吡啶,3-溴-5-[[[(1,1-二甲基乙基)二苯基甲硅烷基]氧代]甲基]- | 153607-77-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 吡啶,3-溴-5-[[[(1,1-二甲基乙基)二苯基甲硅烷基]氧代]甲基]-
• 英文名称: 3-Bromo-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)pyridine
• 英文别名: (5-bromopyridin-3-yl)methoxy-tert-butyl-diphenylsilane
• CAS: 153607-77-3
• 化学式: C₂₂H₂₄BrNOSi
• 分子量: 426.428
• InChiKey: JYCASTDJZWLSKB-UHFFFAOYSA-N

物化性质

• 沸点：
  462.0±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吡啶,3-溴-5-[[[(1,1-二甲基乙基)二苯基甲硅烷基]氧代]甲基]- 在 氟化铵 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 3.08h， 生成 5-羟基甲基烟酸甲酯
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Some Acyclic Pyridine C-Nucleosides. Part Two

  摘要：

  3-Bromo-5-(2-hydroxyethylthiomethyl)pyridine ((7) under bar) was synthesized by reaction of 3-bromo-5-chloromethylpyridine hydrochloride ((6) under bar) with the mono sodium salt of 2-mercaptoethanol. 3-Bromo-5-hydroxymethylpyridine (<(10)under bar>) was, after protection as a silyl ether, converted to the 3-carboxy analogue using BuLi and CO2. After deprotection with NH4F, the alcohol function was chlorinated using SOCl2. Finally, attachment of the acyclic chain and ammonolysis gave the acyclic nicotinamide nucleosides. Treatment of the latter compounds with Lawesson's reagent gave the thioamide analogues. All compounds were identified by NMR and DCI-MS. The acyclic pyridine C-nucleosides were evaluated against a series of tumor-cell lines and a variety of viruses. No marked biological activity was found.

  DOI：

  10.1080/07328319608007388
• 作为产物：
  描述：

  5-溴烟酸甲酯 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 吡啶,3-溴-5-[[[(1,1-二甲基乙基)二苯基甲硅烷基]氧代]甲基]-
  参考文献：
  名称：

  Substituted (Pyridylmethoxy)naphthalenes as Potent and Orally Active 5-Lipoxygenase Inhibitors:  Synthesis, Biological Profile, and Pharmacokinetics of L-739,010

  摘要：

  Dioxabicyclooctanyl naphthalenenitriles have been reported as a class of potent and nonredox 5-lipoxygenase (5-LO) inhibitors. These bicycle derivatives were shown to be metabolically more stable than their tetrahydropyranyl counterparts but were not well orally absorbed. Replacement of the phenyl ring in the naphthalenenitrile 1 by a pyridine ring leads to the potent and orally absorbed inhibitor 3g (L-739,010, 2-cyano-4-(3-furyl)-7-[[6-[3-(3-hydroxy-6,8-dioxabicyclo[3.2.1] octanyl)]-2-pyridyl]methoxy]naphthalene). Compound 3g inhibits 5-HPETE production by human 5-LO and LTB4 biosynthesis by human PMN leukocytes and human whole blood (IC(50)s of 20, 1.6, and 42 nM, respectively). Derivative 3g is orally active in the rat pleurisy model (inhibition of LTB4, ED50 = 0.3 mg/kg) and in the anesthetized dog model (inhibition of ex vivo whole blood LTB4 and urinary LTE4, ED50 = 0.45 and 0.23 mu g/kg/min, respectively, iv infusion). In addition, 3g shows excellent functional activity against ovalbumin-induced dyspnea in rats (60% inhibition at 0.5 mg/kg, 4 h pretreatment) and Ascaris-induced bronchoconstriction in conscious sheep (50% and >85% inhibition in early and late phases, respectively at 2.5 mu g/kg/min, iv infusion) and, more particularly in the conscious antigen sensitive squirrel monkey model (53% inhibition of the increase in R-L and 76% in the decrease of C-dyn, at 0.1 mg/kg, po). In rats and dogs, 3g presents excellent pharmacokinetics (estimated half-lives of 5 and 16 h, respectively) and bioavailabilities (26% and 73% when dosed as its hydrochloride salt at doses of 20 and 10 mg/kg, respectively, in methocel suspension). Based on its overall biological profile, compound 3g has been selected for preclinical animal toxicity studies.

  DOI：

  10.1021/jm970046b

文献信息

• Heteroaryl cinnamic acids as inhibitors of leukotriene biosynthesis
  申请人：Merck Frosst Canada, Inc.

  公开号：US05360815A1

  公开（公告）日：1994-11-01

  Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.

  具有化学式I的化合物是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植物排斥，以及预防动脉粥样硬化斑块的形成。
• Heteroarylnaphthalenes as inhibitors of leukotriene biosynthesis
  申请人：Merck Frosst Canada, Inc.

  公开号：US05308852A1

  公开（公告）日：1994-05-03

  Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.

  具有公式I: ##STR1## 的化合物是白三烯生物合成抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植排斥，并可预防动脉粥样硬化斑块的形成。
• Phenylnaphthalene lactones as inhibitors of leukotriene biosynthesis
  申请人：Merck Frosst Canada, Inc.

  公开号：US05350744A1

  公开（公告）日：1994-09-27

  Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.

  具有以下化学式的化合物I：##STR1## 是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植排斥，以及预防动脉粥样硬化斑块的形成。
• Phenylnaphthalene hydroxy acids
  申请人：Merck Frosst Canada, Inc.

  公开号：US05426109A1

  公开（公告）日：1995-06-20

  Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.

  具有化学式I的化合物是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植排斥，并可预防动脉粥样硬化斑块的形成。
• Heteroarylnaphthalene hydroxy acids as inhibitors of leukotriene
  申请人：Merck Frosst Canada, Inc.

  公开号：US05252599A1

  公开（公告）日：1993-10-12

  Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.

  具有化学式I: ##STR1## 的化合物是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植物排斥反应，并可预防动脉粥样硬化斑块的形成。