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1-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,5-dimethoxyphenyl)ethanone | 864821-46-5

中文名称
——
中文别名
——
英文名称
1-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,5-dimethoxyphenyl)ethanone
英文别名
1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-(2,5-dimethoxyphenyl)ethanone
1-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,5-dimethoxyphenyl)ethanone化学式
CAS
864821-46-5
化学式
C21H25NO5
mdl
——
分子量
371.433
InChiKey
TZOCJRSKUGRULB-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    563.7±50.0 °C(Predicted)
  • 密度:
    1.178±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.7
  • 重原子数:
    27
  • 可旋转键数:
    6
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.38
  • 拓扑面积:
    57.2
  • 氢给体数:
    0
  • 氢受体数:
    5

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    1-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,5-dimethoxyphenyl)ethanone三甲基铵三氧化硫共聚物三溴化硼 作用下, 以 二氯甲烷N,N-二甲基甲酰胺乙腈 为溶剂, 反应 5.17h, 生成 1-(6,7-di-O-sulfonato-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,5-di-O-sulfonato-phenyl)ethanone tetrasodium
    参考文献:
    名称:
    Designing Nonsaccharide, Allosteric Activators of Antithrombin for Accelerated Inhibition of Factor Xa
    摘要:
    Antithrombin is a key regulator of coagulation and prime target of heparins, clinically used anticoagulants. Heparins induce a two-step conformational activation of antithrombin, a process that has remained challenging to target with molecules devoid of the antithrombin-binding pentasaccharide DEFGH. Computational screening of a focused library led to the design of two tetra-sulfated N-arylacyl tetrahydroisoquinoline variants as potential nonsaccharide activators of antithrombin. A high yielding synthetic scheme based on Horner-Wadsworth-Emmons or Pictet-Spengler reactions was developed to facilitate the functionalization of the tetrahydoisoquinoline ring, which upon further amidation, deprotection, and sulfation gave the targeted nonsaccharide activators. Spectrofluorometric measurement of affinity displayed antithrombin binding affinities in the low to high micromolar range at pH 6.0, I 0.05, 25 degrees C. Measurement of second-order rate constants of antithrombin inhibition of factor Xa in the presence and absence of the designed activators showed antithrombin activation in the range of 8-80-fold in the pH 6.0 buffer. This work puts forward 20c, a novel tetra-sulfated N-arylacyl tetrahydroisoquinoline-based molecule, that activates AT only 3.8-fold less than that achieved with DEFGH, suggesting a strong possibility of rationally designing sulfated organic molecules as clinically relevant AT activators.
    DOI:
    10.1021/jm2008387
  • 作为产物:
    参考文献:
    名称:
    富含电子的 N-取代四氢异喹啉 3-羧酸酯:简洁的合成和构象研究
    摘要:
    我们实验室最近的工作表明,高度取代的、富含电子的 1,2,3,4-四氢异喹啉-3-羧酸 (THIQ3CA) 支架是一类新型抗凝剂的关键组成部分。10 THIQ3CA 类似物的合成,尤其是含有特定的、富含电子的取代基,一直是一个挑战,文献中基本上没有报道有效的方法。我们描述了三种互补的、基于甘氨酸供体的策略,用于高产合成高度取代的、富含电子的 THIQ3CA 酯。本文研究的三个甘氨酸供体包括乙内酰脲1、(±)-Boc-α-膦酰甘氨酸三甲酯2和 (±) -Z -α-膦酰甘氨酸三甲酯3. 虽然可以使用这三种中的任何一种来合成 THIQ3CA 类似物,但在三个温和、有效的步骤中使用3 可以最好地实现所需的 THIQ3CA 酯的最佳、高产率方法。使用这种方法,合成了先进的N-芳基酰基、N-芳基烷基和双-THIQ3CA 类似物的重点库。变温和溶剂依赖性 NMR 化学位移研究表明,N-芳基酰基-THIQ3CA
    DOI:
    10.1016/j.tet.2012.01.005
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文献信息

  • Electronically rich N-substituted tetrahydroisoquinoline 3-carboxylic acid esters: concise synthesis and conformational studies
    作者:Rami A. Al-Horani、Umesh R. Desai
    DOI:10.1016/j.tet.2012.01.005
    日期:2012.2
    boxylic acid (THIQ3CA) scaffold is a key building block for a novel class of promising anticoagulants.10 The synthesis of THIQ3CA analogs, especially containing specific, electronically rich substituents, has been a challenge and essentially no efficient methods have been reported in the literature. We describe three complementary, glycine donor-based strategies for high yielding synthesis of highly
    我们实验室最近的工作表明,高度取代的、富含电子的 1,2,3,4-四氢异喹啉-3-羧酸 (THIQ3CA) 支架是一类新型抗凝剂的关键组成部分。10 THIQ3CA 类似物的合成,尤其是含有特定的、富含电子的取代基,一直是一个挑战,文献中基本上没有报道有效的方法。我们描述了三种互补的、基于甘氨酸供体的策略,用于高产合成高度取代的、富含电子的 THIQ3CA 酯。本文研究的三个甘氨酸供体包括乙内酰脲1、(±)-Boc-α-膦酰甘氨酸三甲酯2和 (±) -Z -α-膦酰甘氨酸三甲酯3. 虽然可以使用这三种中的任何一种来合成 THIQ3CA 类似物,但在三个温和、有效的步骤中使用3 可以最好地实现所需的 THIQ3CA 酯的最佳、高产率方法。使用这种方法,合成了先进的N-芳基酰基、N-芳基烷基和双-THIQ3CA 类似物的重点库。变温和溶剂依赖性 NMR 化学位移研究表明,N-芳基酰基-THIQ3CA
  • Designing Nonsaccharide, Allosteric Activators of Antithrombin for Accelerated Inhibition of Factor Xa
    作者:Rami A. Al-Horani、Aiye Liang、Umesh R. Desai
    DOI:10.1021/jm2008387
    日期:2011.9.8
    Antithrombin is a key regulator of coagulation and prime target of heparins, clinically used anticoagulants. Heparins induce a two-step conformational activation of antithrombin, a process that has remained challenging to target with molecules devoid of the antithrombin-binding pentasaccharide DEFGH. Computational screening of a focused library led to the design of two tetra-sulfated N-arylacyl tetrahydroisoquinoline variants as potential nonsaccharide activators of antithrombin. A high yielding synthetic scheme based on Horner-Wadsworth-Emmons or Pictet-Spengler reactions was developed to facilitate the functionalization of the tetrahydoisoquinoline ring, which upon further amidation, deprotection, and sulfation gave the targeted nonsaccharide activators. Spectrofluorometric measurement of affinity displayed antithrombin binding affinities in the low to high micromolar range at pH 6.0, I 0.05, 25 degrees C. Measurement of second-order rate constants of antithrombin inhibition of factor Xa in the presence and absence of the designed activators showed antithrombin activation in the range of 8-80-fold in the pH 6.0 buffer. This work puts forward 20c, a novel tetra-sulfated N-arylacyl tetrahydroisoquinoline-based molecule, that activates AT only 3.8-fold less than that achieved with DEFGH, suggesting a strong possibility of rationally designing sulfated organic molecules as clinically relevant AT activators.
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