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(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic anhydride

中文名称
——
中文别名
——
英文名称
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic anhydride
英文别名
(E)-3-(3,4-dihydroxyphenyl)acrylic anhydride;caffeic anhydride;[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic anhydride化学式
CAS
——
化学式
C18H14O7
mdl
——
分子量
342.305
InChiKey
QDPOOGQUCJJZAO-FCXRPNKRSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.6
  • 重原子数:
    25
  • 可旋转键数:
    6
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    124
  • 氢给体数:
    4
  • 氢受体数:
    7

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    在咖啡中找到有效的Sirt抑制剂:作为Sirt1 / 2抑制剂的Javamide-II(N-Caffeoyltryptophanphan)的分离,确认和合成。
    摘要:
    最近的研究表明,抑制Sirt可能对几种人类疾病(例如神经退行性疾病和癌症)产生有益作用。咖啡是最受欢迎的饮料之一,对健康有积极影响。因此,在本文中,使用咖啡提取物筛选了潜在的Sirt抑制剂。首先,利用HPLC分离咖啡提取物,然后使用Sirt1 / 2抑制试验进行筛选。筛选导致分离出有效的Sirt1 / 2抑制剂,其结构经NMR确定为javamide-II(N-咖啡因色氨酸)。为了确认,化学合成了酰胺,并将其抑制Sirt1 / 2的能力与分离的酰胺进行了比较。Javamide-II抑制Sirt2(IC50; 8.7μM)优于Sirt1(IC50;34μM)。由于javamide-II比Sirt1对Sirt2的抑制作用更强。针对Sirt2进行了动力学研究。酰胺对NAD +表现出非竞争性Sirt2抑制作用(Ki = 9.8μM),对肽底物表现出竞争性抑制作用(Ki = 5.3μM)。而且,对接模
    DOI:
    10.1371/journal.pone.0150392
  • 作为产物:
    参考文献:
    名称:
    在咖啡中找到有效的Sirt抑制剂:作为Sirt1 / 2抑制剂的Javamide-II(N-Caffeoyltryptophanphan)的分离,确认和合成。
    摘要:
    最近的研究表明,抑制Sirt可能对几种人类疾病(例如神经退行性疾病和癌症)产生有益作用。咖啡是最受欢迎的饮料之一,对健康有积极影响。因此,在本文中,使用咖啡提取物筛选了潜在的Sirt抑制剂。首先,利用HPLC分离咖啡提取物,然后使用Sirt1 / 2抑制试验进行筛选。筛选导致分离出有效的Sirt1 / 2抑制剂,其结构经NMR确定为javamide-II(N-咖啡因色氨酸)。为了确认,化学合成了酰胺,并将其抑制Sirt1 / 2的能力与分离的酰胺进行了比较。Javamide-II抑制Sirt2(IC50; 8.7μM)优于Sirt1(IC50;34μM)。由于javamide-II比Sirt1对Sirt2的抑制作用更强。针对Sirt2进行了动力学研究。酰胺对NAD +表现出非竞争性Sirt2抑制作用(Ki = 9.8μM),对肽底物表现出竞争性抑制作用(Ki = 5.3μM)。而且,对接模
    DOI:
    10.1371/journal.pone.0150392
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文献信息

  • Substituted cinnamic anhydrides act as selective inhibitors of acetylcholinesterase
    作者:Josephine M. Gießel、Immo Serbian、Anne Loesche、René Csuk
    DOI:10.1016/j.bioorg.2019.103058
    日期:2019.9
    Cinnamic anhydrides have been shown to be more than reactive reagents, but they also act as inhibitors of the enzyme acetylcholinesterease (AChE). Thus, out of a set of 33 synthesised derivatives, several of them were mixed type inhibitors for AChE (from electric eel). Thus, (E)-3-(2,4-dimethoxyphenyl)acrylic anhydride (2c) showed Ki = 8.30 ± 0.94 µM and Ki' = 9.54 ± 0.38 µM, and for (E)-3-(3-chlorophenyl)acrylic
    肉桂酸酐已被证明比反应性试剂更重要,但它们也可作为乙酰胆碱酯酶(AChE)的抑制剂。因此,在一组33种合成衍生物中,其中几种是AChE的混合型抑制剂(来自鳗鱼)。因此,对于(E)-3-(3-氯苯基)丙烯酸,(E)-3-(2,4-二甲氧基苯基)丙烯酸酐(2c)的Ki = 8.30±0.94μM,Ki’= 9.54±0.38μM。酸酐(2u)的Ki = 8.23±0.93 µM,Ki'= 13.07±0.46 µM。这些化合物虽然对许多人类细胞系无细胞毒性,但它们对AChE却表现出前所未有的且值得注意的抑制作用,但对丁酰胆碱酯酶(BChE)却没有。
  • Berberine salts, ursodeoxycholic salts and combinations, methods of preparation and application thereof
    申请人:SHENZHEN HIGHTIDE BIOPHARMACEUTICAL, LTD.
    公开号:US10301303B2
    公开(公告)日:2019-05-28
    The invention provides various novel compositions of berberine in combination with pharmacologically active organic acids, and related methods of their use in treating various diseases or disorders. The invention further provides various novel compounds prepared from berberine and pharmacologically active organic acids and prepared from ursodeoxycholic acid and pharmacologically active organic bases, and pharmaceutical compositions thereof, and methods of their preparation and therapeutic use in treating and/or preventing various diseases or disorders. The compounds and pharmaceutical compositions of the invention can be utilized to treat various diseases or disorders, such as diabetes, diabetic complications, dyslipidemia, hyperlipidemia, obesity, metabolic syndromes, pre-diabetes, atherosclerosis, heart diseases, neurodegenerative diseases, sarcopenia, muscle atrophy, inflammation, cancer and liver diseases and conditions such as fatty liver, non-alcoholic fatty liver disease, non-alcoholic steatohepatitis, cholestatic liver diseases or graft-versus-host disease of the liver. The compounds of this invention are also useful in improving liver functions in chronic viral associated liver diseases and alcohol-related liver diseases.
    本发明提供了小檗碱与药理活性有机酸结合的各种新型组合物及其用于治疗各种疾病或失调的相关方法。本发明进一步提供了由小檗碱和药理活性有机酸制备的和由熊去氧胆酸和药理活性有机碱制备的各种新型化合物及其药物组合物,以及它们在治疗和/或预防各种疾病或紊乱中的制备和治疗方法。本发明的化合物和药物组合物可用于治疗各种疾病或失调,如糖尿病、糖尿病并发症、血脂异常、高脂血症、肥胖症、代谢综合征、糖尿病前期、动脉粥样硬化、心脏病、神经退行性疾病、骨质疏松症等、神经退行性疾病、肌肉疏松症、肌肉萎缩、炎症、癌症和肝脏疾病,如脂肪肝、非酒精性脂肪肝、非酒精性脂肪性肝炎、胆汁淤积性肝病或肝脏移植物抗宿主疾病。本发明的化合物还可用于改善慢性病毒相关性肝病和酒精相关性肝病的肝功能。
  • Pharmaceutical composition comprising berberine ursodeoxycholic acid salt for the treatment of various diseases or disorders
    申请人:SHENZHEN HIGHTIDE BIOPHARMACEUTICAL, LTD.
    公开号:US10988471B2
    公开(公告)日:2021-04-27
    The invention provides various novel compositions of berberine in combination with pharmacologically active organic acids, and related methods of their use in treating various diseases or disorders. The invention further provides various novel compounds prepared from berberine and pharmacologically active organic acids and prepared from ursodeoxycholic acid and pharmacologically active organic bases, and pharmaceutical compositions thereof, and methods of their preparation and therapeutic use in treating and/or preventing various diseases or disorders. The compounds and pharmaceutical compositions of the invention can be utilized to treat various diseases or disorders, such as diabetes, diabetic complications, dyslipidemia, hyperlipidemia, obesity, metabolic syndromes, pre-diabetes, atherosclerosis, heart diseases, neurodegenerative diseases, sarcopenia, muscle atrophy, inflammation, cancer and liver diseases and conditions such as fatty liver, non-alcoholic fatty liver disease, non-alcoholic steatohepatitis, cholestatic liver diseases or graft-versus-host disease of the liver. The compounds of this invention are also useful in improving liver functions in chronic viral associated liver diseases and alcohol-related liver diseases.
    本发明提供了小檗碱与药理活性有机酸结合的各种新型组合物及其用于治疗各种疾病或失调的相关方法。本发明进一步提供了由小檗碱和药理活性有机酸制备的和由熊去氧胆酸和药理活性有机碱制备的各种新型化合物及其药物组合物,以及它们在治疗和/或预防各种疾病或紊乱中的制备和治疗方法。本发明的化合物和药物组合物可用于治疗各种疾病或失调,如糖尿病、糖尿病并发症、血脂异常、高脂血症、肥胖症、代谢综合征、糖尿病前期、动脉粥样硬化、心脏病、神经退行性疾病、骨质疏松症等、神经退行性疾病、肌肉疏松症、肌肉萎缩、炎症、癌症和肝脏疾病,如脂肪肝、非酒精性脂肪肝、非酒精性脂肪性肝炎、胆汁淤积性肝病或肝脏移植物抗宿主疾病。本发明的化合物还可用于改善慢性病毒相关性肝病和酒精相关性肝病的肝功能。
  • BERBERINE SALTS, URSODEOXYCHOLIC SALTS AND COMBINATIONS, METHODS OF PREPARATION AND APPLICATION THEREOF
    申请人:Shenzhen Hightide Biopharmaceutical Ltd.
    公开号:EP3174874B1
    公开(公告)日:2020-09-02
  • CONJUGATE COMPOUNDS OF URSODEOXYCHOLIC, BERBERINE OR L-CARNITINE, AND COMPOSITIONS AND METHODS THEREOF
    申请人:SHENZHEN HJGHTIDE-BIOPHARMAGEUTiCAL, LTD.
    公开号:US20180050048A1
    公开(公告)日:2018-02-22
    The invention provides novel conjugate compounds having at least one of a moiety derived from ursodeoxycholic acid, or eicosapentaenoic acid, or docosahexaenoic acid, or rhein, or R-(+)-α-lipoic acid, or ursolic acid, or corosolic acid, or hydroxycitric acid, or cinnamic acid, or cholic acid, or oleanolic acid, or salicylic acid, or betulinic acid, or chlorogenic acid, or caffeic acid, or bassic acid, or acetyl L-carnitine, or S-allyl cysteine sulphoxide, or S-methyl cysteine sulfoxide, or pantothenic acid, or ascorbic acid, or retinoic acid, or nicotinic acid, or biotin, or a derivative or analog thereof, and a moiety derived from berberine or L-carnitine or metformin or unsaturated fatty acid, or a derivative or analog thereof. The invention also relates to pharmaceutical compositions, methods of preparation and use of these conjugates in treating and/or preventing, for example, liver diseases or disorders, various diabetes, diabetic complications, dyslipidemia, obesity, metabolic syndromes, pre-diabetes, muscle atrophy, inflammation, and cancers. The compounds of this invention are also useful in improving liver functions in chronic viral associated liver diseases and alcohol-related liver diseases.
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