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

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 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
• 化学式: C₁₈H₁₄O₇
• 分子量: 342.305
• InChiKey: QDPOOGQUCJJZAO-FCXRPNKRSA-N

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

反应信息

• 作为反应物：
  描述：

  (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic anhydride 、 L-色氨酸 在 3-苯丙醇 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 生成 (E)-(3-(3,4-dihydroxyphenyl)acryloyl)tryptophan (N-caffeoyltryptophan)
  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：
  描述：

  TRANS-咖啡酸 在 N,N'-二异丙基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 生成 (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic anhydride
  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

文献信息

• 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.
• [EN] COMPOSITION COMPRISING MESENCHYMAL STEM CELLS TREATED WITH STAT3 INHIBITOR AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING IMMUNE DISEASES<br/>[FR] COMPOSITION COMPRENANT DES CELLULES SOUCHES MÉSENCHYMATEUSES TRAITÉES AVEC UN INHIBITEUR DE STAT3 EN TANT QUE PRINCIPE ACTIF POUR LA PRÉVENTION OU LE TRAITEMENT DE MALADIES IMMUNITAIRES<br/>[KO] STAT3 억제제가 처리된 간엽줄기세포를 유효성분으로 포함하는 면역질환의 예방 또는 치료용 조성물
  申请人：CATHOLIC UNIV KOREA INDUSTRY ACADEMIC COOPERATION FOUNDATION

  公开号：WO2015194710A1

  公开（公告）日：2015-12-23

  본 발명은 STAT3 억제제가 처리된 간엽줄기세포를 유효성분으로 포함하는 면역질환의 예방 또는 치료용 세포치료제 조성물에 관한 것이다. 본 발명에 따른 STAT3 억제제가 처리된 간엽줄기세포는 간엽줄기세포에서의 염증성 사이토카인 및 염증 유발인자의 발현과 생성을 효과적으로 억제할 수 있고, 병인조건 하에서 미분화 T 세포와 공조 배양할 경우, T 세포의 세포 독성 Th17 및 Th1 세포로의 분화를 억제하는 효과가 있으며, 비정상적으로 활성화된 면역세포의 기능을 억제하고 염증 반응을 제어하는 특성을 갖는 면역조절 T 세포(Treg)의 분화 및 활성을 증진시키는 효과가 우수한 특징이 있다. 따라서 STAT3 억제제가 처리된 간엽줄기세포는 각종 면역반응의 조절 이상으로 유발되는 자가면역질환, 염증성질환 및 이식거부질환과 같은 면역질환을 예방 또는 치료할 수 있는 세포치료제 조성물로 사용할 수 있는 효과가 있다.