tert-butyl 6,8-dimethoxy-1-[(4-phenylphenyl)methyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate | 1228098-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: tert-butyl 6,8-dimethoxy-1-[(4-phenylphenyl)methyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1228098-80-3
• 化学式: C₂₉H₃₃NO₄
• 分子量: 459.585
• InChiKey: TXYGJHYJKGQCQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 6,8-dimethoxy-1-[(4-phenylphenyl)methyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 1-[(4-Phenylphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,8-diol;hydrobromide
  参考文献：
  名称：

  Synthesis and evaluation of new 1,2,3,4-tetrahydroisoquinoline analogs as antiglioma agents

  摘要：

  Novel tetrahydroisoquinoline (THI) analogs were designed, synthesized, and their antiglioma activity was evaluated. The results showed that 6,8-dimethoxy-1-(2'-methoxybiphenyl-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (25) demonstrated improved potency, and selectivity on C6 rat glioma vs cultured rat astrocytes (EC50 0.63 mu M vs. 10.85 mu M) compared to our recent lead molecule EDL-155 (EC50 1.5 mu M vs. 27.4 mu M). The isomers of 25 were isolated using a semi-preparative high-performance liquid chromatography (HPLC) method, and their in vitro biological evaluation revealed that (+) 25 was the most active, and it was nearly 21 fold more potent than (-) 25, suggesting the antiglioma profile is influenced by stereochemical factors.

  DOI：

  10.1007/s00044-010-9356-8
• 作为产物：
  描述：

  4-联苯乙酸 在 sodium tetrahydroborate 、 氰基磷酸二乙酯 、 三乙胺 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 tert-butyl 6,8-dimethoxy-1-[(4-phenylphenyl)methyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of new 1,2,3,4-tetrahydroisoquinoline analogs as antiglioma agents

  摘要：

  Novel tetrahydroisoquinoline (THI) analogs were designed, synthesized, and their antiglioma activity was evaluated. The results showed that 6,8-dimethoxy-1-(2'-methoxybiphenyl-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (25) demonstrated improved potency, and selectivity on C6 rat glioma vs cultured rat astrocytes (EC50 0.63 mu M vs. 10.85 mu M) compared to our recent lead molecule EDL-155 (EC50 1.5 mu M vs. 27.4 mu M). The isomers of 25 were isolated using a semi-preparative high-performance liquid chromatography (HPLC) method, and their in vitro biological evaluation revealed that (+) 25 was the most active, and it was nearly 21 fold more potent than (-) 25, suggesting the antiglioma profile is influenced by stereochemical factors.

  DOI：

  10.1007/s00044-010-9356-8

文献信息

• Synthesis and evaluation of new 1,2,3,4-tetrahydroisoquinoline analogs as antiglioma agents
  作者：Renukadevi Patil、Shivaputra Patil、XiangDi Wang、Fei Ma、William E. Orr、Wei Li、Charles R. Yates、Eldon E. Geisert、Duane D. Miller

  DOI：10.1007/s00044-010-9356-8

  日期：2011.1

  Novel tetrahydroisoquinoline (THI) analogs were designed, synthesized, and their antiglioma activity was evaluated. The results showed that 6,8-dimethoxy-1-(2'-methoxybiphenyl-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (25) demonstrated improved potency, and selectivity on C6 rat glioma vs cultured rat astrocytes (EC50 0.63 mu M vs. 10.85 mu M) compared to our recent lead molecule EDL-155 (EC50 1.5 mu M vs. 27.4 mu M). The isomers of 25 were isolated using a semi-preparative high-performance liquid chromatography (HPLC) method, and their in vitro biological evaluation revealed that (+) 25 was the most active, and it was nearly 21 fold more potent than (-) 25, suggesting the antiglioma profile is influenced by stereochemical factors.