diacetylcurcumin | 814919-70-5

• 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: diacetylcurcumin
• 英文别名: [4-[(1E,3Z,6E)-7-(4-acetyloxy-3-methoxyphenyl)-3-hydroxy-5-oxohepta-1,3,6-trienyl]-2-methoxyphenyl] acetate
• CAS: 814919-70-5
• 化学式: C₂₅H₂₄O₈
• 分子量: 452.461
• InChiKey: MDUJMNGOOWUELB-OEHUVLJNSA-N

物化性质

• 沸点：
  596.9±50.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diacetylcurcumin 在 盐酸羟胺 、 溶剂黄146 作用下， 反应 0.08h， 以98%的产率得到3,5-bis(4-hydroxy-3-methoxystyryl)isoxazole
  参考文献：
  名称：

  姜黄素的合成及其细胞毒性和抗氧化性能的评估。

  摘要：

  合成姜黄素（1）和十种衍生物（2-11）并作为细胞毒性和抗氧化剂进行评估。通过Sulforhodamine B分析对五种人类癌细胞系（U-251 MG，胶质母细胞瘤; PC-3，人类的前列腺癌; HCT-15，人类的结肠直肠癌; K562，人类的慢性粒细胞白血病; SKLU-1，非人类）进行初步筛选的结果-小细胞肺癌）使我们能够计算出对HCT-15和K562细胞系更具活性的化合物的半数最大抑制浓度（IC50）值。化合物2和10对两种细胞系均最具活性，并且比姜黄素本身更具活性。硫代巴比妥酸反应性物质（TBARS）分析表明，其中7种具有强活性。甚至比姜黄素，α-生育酚和槲皮素更强。

  DOI：

  10.3390/molecules22040633
• 作为产物：
  描述：

  在 水 、 sodium oxalate 作用下， 以 甲醇 为溶剂， 以85%的产率得到diacetylcurcumin
  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：US11117907B2

  公开（公告）日：2021-09-14

  Novel CUR— and CUR—BF2 compounds as well as novel bis and mono-NSAID/CUR—BF2 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—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 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.

  本文介绍了新型 CUR 和 CUR-BF2 化合物以及新型双、单 NSAID/CUR-BF2 和 NSAID/CUR 混合物，这些化合物具有抗肿瘤特性。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。这些杂化物、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。与单独的非甾体抗炎药或姜黄素相比，非甾体抗炎药/姜黄素混合化合物还表现出卓越的抗炎活性。
• Pedersen, Uffe; Rasmussen, Preben B.; Lawesson, Sven-Olov, Liebigs Annalen der Chemie, 1985, # 8, p. 1557 - 1569
  作者：Pedersen, Uffe、Rasmussen, Preben B.、Lawesson, Sven-Olov

  DOI：——

  日期：——
• Antitumor Agents. Part 214:††For paper 213, see ref 1. Synthesis and Evaluation of Curcumin Analogues as Cytotoxic Agents
  作者：Junko Ishida、Hironori Ohtsu、Yoko Tachibana、Yuka Nakanishi、Kenneth F Bastow、Masahiro Nagai、Hui-Kang Wang、Hideji Itokawa、Kuo-Hsiung Lee

  DOI：10.1016/s0968-0896(02)00249-3

  日期：2002.11

  Fifty-eight curcumin analogues were prepared and evaluated for in vitro cytotoxicity against a panel of human tumor cell lines. Compound 50 was the most potent analogue against several cell lines, including HOS (bone cancer) and 1A9 (breast cancer), with ED50 values of 0.97 and <0.63 mug/mL, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Gomes, Denise De C. F.; Alegrio, Leila Vilela; Freire de Lima, Marco Edilson, Arzneimittel-Forschung/Drug Research, 2002, vol. 52, # 2, p. 120 - 124
  作者：Gomes, Denise De C. F.、Alegrio, Leila Vilela、Freire de Lima, Marco Edilson、Leon, Leonor L.、Araujo, Catarina A. C.

  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.