(1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid | 25514-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• 英文别名: (1S,3S,4R,5R)-3-{3-(3,4-dihydroxyphenyl)acryloyloxy}-1,4,5-trihydroxycyclohexanecarboxylic acid；dihydrocaffeoylquinic acid；reduced chlorogenic acid；(1S)-1.4t.5t-trihydroxy-3c-[3-(3.4-dihydroxy-phenyl)-propionyloxy]-cyclohexane-carboxylic acid-(1r)；(1S)-1.4t.5t-Trihydroxy-3c-[3-(3.4-dihydroxy-phenyl)-propionyloxy]-cyclohexan-carbonsaeure-(1r)；(1S)-3c-[3-(3,4-Dihydroxy-phenyl)-propionyloxy]-1,4t,5t-trihydroxy-cyclohexan-r-carbonsaeure；(1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)propanoyloxy]-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• CAS: 25514-46-9
• 化学式: C₁₆H₂₀O₉
• 分子量: 356.329
• InChiKey: RLGFSACCIOSKQS-NCZKRNLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  165
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid 在 盐酸 作用下， 生成 右旋奎宁酸
  参考文献：
  名称：

  Watanabe, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1936, vol. 56, p. 71,73; dtsch. Ref. S. 13

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-5-咖啡酰奎宁酸 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以67%的产率得到(1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid
  参考文献：
  名称：

  咖啡酸衍生物作为α-MSH刺激的黑色素生成的有效抑制剂的合成和生物学评估

  摘要：

  我们已经公开了开发咖啡酸衍生物作为α-MSH刺激的黑色素生成的有效和无毒抑制剂的努力，以治疗色素沉着症和包括美容性皮肤增白剂的皮肤药物。SAR研究表明，咖啡酸的环己酯和仲酰胺衍生物表现出显着的抑制活性。

  DOI：

  10.1016/j.bmcl.2017.06.011

文献信息

• MYOCARDIAL REGENERATION PROMOTING COMPOUNDS, PREPARATION METHOD THEREOF, PHARMACEUTICAL COMPOSITION, AND THEIR USE
  申请人：GENHEALTH PHARMA CO., LTD.

  公开号：US20200317602A1

  公开（公告）日：2020-10-08

  The present invention discloses a novel 3-aryl-2-propen-1-one series derivative and the synthesis processes thereof. Besides, the present invention also discloses the series derivative as a pharmaceutical composition and their use for promoting myocardial regeneration.

  本发明公开了一种新型的3-芳基-2-丙烯-1-酮系列衍生物及其合成方法。此外，本发明还公开了该系列衍生物作为一种药物组合物，以及它们用于促进心肌再生的用途。
• 신규 클로로겐산 유도체 및 이를 유효성분으로 포함하는 염증성 질환 치료용 조성물
  申请人：Chungbuk National University Industry-Academic Cooperation Foundation 충북대학교 산학협력단(220040168226) BRN ▼301-82-16304

  公开号：KR101693033B1

  公开（公告）日：2017-01-09

  본 발명은 항염증 활성을 갖는 신규 클로로겐산 유도체 화합물 및 이를 유효성분으로 포함하는 항염증 조성물에 관한 것이다. 본 발명의 클로로겐산 유도체 화합물은 대식세포에서 LPS에 처리에 의해 유도되는 산화질소(NO)의 과생성을 억제한다. 본 발명의 클로로겐산 유도체 화합물은 산화적 스트레스 및 염증 촉진 경로에서 중요한 신호전달 매개 전사인자인 NF-κB의 활성화를 저해한다. 본 발명의 클로로겐산 유도체 화합물은 산화질소 과생성과 NF-κB의 활성화를 저해함으로써 다양한 염증성질환의 치료제로 개발될 가능성이 높다.

  本发明涉及具有抗炎活性的新型克罗洛糖酸衍生物化合物及其作为有效成分包含的抗炎组合物。本发明的克罗洛糖酸衍生物化合物可以抑制由大食细胞对LPS处理引起的氧化氮(NO)的过度产生。本发明的克罗洛糖酸衍生物化合物还可以抑制在氧化应激和炎症促进途径中重要的信号传导介质转录因子NF-κB的活化。通过抑制氧化氮的过度产生和NF-κB的活化，本发明的克罗洛糖酸衍生物化合物有望被开发为治疗各种炎症性疾病的治疗剂。
• Structure-Activity Relationship of Caffeoylquinic Acids on the Accelerating Activity on ATP Production
  作者：Yusaku Miyamae、Manami Kurisu、Junkyu Han、Hiroko Isoda、Hideyuki Shigemori

  DOI：10.1248/cpb.59.502

  日期：——

  Caffeoylquinic acid (CQA) is one of the phenylpropanoids which have various bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. We previously reported that 3,5-di-O-caffeoylquinic acid inhibited amyloid β1—42-induced cellular toxicity on human neuroblastoma SH-SY5Y cells and increased the mRNA expression level of glycolytic enzymes and the intracellular ATP level. To investigate structure–activity relationship on the accelerating activity on ATP production, we synthesized 1,4,5-tri-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 3,4,5-tri-O-caffeoylquinic acid, and other derivatives. Additionally, we evaluated intracellular ATP level in SH-SY5Y treated with each CQA derivative. As a result, 3,4,5-tri-O-caffeoylquinic acid showed the highest accelerating activity on ATP production among tested compounds. It was suggested that caffeoyl groups bound to quinic acid are important for activity and the more caffeoyl groups are bound to quinic acid, the higher accelerating activity on ATP production exhibits.

  咖啡酰奎宁酸（CQA）是一种酚丙烷类化合物，具有多种生物活性，如抗氧化、抗菌、抗癌、抗组胺和其他生物效应。我们之前报道过，3,5-二-O-咖啡酰奎宁酸抑制了淀粉样蛋白β1—42引起的人类神经母细胞瘤SH-SY5Y细胞的细胞毒性，并提高了糖酵解酶的mRNA表达水平和细胞内ATP水平。为了研究结构—活性关系对ATP生产加速活性的影响，我们合成了1,4,5-三-O-咖啡酰奎宁酸、4,5-二-O-咖啡酰奎宁酸、3,4,5-三-O-咖啡酰奎宁酸及其他衍生物。此外，我们评估了用每种CQA衍生物处理的SH-SY5Y细胞的细胞内ATP水平。结果显示，3,4,5-三-O-咖啡酰奎宁酸在测试化合物中对于ATP生产的加速活性最高。研究表明，结合在奎宁酸上的咖啡酰基团对活性至关重要，结合到奎宁酸上的咖啡酰基团越多，ATP生产的加速活性就越高。
• Myocardial regeneration promoting compounds, preparation method thereof, and pharmaceutical composition
  申请人：GENHEALTH PHARMA CO., LTD.

  公开号：US11124472B2

  公开（公告）日：2021-09-21

  The present invention discloses a novel 3-aryl-2-propen-1-one series derivative and the synthesis processes thereof. Besides, the present invention also discloses the series derivative as a pharmaceutical composition and their use for promoting myocardial regeneration.

  本发明公开了一种新型 3-芳基-2-丙烯-1-酮系列衍生物及其合成工艺。此外，本发明还公开了该系列衍生物作为药物组合物及其在促进心肌再生方面的用途。
• Gorter, Justus Liebigs Annalen der Chemie, 1911, vol. 379, p. 122
  作者：Gorter

  DOI：——

  日期：——