二氢桑色素 | 18422-83-8

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 二氢桑色素
• 英文名称: dihydromorin
• 英文别名: trans-dihydromorin；(2R,3R)-2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
• CAS: 18422-83-8
• 化学式: C₁₅H₁₂O₇
• 分子量: 304.256
• InChiKey: QIWOFDHUQPJCJF-LSDHHAIUSA-N

物化性质

• 熔点：
  224 °C
• 沸点：
  693.8±55.0 °C(Predicted)
• 密度：
  1.702±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

制备方法与用途

概述

二氢桑色素是一种有机化合物，其可用作医药合成中间体。

用途

二氢桑色素是一种有机化合物，其可用作医药合成中间体；也可与其他成分构成组合物，用于治疗结核等疾病。

反应信息

• 作为反应物：
  描述：

  二氢桑色素 在 potassium carbonate 、 丙酮 作用下， 生成 (+/-)-3t-acetoxy-2r-(2,4-dimethoxy-phenyl)-5,7-dimethoxy-chroman-4-one
  参考文献：
  名称：

  Carruthers et al., Journal of the Chemical Society, 1957, p. 4440,4441

  摘要：

  DOI：
• 作为产物：
  描述：

  1-[2,4,6-三(甲氧基甲氧基)苯基]乙酮 在 盐酸 、 双氧水 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 正己烷 、 水 为溶剂， 反应 6.42h， 生成 2,3-trans-Dihydromorin 、 二氢桑色素
  参考文献：
  名称：

  Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure–activity relationship

  摘要：

  To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.042

文献信息

• Aromatase inhibitors from Broussonetia papyrifera
  申请人：——

  公开号：US20030125377A1

  公开（公告）日：2003-07-03

  A composition and method of cancer treatment is disclosed. The composition and method utilized the extract of B. papyrifera , or compounds included therein having aromatase inhibition properties, as active cancer chemopreventative and treating agents in mammals, including humans.

  本发明揭示了一种癌症治疗的组合物和方法。该组合物和方法利用B. papyrifera的提取物，或者包括具有芳香化酶抑制作用的化合物，作为哺乳动物，包括人类的活性癌症化学预防和治疗剂。
• US6737439B2
  申请人：——

  公开号：US6737439B2

  公开（公告）日：2004-05-18