1-[(Benzyloxy)methyl]-1,2,3,4-tetrahydroisoquinolin-6-ol | 193682-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-[(Benzyloxy)methyl]-1,2,3,4-tetrahydroisoquinolin-6-ol
• 英文别名: 1-(phenylmethoxymethyl)-1,2,3,4-tetrahydroisoquinolin-6-ol
• CAS: 193682-76-7
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: MANVAJPPBZRENS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(Benzyloxy)methyl]-1,2,3,4-tetrahydroisoquinolin-6-ol 在 palladium on activated charcoal 叠氮磷酸二苯酯 、 氢气 、 sodium hydride 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 41.75h， 生成 tert-butyl 1-(aminomethyl)-6-(2-methoxyethoxymethoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylate
  参考文献：
  名称：

  Synthesis of a Tetradentate Oxorhenium(V) Complex Mimic of a Steroidal Estrogen

  摘要：

  We are developing oxometal(V) complexes as high affinity ligands for the estrogen receptor. When labeled with technetium-99m, these complexes might be used as imaging agents for estrogen receptor-positive breast tumors. We describe the synthesis of a tetradentate oxorhenium(V) amino amido thioether thiol (AATT) complex in which the metal complex replaces the CD ring portion of estradiol. This complex is a close steric congener of the steroid and has a similar molecular volume. It was synthesized from norphenylephrine via an efficient Pictet-Spengler cyclization to give a tetrahydroisoquinoline that was then readily elaborated into the tetradentate chelate system. Treatment with an oxorhenium(V) salt led to the formation of the desired complex as a mixture of two diastereomers in modest yield. The relative stereochemistry of these isomers was easily assigned from their NMR spectra. On the basis of their octanol-water partition coefficients, these complexes are considerably more hydrophilic than is estradiol, and their binding affinity for the estrogen receptor is low. The AATT unit in these complexes represents a new chelation system for the oxometal(V) complexes of group 7 transition metals, and compared to other closely related bisbidentate and other tetradentate systems we have studied, these complexes are quite stable. Nevertheless, the low binding affinity of these complexes for the estrogen receptor emphasizes the fact that metal complexes must most likely have an electronic complementarity with good receptor ligands, as well as a size and shape complementarity, in order for them to exhibit high affinity receptor binding.

  DOI：

  10.1021/jo970471c
• 作为产物：
  描述：

  3-甲氧基苯乙胺 在 氢溴酸 作用下， 以 甲醇 为溶剂， 反应 53.0h， 生成 1-[(Benzyloxy)methyl]-1,2,3,4-tetrahydroisoquinolin-6-ol
  参考文献：
  名称：

  化合物及其作为L-型钙通道阻滞剂或/和乙酰 胆碱酯酶抑制剂的应用

  摘要：

  本发明公开了化合物及其作为L-型钙通道阻滞剂或/和乙酰胆碱酯酶抑制剂的应用。100nmol/L的本发明所述化合物对L-型钙通道的抑制率为8.71-35.77％，1000nmol/L的本发明所述化合物对L-型钙通道的抑制率为26.43-83.54％，本发明所述化合物对乙酰胆碱酯酶活性的IC50为16-1470nmol/L，可见，本发明所述化合物对L-型钙通道具有有效地阻滞作用，对乙酰胆碱酯酶具有明显的抑制作用，因此，本发明还提供所述化合物在制备治疗心血管疾病、中风或老年性痴呆药物中的应用。

  公开号：

  CN102464608B

文献信息

• 化合物及其作为L-型钙通道阻滞剂或/和乙酰 胆碱酯酶抑制剂的应用
  申请人：江苏先声药物研究有限公司

  公开号：CN102464608B

  公开（公告）日：2016-05-11

  本发明公开了化合物及其作为L-型钙通道阻滞剂或/和乙酰胆碱酯酶抑制剂的应用。100nmol/L的本发明所述化合物对L-型钙通道的抑制率为8.71-35.77％，1000nmol/L的本发明所述化合物对L-型钙通道的抑制率为26.43-83.54％，本发明所述化合物对乙酰胆碱酯酶活性的IC50为16-1470nmol/L，可见，本发明所述化合物对L-型钙通道具有有效地阻滞作用，对乙酰胆碱酯酶具有明显的抑制作用，因此，本发明还提供所述化合物在制备治疗心血管疾病、中风或老年性痴呆药物中的应用。
• Synthesis of a Tetradentate Oxorhenium(V) Complex Mimic of a Steroidal Estrogen
  作者：Roy K. Hom、John A. Katzenellenbogen

  DOI：10.1021/jo970471c

  日期：1997.9.1

  We are developing oxometal(V) complexes as high affinity ligands for the estrogen receptor. When labeled with technetium-99m, these complexes might be used as imaging agents for estrogen receptor-positive breast tumors. We describe the synthesis of a tetradentate oxorhenium(V) amino amido thioether thiol (AATT) complex in which the metal complex replaces the CD ring portion of estradiol. This complex is a close steric congener of the steroid and has a similar molecular volume. It was synthesized from norphenylephrine via an efficient Pictet-Spengler cyclization to give a tetrahydroisoquinoline that was then readily elaborated into the tetradentate chelate system. Treatment with an oxorhenium(V) salt led to the formation of the desired complex as a mixture of two diastereomers in modest yield. The relative stereochemistry of these isomers was easily assigned from their NMR spectra. On the basis of their octanol-water partition coefficients, these complexes are considerably more hydrophilic than is estradiol, and their binding affinity for the estrogen receptor is low. The AATT unit in these complexes represents a new chelation system for the oxometal(V) complexes of group 7 transition metals, and compared to other closely related bisbidentate and other tetradentate systems we have studied, these complexes are quite stable. Nevertheless, the low binding affinity of these complexes for the estrogen receptor emphasizes the fact that metal complexes must most likely have an electronic complementarity with good receptor ligands, as well as a size and shape complementarity, in order for them to exhibit high affinity receptor binding.