1-(bromomethyl)-4-(tetradecyloxy)benzene | 108003-51-6

• 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: 1-(bromomethyl)-4-(tetradecyloxy)benzene
• 英文别名: 1-(bromomethyl)-4-tetradecoxybenzene
• CAS: 108003-51-6
• 化学式: C₂₁H₃₅BrO
• 分子量: 383.412
• InChiKey: BODOSVSSNFXFFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(bromomethyl)-4-(tetradecyloxy)benzene 在 sodium hydride 作用下， 生成 3-[[Acetyl[[4-(tetradecyloxy)phenyl]methyl]amino]methyl]-1-methylpyridinium iodide
  参考文献：
  名称：

  Analogs of platelet activating factor. 8. Antagonists of PAF containing an aromatic ring linked to a pyridinium ring

  摘要：

  A series of platelet activating factor (PAF) antagonists containing a quaternary pyridinium ring connected through an amide, imide, or carbamate linkage to a substituted aromatic ring was prepared. Of these compounds, those containing a branched imide linkage of the form (CON-(COCH3)CH2, 37-51, and 59) generally showed excellent PAF antagonist properties in vitro. Structure-activity relationships within this series of compounds were studied extensively with respect to substituents and the position of substitution in both the aromatic and pyridinium rings. Several of these compounds (40 and 44) showed in vitro PAF antagonism at less than 0.1 muM and are as potent as CV-6209, the most potent PAF antagonist reported in the literature. Less active PAF antagonists were those bearing simple amide linkages (20-23, 27-29, and 31-35), linear imide linkages (62-63), or carbamate linkages (66 and 68), between the two aromatic rings. A number of our PAF antagonists were tested in vivo in mice and rabbits for their ability to protect these animals against a lethal injection of PAF. Those antagonists that are particularly potent (IC50 <0.1 muM) provide excellent protection against an LD97 dose of PAF in rabbits. The relationships between structure and activity in vitro and in vivo are presented and compared to literature standards.

  DOI：

  10.1021/jm00057a008
• 作为产物：
  描述：

  4-(Tetradecyloxy)-benzyl alcohol 在 二溴亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 1-(bromomethyl)-4-(tetradecyloxy)benzene
  参考文献：
  名称：

  1-(4-Alkyloxybenzyl)-3-methyl-1H-imidazol-3-ium organic backbone: A versatile smectogenic moiety

  摘要：

  离子液体和液晶领域的合并，通过使用咪唑环作为共同元素，使我们能够定制一组新材料，这些材料具有特定的功能。这些功能是组分的原始性质——离子液体、液晶及它们在单一化合物中的结合——的结果。对这种有趣的结合的研究使我们能够从中制定出环境灵活的阳离子结构，从中产生出介向性质。此外，我们还探讨了不同阴离子对介向性质的影响。

  DOI：

  10.3762/bjoc.5.62

文献信息

• Pyridinium compounds which are useful as antagonists of platelet
  申请人：American Cyanamid Company

  公开号：US05208247A1

  公开（公告）日：1993-05-04

  The invention is aryl, amide, imide and carbamate pyridine antagonists of platelet activating factor.

  这项发明是有机芳基、酰胺、亚胺和碳酸酯吡啶拮抗剂，用于抑制血小板活化因子。
• Phosphocholine derivatives having antihypertensive action
  申请人：American Cyanamid Company

  公开号：US04640913A1

  公开（公告）日：1987-02-03

  Phosphocholine derivatives and compositions are described which are useful as hypotensive agents and in the treatment of hypertension in warm-blooded animals.

  磷酸胆碱衍生物和组合物被描述为在温血动物中作为降压剂和治疗高血压的有用药物。
• Benzyl and Naphthalene Methylphosphonic Acid Inhibitors of Autotaxin with Anti-invasive and Anti-metastatic Activity
  作者：Renuka Gupte、Renukadevi Patil、Jianxiong Liu、Yaohong Wang、Sue C. Lee、Yuko Fujiwara、James Fells、Alyssa L. Bolen、Karin Emmons-Thompson、C. Ryan Yates、Anjaih Siddam、Nattapon Panupinthu、Truc-Chi T. Pham、Daniel L. Baker、Abby L. Parrill、Gordon B. Mills、Gabor Tigyi、Duane D. Miller

  DOI：10.1002/cmdc.201000425

  日期：2011.5.2

  report the synthesis and pharmacological characterization of ATX inhibitors based on the 4‐tetradecanoylaminobenzylphosphonic acid scaffold, which was previously found to lack sufficient stability in cellular systems. The new 4‐substituted benzylphosphonic acid and 6‐substituted naphthalen‐2‐ylmethylphosphonic acid analogues block ATX activity with Ki values in the low micromolar to nanomolar range against

  Autotaxin (ATX, NPP2) 是核苷酸焦磷酸磷酸二酯酶家族的成员。ATX 通过溶血磷脂酶 D 的活性催化溶血磷脂酰胆碱 (LPC) 的水解裂解，从而产生生长因子样脂质介质溶血磷脂酸 (LPA)。ATX 在转移性和化疗耐药性癌症中高度上调，是介导癌症侵袭和转移的潜在靶点。在此，我们报告了基于 4-十四烷酰氨基苄基膦酸支架的 ATX 抑制剂的合成和药理学表征，此前发现该支架在细胞系统中缺乏足够的稳定性。新的 4-取代苄基膦酸和 6-取代萘-2-基甲基膦酸类似物通过K i阻断 ATX 活性通过混合模式抑制机制，对 FS3、LPC 和核苷酸底物的低微摩尔至纳摩尔范围内的值。所测试的化合物均不抑制相关酶（NPP6 和 NPP7）的活性。此外，这些化合物被评估为七种 LPA 受体 (LPAR) 亚型的激动剂或拮抗剂。类似物22和30 b是两种最有效的 ATX 抑制剂，在体外以剂量依赖性方式抑制
• Inhibitors of Autotaxin
  申请人：Gupte Renuka

  公开号：US20120190650A1

  公开（公告）日：2012-07-26

  Stabilized benzyl phosphonic acid and naphthyl phosphonic acid analog compounds are effective in inhibiting the activity of autotaxin.

  稳定的苄基膦酸和萘基膦酸类似化合物在抑制自动税脂酶活性方面有效。
• The synthesis and properties of surfactant aza macrocycles
  作者：Andrew D. Pidwell、Simon R. Collinson、Duncan W. Bruce、Simon J. Coles、Michael B. Hursthouse、Martin Schröder

  DOI：10.1039/b003368p

  日期：——

  Surfactant derivatives of [9]aneN3 and [12]aneN3 are prepared; micelles are formed at low concentrations in water while at higher concentrations lyotropic hexagonal, cubic and lamellar phases are characterised.

  制备了 [9]aneN3 和 [12]aneN3 的表面活性剂衍生物；在水中低浓度时形成胶束，高浓度时形成各向同性的六方相、立方相和片状相。