4-(4-苯基丁基)苯-1,2-二醇 | 119189-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-(4-苯基丁基)苯-1,2-二醇
• 中文别名: 1,2-苯二醇,4-(4-苯基丁基)-
• 英文名称: 1-(3,4-dihydroxyphenyl)-4-phenylbutane
• 英文别名: 4-(4-phenylbutyl)benzene-1,2-diol
• CAS: 119189-32-1
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: PEMMCHVJDAVCMU-UHFFFAOYSA-N

物化性质

• 沸点：
  418.4±30.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3-(3,4-dimethoxyphenyl)propyl)triphenylphosphonium bromide 在 正丁基锂 、 palladium on activated charcoal 、 氢气 、 三溴化硼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 30.0h， 生成 4-(4-苯基丁基)苯-1,2-二醇
  参考文献：
  名称：

  天然产物去氢二氢瓜二酸的结构优化，以发现新型类似物作为AcrB抑制剂。

  摘要：

  药物外排泵对危险的细菌病原体具有多重耐药性，这使这些蛋白质成为有希望的药物靶标。在本文中，我们围绕先前描述的外排泵抑制剂降冰片二氢乙酸（NDGA）提出了初始化学优化和结构-活性关系（SAR）数据。设计，合成和评估了针对大肠杆菌AcrB的四个系列的新型NDGA类似物，以评估它们增强抗生素活性，抑制AcrB介导的底物外流并降低脱靶活性的能力。鉴定出九种新颖结构，这些结构提高了一组抗生素的功效，抑制了药物外排并降低了细菌外膜和内膜的通透性。其中，WA7，具有广谱抗菌增敏活性的WB11和WD6被鉴定为具有良好特性的NDGA类似物，可作为潜在的AcrB抑制剂，与NDGA相比，其效能有中等程度的提高。尤其是，WD6是最广泛活性的类似物，可提高所有四类抗菌药物的活性。

  DOI：

  10.1016/j.ejmech.2019.111910

文献信息

• Pharmaceutical compositions comprising catecholic butanes
  申请人：BLOCK DRUG COMPANY, INC.

  公开号：EP0297733A2

  公开（公告）日：1989-01-04

  The invention relates to pharmaceutical compositions useful in the treatment of benign, premalignant and malignant solid tumours, especially those of the skin, and in the treatment of other disorders of the skin e.g. psoriasis and acne. The compositions comprise at least one catecholic butane. The preferred catecholic butane is nordihydroguaiaretic acid. The compositions are preferably applied topically or by intratumor or subcutaneous injection. The invention also includes sunscreening agents comprising at least one catecholic butane.

  本发明涉及可用于治疗良性、恶性前和恶性实体瘤（尤其是皮肤肿瘤）以及其他皮肤疾病（如牛皮癣和痤疮）的药物组合物。组合物包含至少一种儿茶酚丁烷。首选的儿茶酚丁烷是去氢愈创木酚酸。组合物最好局部使用或通过瘤内注射或皮下注射。本发明还包括包含至少一种儿茶酚丁烷的防晒剂。
• 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.
• COMPOSITIONS OF CATECHOLIC BUTANES WITH ZINC
  申请人：CHEMEX PHARMACEUTICALS, INC.

  公开号：EP0288534A1

  公开（公告）日：1988-11-02
• PHARMACOLOGICALLY ACTIVE COMPOUNDS AND MIXTURES THEREOF, ORGANIC COMPOSITIONS AND METAL SALTS
  申请人：CHEMEX PHARMACEUTICALS, INC.

  公开号：EP0290442A1

  公开（公告）日：1988-11-17
• EP0288534A4
  申请人：——

  公开号：EP0288534A4

  公开（公告）日：1989-02-23