methyl (1R,3S)-2-formyl-6,7-dihydroxy-1-(phenylmethoxymethyl)-3,4-dihydro-1H-isoquinoline-3-carboxylate | 880262-26-0

• 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: methyl (1R,3S)-2-formyl-6,7-dihydroxy-1-(phenylmethoxymethyl)-3,4-dihydro-1H-isoquinoline-3-carboxylate
• CAS: 880262-26-0
• 化学式: C₂₀H₂₁NO₆
• 分子量: 371.39
• InChiKey: AZIVLSVUKSKUTN-IRXDYDNUSA-N

物化性质

• 沸点：
  592.3±50.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1R,3S)-2-formyl-6,7-dihydroxy-1-(phenylmethoxymethyl)-3,4-dihydro-1H-isoquinoline-3-carboxylate 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 甲酸 、 草酰氯 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 potassium carbonate 、 二甲基亚砜 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， -17.0~70.0 ℃ 、344.74 kPa 条件下， 反应 24.0h， 生成 [(1R,2S,10R,12R,13S)-12-cyano-6,7,17,18-tetramethoxy-21-methyl-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4,6,8,15,17,19-hexaen-10-yl]methyl propanoate
  参考文献：
  名称：

  Synthesis and antitumor activity of simplified ecteinascidin–saframycin analogs

  摘要：

  Two series of simplified analogs of the ecteinascidin-saframycin type alkaloids were prepared from L-DOPA. Their in vitro antitumor activity was tested against three human cancer cell lines (HCT-8 colon carcinoma, Bel-7402 liver carcinoma, and BGC-823 gastric carcinoma). Among these compounds, the ester analogs have stronger activities than those of amide analogs in general. Among them, 1-naphthalene carboxylate ester analog 31 has the strongest activity against BGC-823 cells. F (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.069
• 作为产物：
  描述：

  L-3,4-二羟基苯基丙氨酸甲酯盐酸 在 sodium acetate 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 生成 methyl (1R,3S)-2-formyl-6,7-dihydroxy-1-(phenylmethoxymethyl)-3,4-dihydro-1H-isoquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and antitumor activity of simplified ecteinascidin–saframycin analogs

  摘要：

  Two series of simplified analogs of the ecteinascidin-saframycin type alkaloids were prepared from L-DOPA. Their in vitro antitumor activity was tested against three human cancer cell lines (HCT-8 colon carcinoma, Bel-7402 liver carcinoma, and BGC-823 gastric carcinoma). Among these compounds, the ester analogs have stronger activities than those of amide analogs in general. Among them, 1-naphthalene carboxylate ester analog 31 has the strongest activity against BGC-823 cells. F (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.069