Methyl 1-(2-naphthylsulfonyl)pyrrolidine-2-carboxylate | 941599-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 1-(2-naphthylsulfonyl)pyrrolidine-2-carboxylate
• 英文别名: methyl 1-naphthalen-2-ylsulfonylpyrrolidine-2-carboxylate
• CAS: 941599-79-7
• 化学式: C₁₆H₁₇NO₄S
• 分子量: 319.381
• InChiKey: DPFCYDDFRCUWGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 1-(2-naphthylsulfonyl)pyrrolidine-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到1-(2-Naphthylsulfonyl)proline
  参考文献：
  名称：

  Small molecule antagonists of the CC chemokine receptor 4 (CCR4)

  摘要：

  The identification, optimization, and structure-activity relationship (SAR) of small-molecule CCR4 antagonists is described. An initial screening hit with micromolar potency was identified that was optimized to sub-micromolar binding potency by enantiomer resolution, halogenation of the naphthalene ring, and extension of the alkyl chain linker between the central piperidine ring and the terminal aryl group. An antagonist was identified that showed good cross-reactivity against the mouse receptor and inhibited CCR4-based cell recruitment in dose-dependent fashion. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.03.030
• 作为产物：
  描述：

  甲基吡咯烷-2-羧酸 、 2-萘磺酰氯 在 TEA 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到Methyl 1-(2-naphthylsulfonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Small molecule antagonists of the CC chemokine receptor 4 (CCR4)

  摘要：

  The identification, optimization, and structure-activity relationship (SAR) of small-molecule CCR4 antagonists is described. An initial screening hit with micromolar potency was identified that was optimized to sub-micromolar binding potency by enantiomer resolution, halogenation of the naphthalene ring, and extension of the alkyl chain linker between the central piperidine ring and the terminal aryl group. An antagonist was identified that showed good cross-reactivity against the mouse receptor and inhibited CCR4-based cell recruitment in dose-dependent fashion. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.03.030

文献信息

• Small molecule antagonists of the CC chemokine receptor 4 (CCR4)
  作者：Douglas F. Burdi、Shannon Chi、Karen Mattia、Celeste Harrington、Zhan Shi、Shaowu Chen、Swanee Jacutin-Porte、Robert Bennett、Kenneth Carson、Wei Yin、Vikram Kansra、Jose-Angel Gonzalo、Anthony Coyle、Bruce Jaffee、Timothy Ocain、Marty Hodge、Gregory LaRosa、Geraldine Harriman

  DOI：10.1016/j.bmcl.2007.03.030

  日期：2007.6

  The identification, optimization, and structure-activity relationship (SAR) of small-molecule CCR4 antagonists is described. An initial screening hit with micromolar potency was identified that was optimized to sub-micromolar binding potency by enantiomer resolution, halogenation of the naphthalene ring, and extension of the alkyl chain linker between the central piperidine ring and the terminal aryl group. An antagonist was identified that showed good cross-reactivity against the mouse receptor and inhibited CCR4-based cell recruitment in dose-dependent fashion. Published by Elsevier Ltd.