(2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid (R)-PGME amide | 1174681-32-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid (R)-PGME amide
• 英文别名: methyl (2R)-2-[[(2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoyl]amino]-2-phenylacetate
• CAS: 1174681-32-3
• 化学式: C₁₈H₁₉NO₆
• 分子量: 345.352
• InChiKey: FYOWCERNAXEHRR-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  salvianolic acid B 在 N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid (R)-PGME amide
  参考文献：
  名称：

  Diastereomers of lithospermic acid and lithospermic acid B from Monarda fistulosa and Lithospermum erythrorhizon

  摘要：

  Monardic acids A (1) and B (2), which are (7R,8R) diastereomers of lithospermic acid (LA) and lithospermic acid B, respectively, were isolated from Monarda fistulosa. A (75,8R) isomer (3) of LA was also isolated from this plant, and a (7R,8S) isomer (7) of LA was obtained from Lithospermum erythrorhizon. The absolute configuration of 1 was confirmed by analysis of its hydrolysates, 7-epiblechnic acid and 2R-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid. The configuration in the dihydrobenzofuran moieties of 2, 3, and 7 was extrapolated by using the phenylglycine methyl ester method and a Cotton effect at approximately 250-260 nm in their electronic circular dichroism spectra. Diastereomers (1-3 and 7) displayed moderate hyaluronidase inhibitory and histamine release inhibitory activities. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2013.08.009

文献信息

• Hyaluronidase Inhibitory Rosmarinic Acid Derivatives from Meehania urticifolia
  作者：Toshihiro Murata、Toshio Miyase、Fumihiko Yoshizaki

  DOI：10.1248/cpb.59.88

  日期：——

  Nine new phenylpropanoids, rashomonic acids A—D (1—4) and meehaniosides A—E (5—9), along with four known compounds were isolated from Meehania urticifolia. The structure of each new compound was elucidated based on the results of spectroscopic analyses. Compounds 3—8 showed moderate hyaluronidase inhibitory activity with IC50 values of 183—1049 μM.

  从 Meehania urticifolia 中分离出九种新的苯丙素、罗素酸 A—D (1—4) 和 meehanioside A—E (5—9)，以及四种已知化合物。根据光谱分析的结果阐明了每种新化合物的结构。化合物3-8表现出中等的透明质酸酶抑制活性，IC50值为183-1049 μM。
• Caffeic Acid Oligomers with Hyaluronidase Inhibitory Activity from <i>Clinopodium gracile</i>
  作者：Hiroaki Aoshima、Toshio Miyase、Tsutomu Warashina

  DOI：10.1248/cpb.60.499

  日期：——

  Eight new caffeic acid oligomers, clinopodic acids J–Q (1–8), were isolated from whole plants of Clinopodium gracile, together with nine known caffeic acid oligomers. The caffeic acid oligomers with two to four dihydrobenzofuran rings were isolated as natural products for the first time. Clinopodic acid M (4) showed the strongest hyaluronidase inhibitory activity, IC50 (19 µM) among the 22 compounds isolated from this plant.

  从蟛蜞菊全株中分离出八种新的咖啡酸低聚物，即蟛蜞菊酸 J-Q（1-8），以及九种已知的咖啡酸低聚物。首次分离出具有 2 至 4 个二氢苯并呋喃环的咖啡酸低聚物天然产物。在从该植物中分离出的 22 种化合物中， Clinopodic 酸 M (4) 显示出最强的透明质酸酶抑制活性，IC50（19 µM）。
• Hyaluronidase Inhibitors from Takuran, <i>Lycopus lucidus</i>
  作者：Toshihiro Murata、Mai Watahiki、Yu Tanaka、Toshio Miyase、Fumihiko Yoshizaki

  DOI：10.1248/cpb.58.394

  日期：——

  Takuran is a traditional herbal medicine that is produced from the herbal plant Lycopus lucidas TURCZ. (Lamiaceae). Takuran is used as a treatment for diseases in women. From Takuran, four new phenylpropanoids along with 18 known compounds were isolated, and their structures were elucidated by spectroscopic analyses. Five phenylpropanoids isolated from the plant showed hyaluronidase inhibitory activity comparable to that of rosmarinic acid.

  Takuran是一种传统草药，由草本植物Lycopus lucidas TURCZ.（唇形科）制成。Takuran用于治疗女性疾病。从Takuran中分离出四种新的苯丙烷类化合物和18种已知化合物，并通过光谱分析阐明了它们的结构。从植物中分离出的五种苯丙烷类化合物显示出与迷迭香酸相当的透明质酸酶抑制活性。
• Matrix Metalloproteinase-2 Inhibitors from <i>Clinopodium chinense</i> var. <i>parviflorum</i>
  作者：Toshihiro Murata、Kenroh Sasaki、Kumiko Sato、Fumihiko Yoshizaki、Haruna Yamada、Hiromichi Mutoh、Kaoru Umehara、Toshio Miyase、Tsutomu Warashina、Hiroaki Aoshima、Homare Tabata、Kouichi Matsubara

  DOI：10.1021/np800781t

  日期：2009.8.28

  From the aerial parts of Clinopodium chinense var. parviflorum, nine new phenylpropanoids, clinopodic acids A-1 (2-10), were isolated together with a known phenylpropanoid, rosmarinic acid (1). The structures of these new compounds were elucidated on the basis of spectroscopic analysis. Clinopodic acid C (4) showed NIMP-2 inhibitory activity (IC50 3.26 mu M).
• Monoterpene glycosides, phenylpropanoids, and acacetin glycosides from Dracocephalum foetidum
  作者：Erdenechimeg Selenge、Toshihiro Murata、Shiho Tanaka、Kenroh Sasaki、Javzan Batkhuu、Fumihiko Yoshizaki

  DOI：10.1016/j.phytochem.2014.02.007

  日期：2014.5

  Chemical investigation of the acetone extract from the aerial parts of the Mongolian medicinal plant Dracocephalum foetidum resulted in the isolation of three limonene glycosides, a caffeic acid trimer, four rosmarinic acid glucosides, and five acacetin acyl glycosides, together with 13 known natural products. The chemical structures of all of the compounds were determined by spectroscopic analyses. Among these compounds three showed hyaluronidase inhibitory activity. In addition, one other compound showed stronger 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity than the positive control Trolox, whereas three other compounds demonstrated a similar activity to that of Trolox.