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(E)-3-(2,4-Dihydroxy-6-methyl-phenyl)-acrylic acid ethyl ester | 921882-87-3

中文名称
——
中文别名
——
英文名称
(E)-3-(2,4-Dihydroxy-6-methyl-phenyl)-acrylic acid ethyl ester
英文别名
Ethyl 3-(2,4-dihydroxy-6-methylphenyl)prop-2-enoate;ethyl 3-(2,4-dihydroxy-6-methylphenyl)prop-2-enoate
(E)-3-(2,4-Dihydroxy-6-methyl-phenyl)-acrylic acid ethyl ester化学式
CAS
921882-87-3
化学式
C12H14O4
mdl
——
分子量
222.241
InChiKey
RLXWPAIKNDQALF-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    385.6±11.0 °C(Predicted)
  • 密度:
    1.234±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.2
  • 重原子数:
    16
  • 可旋转键数:
    4
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.25
  • 拓扑面积:
    66.8
  • 氢给体数:
    2
  • 氢受体数:
    4

反应信息

  • 作为反应物:
    描述:
    参考文献:
    名称:
    抗艾滋病剂。37.(3′R,4′R)-(+)-顺式-甲壳酮衍生物作为新型有效的抗HIV剂的合成和构效关系。
    摘要:
    为了探索作为新型抗HIV药物的(+)-顺式-khellactone衍生物的结构要求,使用24个单取代的3',4'-di-O-(S)-樟脑酰基-(+)-顺式-khellactone(DCK)衍生物不对称合成。这些化合物包括4个异构的单甲氧基类似物(3-6),4个异构的单甲基类似物(7-10),4个4-烷基/芳基取代的类似物(11-14)和12个4-甲基-(+)-顺式具有3',4'取代基的khellactone衍生物(15-26)。这些(+)-顺式-khellactone衍生物被筛选针对急性感染的H9淋巴细胞中的HIV-1复制。结果表明,(3'R,4'R)-(+)-顺式-khellactone骨架,3'-和4'-位置的两个(S)-(-)-樟脑酰基和甲基除6-位以外,香豆素环上的α是抗HIV活性的最佳结构部分。3-甲基-(7),4-甲基-(8)和5-甲基-(9)3',4'-二-O-(S)-樟脑酰基-(3'R,4'R)-
    DOI:
    10.1021/jm9900624
  • 作为产物:
    参考文献:
    名称:
    Synthesis and cytotoxic activities of novel 4-methoxy-substituted and 5-methyl-substituted (3&prime;<em>S</em>,4&prime;<em>S</em>)-(-)-<em>cis</em>-khellactone derivatives that induce apoptosis via the intrinsic pathway
    摘要:
    This study deals with the design and synthesis of a series of novel 4-methoxy-substituted and 5-methyl-substituted (3'S, 4'S)-(-)-cis-khellactones. The newly synthesized compounds were characterized by H-1 nuclear magnetic resonance (NMR), C-13-NMR, mass spectrometry, and elemental analysis. All the derivatives were subjected to in vitro cytotoxicity screening against HEPG-2 (human liver carcinoma), SGC-7901 (human gastric carcinoma), and LS174T (human colon carcinoma), by using the MTT assay. The results revealed that several of the 4-methoxy-substituted compounds exhibited potent cytotoxicity. Among these, compound 12e showed the highest activity against cancer cells which 50% inhibitory concentration (IC50) values were in the range of 6.1-9.2 mu M with low toxicity on normal human hepatocyte. Preliminary investigation of possible mechanisms of action of compound 12e against HEPG-2 cells indicated possible induction of apoptosis, as determined by morphological observations and Annexin V/propidium iodide (PI) double staining, in addition to apparent dissipation of mitochondrial membrane potential (MMP), as measured by 5,5', 6,6'-tetrachloro-1,1', 3,3'-tetraethyl-imidacarbocyanine iodide (JC-1) staining in combination with the activation of caspase-9 and caspase-3 by Western blot analysis. Overall, the data suggest that compound 12e may be a promising potential anticancer agent that could act primarily by inducing apoptosis through the mitochondria-mediated intrinsic pathway in human hepatoma cells.
    DOI:
    10.2147/dddt.s131753
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