1-[3-[[6-(cyclohexylmethoxy)-7H-purin-2-yl]amino]phenyl]-1-deuterio-N-(3-phenylpropyl)methanesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1-[3-[[6-(cyclohexylmethoxy)-7H-purin-2-yl]amino]phenyl]-1-deuterio-N-(3-phenylpropyl)methanesulfonamide
• 化学式: C₆₅H₁₀₄N₁₃O₁₉Pol
• 分子量: 535.7
• InChiKey: AMKDKSXSUHPPCW-YUIGOLOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[3-[[6-(cyclohexylmethoxy)-7H-purin-2-yl]amino]phenyl]-1-deuterio-N-(3-phenylpropyl)methanesulfonamide 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Efficient Solid-Phase Synthesis of a Series of Cyclic and Linear Peptoid−Dexamethasone Conjugates for the Cell Permeability Studies

  摘要：

  Cyclic peptides and their cyclic analogs have received a great deal of attention because of their numerous interesting biological activities and their challenging chemical synthesis. It has also been hypothesized that they might improve the cell permeability compared to linear molecules by providing internal hydrogen bonding and generally decreasing the conformational flexibility. In this study, a series of cyclic and linear peptoid dexamethasone conjugates were rationally designed and efficiently synthesized on solid-phase for systematic cell permeability studies using reporter gene-based assays. These model compounds should be used to reveal how the cell permeability of cyclic molecules is affected by several physicochemical properties, especially, the reduced conformational flexibility and the ring size. In addition, the synthetic strategy that was adopted in this study can also provide a robust platform for postchemical modifications of various molecular scaffolds in solid-phase or solution-phase syntheses.

  DOI：

  10.1021/cc9001857
• 作为产物：
  描述：

  Fmoc-Dpr(ivDde)-OH 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 1-[3-[[6-(cyclohexylmethoxy)-7H-purin-2-yl]amino]phenyl]-1-deuterio-N-(3-phenylpropyl)methanesulfonamide
  参考文献：
  名称：

  Efficient Solid-Phase Synthesis of a Series of Cyclic and Linear Peptoid−Dexamethasone Conjugates for the Cell Permeability Studies

  摘要：

  Cyclic peptides and their cyclic analogs have received a great deal of attention because of their numerous interesting biological activities and their challenging chemical synthesis. It has also been hypothesized that they might improve the cell permeability compared to linear molecules by providing internal hydrogen bonding and generally decreasing the conformational flexibility. In this study, a series of cyclic and linear peptoid dexamethasone conjugates were rationally designed and efficiently synthesized on solid-phase for systematic cell permeability studies using reporter gene-based assays. These model compounds should be used to reveal how the cell permeability of cyclic molecules is affected by several physicochemical properties, especially, the reduced conformational flexibility and the ring size. In addition, the synthetic strategy that was adopted in this study can also provide a robust platform for postchemical modifications of various molecular scaffolds in solid-phase or solution-phase syntheses.

  DOI：

  10.1021/cc9001857

文献信息

• Synthesis of sulfonamide-based kinase inhibitors from sulfonates by exploiting the abrogated SN2 reactivity of 2,2,2-trifluoroethoxysulfonates
  作者：Christopher Wong、Roger J. Griffin、Ian R. Hardcastle、Julian S. Northen、Lan-Zhen Wang、Bernard T. Golding

  DOI：10.1039/b922717b

  日期：——

  methylene group. These were required as potential inhibitors of serine-threonine kinases of interest for the treatment of cancer. 3-Nitrophenylmethanesulfonyl chloride was converted into the corresponding 2,2,2-trifluoroethoxysulfonyl ester by reaction with 2,2,2-trifluoroethanol in the presence of triethylamine/4-dimethylaminopyridine. Catalytic hydrogenation of the nitro group employing 2,2,2-trifluoroethanol

  的减毒小号Ñ的2,2,2-三氟乙基的2反应性已被开发用于一系列6-环己基-2- arylaminopurines其中磺酰胺部分被附连到芳基环的合成通过一个亚甲基。这些被要求作为潜在的抑制剂丝氨酸--苏氨酸 用于治疗癌症的目的激酶。 3-硝基苯基甲磺酰氯 被转换成对应的 2,2,2-三氟乙氧基磺酰基酯 通过与 2,2,2-三氟乙醇 在......的存在下 三乙胺/4-二甲基氨基吡啶。使用硝基催化加氢2,2,2-三氟乙醇 作为溶剂给 3-氨基苯基甲磺酸2,2,2-三氟乙酯，与 6-环己基甲氧基-2-氟嘌呤 在 2,2,2-三氟乙醇/三氟乙酸 负担 3-（6-环己基甲氧基-9 H-嘌呤-2-基氨基）苯基甲磺酸2,2,2-三氟乙基酯。3-（6-环己基甲氧9 ħ -嘌呤-2-基氨基）phenylmethanesulfonamides通过的微波加热合成三氟乙氧基磺酸盐 用胺和 1,8-二氮杂双环十一碳-7-烯