3-Methoxy-4(2-methoxyethoxy)nitrobenzol | 26181-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Methoxy-4(2-methoxyethoxy)nitrobenzol
• 英文别名: 2-Methoxy-1-(2-methoxyethoxy)-4-nitrobenzene
• CAS: 26181-50-0
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: VLMAEPMMCOTHKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Methoxy-4(2-methoxyethoxy)nitrobenzol 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-methoxy-4-(2-methoxyethoxy)-aniline
  参考文献：
  名称：

  Discovery of novel anti-breast cancer agents derived from deguelin as inhibitors of heat shock protein 90 (HSP90)

  摘要：

  A series of O-substituted analogues of the B,C-ring truncated scaffold of deguelin were designed as C-terminal inhibitors of heat shock protein 90 (HSP90) and investigated as novel antiproliferative agents against HER2-positive breast cancer. Among the synthesized compounds, compound 80 exhibited significant inhibition in both trastuzumab-sensitive and trastuzumab-resistant breast cancer cells, whereas compound 80 did not show any cytotoxicity in normal cells. Compound 80 markedly downregulated the expression of the major client proteins of HSP90 in both cell types, indicating that the cytotoxicity of 80 in breast cancer cells is attributed to the destabilization and inactivation of HSP90 client proteins and that HSP90 inhibition represents a promising strategy to overcome trastuzumab resistance. A molecular docking study of 80 with the homology model of a HSP90 homodimer showed that 80 fit nicely in the C-terminal domain with a higher electrostatic complementary score than that of ATP.

  DOI：

  10.1016/j.bmcl.2020.127374
• 作为产物：
  描述：

  1-甲氧基-2-(2-甲氧基乙氧基)苯 生成 3-Methoxy-4(2-methoxyethoxy)nitrobenzol
  参考文献：
  名称：

  Budesinsky,Z.; Valenta,A., Collection of Czechoslovak Chemical Communications, 1971, vol. 36, p. 2527 - 2539

  摘要：

  DOI：

文献信息

• Budesinsky,Z.; Valenta,A., Collection of Czechoslovak Chemical Communications, 1971, vol. 36, p. 2527 - 2539
  作者：Budesinsky,Z.、Valenta,A.

  DOI：——

  日期：——
• Discovery of novel anti-breast cancer agents derived from deguelin as inhibitors of heat shock protein 90 (HSP90)
  作者：Cong-Truong Nguyen、Jihyae Ann、Raghaba Sahu、Woong Sub Byun、Sangkook Lee、Gibeom Nam、Hyun-Ju Park、Soeun Park、Yoon-Jae Kim、Ji Young Kim、Jae Hong Seo、Jeewoo Lee

  DOI：10.1016/j.bmcl.2020.127374

  日期：2020.9

  A series of O-substituted analogues of the B,C-ring truncated scaffold of deguelin were designed as C-terminal inhibitors of heat shock protein 90 (HSP90) and investigated as novel antiproliferative agents against HER2-positive breast cancer. Among the synthesized compounds, compound 80 exhibited significant inhibition in both trastuzumab-sensitive and trastuzumab-resistant breast cancer cells, whereas compound 80 did not show any cytotoxicity in normal cells. Compound 80 markedly downregulated the expression of the major client proteins of HSP90 in both cell types, indicating that the cytotoxicity of 80 in breast cancer cells is attributed to the destabilization and inactivation of HSP90 client proteins and that HSP90 inhibition represents a promising strategy to overcome trastuzumab resistance. A molecular docking study of 80 with the homology model of a HSP90 homodimer showed that 80 fit nicely in the C-terminal domain with a higher electrostatic complementary score than that of ATP.