6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene | 78238-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene
• CAS: 78238-94-5
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: AKLOQUHTKMBFQX-UHFFFAOYSA-N

物化性质

• 沸点：
  387.3±42.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到5-Phenyl-5,6,7,8-tetrahydronaphthalene-2,3-diol
  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 platinum(IV) oxide 硫酸 、 氢气 、 magnesium 、 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 25.0~95.0 ℃ 、354.64 kPa 条件下， 反应 19.5h， 生成 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Bandaranayake, Wickramasinghe M.; Riggs, Noel V., Australian Journal of Chemistry, 1981, vol. 34, # 1, p. 115 - 129

  摘要：

  DOI：

文献信息

• Bandaranayake, Wickramasinghe M.; Riggs, Noel V., Australian Journal of Chemistry, 1981, vol. 34, # 1, p. 115 - 129
  作者：Bandaranayake, Wickramasinghe M.、Riggs, Noel V.

  DOI：——

  日期：——
• BANDARANAYAKE W. M.; RIGGS N. V., AUSTRAL. J. CHEM., 1981, 34, NO 1, 115-129
  作者：BANDARANAYAKE W. M.、 RIGGS N. V.

  DOI：——

  日期：——
• 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.