2--amino-1.2.3.4-tetrahydro-isochinolin | 90917-74-1

• 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: 2--amino-1.2.3.4-tetrahydro-isochinolin
• 英文别名: N-(3,4-dihydro-1H-isoquinolin-2-yl)-formamide；N-(3,4-dihydro-1H-isoquinolin-2-yl)formamide
• CAS: 90917-74-1
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: MNDRBMDNFBQJDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2--amino-1.2.3.4-tetrahydro-isochinolin 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.67h， 以1.3 g的产率得到N-methyl-3,4-dihydroisoquinolin-2(1H)-amine
  参考文献：
  名称：

  Discovery and structural analyses of S-adenosyl-l-homocysteine hydrolase inhibitors based on non-adenosine analogs

  摘要：

  Optimization of a new series of S-adenosyl-L-homocysteine hydrolase (AdoHcyase) inhibitors based on non-adenosine analogs led to very potent compounds 14n, 18a, and 18b with IC50 values of 13 +/- 3, 5.0 +/- 2.0, and 8.5 +/- 3.1 nM, respectively. An X-ray crystal structure of AdoHcyase with NAD(+) and 18a showed a novel open form co-crystal structure. 18a in the co-crystals formed intramolecular eight membered ring hydrogen bond formations. A single crystal X-ray structure of 14n also showed an intramolecular eight-membered ring hydrogen bond interaction. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.018
• 作为产物：
  描述：

  2-硝基-1,2,3,4-四氢异喹啉 在 溶剂黄146 、 锌 作用下， 以 甲醇 、 水 为溶剂， 反应 0.17h， 生成 2--amino-1.2.3.4-tetrahydro-isochinolin
  参考文献：
  名称：

  Discovery and structural analyses of S-adenosyl-l-homocysteine hydrolase inhibitors based on non-adenosine analogs

  摘要：

  Optimization of a new series of S-adenosyl-L-homocysteine hydrolase (AdoHcyase) inhibitors based on non-adenosine analogs led to very potent compounds 14n, 18a, and 18b with IC50 values of 13 +/- 3, 5.0 +/- 2.0, and 8.5 +/- 3.1 nM, respectively. An X-ray crystal structure of AdoHcyase with NAD(+) and 18a showed a novel open form co-crystal structure. 18a in the co-crystals formed intramolecular eight membered ring hydrogen bond formations. A single crystal X-ray structure of 14n also showed an intramolecular eight-membered ring hydrogen bond interaction. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.018

文献信息

• Carbazates as potent inhibitors of hormone-sensitive lipase
  作者：Johannes C. de Jong、Lotte G. Sørensen、Hans Tornqvist、Poul Jacobsen

  DOI：10.1016/j.bmcl.2004.01.038

  日期：2004.4

  The central role of adipose tissue hormone-sensitive lipase in regulating fatty acid metabolism makes it a potential pharmacological target for the prevention of peripheral insulin resistance in obese, prediabetic and diabetic individuals. The synthesis of a new series of carbazates is presented. Modification of the phenolic 4-position in a series of 1,2,3,4-tetrahydroisoquinoline and morpholine derived carbazates, yielded inhibitors of the catalytic activity of this enzyme with nanomolar potency. (C) 2004 Elsevier Ltd. All rights reserved.
• Discovery and structural analyses of S-adenosyl-l-homocysteine hydrolase inhibitors based on non-adenosine analogs
  作者：Akira Nakao、Hiroko Suzuki、Hiroaki Ueno、Hiroshi Iwasaki、Tomofumi Setsuta、Akiko Kashima、Shinji Sunada

  DOI：10.1016/j.bmc.2015.05.018

  日期：2015.8

  Optimization of a new series of S-adenosyl-L-homocysteine hydrolase (AdoHcyase) inhibitors based on non-adenosine analogs led to very potent compounds 14n, 18a, and 18b with IC50 values of 13 +/- 3, 5.0 +/- 2.0, and 8.5 +/- 3.1 nM, respectively. An X-ray crystal structure of AdoHcyase with NAD(+) and 18a showed a novel open form co-crystal structure. 18a in the co-crystals formed intramolecular eight membered ring hydrogen bond formations. A single crystal X-ray structure of 14n also showed an intramolecular eight-membered ring hydrogen bond interaction. (C) 2015 Elsevier Ltd. All rights reserved.