1,7-bis(3,4-dibenzyloxyphenyl)-1,6-heptadiene-1,5-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,7-bis(3,4-dibenzyloxyphenyl)-1,6-heptadiene-1,5-dione
• 英文别名: (1E,4Z,6E)-1,7-bis[3,4-bis(phenylmethoxy)phenyl]-5-hydroxyhepta-1,4,6-trien-3-one
• 化学式: C₄₇H₄₀O₆
• 分子量: 700.831
• InChiKey: AWFUTNWGPKHOQC-MMMGWEFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  53
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三氟化硼乙醚 、 1,7-bis(3,4-dibenzyloxyphenyl)-1,6-heptadiene-1,5-dione 以 二氯甲烷 为溶剂， 以93%的产率得到
  参考文献：
  名称：

  姜黄素-BF2 /姜黄素对的模块化合成及其在人癌细胞系中比较抗增殖活性的灵活策略。

  摘要：

  描述了一种实现CUR-BF2和CUR化合物合成相互转化的简便协议，该协议显着拓宽了姜黄素的制备范围，提供了更大的化合物库，从而能够对癌细胞中更大的合成类似物库进行比较抗增殖和凋亡研究线。

  DOI：

  10.1002/cmdc.201900640
• 作为产物：
  描述：

  在 水 、 sodium oxalate 作用下， 以 甲醇 为溶剂， 以88%的产率得到1,7-bis(3,4-dibenzyloxyphenyl)-1,6-heptadiene-1,5-dione
  参考文献：
  名称：

  姜黄素-BF2 /姜黄素对的模块化合成及其在人癌细胞系中比较抗增殖活性的灵活策略。

  摘要：

  描述了一种实现CUR-BF2和CUR化合物合成相互转化的简便协议，该协议显着拓宽了姜黄素的制备范围，提供了更大的化合物库，从而能够对癌细胞中更大的合成类似物库进行比较抗增殖和凋亡研究线。

  DOI：

  10.1002/cmdc.201900640

文献信息

• Curcuminoid-inspired synthetic compounds as anti-tumor agents
  申请人：Laali Kenneth K.

  公开号：US10934241B2

  公开（公告）日：2021-03-02

  Novel CUR— and CUR—BF2 compounds exhibiting anti-tumor properties are presented. CUR compounds bearing fluorinated moieties with selective fluorine introduction into the α-carbonyl moiety as well as CUR—BF2 adducts and CURs with diverse substitution patterns in the phenyl rings including fluorinated substituents (SCF3, OCF3, and F) and/or bulky activating groups (OMe, OAc, and OBz) are presented. Fluorinated aryl-pyrazoles and isoxazoles as well as novel CUR and CUR—BF2 compounds with monocyclic aromatic and bicyclic-heteroaromatic lateral rings, bearing fluorine(s), OCF3, CF3, and SCF3 groups, and their alpha-carbonyl-fluorinated analogs, as well as their pyrazole and isoxazole derivatives are presented. The CUR-pyrazoles embody analogs that are fluorinated at the phenyl-pyrazole moiety. The compounds and their derivatives exhibited exceptional cytotoxic and anti-proliferative activity against several cancer cell-lines. Deuterated CUR—BF2 and CUR compounds were also synthesized.

  本文介绍了具有抗肿瘤特性的新型 CUR 和 CUR-BF2 化合物。介绍了在 α-羰基中选择性引入氟的含氟 CUR 化合物，以及 CUR-BF2 加合物和在苯环中具有不同取代模式的 CUR，包括含氟取代基（SCF3、OCF3 和 F）和/或大块活化基团（OMe、OAc 和 OBz）。介绍了含氟芳基吡唑和异噁唑，以及带有氟、OCF3、CF3 和 SCF3 基团的单环芳香族和双环异芳香族侧环的新型 CUR 和 CUR-BF2 化合物及其α-羰基氟化类似物，以及它们的吡唑和异噁唑衍生物。CUR 吡唑包含在苯基吡唑分子上氟化的类似物。这些化合物及其衍生物对几种癌细胞系具有卓越的细胞毒性和抗增殖活性。此外，还合成了氚代 CUR-BF2 和 CUR 化合物。
• Nurfina, A. N.; Reksohadiprodjo, M. S.; Timmerman, H., European Journal of Medicinal Chemistry, 1997, vol. 32, # 4, p. 320 - 328
  作者：Nurfina, A. N.、Reksohadiprodjo, M. S.、Timmerman, H.、Jenie, U. A.、Sugiyanto, D.、Goot, H. van der

  DOI：——

  日期：——
• NOVEL CURCUMINOID-INSPIRED SYNTHETIC COMPOUNDS AS ANTI-TUMOR AGENTS
  申请人：Laali Kenneth K.

  公开号：US20210087208A1

  公开（公告）日：2021-03-25

  Novel CUR- and CUR-BF 2 compounds as well as novel bis and mono-NSAID/CUR-BF 2 and NSAID/CUR hybrids exhibiting anti-tumor properties are presented. CUR compounds bearing fluorinated moieties with selective fluorine introduction into the α-carbonyl moiety as well as CUR-BF 2 adducts and CURs with diverse substitution patterns in the phenyl rings including fluorinated substituents (SCF 3 , OCF 3 , and F) and/or bulky activating groups (OMe, OAc, and OBz) are presented. Fluorinated aryl-pyrazoles and isoxazoles as well as novel CUR and CUR-BF 2 compounds with monocyclic aromatic and bicyclic-heteroaromatic lateral rings, bearing fluorine(s), OCF 3 , CF 3 , and SCF 3 groups, and their alpha-carbonyl-fluorinated analogs, as well as their pyrazole and isoxazole derivatives are presented. The CUR-pyrazoles embody analogs that are fluorinated at the phenyl-pyrazole moiety. The hybrids, compounds, and their derivatives exhibited exceptional cytotoxic and anti-proliferative activity against several cancer cell-lines. The hybrid NSAID/CUR compounds also exhibited exceptional anti-inflammatory activity over NSAID or curcumin alone.
• A Flexible Strategy for Modular Synthesis of Curcuminoid‐BF ₂ /Curcuminoid Pairs and Their Comparative Antiproliferative Activity in Human Cancer Cell Lines
  作者：Rodrigo Abonia、Kenneth K. Laali、Dawn Raja Somu、Scott D. Bunge、Esther C. Wang

  DOI：10.1002/cmdc.201900640

  日期：2020.2.17

  interconversion of CUR-BF2 and CUR compounds is described that significantly widens the preparative scope of curcuminoids, providing access to larger libraries of compounds, thus enabling comparative antiproliferative and apoptotic study of a larger library of synthetic analogs in cancer cell lines.

  描述了一种实现CUR-BF2和CUR化合物合成相互转化的简便协议，该协议显着拓宽了姜黄素的制备范围，提供了更大的化合物库，从而能够对癌细胞中更大的合成类似物库进行比较抗增殖和凋亡研究线。