3-(3,4-dimethoxyphenyl)propylamine hydrochloride | 59734-58-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3,4-dimethoxyphenyl)propylamine hydrochloride
• 英文别名: 3-(3,4-dimethoxyphenyl)propan-1-amine;hydron;chloride
• CAS: 59734-58-6
• 化学式: C₁₁H₁₇NO₂*ClH
• 分子量: 231.722
• InChiKey: OTMANLIKOBIDOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  162-163 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,4-dimethoxyphenyl)propylamine hydrochloride 在 吡啶 、 三溴化硼 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 N-(3-[3,4-diacetoxyphenyl]propyl)-6,7-diacetoxy-2-naphthamide
  参考文献：
  名称：

  作为新型非嘌呤黄嘌呤氧化酶抑制剂的 N-芳基烷基 2-萘酰胺的计算机设计与合成

  摘要：

  合成了一系列N-芳基烷基 2-萘酰胺 ( Xa ~ e )，这些化合物是从构建的黄嘌呤氧化酶模板上的虚拟分子对接预测的，作为潜在的抑制剂。测定了它们对黄嘌呤氧化酶的抑制活性。在这些制备物中，化合物Xb (IC 50 13.6 μM)、Xc (IC 50 13.1 μM)和Xd (IC 50 12.5 μM)显示出与别嘌醇(IC 50 22.1 μM)相当的抑制活性。体外测定结果与分子对接分数 Δ G有很好的相关性 = -16.99、-17.66 和 -17.13 Kcal/mol，分别。在氧酸钾诱导的高尿酸血症小鼠模型中，口服Xc - Ac（40mg/Kg）过氧乙酰化Xc可使血尿酸水平较正常对照组降低 60%， 与高尿酸血症小鼠组相比，具有统计学意义 ( p < .01)。

  DOI：

  10.1002/ddr.21782
• 作为产物：
  描述：

  3,4-二甲氧基肉桂酸 在 盐酸 、 lithium aluminium tetrahydride 、 硫酸 、 palladium 10% on activated carbon 、 盐酸羟胺 、 氢气 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 3-(3,4-dimethoxyphenyl)propylamine hydrochloride
  参考文献：
  名称：

  作为新型非嘌呤黄嘌呤氧化酶抑制剂的 N-芳基烷基 2-萘酰胺的计算机设计与合成

  摘要：

  合成了一系列N-芳基烷基 2-萘酰胺 ( Xa ~ e )，这些化合物是从构建的黄嘌呤氧化酶模板上的虚拟分子对接预测的，作为潜在的抑制剂。测定了它们对黄嘌呤氧化酶的抑制活性。在这些制备物中，化合物Xb (IC 50 13.6 μM)、Xc (IC 50 13.1 μM)和Xd (IC 50 12.5 μM)显示出与别嘌醇(IC 50 22.1 μM)相当的抑制活性。体外测定结果与分子对接分数 Δ G有很好的相关性 = -16.99、-17.66 和 -17.13 Kcal/mol，分别。在氧酸钾诱导的高尿酸血症小鼠模型中，口服Xc - Ac（40mg/Kg）过氧乙酰化Xc可使血尿酸水平较正常对照组降低 60%， 与高尿酸血症小鼠组相比，具有统计学意义 ( p < .01)。

  DOI：

  10.1002/ddr.21782

文献信息

• Die Synthese von 6,7-Dihydro-2<i>H</i>-pyrimido[6, 1-<i>a</i>]isochinolin-4(3<i>H</i>)-onen und analogen Verbindungen und deren Wirkung als Blutpättchenaggregationshemmer
  作者：Frank Kienzle、Yves Bounameaux、Rudolf E. Minder、Reto Muggli

  DOI：10.1002/hlca.19860690722

  日期：1986.10.29

  Synthesis of 6,7-Dihydro-2H-pyrimido[6,1-a]isoquinolin-4(3H)-ones and Analogous Compounds and their Activity as Blood-Platelet Inhibitors

  6,7-二氢-2 H-嘧啶基[6,1 - a ]异喹啉-4（3 H）-ones及其类似化合物的合成及其作为血小板抑制剂的活性
• The Discovery of Capsazepine, the First Competitive Antagonist of the Sensory Neuron Excitants Capsaicin and Resiniferatoxin
  作者：Christopher S. J. Walpole、Stuart Bevan、Guenter Bovermann、Johann J. Boelsterli、Robin Breckenridge、John W. Davies、Glyn A. Hughes、Iain James、Lukas Oberer、Janet Winter、Roger Wrigglesworth

  DOI：10.1021/jm00039a006

  日期：1994.6.1

  Capsaicin and resiniferatoxin are natural products which act specifically on a subset of primary afferent sensory neurons to open a novel cation-selective ion channel in the plasma membrane. These sensory neurons are involved in nociception, and so, these agents are targets for the design of a novel class of analgesics. Although synthetic agonists at the capsaicin receptor have been described previously, competitive antagonists at this receptor would be interesting and novel pharmacological agents. Structure-activity relationships for capsaicin agonists have previously been rationalized, by ourselves and others, by dividing the capsaicin molecule into three regions-the A (aromatic ring)-, B (amide bond)-, and C (hydrophobic side chain)-regions. In this study, the effects on biological activity of conformational constraint of the A-region with respect to the B-region are discussed. Conformational constraint was achieved by the introduction of saturated ring systems of different sizes. The resulting compounds provided agonists of comparable potency to unconstrained analogues as well as a moderately potent antagonist, capsazepine. This compound is the first competitive antagonist of capsaicin and resiniferatoxin to be described and is active in various systems, in vitro and in vivo. It has recently attracted considerable interest as a tool for dissecting the mechanisms by which capsaicin analogues evoke their effects. NMR spectroscopy and X-ray crystallography experiments, as well as molecular modeling techniques, were used to study the conformational behavior of a representative constrained agonist and antagonist. The conformation of the saturated ring contraint in the two cases was found to differ markedly, dramatically affecting the relative disposition of the A-ring and B-region pharmacophores. In agonist structures, the A- and B-regions were virtually coplanar in contrast to those in the antagonist, in which they were approximately orthogonal. A rationale for agonist and antagonist activity at the capsaicin receptor is proposed, based on the consideration of these conformational differences.
• KIENZLE F.; BOUNAMEAUX Y.; MINDER R. E.; MUGGLI R., HELV. CHIM. ACTA, 69,(1986) N 7, 1671-1680
  作者：KIENZLE F.、 BOUNAMEAUX Y.、 MINDER R. E.、 MUGGLI R.

  DOI：——

  日期：——
• In silico design and synthesis of N‐arylalkanyl 2‐naphthamides as a new class of non‐purine xanthine oxidase inhibitors
  作者：Sheau Ling Ho、Ching‐Ting Lin、Shoei‐Sheng Lee

  DOI：10.1002/ddr.21782

  日期：2021.9

  A series of N-arylalkanyl 2-naphthamides (Xa~e), which were predicted from virtual molecular docking on a built xanthine oxidase template as potential inhibitors, were synthesized. Their inhibitory activity against xanthine oxidase was assayed. Among these prepared, compounds Xb (IC50 13.6 μM), Xc (IC50 13.1 μM), and Xd (IC50 12.5 μM) showed comparable inhibitory activity to allopurinol (IC50 22.1 μM)

  合成了一系列N-芳基烷基 2-萘酰胺 ( Xa ~ e )，这些化合物是从构建的黄嘌呤氧化酶模板上的虚拟分子对接预测的，作为潜在的抑制剂。测定了它们对黄嘌呤氧化酶的抑制活性。在这些制备物中，化合物Xb (IC 50 13.6 μM)、Xc (IC 50 13.1 μM)和Xd (IC 50 12.5 μM)显示出与别嘌醇(IC 50 22.1 μM)相当的抑制活性。体外测定结果与分子对接分数 Δ G有很好的相关性 = -16.99、-17.66 和 -17.13 Kcal/mol，分别。在氧酸钾诱导的高尿酸血症小鼠模型中，口服Xc - Ac（40mg/Kg）过氧乙酰化Xc可使血尿酸水平较正常对照组降低 60%， 与高尿酸血症小鼠组相比，具有统计学意义 ( p < .01)。