(E)-1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-[4-[2-[4-[(E)-3-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-oxoprop-1-enyl]phenoxy]ethoxy]phenyl]prop-2-en-1-one | 916330-62-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-[4-[2-[4-[(E)-3-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-oxoprop-1-enyl]phenoxy]ethoxy]phenyl]prop-2-en-1-one
• CAS: 916330-62-6
• 化学式: C₆₀H₅₀O₁₀
• 分子量: 931.051
• InChiKey: UNWAZPUBUOPGFM-YESHOFFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  70
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (E)-1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-[4-[2-[4-[(E)-3-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-oxoprop-1-enyl]phenoxy]ethoxy]phenyl]prop-2-en-1-one 在 palladium on activated charcoal 氢气 、 碘 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 1,4-bis[4-((5,7-dihydroxy)-4H-chromen-4-on-2-yl)phenyl]-1,4-dioxabutane
  参考文献：
  名称：

  Flavonoid Dimers as Bivalent Modulators for P-Glycoprotein-Based Multidrug Resistance:  Synthetic Apigenin Homodimers Linked with Defined-Length Poly(ethylene glycol) Spacers Increase Drug Retention and Enhance Chemosensitivity in Resistant Cancer Cells

  摘要：

  Much effort has been spent on searching for better P-glycoprotein- ( P-gp-) based multidrug resistance ( MDR) modulators. Our approach was to target the binding sites of P-gp using dimers of dietary flavonoids. A series of apigenin-based flavonoid dimers, linked by poly( ethylene glycol) chains of various lengths, have been synthesized. These flavonoid dimers modulate drug chemosensitivity and retention in breast and leukemic MDR cells with the optimal number of ethylene glycol units equal to 2-4. Compound 9d bearing four ethylene glycol units increased drug accumulation in drug-resistant cells and enhanced cytotoxicity of paclitaxel, doxorubicin, daunomycin, vincristine, and vinblastine in drug- resistant breast cancer and leukemia cells in vitro, resulting in reduction of IC50 by 5-50 times. This compound also stimulated P-gp's ATPase activity by 3.3-fold. Its modulating activity was presumably by binding to the substrate binding sites of P-gp and disrupting drug efflux.

  DOI：

  10.1021/jm060593+
• 作为产物：
  描述：

  4,4-乙烷二氧基二苯甲醛 、 2-乙酰基-3,5-双(苄氧基)苯酚 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (E)-1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-[4-[2-[4-[(E)-3-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-oxoprop-1-enyl]phenoxy]ethoxy]phenyl]prop-2-en-1-one
  参考文献：
  名称：

  Flavonoid Dimers as Bivalent Modulators for P-Glycoprotein-Based Multidrug Resistance:  Synthetic Apigenin Homodimers Linked with Defined-Length Poly(ethylene glycol) Spacers Increase Drug Retention and Enhance Chemosensitivity in Resistant Cancer Cells

  摘要：

  Much effort has been spent on searching for better P-glycoprotein- ( P-gp-) based multidrug resistance ( MDR) modulators. Our approach was to target the binding sites of P-gp using dimers of dietary flavonoids. A series of apigenin-based flavonoid dimers, linked by poly( ethylene glycol) chains of various lengths, have been synthesized. These flavonoid dimers modulate drug chemosensitivity and retention in breast and leukemic MDR cells with the optimal number of ethylene glycol units equal to 2-4. Compound 9d bearing four ethylene glycol units increased drug accumulation in drug-resistant cells and enhanced cytotoxicity of paclitaxel, doxorubicin, daunomycin, vincristine, and vinblastine in drug- resistant breast cancer and leukemia cells in vitro, resulting in reduction of IC50 by 5-50 times. This compound also stimulated P-gp's ATPase activity by 3.3-fold. Its modulating activity was presumably by binding to the substrate binding sites of P-gp and disrupting drug efflux.

  DOI：

  10.1021/jm060593+

文献信息

• US8710097B2
  申请人：——

  公开号：US8710097B2

  公开（公告）日：2014-04-29
• Flavonoid Dimers as Bivalent Modulators for P-Glycoprotein-Based Multidrug Resistance:  Synthetic Apigenin Homodimers Linked with Defined-Length Poly(ethylene glycol) Spacers Increase Drug Retention and Enhance Chemosensitivity in Resistant Cancer Cells
  作者：Kin-Fai Chan、Yunzhe Zhao、Brendan A. Burkett、Iris L. K. Wong、Larry M. C. Chow、Tak Hang Chan

  DOI：10.1021/jm060593+

  日期：2006.11.1

  Much effort has been spent on searching for better P-glycoprotein- ( P-gp-) based multidrug resistance ( MDR) modulators. Our approach was to target the binding sites of P-gp using dimers of dietary flavonoids. A series of apigenin-based flavonoid dimers, linked by poly( ethylene glycol) chains of various lengths, have been synthesized. These flavonoid dimers modulate drug chemosensitivity and retention in breast and leukemic MDR cells with the optimal number of ethylene glycol units equal to 2-4. Compound 9d bearing four ethylene glycol units increased drug accumulation in drug-resistant cells and enhanced cytotoxicity of paclitaxel, doxorubicin, daunomycin, vincristine, and vinblastine in drug- resistant breast cancer and leukemia cells in vitro, resulting in reduction of IC50 by 5-50 times. This compound also stimulated P-gp's ATPase activity by 3.3-fold. Its modulating activity was presumably by binding to the substrate binding sites of P-gp and disrupting drug efflux.