留言板

尊敬的读者、作者、审稿人, 关于本刊的投稿、审稿、编辑和出版的任何问题, 您可以本页添加留言。我们将尽快给您答复。谢谢您的支持!

姓名
邮箱
手机号码
标题
留言内容
验证码
x 关闭 永久关闭

应中央军委要求，2022年9月起，《药学实践杂志》将更名为《药学实践与服务》，双月刊，正文96页；2023年1月起，拟出版月刊，正文64页，数据库收录情况与原《药学实践杂志》相同。欢迎作者踊跃投稿！

二氢黄酮类化合物的合成研究进展

梁海,  向卓,  张学辉,  吴久鸿

downloadPDF
文章导航 > 药学实践与服务  > 2015 >  33(2): 97-101,130
梁海, 向卓, 张学辉, 吴久鸿. 二氢黄酮类化合物的合成研究进展[J]. 药学实践与服务, 2015, 33(2): 97-101,130. doi: 10.3969/j.issn.1006-0111.2015.02.001
引用本文: 梁海, 向卓, 张学辉, 吴久鸿. 二氢黄酮类化合物的合成研究进展[J]. 药学实践与服务, 2015, 33(2): 97-101,130. doi: 10.3969/j.issn.1006-0111.2015.02.001
shu
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
shu

二氢黄酮类化合物的合成研究进展

doi: 10.3969/j.issn.1006-0111.2015.02.001
  • 1.

    安徽医科大学药学院, 安徽 合肥 230032;解放军306医院药学部, 北京 100101

  • 2.

    解放军306医院药学部, 北京 100101

基金项目: 国家自然科学基金项目(No.81072546)

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

  • 摘要: 综述二氢黄酮类化合物的合成研究进展, 总结已报道的各种类型的二氢黄酮合成方法, 为二氢黄酮类新药研发提供方法学支持。合成方法包括:查尔酮环合、Friedel-Crafts反应、Knoevenagel缩合和Hoesch单酰基化反应, 以及二氢黄酮的不对称合成, 并简要介绍无溶剂合成二氢黄酮等"绿色"化学方法。
    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.
  • [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.
  • [1] 毛智毅, 王筱燕, 陈晓颖, 汤逸斐.  度拉糖肽联合二甲双胍对肥胖型2型糖尿病患者机体代谢、体脂成分及血清脂肪因子的影响 . 药学实践与服务, 2024, 42(7): 305-309. doi: 10.12206/j.issn.2097-2024.202305032
    [2] 戴菲菲, 傅翔, 陈琼年, 俞苏纯.  上海某二级医院革兰阴性菌流行特征的回顾性分析 . 药学实践与服务, 2024, 42(): 1-5. doi: 10.12206/j.issn.2097-2024.202305005
    [3] 夏哲炜, 曾垣烨, 朱海菲, 李育, 陈啸飞.  核磁共振磷谱法测定磷酸氢钙咀嚼片中药物含量 . 药学实践与服务, 2024, 42(9): 399-401, 406. doi: 10.12206/j.issn.2097-2024.202404063
    [4] 宋雨桐, 夏德润, 顾珩, 唐少文, 易洪刚, 沃红梅.  帕博利珠单抗与铂类化疗方案在晚期非小细胞肺癌一线治疗中的药物经济学评价 . 药学实践与服务, 2024, 42(8): 334-340. doi: 10.12206/j.issn.2097-2024.202303023
    [5] 冯志惠, 邓仪卿, 叶冰, 安培, 张宏, 张海军.  雀梅藤石油醚提取物诱导三阴性乳腺癌细胞凋亡的实验研究 . 药学实践与服务, 2024, 42(6): 253-259. doi: 10.12206/j.issn.2097-2024.202311055
    [6] 陈方剑, 骆锦前, 王志君, 胡叶帅, 孙煜昕, 宋洪杰.  HPLC-MS/MS同时测定感冒安颗粒中5种黄酮成分的含量 . 药学实践与服务, 2024, 42(9): 402-406. doi: 10.12206/j.issn.2097-2024.202403030
    [7] 张艺昕, 关欣怡, 王博宁, 闻俊, 洪战英.  二氢吡啶类钙离子拮抗药物手性分析及其立体选择性药动学研究进展 . 药学实践与服务, 2024, 42(8): 319-324. doi: 10.12206/j.issn.2097-2024.202308062
    [8] 陈炳辰, 王思真, 郭贝贝, 杨峰.  紫杉醇棕榈酸酯的合成及其脂质体的制备与处方研究 . 药学实践与服务, 2024, 42(9): 379-384, 410. doi: 10.12206/j.issn.2097-2024.202404062
  • 加载中
WeChat 点击查看大图
计量
  • 文章访问数:  4233
  • HTML全文浏览量:  382
  • PDF下载量:  179
  • 被引次数: 0
出版历程
  • 收稿日期:  2013-11-28
  • 修回日期:  2014-04-21

二氢黄酮类化合物的合成研究进展

doi: 10.3969/j.issn.1006-0111.2015.02.001
  • 1. 安徽医科大学药学院, 安徽 合肥 230032;解放军306医院药学部, 北京 100101
  • 2. 解放军306医院药学部, 北京 100101
    • 基金项目:  国家自然科学基金项目(No.81072546)
  • 收稿日期: 2013-11-28
  • 修回日期: 2014-04-21

摘要: 综述二氢黄酮类化合物的合成研究进展, 总结已报道的各种类型的二氢黄酮合成方法, 为二氢黄酮类新药研发提供方法学支持。合成方法包括:查尔酮环合、Friedel-Crafts反应、Knoevenagel缩合和Hoesch单酰基化反应, 以及二氢黄酮的不对称合成, 并简要介绍无溶剂合成二氢黄酮等"绿色"化学方法。

English Abstract

梁海, 向卓, 张学辉, 吴久鸿. 二氢黄酮类化合物的合成研究进展[J]. 药学实践与服务, 2015, 33(2): 97-101,130. doi: 10.3969/j.issn.1006-0111.2015.02.001
引用本文: 梁海, 向卓, 张学辉, 吴久鸿. 二氢黄酮类化合物的合成研究进展[J]. 药学实践与服务, 2015, 33(2): 97-101,130. doi: 10.3969/j.issn.1006-0111.2015.02.001
shu
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
shu

    全文HTML

参考文献 (39)

目录

    /

    返回文章
    返回

    版权所有：《药学实践与服务》编辑委员会

    主管、主办: 中国人民解放军海军军医大学地址: 上海市杨浦区国和路325号邮政编码: 200433

    电话: （021）81871324,81871397 E-mail: yxsjzzs@163.com

    网站备案号 沪ICP备05003363号-1

    本系统由 北京仁和汇智信息技术有限公司 开发    百度统计