(3S)-1-(3',4'-dimethoxyphenyl)-7-(4''-methoxyphenyl)-(6E)-6-hepten-3-ol | 1251830-66-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (3S)-1-(3',4'-dimethoxyphenyl)-7-(4''-methoxyphenyl)-(6E)-6-hepten-3-ol
• 英文别名: (E,3S)-1-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)hept-6-en-3-ol
• CAS: 1251830-66-6
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: WENLBDGVNFNXLQ-OQBYNLHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-1-(3',4'-dimethoxyphenyl)-7-(4''-methoxyphenyl)-(6E)-6-hepten-3-ol 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 反应 12.0h， 以1.1 mg的产率得到[(E,3S)-1-(3,4-dimethoxyphenyl)-7-(4-methoxyphenyl)hept-6-en-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Diarylheptanoids with inhibitory effects on melanogenesis from the rhizomes of Curcuma comosa in B16 melanoma cells

  摘要：

  The methanolic extract from the dried rhizomes of Curcuma comosa cultivated in Thailand was found to inhibit melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extract, three new diarylheptanoids, diarylcomosols I-III, were isolated together with 12 known diarylheptanoids. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The diarylheptanoids inhibited melanogenesis, and several structural requirements of the active constituents for the inhibition were clarified. In particular, (3R)-1,7-bis(4-hydroxyphenyl)-(6E)-6-hepten-3-ol exhibited stronger inhibitory effect [IC50 = 0.36 mu M] without inducing cytotoxicity. The biological effect was much stronger than that of a reference compound, arbutin [IC50 = 174 mu M]. We conclude that diarylheptanoid analogs are promising therapeutic agents for the treatment of skin disorders. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.010
• 作为产物：
  描述：

  (3S)-1-(3'-methoxy-4'-hydroxyphenyl)-7-(4''-hydroxyphenyl)-(6E)-6-hepten-3-ol 、 三甲基硅烷化重氮甲烷 以 甲醇 、 正己烷 为溶剂， 反应 15.0h， 以4 mg的产率得到(3S)-1-(3',4'-dimethoxyphenyl)-7-(4''-methoxyphenyl)-(6E)-6-hepten-3-ol
  参考文献：
  名称：

  Diarylheptanoids with inhibitory effects on melanogenesis from the rhizomes of Curcuma comosa in B16 melanoma cells

  摘要：

  The methanolic extract from the dried rhizomes of Curcuma comosa cultivated in Thailand was found to inhibit melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extract, three new diarylheptanoids, diarylcomosols I-III, were isolated together with 12 known diarylheptanoids. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The diarylheptanoids inhibited melanogenesis, and several structural requirements of the active constituents for the inhibition were clarified. In particular, (3R)-1,7-bis(4-hydroxyphenyl)-(6E)-6-hepten-3-ol exhibited stronger inhibitory effect [IC50 = 0.36 mu M] without inducing cytotoxicity. The biological effect was much stronger than that of a reference compound, arbutin [IC50 = 174 mu M]. We conclude that diarylheptanoid analogs are promising therapeutic agents for the treatment of skin disorders. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.010

文献信息

• Diarylheptanoids from the Rhizomes of <i>Curcuma kwangsiensis</i>
  作者：Jun Li、Feng Zhao、Ming Zhi Li、Li Xia Chen、Feng Qiu

  DOI：10.1021/np100392m

  日期：2010.10.22

  Twelve new diarylheptanoids and six known compounds were isolated from rhizomes of Curcuma kwangsiensis. Structures of the new compounds were elucidated by spectroscopic and chemical methods as (3S)- and (3R)-1,7-bis(4-hydroxyphenyl)-(6E)-6-hepten-3-ol (1a and 1b), (3S)- and (3R)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)-(6E)-6-hepten-3-ol (2a and 2b), (3S)- and (3R)-1-(3,4-dihydroxyphenyl)-7-(4

  从姜黄的根茎中分离出12种新的二芳基庚烷类化合物和6种已知化合物。通过光谱和化学方法阐明了新化合物的结构，分别为（3 S）-和（3 R）-1,7-双（4-羟苯基）-（6 E）-6-庚烯-3-醇（1a和1b），（3 S）-和（3 R）-1-（3,4-二羟基苯基）-7-（4-羟基苯基）-（6 E）-6-庚烯-3-醇（2a和2b）， （3 S）-和（3 R）-1-（3,4-二羟基苯基）-7-（4-羟基苯基）庚烷-3-醇（3a和3b），（3 R）-1-（3,4-二羟基苯基）-7-苯基-（6 E）-6-庚烯-3-醇（4b），（3 S）-和（3 R）-3-乙酰氧基-1-（ 3,4-二羟基苯基）-7-（4-羟基苯基）-（6 E）-6-庚烯（5a和5b），（3 S）-和（3 R）-3-乙酰氧基-1-（3,4 -二羟基苯基）-7-（4-羟基苯基）庚烷（6a和6b）和（E）-1,7-双（4-羟基苯基）-6-庚