(1R,3S)‐1‐[(benzyloxy)methyl]‐6,7‐dihydroxy‐1,2,3,4‐tetrahydroisoquinoline‐3‐carboxylate methy | 880262-24-8

• 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: (1R,3S)‐1‐[(benzyloxy)methyl]‐6,7‐dihydroxy‐1,2,3,4‐tetrahydroisoquinoline‐3‐carboxylate methy
• 英文别名: methyl (1R,3S)-6,7-dihydroxy-1-(phenylmethoxymethyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
• CAS: 880262-24-8
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: UGTWUMNWXIDHNE-HOTGVXAUSA-N

物化性质

• 沸点：
  524.2±50.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  88.02
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,3S)‐1‐[(benzyloxy)methyl]‐6,7‐dihydroxy‐1,2,3,4‐tetrahydroisoquinoline‐3‐carboxylate methy 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 甲酸 、 草酰氯 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 乙酸酐 、 potassium carbonate 、 二甲基亚砜 、 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 23.0h， 生成 (6S,7R,9R,15R)‐9‐(hydroxymethyl)‐2,3,11,12‐tetramethoxy‐16‐methyl‐6,7,9,14,14a,15‐hexahydro‐5H‐6,15‐ep‐iminobenzo[4,5]azocino[1,2‐b]isoquinoline‐7‐carbonitrile
  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：

  左旋多巴 在 氯化亚砜 、 sodium acetate 、 溶剂黄146 作用下， 生成 (1R,3S)‐1‐[(benzyloxy)methyl]‐6,7‐dihydroxy‐1,2,3,4‐tetrahydroisoquinoline‐3‐carboxylate methy
  参考文献：
  名称：

  Simplified hybrids of two anticancer bistetrahydroisoquinoline alkaloids ecteinascidin 743 and cribrostatin 4 and inhibitory activity against proliferation of cancer cells

  摘要：

  一系列简化的天然生物碱ecteinascidin 743和cribrostatin 4的杂交/类似物已被合成和评估。

  DOI：

  10.1039/d2ob01707e

文献信息

• Design, synthesis, and biological evaluation of simplified tetrahydroisoquinoline analogs
  作者：Yang Yang、Yi Gao、Siyu Chen、Ju Guo、Yanggen Hu

  DOI：10.1002/ardp.202300453

  日期：2023.12

  were prepared and their antitumor activity was studied against several human carcinoma cell lines, including Ketr3, BEL-7402, BGC-823, KB, HCT-8, MCF-7, HeLa, A2780, A549, and HT-1080. Compound 20, an analog of phthalascidin 650, exhibited good broad-spectrum antitumor activity in vitro. However, compounds 19 and 21, in which the side chains at C-22 are simplified, showed no obvious antitumor activity

  制备了一系列四氢异喹啉衍生物，并研究了其对几种人癌细胞系的抗肿瘤活性，包括 Ketr3、BEL-7402、BGC-823、KB、HCT-8、MCF-7、HeLa、A2780、A549 和 HT- 1080.化合物20是Phascidin 650的类似物，在体外表现出良好的广谱抗肿瘤活性。然而，C-22位侧链简化的化合物19和21并没有表现出明显的抗肿瘤活性，表明该类化合物的C-22位侧链对其活性影响较大。化合物20和酞菁650体内活性的差异也表明骨架结构上的取代基对体内活性的显着影响。
• RCM-mediated stereoselective synthesis of three novel tetrahydroisoquinoline tetracyclic core frameworks
  作者：Qing-Qing Huang、Lin-Hai Chen、Fa-Jun Nan

  DOI：10.1016/j.tetlet.2008.06.094

  日期：2008.8

  Three novel tetrahydroisoquinoline tetracyclic core frameworks were sterectselectively synthesized. The key steps included a ring-closing metathesis (RCM)-mediated cyclization and a subsequent intramolecular S(N)2 N(O)-substituted reaction. This simple method for tetracyclic core synthesis facilitates the further exploration of the chemical space of tetrahydroisoquinoline alkaloids. (C) 2008 Elsevier Ltd. All rights reserved.