[4-acetyloxy-6-(3-oxopropyl)-5,6,7,8-tetrahydronaphthalen-1-yl] acetate | 289633-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: [4-acetyloxy-6-(3-oxopropyl)-5,6,7,8-tetrahydronaphthalen-1-yl] acetate
• CAS: 289633-38-1
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: VHQSLLOZUZVWLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [4-acetyloxy-6-(3-oxopropyl)-5,6,7,8-tetrahydronaphthalen-1-yl] acetate 在 重铬酸吡啶 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 methyl 3-(5,8-diacetyloxy-1,2,3,4-tetrahydronaphthalen-2-yl)propanoate
  参考文献：
  名称：

  New antineoplastic prenylhydroquinones. Synthesis and evaluation

  摘要：

  Several prenylhydroquinones have been prepared through Diels-Alder condensation, further functionalized or degraded chemically and then evaluated for their cytotoxic activity against some neoplastic cultured cell lines. A number of them have shown IC50 values under the mu M level. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00032-8
• 作为产物：
  描述：

  [4-Acetyloxy-6-[2-(3,3-dimethyloxiran-2-yl)ethyl]-5,8-dihydronaphthalen-1-yl] acetate 在 Lindlar's catalyst 氢气 、 高碘酸 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 19.0h， 生成 [4-acetyloxy-6-(3-oxopropyl)-5,6,7,8-tetrahydronaphthalen-1-yl] acetate
  参考文献：
  名称：

  New antineoplastic prenylhydroquinones. Synthesis and evaluation

  摘要：

  Several prenylhydroquinones have been prepared through Diels-Alder condensation, further functionalized or degraded chemically and then evaluated for their cytotoxic activity against some neoplastic cultured cell lines. A number of them have shown IC50 values under the mu M level. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00032-8

文献信息

• Synthesis and Cytotoxic Evaluation of 6-(3-Pyrazolylpropyl) Derivatives of 1,4-Naphthohydroquinone-1,4-diacetate
  作者：Aurora Molinari、Alfonso Oliva、Claudia Ojeda、José M. Miguel del Corral、M. Angeles Castro、Carmen Cuevas、Arturo San Feliciano

  DOI：10.1002/ardp.200900041

  日期：2009.10

  Several new 6‐(3‐pyrazolylpropyl) derivatives of 1,4‐naphthohydroquinone‐1,4‐diacetate (NHQ‐DA) have been prepared by chemical modifications of the Diels–Alder adduct of α‐myrcene and 1,4‐benzoquinone. All these new compounds and precursors have been evaluated in vitro for their cytotoxicity against cultured human cancer cells of MB‐231 breast‐adeno carcinoma, A‐549 lung carcinoma, and HT‐29 colon

  通过对 α-月桂烯和 1,4-苯醌的 Diels-Alder 加合物进行化学修饰，已经制备了 1,4-萘并氢醌-1,4-二乙酸酯 (NHQ-DA) 的几种新的 6-(3-吡唑基丙基) 衍生物。所有这些新化合物和前体都已在体外评估了它们对培养的人癌细胞 MB-231 乳腺癌、腺癌、A-549 肺癌和 HT-29 结肠癌的细胞毒性。GI50 值的范围在微摩尔浓度水平和以下。
• Synthesis and Evaluation as Antitumor Agents of 1,4-Naphthohydroquinone Derivatives Conjugated with Amino Acids and Purines
  作者：Aurora Molinari、Alfonso Oliva、Claudia Ojeda、José M. Miguel del Corral、Maria A. Castro、Faustino Mollinedo、Arturo San Feliciano

  DOI：10.1002/ardp.201300137

  日期：2013.12

  We report on the synthesis of two series of 1,4‐naphthohydroquinone derivatives conjugated with amino acids (Gly, Ala, Phe, and Glu) and with substituted purines linked by an aliphatic chain. The compounds were obtained through Diels–Alder cycloaddition between myrcene and 1,4‐benzoquinone and evaluated in vitro for their cytotoxicity (GI50) against cultured human cancer cells of A‐549 lung carcinoma

  我们报告了与氨基酸（Gly、Ala、Phe 和 Glu）结合的两个系列 1,4-萘并氢醌衍生物和通过脂肪链连接的取代嘌呤的合成。这些化合物是通过月桂烯和 1,4-苯醌之间的 Diels-Alder 环加成获得的，并在体外评估了它们对培养的 A-549 肺癌、HT-29 结肠腺癌和 MCF-7 乳腺癌细胞的细胞毒性 (GI50)癌。某些对苯二酚-氨基酸和对苯二酚-嘌呤杂合物对 MCF-7 的 GI50 值与参考药物多柔比星的活性范围相当。