(S)-3-(N'-tert-Butoxycarbonyl-hydrazinocarbonyl)-2-((R)-4-methyl-2-methylamino-pentanoyl)-tetrahydro-pyridazine-1-carboxylic acid benzyl ester | 439292-91-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-(N'-tert-Butoxycarbonyl-hydrazinocarbonyl)-2-((R)-4-methyl-2-methylamino-pentanoyl)-tetrahydro-pyridazine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (3S)-2-[(2R)-4-methyl-2-(methylamino)pentanoyl]-3-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]diazinane-1-carboxylate
• CAS: 439292-91-8
• 化学式: C₂₅H₃₉N₅O₆
• 分子量: 505.615
• InChiKey: BYHDFKPKHAJFAT-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-3-(N'-tert-Butoxycarbonyl-hydrazinocarbonyl)-2-((R)-4-methyl-2-methylamino-pentanoyl)-tetrahydro-pyridazine-1-carboxylic acid benzyl ester 在 2,3,5-三甲基吡啶 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 二乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.58h， 生成 (S)-2-[(R)-2-({(S)-2-[Benzyloxy-((R)-1-benzyloxycarbonyl-hexahydro-pyridazine-3-carbonyl)-amino]-propionyl}-methyl-amino)-4-methyl-pentanoyl]-3-(N'-tert-butoxycarbonyl-hydrazinocarbonyl)-tetrahydro-pyridazine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthetic Route to the GE3 Cyclodepsipeptide

  摘要：

  [GRAPHICS]A reasonably efficient [2 + 2 + 2] fragment condensation strategy has been developed for assembling the cyclodepsipeptide sector of GE3 that involves 5-7. A Carpino HATU-mediated macrolactamization was used to close the 19-membered cyclodepsipeptide ring.

  DOI：

  10.1021/ol025895u
• 作为产物：
  描述：

  N-Fmoc-N-methyl-D-leucinoyl chloride 在 silver cyanide 、 二乙胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 1.08h， 生成 (S)-3-(N'-tert-Butoxycarbonyl-hydrazinocarbonyl)-2-((R)-4-methyl-2-methylamino-pentanoyl)-tetrahydro-pyridazine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthetic Route to the GE3 Cyclodepsipeptide

  摘要：

  [GRAPHICS]A reasonably efficient [2 + 2 + 2] fragment condensation strategy has been developed for assembling the cyclodepsipeptide sector of GE3 that involves 5-7. A Carpino HATU-mediated macrolactamization was used to close the 19-membered cyclodepsipeptide ring.

  DOI：

  10.1021/ol025895u

文献信息

• 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).
• Synthetic Route to the GE3 Cyclodepsipeptide
  作者：Karl J. Hale、Linos Lazarides

  DOI：10.1021/ol025895u

  日期：2002.5.1

  [GRAPHICS]A reasonably efficient [2 + 2 + 2] fragment condensation strategy has been developed for assembling the cyclodepsipeptide sector of GE3 that involves 5-7. A Carpino HATU-mediated macrolactamization was used to close the 19-membered cyclodepsipeptide ring.