(3S)-(+)-3-(1-甲基吲哚)-3-苯丙酸 | 406920-62-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (3S)-(+)-3-(1-甲基吲哚)-3-苯丙酸
• 英文名称: (S)-3-(1-Methyl-1H-indol-3-yl)-3-phenylpropanoic acid
• 英文别名: (3S)-3-(1-methylindol-3-yl)-3-phenylpropanoic acid
• CAS: 406920-62-5
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.3
• InChiKey: XVWRQAZBQVTVJA-HNNXBMFYSA-N

物化性质

• 熔点：
  63-67 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S)-(+)-3-(1-甲基吲哚)-3-苯丙酸 、 Centratherin 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以56 %的产率得到centratherin (S)-3-(1-methyl-1H-indol-3-yl)-3-phenylpropanoate
  参考文献：
  名称：

  新型中心草素衍生物：分子对接设计、不对称合成和抗肿瘤活性

  摘要：

  Centratherin 是一种倍半萜内酯，具有抑制癌症治疗靶蛋白的潜力，例如炎症介质 NF-κB。吲哚还具有抗肿瘤活性，并且可以调节 NF-κB 信号通路。在这里，我们描述了一种分子对接引导的含吲哚中心草素衍生物的半合成。研究表明，这些化合物与 NF-κB 具有高亲和力，并且不存在毒性或致癌性。采用有机催化的Friedel-Crafts烷基化作为关键步骤，分三步合成了两个对映体系列的吲哚-中心蛋白杂化物，收率良好。这些化合物针对人类白血病 K562 细胞进行了评估，显示出良好的抗肿瘤活性，IC 范围为 0.49 至 7.83 μM。

  DOI：

  10.1016/j.tet.2024.134112
• 作为产物：
  描述：

  (3S)-(+)-3-(1-甲基吲哚-3-基)-3-苯基丙醛 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 异丁烯 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 以71 %的产率得到(3S)-(+)-3-(1-甲基吲哚)-3-苯丙酸
  参考文献：
  名称：

  新型中心草素衍生物：分子对接设计、不对称合成和抗肿瘤活性

  摘要：

  Centratherin 是一种倍半萜内酯，具有抑制癌症治疗靶蛋白的潜力，例如炎症介质 NF-κB。吲哚还具有抗肿瘤活性，并且可以调节 NF-κB 信号通路。在这里，我们描述了一种分子对接引导的含吲哚中心草素衍生物的半合成。研究表明，这些化合物与 NF-κB 具有高亲和力，并且不存在毒性或致癌性。采用有机催化的Friedel-Crafts烷基化作为关键步骤，分三步合成了两个对映体系列的吲哚-中心蛋白杂化物，收率良好。这些化合物针对人类白血病 K562 细胞进行了评估，显示出良好的抗肿瘤活性，IC 范围为 0.49 至 7.83 μM。

  DOI：

  10.1016/j.tet.2024.134112

文献信息

• [EN] DNA-ENCODED CHEMICAL LIBRARIES<br/>[FR] BIBLIOTHÈQUES DE PRODUITS CHIMIQUES CODÉS PAR ADN
  申请人：PHILOCHEM AG

  公开号：WO2009077173A2

  公开（公告）日：2009-06-25

  A method of preparing a DNA-encoded chemical library comprising members which comprise a chemical moiety, a linking moiety and a DNA moiety, comprising for each member the steps of: (I) coupling a initial building block to a initial coding single strand oligomer via a linking moiety to form a initial conjugate, the initial coding single strand oligomer comprising a first primer region, an initial coding region and a first annealing region; (II) optionally coupling a middle building block and middle coding single strand oligomer to said initial conjugate to form a middle conjugate, the coupling take place in either order, wherein: (a) the middle building block is coupled to the residue of the initial building block; and (b) the middle coding single strand oligomer comprises a middle coding region and second annealing region, and is coupled by: (i) annealing a complementary single strand oligomer which comprises a chemical modifier, a complementary first annealing region, a complementary middle coding region and a complementary second annealing region by interaction between the first annealing region and the complementary first annealing region; (ii) treating the conjugate formed with a DNA polymerase to elongate the initial coding single strand oligomer to be complementary to the complementary middle coding region and the complementary second annealing region; (iii) removing the complementary single strand oligomer by denaturing the DNA and capturing the complementary single strand oligomer via the chemical modifier; (III) coupling a final building block and final coding single strand oligomer to the initial or middle conjugate as appropriate to form a final conjugate, the coupling take place in either order, wherein: (a) the final building block is coupled to the residue of the initial building block, or may be additionally or alternatively be coupled to the residue of the middle building block (if present); and (b) the final coding single strand oligomer comprises a final coding region and a second primer region, and is coupled by: (i) annealing a complementary single strand oligomer which comprises a complementary first or second annealing region as appropriate, a complementary final coding region and a complementary second primer region, by interaction between the first or second annealing region and the complementary first or second annealing region, as appropriate; (ii) treating the conjugate formed with a DNA polymerase to elongate the initial coding single strand oligomer to be complementary to the complementary final coding region and the complementary second primer region, and to elongate the complementary coding strand to be complementary to the initial coding single strand oligomer.