5-[4-(3,4-dimethoxyphenyl)butyl]-1,3-benzodioxole | 611211-74-6

• 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: 5-[4-(3,4-dimethoxyphenyl)butyl]-1,3-benzodioxole
• 英文别名: 5-[4-(3,4-dimethoxyphenyl)butyl]benzo[1,3]dioxole
• CAS: 611211-74-6
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: NRORQTDYXIMAJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[4-(3,4-dimethoxyphenyl)butyl]-1,3-benzodioxole 在 五氯化磷 作用下， 以 甲苯 为溶剂， 生成 4-[4-(4-chlorophenyl)butyl]-1,2-dimethoxybenzene
  参考文献：
  名称：

  Inhibition of IGF-1R and lipoxygenase by nordihydroguaiaretic acid (NDGA) analogs

  摘要：

  Herein, we pursue the hypothesis that the structure of nordihydroguaiaretic acid (NDGA) can be refined for selective potency against the insulin-like growth factor 1 receptor (IGF-1R) as a potential therapeutic target for breast cancer while diminishing its action against other cellular targets. Thus, a set of NDGA analogs (7a-7h) was prepared and examined for inhibitory potency against IGF-1R kinase and an alternative target, 15-lipoxygenase (15 LOX). The anti-cancer effects of these compounds were determined by their ability to inhibit IGF-1 mediated cell growth of MCF-7 breast cancer cells. The design of the analogs was based upon a cursory Topliss approach in which one of NDGA's aromatic rings was modified with various substituents. Structural modification of one of the two catechol rings of NDGA was found to have little effect upon the inhibitory potency against both kinase activity of the IGF-1R and IGF-1 mediated cell growth of MCF-7 cells. 15-LOX was found to be most sensitive to structural modifications of NDGA. From the limited series of NDGA analogs examined, the compound that exhibited the greatest selectivity for IGF-1 mediated growth compared to 15-LOX inhibition was a cyclic analog 7h with a framework similar to a natural product isolated from Larrea divaricata. The results for 7h are significant because while NDGA displays biological promiscuity, 7h exhibits greater specificity toward the breast cancer target IGF-IR with that added benefit of possessing a 10-fold weaker potency against 15-LOX, an enzyme which has a purported tumor suppressing role in breast cancer. With increased specificity and potency, 7h may serve as a new lead in developing novel therapeutic agents for breast cancer. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.092
• 作为产物：
  描述：

  4-(3,4-二甲氧苯基)丁酸 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成 5-[4-(3,4-dimethoxyphenyl)butyl]-1,3-benzodioxole
  参考文献：
  名称：

  Inhibition of IGF-1R and lipoxygenase by nordihydroguaiaretic acid (NDGA) analogs

  摘要：

  Herein, we pursue the hypothesis that the structure of nordihydroguaiaretic acid (NDGA) can be refined for selective potency against the insulin-like growth factor 1 receptor (IGF-1R) as a potential therapeutic target for breast cancer while diminishing its action against other cellular targets. Thus, a set of NDGA analogs (7a-7h) was prepared and examined for inhibitory potency against IGF-1R kinase and an alternative target, 15-lipoxygenase (15 LOX). The anti-cancer effects of these compounds were determined by their ability to inhibit IGF-1 mediated cell growth of MCF-7 breast cancer cells. The design of the analogs was based upon a cursory Topliss approach in which one of NDGA's aromatic rings was modified with various substituents. Structural modification of one of the two catechol rings of NDGA was found to have little effect upon the inhibitory potency against both kinase activity of the IGF-1R and IGF-1 mediated cell growth of MCF-7 cells. 15-LOX was found to be most sensitive to structural modifications of NDGA. From the limited series of NDGA analogs examined, the compound that exhibited the greatest selectivity for IGF-1 mediated growth compared to 15-LOX inhibition was a cyclic analog 7h with a framework similar to a natural product isolated from Larrea divaricata. The results for 7h are significant because while NDGA displays biological promiscuity, 7h exhibits greater specificity toward the breast cancer target IGF-IR with that added benefit of possessing a 10-fold weaker potency against 15-LOX, an enzyme which has a purported tumor suppressing role in breast cancer. With increased specificity and potency, 7h may serve as a new lead in developing novel therapeutic agents for breast cancer. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.092

文献信息

• Oxidative Coupling Reactions Mediated by MoCl5 Leading to 2,2′-Cyclolignans: The Specific Role of HCl
  作者：Beate Kramer、Roland Fröhlich、Siegfried R. Waldvogel

  DOI：10.1002/ejoc.200300263

  日期：2003.9

  The scope and performance of oxidative coupling reaction using MoCl5 can be significantly improved by employing Lewis-acidic additives such as TiCl4, SnCl4, or SiCl4. Since the by-product, HCl, plays a particular function as an inhibitor for MoCl5 by forming chloro complexes, exploiting typical chloride scavengers, like silver salts or molecular sieves, is also successful. A variety of differently

  通过使用路易斯酸性添加剂，如 TiCl4、SnCl4 或 SiCl4，可以显着改善使用 MoCl5 的氧化偶联反应的范围和性能。由于副产物 HCl 通过形成氯配合物而起到作为 MoCl5 抑制剂的特殊功能，因此利用典型的氯化物清除剂（如银盐或分子筛）也很成功。通过模块化方法很容易合成的各种不同取代的 1,4-二芳基丁烷 4a-g 进行了脱氢二聚反应。对于氧化偶联反应，对位取代模式 - 在芳基系统上具有供体基团 - 是允许访问 2,2'-环木脂体 5a，例如。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Electrochemical Synthesis of Fluorinated Orthoesters from 1,3‐Benzodioxoles
  作者：Johannes L. Röckl、Adrian V. Hauck、Dieter Schollmeyer、Siegfried R. Waldvogel

  DOI：10.1002/open.201900127

  日期：2019.9

  A scalable, dehydrogenative, and electrochemical synthesis of novel highly fluorinated orthoesters is reported. This protocol provides easy and direct access to a wide variety of derivatives, using a very simple electrolysis setup. These compounds are surprisingly robust towards base and acid with an unusual high lipophilicity, making them interesting motifs for potentially active compounds in medicinal

  报道了新型高度氟化原酸酯的可扩展、脱氢和电化学合成。该协议使用非常简单的电解设置，可以轻松直接地访问各种衍生物。这些化合物对碱和酸具有令人惊讶的鲁棒性，具有异常高的亲脂性，使它们成为药物化学或农业应用中潜在活性化合物的有趣主题。由于只有电子作为氧化剂，电力的使用可以实现安全且环保的化学转化。
• Inhibition of IGF-1R and lipoxygenase by nordihydroguaiaretic acid (NDGA) analogs
  作者：Joseph E. Blecha、Marc O. Anderson、Jennifer M. Chow、Christle C. Guevarra、Celia Pender、Cristina Penaranda、Marianna Zavodovskaya、Jack F. Youngren、Clifford E. Berkman

  DOI：10.1016/j.bmcl.2007.04.092

  日期：2007.7

  Herein, we pursue the hypothesis that the structure of nordihydroguaiaretic acid (NDGA) can be refined for selective potency against the insulin-like growth factor 1 receptor (IGF-1R) as a potential therapeutic target for breast cancer while diminishing its action against other cellular targets. Thus, a set of NDGA analogs (7a-7h) was prepared and examined for inhibitory potency against IGF-1R kinase and an alternative target, 15-lipoxygenase (15 LOX). The anti-cancer effects of these compounds were determined by their ability to inhibit IGF-1 mediated cell growth of MCF-7 breast cancer cells. The design of the analogs was based upon a cursory Topliss approach in which one of NDGA's aromatic rings was modified with various substituents. Structural modification of one of the two catechol rings of NDGA was found to have little effect upon the inhibitory potency against both kinase activity of the IGF-1R and IGF-1 mediated cell growth of MCF-7 cells. 15-LOX was found to be most sensitive to structural modifications of NDGA. From the limited series of NDGA analogs examined, the compound that exhibited the greatest selectivity for IGF-1 mediated growth compared to 15-LOX inhibition was a cyclic analog 7h with a framework similar to a natural product isolated from Larrea divaricata. The results for 7h are significant because while NDGA displays biological promiscuity, 7h exhibits greater specificity toward the breast cancer target IGF-IR with that added benefit of possessing a 10-fold weaker potency against 15-LOX, an enzyme which has a purported tumor suppressing role in breast cancer. With increased specificity and potency, 7h may serve as a new lead in developing novel therapeutic agents for breast cancer. (C) 2007 Elsevier Ltd. All rights reserved.