(S)-methyl-6,7-bis(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydroisoquinoline | 1449405-95-1

• 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)-methyl-6,7-bis(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: methyl (3S)-6,7-bis[[tert-butyl(dimethyl)silyl]oxy]-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
• CAS: 1449405-95-1
• 化学式: C₂₃H₄₁NO₄Si₂
• 分子量: 451.754
• InChiKey: RADBSTANJCUXST-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl-6,7-bis(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydroisoquinoline 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以78%的产率得到(S)-6,7-bis(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydroisoquin-3-yl methanol
  参考文献：
  名称：

  Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands

  摘要：

  Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 mu M for the cis-diastereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.048
• 作为产物：
  描述：

  左旋多巴 在 氯化亚砜 、 硫酸 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 生成 (S)-methyl-6,7-bis(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydroisoquinoline 、 (S)-methyl 6-(tert-butyldimethylsilyloxy)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
  参考文献：
  名称：

  Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands

  摘要：

  Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 mu M for the cis-diastereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.048

文献信息

• Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands
  作者：Madichaba P. Chelopo、Sachin A. Pawar、Mxolisi K. Sokhela、Thavendran Govender、Hendrik G. Kruger、Glenn E.M. Maguire

  DOI：10.1016/j.ejmech.2013.05.048

  日期：2013.8

  Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 mu M for the cis-diastereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4. (C) 2013 Elsevier Masson SAS. All rights reserved.