4-(4-bromobutoxy)phenol | 66619-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(4-bromobutoxy)phenol
• 英文别名: 4-(4-Bromo-butoxy)-phenol
• CAS: 66619-92-9
• 化学式: C₁₀H₁₃BrO₂
• 分子量: 245.116
• InChiKey: WSTXXXZXZBLOCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  361.1±22.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-bromobutoxy)phenol 在 三乙胺 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 132.0h， 生成 4-[4-[benzyl-(2-hydroxy-3-phenoxypropyl)amino]butoxy]phenol
  参考文献：
  名称：

  Selective .beta.3-adrenergic agonists of brown adipose tissue and thermogenesis. 2. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetamides

  摘要：

  The ester methyl [4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetate (1) (R1 = OMe) had previously been identified as the most interesting member of a series of selective beta-3-adrenergic agonists of brown adipose tissue and thermogenesis in the rat. In vivo it acts mainly via the related acid 1 (R1 = OH). Amides have been examined to determine whether they have advantages over the ester. In particular, in the rat and dog the half-lives of amides of appropriate potency were no longer than those of the ester. The amide (S)-4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]-N-(2-methoxyethyl)phenoxyacetamide [S-27, ICI D7114] was selected as having properties consistent with a sustained-release formulation should that prove necessary. Unlike the ester it is resistant to hydrolysis in the gut lumen. Further testing of ICI D7114 has shown that in the rat, cat, and dog it stimulates the beta-3-adrenergic receptor in brown adipose tissue at doses lower than those at which it affects beta-1- and beta-2-adrenergic receptors in other tissues. Slimming effects were observed in the dog. ICI D7114 may be a selective thermogenic agent in man and may be useful in the treatment of obesity and diabetes.

  DOI：

  10.1021/jm00088a010
• 作为产物：
  描述：

  1,4-二溴丁烷 、 对苯二酚 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.5h， 以18%的产率得到4-(4-bromobutoxy)phenol
  参考文献：
  名称：

  ROS-Activated Compounds as Selective Anti-Cancer Therapeutics

  摘要：

  根据以下的公式I提供了化合物：公式I化合物在存在活性氧气体（ROS）的情况下被激活，因此对于与增加ROS相关的癌症是选择性的抗癌治疗药物。还提供了用于治疗与增加ROS相关的癌症的方法和药物组合物。

  公开号：

  US20130230542A1

文献信息

• ROS-activated compounds as selective anti-cancer therapeutics
  申请人：University of Cincinnati

  公开号：US09394233B2

  公开（公告）日：2016-07-19

  Provided are compounds according to the following Formula I: The Formula I compounds are activated in the presence of reactive oxygen species (ROS) and are therefore selective anti-cancer therapeutics for cancers associated with elevated ROS. Also provided are methods and pharmaceutical compositions for treating cancers associated with increased ROS.

  提供的化合物符合以下公式I：公式I化合物在反应性氧化物种（ROS）存在下被激活，因此是选择性的抗癌治疗药物，用于与增高ROS相关的癌症。同时提供了治疗与增加ROS相关的癌症的方法和制药组合物。
• Supramolecular Enhancement of Charge Transport through Pillar[5]arene‐Based Self‐Assembled Monolayers
  作者：Xiaobing Li、Siyuan Zhou、Qi Zhao、Yi Chen、Pan Qi、Yongkang Zhang、Lu Wang、Cunlan Guo、Shigui Chen

  DOI：10.1002/anie.202216987

  日期：——

  transport at a molecular junction is realized in pillar[5]arene-based self-assembled monolayers through host–guest interactions with cationic guest molecules. The improved charge transport is positively correlated with the strong binding affinity between pillar[5]arene and cationic guest molecules, which results in a delocalized structure in the supramolecular complex and a reduced energy offset.

  通过主客体与阳离子客体分子的相互作用，在基于柱 [5] 芳烃的自组装单分子层中实现了分子连接处电荷传输的显着增强。改进的电荷传输与柱 [5] 芳烃和阳离子客体分子之间的强结合亲和力正相关，这导致超分子复合物中的离域结构和减少的能量偏移。
• Novel ROS-activated agents utilize a tethered amine to selectively target acute myeloid leukemia
  作者：Tiffany R. Bell-Horwath、Anish K. Vadukoot、Fathima Shazna Thowfeik、Guorui Li、Mark Wunderlich、James C. Mulloy、Edward J. Merino

  DOI：10.1016/j.bmcl.2013.03.048

  日期：2013.5

  This study explores the possible use of reactive oxygen-activated DNA modifying agents against acute myeloid leukemia (AML). A key amine on the lead agent was investigated via cytotoxicity assays and was found necessary for potency. The two best compounds were screened via the NCI-60 cell panel. These two compounds had potency between 200 and 800 nM against many of the leukemia cancer cell types. Subsequent experiments explored activity against a transformed AML model that mimics the molecular signatures identified in primary AML patient samples. A lead compound had an IC50 of 760 nM against this AML cell line as well as a therapeutic index of 7.7 +/- 3 between the transformed AML model cell line and non-cancerous human CD34+ blood stem/progenitor cells (UCB). The selectivity was much greater than the mainstays of AML treatment: doxorubicin and cytarabine. This manuscript demonstrates that this novel type of agent may be useful against AML. (C) 2013 Elsevier Ltd. All rights reserved.
• Antiviral activity of some .beta.-diketones. 3. Aryl bis(.beta.-diketones). Antiherpetic activity
  作者：Guy D. Diana、Philip M. Carabateas、U. Joseph Salvador、Gordon L. Williams、Ethel S. Zalay、Francis Pancic、B. A. Steinberg、Joseph C. Collins

  DOI：10.1021/jm00205a019

  日期：1978.7

  A series of bis(beta-diketones) was synthesized and tested in vitro for antiviral actitity against herpes simplex type 2. Two parameters which were studied in an effort to optimize activity were the nature of the aryl group and the length of the alkyl bridge. One of the more active compounds, 4,4'-[(1,4-phenylenedioxy)bis(6,1-hexanediyl)]-bis[3,5-heptanedione] (6), was evaluated more extensively and found to inhibit the cytopathic effect in tissue culture of herpes simplex virus type 1 as well as type 2. Compound 6 was evaluated in vivo topically against herpes simplex type 1 in experimentally induced skin infections in guinea pigs. A topical treatment with 2% of 6 in a vanishing cream base, administered 24 h postinfection applied five times daily for 4 days, significantly reduced the number and size of herpetic vesicles.
• DIANA G. D.; CARABATEAS P. M.; SALVADOR U. J.; WILLIAMS G. L.; ZALAY E. S+, J. MED. CHEM., 1978, 21, NO 7, 689-692
  作者：DIANA G. D.、 CARABATEAS P. M.、 SALVADOR U. J.、 WILLIAMS G. L.、 ZALAY E. S+

  DOI：——

  日期：——