(2S,3R)-(-)-erythrin | 480-57-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: (2S,3R)-(-)-erythrin
• 英文别名: erythrin；Erythrin；[3-hydroxy-5-methyl-4-[(2S,3R)-2,3,4-trihydroxybutoxy]carbonylphenyl] 2,4-dihydroxy-6-methylbenzoate
• CAS: 480-57-9
• 化学式: C₂₀H₂₂O₁₀
• 分子量: 422.389
• InChiKey: BUBBEHCXSMCYNY-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3R)-(-)-erythrin 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以47%的产率得到
  参考文献：
  名称：

  5-脱羧二苯并呋喃的新进入通过地衣对-depside，红蛋白的Smiles重排

  摘要：

  从地衣 Roccella montagnei 中以 7.3% 的产率分离出的红蛋白通过 Smiles 重排转化为一系列二苯醚。那些在 C-1 处具有游离羧酸的化合物在 Pd(OAc)2 存在下经历了一种新型的脱羧氧化环化反应，生成 5-脱羧基二苯并呋喃。测定了所有化合物的抗氧化和β-葡萄糖醛酸酶抑制活性。

  DOI：

  10.3184/030823410x12677394014276
• 作为产物：
  描述：

  2,4-二羟基-6-甲基苯甲酸 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 sodium 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 反应 40.0h， 生成 (2S,3R)-(-)-erythrin
  参考文献：
  名称：

  Facile syntheses of (−)-montagnetol and (−)-erythrin

  摘要：

  A novel synthetic method is introduced to prepare the biologically important montagnetol and erythrin compounds starting from a 1,3-benzodioxin-4-one, synthesized from commercially available orsellinic acid and erythritol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.071

文献信息

• Study of Binding Epitopes by STD-NMR Spectroscopy and Molecular Docking of Urease Inhibitors from Lichens
  作者：Vinitha Moolchand Thadhani、Ajmal Khan、. Atia-tul-Wahab、Sumaira Javaid、Amsal Shafqat、. Zaheer-ul-Haq、M. Iqbal Choudhary

  DOI：10.2174/1570180812666150907204007

  日期：2016.3.3

  responsible for the inhibition of urease enzyme at the atomic levels. STD-NMR technique revealed that aromatic moiety and methyl protons of the compound 5 are involved in interactions with the receptor protein. Since C-8 and C-10 methyl protons received the maximum saturation from the receptor protein, this indicated their close proximity to the protein. Weak STDNMR signals for lecanoric acid (8) could

  评估了从罗氏菌（Roccella montagnei）和金盏花（Parmotrema cooperi）分离的地衣聚酮化合物（1-14）的脲酶抑制潜力。与标准硫脲（IC 50）相比，发现化合物5（甲基-β-蓖麻酚羧酸甲酯）是该系列中最有效的抑制剂，IC 50 = 17.4±3.0μM= 21.0±0.1μM）。SAR研究表明，与核苷，二苯醚和二苯并呋喃相比，单核聚酮化合物是更有效的抑制剂。使用饱和转移差异（STD）NMR实验来鉴定负责在原子水平上抑制脲酶的结构特征。STD-NMR技术表明，化合物5的芳族部分和甲基质子参与与受体蛋白的相互作用。由于C-8和C-10甲基质子从受体蛋白质获得最大饱和度，因此表明它们与蛋白质非常接近。Lecanoric acid（8）的STDNMR信号弱可能归因于其较大的尺寸。分子对接研究预测，这些聚酮的羧基部分充当与尿素酶双金属活性位点结合的锚。
• Studies on the resorcylates: biomimetic total syntheses of (+)-montagnetol and (+)-erythrin
  作者：Jean-François Basset、Colin Leslie、Dieter Hamprecht、Andrew J.P. White、Anthony G.M. Barrett

  DOI：10.1016/j.tetlet.2009.11.134

  日期：2010.2

  6-(2,4-Dioxopentyl)-2,2-trimethyl-4H-1,3-dioxin-4-one on reflux in toluene gave MeCOCH2COCH2 COCH=C=O, which cyclized to 6-(2-oxopropyl)-4-hydroxy-2H-pyrin-2-one or was trapped with alcohols to produce resorcylate esters. The method was used for the synthesis of both enantiomers of montagnetol and erythrin. (c) 2009 Elsevier Ltd. All rights reserved.
• Optimism, distress, and immunologic status in HIV-infected gay men following hurricane andrew
  作者：Stacy Cruess、Michael Antoni、Kristin Kilbourn、Gail Ironson、Nancy Klimas、Mary Ann Fletcher、Andy Baum、Neil Schneiderman

  DOI：10.1207/s15327558ijbm0702_5

  日期：2000.6

  This study investigated how dispositional optimism relates to psychological and immunologic status in 40 HIV-infected gay men residing in areas of South Florida hard hit by Hurricane Andrew. In the months following the storm, participants' levers of psychological distress (hurricane-related and overall distress) and antibody titers to several herpesviruses (Herpes Simplex Virus-2, Epstein-Barr Virus [EBV], Cytomegalovirus, and Human Herpes Virus-6 [HHV-6]) were measured. Overall, participants had elevated mean levels of hurricane-specific and general distress. Higher levels of optimism were related to lower levels of depression, overall distress, and hurricane-specific posttraumatic stress disorder symptoms. After controlling for nonspecific polyclonal B cell activation, greater optimism was also associated with lower levels of circulating antibodies to EBV and HHV-6, suggesting better cellular immunologic control over these viruses among optimists. Regression analyses showed that the relation between optimism and lower EBV titers was partially mediated by the lower depression levels experienced by optimists.
• Sakurai, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 108,115; dtsch. Ref. S. 45
  作者：Sakurai

  DOI：——

  日期：——