(R)-1-(Naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid | 126522-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-1-(Naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid
• 英文别名: (2R)-1-naphthalen-2-ylsulfonylpyrrolidine-2-carboxylic acid
• CAS: 126522-73-4
• 化学式: C₁₅H₁₅NO₄S
• 分子量: 305.354
• InChiKey: GVNYVKRDASNULU-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl bromo-<6-cyano-1,1-(ethylenedioxy)-5-oxo-1,2,3,5-tetrahydroindolizin-7-yl> acetate 、 (R)-1-(Naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  （S）-喜树碱的不对称合成

  摘要：

  通过新颖的非对映选择性乙基化方法，从带有N-甲苯磺酰基-脯氨酸的吲哚嗪衍生物5a合成标题化合物。

  DOI：

  10.1016/s0040-4039(00)99086-5
• 作为产物：
  描述：

  methyl (2R)-1-naphthalen-2-ylsulfonylpyrrolidine-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-1-(Naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid
  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

• EJIMA, AKIO;TERASAWA, HIROFUMI;SUGIMORI, MASAMICHI;TAGAWA, HIROAKI, TETRAHEDRON LETT., 30,(1989) N0, C. 2639-2640
  作者：EJIMA, AKIO、TERASAWA, HIROFUMI、SUGIMORI, MASAMICHI、TAGAWA, HIROAKI

  DOI：——

  日期：——
• Asymmetric synthesis of (S)-camptothecin
  作者：Akio Ejima、Hirofumi Terasawa、Masamichi Sugimori、Hiroaki Tagawa

  DOI：10.1016/s0040-4039(00)99086-5

  日期：1989.1

  The title compound was synthesized via a novel diastereoselective ethylation process from indolizine derivative 5a bearing N-tosyl-(R)-proline.

  通过新颖的非对映选择性乙基化方法，从带有N-甲苯磺酰基-脯氨酸的吲哚嗪衍生物5a合成标题化合物。
• 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.