(2S)-2-[[(3R)-2-(9H-fluoren-9-ylmethoxycarbonyl)-1-phenylmethoxycarbonyldiazinane-3-carbonyl]-phenylmethoxyamino]-3-methoxypropanoic acid | 1104899-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S)-2-[[(3R)-2-(9H-fluoren-9-ylmethoxycarbonyl)-1-phenylmethoxycarbonyldiazinane-3-carbonyl]-phenylmethoxyamino]-3-methoxypropanoic acid
• CAS: 1104899-89-9
• 化学式: C₃₉H₃₉N₃O₉
• 分子量: 693.753
• InChiKey: APSFIAOBQYWXPM-GPOMZPHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(3R)-2-(9H-fluoren-9-ylmethoxycarbonyl)-1-phenylmethoxycarbonyldiazinane-3-carbonyl]-phenylmethoxyamino]-3-methoxypropanoic acid 、 (S)-3-(N'-tert-Butoxycarbonyl-hydrazinocarbonyl)-2-((R)-4-methyl-2-methylamino-pentanoyl)-tetrahydro-pyridazine-1-carboxylic acid benzyl ester 在 2,4,6-三甲基吡啶 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 二氯甲烷 为溶剂， 以12.4 g的产率得到
  参考文献：
  名称：

  Synthesis of A83586C Analogs with Potent Anticancer and β-Catenin/ TCF4/Osteopontin Inhibitory Effects and Insights Into How A83586C Modulates E2Fs and pRb

  摘要：

  The synthesis of three potent new antitumor agents is described: the A83586C-citropeptin hybrid (1), the A83586C-GE3 hybrid (2), and L-Pro-A83586C (3). Significantly, compounds 1 and 2 function as highly potent inhibitors of beta-catenin/TCF4 signaling within cancer cells, while simultaneously downregulating osteopontin (Opn) expression. A83586C antitumor cyclodepsipeptides also inhibit E2F-mediated transcription by downregulating E2F1 expression and inducing dephosphorylation of the oncogenic hyperphosphorylated retinoblastoma protein (pRb).

  DOI：

  10.1021/ol802818f
• 作为产物：
  描述：

  在 四(三苯基膦)钯 、 苯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到(2S)-2-[[(3R)-2-(9H-fluoren-9-ylmethoxycarbonyl)-1-phenylmethoxycarbonyldiazinane-3-carbonyl]-phenylmethoxyamino]-3-methoxypropanoic acid
  参考文献：
  名称：

  Total Synthesis of (+)-Azinothricin and (+)-Kettapeptin

  摘要：

  Asymmetric total syntheses of (+)-azinothricin and (+)-kettapeptin have been completed through a common new pathway that exploits a highly chemoselective coupling reaction between the fully elaborated cyclodepsipeptide 5 and the glycal activated esters 3 and 4 at the final stages of both respective syntheses.

  DOI：

  10.1021/ol802817t

文献信息

• Total Synthesis of (+)-Azinothricin and (+)-Kettapeptin
  作者：Karl J. Hale、Soraya Manaviazar、Jonathan H. George、Marcus A. Walters、Stephen M. Dalby

  DOI：10.1021/ol802817t

  日期：2009.2.5

  Asymmetric total syntheses of (+)-azinothricin and (+)-kettapeptin have been completed through a common new pathway that exploits a highly chemoselective coupling reaction between the fully elaborated cyclodepsipeptide 5 and the glycal activated esters 3 and 4 at the final stages of both respective syntheses.
• Synthesis of A83586C Analogs with Potent Anticancer and β-Catenin/ TCF4/Osteopontin Inhibitory Effects and Insights Into How A83586C Modulates E2Fs and pRb
  作者：Karl J. Hale、Soraya Manaviazar、Linos Lazarides、Jonathan George、Marcus A. Walters、Jiaqiang Cai、Vern M. Delisser、Gurpreet S. Bhatia、S. Andrew Peak、Stephen M. Dalby、Amandine Lefranc、Ying-Nan P. Chen、Alexander W. Wood、Paul Crowe、Pauline Erwin、Mohamed El-Tanani

  DOI：10.1021/ol802818f

  日期：2009.2.5

  The synthesis of three potent new antitumor agents is described: the A83586C-citropeptin hybrid (1), the A83586C-GE3 hybrid (2), and L-Pro-A83586C (3). Significantly, compounds 1 and 2 function as highly potent inhibitors of beta-catenin/TCF4 signaling within cancer cells, while simultaneously downregulating osteopontin (Opn) expression. A83586C antitumor cyclodepsipeptides also inhibit E2F-mediated transcription by downregulating E2F1 expression and inducing dephosphorylation of the oncogenic hyperphosphorylated retinoblastoma protein (pRb).