(7′R,8′R)-cleomiscosin C

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 香豆素木脂素
• 英文名称: (7′R,8′R)-cleomiscosin C
• 英文别名: cleomiscosin A；cleomiscosin B；cleomiscosin C；cleomiscosin D；aquillochin；(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• 化学式: C₂₁H₂₀O₉
• 分子量: 416.384
• InChiKey: GZXPCBAETDEQAX-CRAIPNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (7′R,8′R)-cleomiscosin C 在 吡啶 作用下， 生成 aquillochin diacetate
  参考文献：
  名称：

  Lin, Lee-Juian; Cordell, Geoffrey A., Journal of Chemical Research, Miniprint, 1988, # 12, p. 3052 - 3080

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 在 吡啶 、 lithium aluminium tetrahydride 、 silver(l) oxide 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 39.0h， 生成 (7′R,8′R)-cleomiscosin C
  参考文献：
  名称：

  Lin, Lee-Juian; Cordell, Geoffrey A., Journal of Chemical Research, Miniprint, 1988, # 12, p. 3052 - 3080

  摘要：

  DOI：

文献信息

• Total synthesis of coumarinolignans, aquillochin (cleomiscosin C) and cleomiscosin D.
  作者：HITOSHI TANAKA、MASAYA ISHIHARA、KAZUHIKO ICHINO、KAZUO ITO

  DOI：10.1248/cpb.36.3833

  日期：——

  The reaction of 8-hydroxy-6-methoxy-7-methoxymethoxycoumarin (3) with ethyl 2-bromo-3-(4-benzyloxy-3, 5-dimethoxypheny1)-3-oxopropionate (5) in the presence of potassium tert-butoxide gave the condensation product (6), which, on treatment with hydrochloric acid followed by reduction with lithium borohydride, was converted into a diastereomeric mixture of alcohols (8a, b). Treatment of the alcohols (8a, b) with 35% hydrochloric acid in acetic acid furnished aquillochin (cleomiscosin C)(1). The regioisomer cleomiscosin D (2) was similarly synthesized from 10.

  8-hydroxy-6-methoxy-7-methoxymethoxycoumarin (3) 与 2-bromo-3-(4-benzyloxy-3,5-dimethoxypheny1)-3-oxopropionate(5)乙酯在叔丁醇钾存在下反应生成缩合产物 (6)，用盐酸处理后再用硼氢化锂还原，可转化为非对映的醇类混合物 (8a，b)。用醋酸中 35% 的盐酸处理醇（8a、b），可得到水黄素（裂米黄素 C）(1)。类似的方法还可以从 10 中合成出半木香苷 D（2）。
• Synthesis of coumarinolignans through chemical and enzymic Oxidation
  作者：Lee-Juian Lin、Geoffrey A. Cordell

  DOI：10.1039/c39840000160

  日期：——

  The first syntheses of coumarinolignans through chemical or enzymic oxidation of a dihydroxycoumarin and a phenylpropene are described.

  描述了通过二羟基香豆素和苯丙烯的化学或酶促氧化来香豆素的第一合成。
• Syntheses of Natural Coumarinolignans: Oxidative Coupling of 7,8-Dihydroxycoumarins and Phenylpropenes in the Presence of Diphenyl Selenoxide
  作者：Hitoshi Tanaka、Masaya Ishihara、Kazuhiko Ichino、Kazuo Ito

  DOI：10.3987/com-88-4747

  日期：——
• Total synthesis of cleomiscosin C via a regioselective cycloaddition reaction of o-quinone
  作者：Atsuhito Kuboki、Chie Maeda、Tetsuya Arishige、Kohei Kuyama、Mami Hamabata、Susumu Ohira

  DOI：10.1016/j.tetlet.2008.05.051

  日期：2008.7

  We have achieved total synthesis of cleomiscosin C (aquillochin) through regioselective cycloaddition of o-quinone and protected sinapyl alcohol as a key step. During preparation of o-quinone from phenol by IBX oxidation, silyl substituents adjacent to the phenolic hydroxyl group afforded effective inhibition of an undesired oxidative elimination. (c) 2008 Elsevier Ltd. All rights reserved.
• Immunomodulatory pharmaceutical composition and a process for preparation thereof
  申请人：Khanuja Preet Singh Suman

  公开号：US20070258989A1

  公开（公告）日：2007-11-08

  The present invention provides a novel pharmaceutical composition consisting of a combination of three coumarinolignoids of formula 1, 2 and 3 isolated from the seeds of the plant Cleome viscose along with a pharmaceutically acceptable carrier useful as a immunomodulator. The invention also describes the ability of the compounds to modulate humorral and cell mediated immune response. It further provides a process for the preparation of a novel pharmaceutical composition of the said three coumarinolignoids in an optimized ratio to modulate humorral and cell mediated immune response.