Huang WL, et al. Synthesis and preliminary anti-HIV activities of andrographolide derivatives[J]. J Med Chem, 2010, 6(4): 252-258.
[5]	Resende FA, Vilegas W, Dos Santos LC, et al. Mutagenicity of flavonoids assayed by bacterial reverse mutation (Ames) test[J]. Molecules, 2012, 17(5): 5255-5268.
[6]	Zhou ZL, Fu CY. A new flavanone and other constituents from the rhizomes of Cyperus rotundus and their antioxidant activities[J]. Chem Nat Compd, 2013, 48(6): 963-965.
[7]	Bhattachaqryya A, Chaudhuri A. Synthesis of didymocarpin-A, a new flavanone isolated from didymocarpus pedicellata[J]. Indian J Chem, 1980, 19B: 428-429.
[8]	Anguly A, Bhattacharyya P, Bhattacharyya A, et al. A synthesis of candidone—a new flavanone isolated from Tephrosia candida[J]. Indian J Chem, 1988, 27(5): 462-463.
[9]	郭冬冬, 杨金会, 梁西周, 等. 两种天然异戊烯基黄烷酮的全合成[J]. 合成化学, 2013, 21(5): 550-553.
[10]	Deshpande VH. Synthesis of 5,3'-dihydroxy-4'-methoxy-flavanone[J]. Indian J Chem, 1981, 20(10): 917-918.
[11]	何文香, 郑旭煦, 殷钟意, 等. 基于吡啶-水体系的2'-羟基查尔酮的环化反应研究[J]. 化学研究与应用, 2010, 22(9): 1142-1146.
[12]	Namrata A, Priyanka S, Anindra S, et al. Synthesis and evaluation of small libraries of triazolylmethoxy chalcones, flavanones and 2-aminopyrimidines as inhibitors of mycobacterial FAS-II and PknG[J]. J Med Chem, 2012, 20(17): 5150-5163.
[13]	Sangwan MK, Verma BS. Association and path-coefficients in Plantago ovata Forsk[J]. Indian J Chem, 1984: 54(12) 1090-1091.
[14]	Bagade MB, Thool AW, Lokhande PD, et al. Simple technics for isomerization of 2'-hydroxychalcones to flavanones—use of silicagel, ethylenediamine and hydroxylamine hydrochloride[J]. Ind J Chem, 1991, 30B: 973-975.
[15]	Naseem A, Ansare WH. An improved procedure for the isomerisation of 2'-hydroxy substituted chalcones to flavaones using silica supported-BiCl3 under dry conditions[J]. J Chem Res, 2004,35(17):572-573.
[16]	Naseem A, Johan EVL. Silica gel supported TaBr5: new catalyst for the facile and rapid cyclization of 2'-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent-free conditions[J]. Tetrahedron Lett, 2006, 47(16): 2725-2729.
[17]	Beena N, Sharad F, Abdul R, et al. Efficient synthesis of 3-methyl-flavanones and evaluation of their anti-bacterial activity[J]. Chin J Chem, 2012, 30(8): 1695-1698.
[18]	Michele TD, Michael DA. Kinetic investigation of the heterogeneous synthesis of flavanone over MgO[J]. Catal Lett, 2002, 79(1-4): 175-181.
[19]	Liu Z, Cortés-Concepción JA, Mustian M, et al. Effect of basic properties of MgO on the heterogeneous synthesis of flavanone[J]. Appl Catal A-Gen, 2006, 302(2): 232-236.
[20]	Choudary BM, Ranganath KVS, Yadav J, et al. Synthesis of flavanones using nanocrystalline MgO[J]. Tetrahedron Lett, 2005, 46(8): 1369-1371.
[21]	Saravanamurugan S, Palanichamy M, Arabmdoo B, et al. Solvent free synthesis of chalcone and flavanone over zinc oxide supported metal oxide catalysts[J]. Catal Commun, 2005, 6(6): 399-403.
[22]	Makrandi JK,Shasi B.Potassium ferricyanide mediated cyclisation of 2'-hydroxychalcones to flavanones using phase transfer catalysis [J].Synth Commun,2000,30(19):3555-3558.
[23]	Hemanth KK, Perumal TP. A simple and facile solventless procedure for the cyclization of 2'-amino-and-2'-hydroxychalcones sodium hydrogen sulphate as heterogenous catalyst[J]. Can J Chem, 2006, 84(8): 1079-1083.
[24]	Raghavendra S, Marzieh Y, Noorsaadah AR. Synthesis of flavanones, azaflavanones, and thioflavanones catalyzed by PMA-SiO₂ as a mild, efficient, and reusable catalyst[J]. Monatsh Chem, 2012, 143(5): 797-800.
[25]	Koichi T, Teize S. Efficient conversion of 2'-hydroxychalcones into flavanones and flavanols[J]. Green Chem, 2001, 3(3): 133-134.
[26]	Jiang HY, Zheng XX, Yin ZY, et al. An efficient catalytic synthesis of flavanones under green conditions[J]. J Chem Res, 2011, 35(4): 220-221.
[27]	Chandrasekhar S, Vijeender K, Venkatram RK. New synthesis of flavanone catalyzed by L-proline[J]. Tetrahedron Lett, 2005, 46(41): 6991-6993.
[28]	Wang X, Cheng S. Solvent-free synthesis of flavanones over aminopropyl-functionalized SBA-15[J]. Catal Commun, 2006, 7(9): 689-695.
[29]	Shunmugavel S, Sujandia, Prasetyantoa EA, et al. Liquid-phase reaction of 2'-hydroxyacetophenone and benzaldehyde over SO₃H-SBA-15 catalysts: influence of microwave and thermal effects[J]. Micropor Mesopor Mat, 2008, 112(1): 97-107.
[30]	Wang H, Nu XD, Zhao M, et al. Solvent-free synthesis of flavanone over new hybrid mesoporous base- catalysts[J]. Chem Res Chin U, 2011, 27(4): 664-668.
[31]	Tibor T.A novel synthesis of precocenes. Efficient synthesis and regioselective o-alkylation of dihydroxy-2,2-dimethyl-4-chromanones[J].J Heterocycl Chem,1988,25(3):871-877.
[32]	覃章兰, 李文新, 黄天宝, 等. 5,7-二羟基-4'-苄氧基黄烷酮的合成及生物活性[J]. 武汉大学学报(自然科学版), 2000, 46(6): 706-708.
[33]	陈俊杰, 李裕林. 黄酮类化合物的合成方法[J]. 厦门大学学报(自然科学版), 1992, 31(6): 651-655.
[34]	Zhang WH, Chan WL, Lin YH,et al. Synthesis of hydroxyflavanones from substituted acetophenones and benzaldehydes in the presence of silica gel, boric acid and piperidine[J]. Heterocycles, 1997, 45(1): 71-75.
[35]	Takashi Y, Kodai N, Kanji S, et al. Synthesis of chalcone and flavanone derivatives from condensation of 2'-hydroxyacetophenones and benzaldehyde over basic β-zeolites[J]. J Jpn Petrol Inst, 2010, 53(6): 351-354.
[36]	Solladie G, Gehrold N, Maignan J. Synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methyl-flavanone[J]. Tetrahedron Asymmetr, 1999, 10(14): 2739-2747.
[37]	Biddle MM, Lin M, Scheidt KA. Enantioselective synthesis of flavanones and chromanones[J]. J Am Chem Soc, 2007, 129(13): 3830-3831.
[38]	Wang LJ, Liu XH, Dong ZH, et al. Asymmetric intramolecular Oxa-Michael addition of activated a,b-unsaturated ketones catalyzed by a chiral N,N'-dioxide nickel(II) complex: highly enantioselective synthesis of flavanoneses[J]. Angew Chem Int Ed, 2008, 47(45): 8670-8673.
[39]	Nibbs AE, Scheidt KA. Asymmetric methods for the synthesis of flavanones, chromanones and azaflavanones[J]. Eur J Org Chem, 2012, 2012(3): 449-462.

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Reviews on flavanone compounds synthesis research

doi: 10.3969/j.issn.1006-0111.2015.02.001

Abstract

References

Proportional views

通讯作者: 陈斌, bchen63@163.com

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