carbamic acid, [(5-amino-2,3-dihydro-1H-inden-2-yl)methyl]-, methyl ester | 391655-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: carbamic acid, [(5-amino-2,3-dihydro-1H-inden-2-yl)methyl]-, methyl ester
• 英文别名: methyl N-[(5-amino-2,3-dihydro-1H-inden-2-yl)methyl]carbamate
• CAS: 391655-61-1
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: AIEYCZJKGBOQIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  413.8±38.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  carbamic acid, [(5-amino-2,3-dihydro-1H-inden-2-yl)methyl]-, methyl ester 在 吡啶 、 碘代三甲硅烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 N-[2-(methanesulfonamidomethyl)-2,3-dihydro-1H-inden-5-yl]-3-methyl-2-[4-(trifluoromethyl)phenyl]benzamide
  参考文献：
  名称：

  Diaminoindanes as Microsomal Triglyceride Transfer Protein Inhibitors

  摘要：

  The synthesis and biological activities of biarylamide-substituted diaminoindanes as microsomal triglyceride transfer protein (MTP) inhibitors are described. One of the more potent compounds, 8aR, inhibited both the secretion of apoB from Hep G2 cells and the MTP-mediated transfer of triglycerides between synthetic acceptor and donor liposomes with IC50 values of 0.7 and 70 nM, respectively. In normolipidemic rats and dogs, oral administration of 8aR dose-dependently reduced both plasma triglycerides and total cholesterol. Moreover, in rats and dogs, 8aR also prevented the postprandial rise in plasma triglycerides following a bolus administration of a fat load. Because MTP inhibitors decrease very low density lipoprotein assembly in the liver, the potential for hepatic lipid accumulation was evaluated. In normolipidemic rats, hepatic cholesterol and triglyceride contents were dose-dependently increased by 8aR. However, hepatic lipid accumulation resulted in negligible change in total liver weight and was reversible after withdrawal of the compound.

  DOI：

  10.1021/jm010294e
• 作为产物：
  描述：

  2-茚醇 在 10percent Pd/C 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 硝酸 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、344.75 kPa 条件下， 反应 42.5h， 生成 carbamic acid, [(5-amino-2,3-dihydro-1H-inden-2-yl)methyl]-, methyl ester
  参考文献：
  名称：

  Diaminoindanes as Microsomal Triglyceride Transfer Protein Inhibitors

  摘要：

  The synthesis and biological activities of biarylamide-substituted diaminoindanes as microsomal triglyceride transfer protein (MTP) inhibitors are described. One of the more potent compounds, 8aR, inhibited both the secretion of apoB from Hep G2 cells and the MTP-mediated transfer of triglycerides between synthetic acceptor and donor liposomes with IC50 values of 0.7 and 70 nM, respectively. In normolipidemic rats and dogs, oral administration of 8aR dose-dependently reduced both plasma triglycerides and total cholesterol. Moreover, in rats and dogs, 8aR also prevented the postprandial rise in plasma triglycerides following a bolus administration of a fat load. Because MTP inhibitors decrease very low density lipoprotein assembly in the liver, the potential for hepatic lipid accumulation was evaluated. In normolipidemic rats, hepatic cholesterol and triglyceride contents were dose-dependently increased by 8aR. However, hepatic lipid accumulation resulted in negligible change in total liver weight and was reversible after withdrawal of the compound.

  DOI：

  10.1021/jm010294e

文献信息

• Diaminoindanes as Microsomal Triglyceride Transfer Protein Inhibitors
  作者：Gary M. Ksander、Reynalda deJesus、Andrew Yuan、Cynthia Fink、Michael Moskal、Eric Carlson、Paivi Kukkola、Natalie Bilci、Eli Wallace、Alan Neubert、David Feldman、Therese Mogelesky、Kevin Poirier、Michael Jeune、Ronald Steele、Jong Wasvery、Zouhair Stephan、Edna Cahill、Randy Webb、Aida Navarrete、Warren Lee、Joyce Gibson、Natalya Alexander、Haamid Sharif、Ashok Hospattankar

  DOI：10.1021/jm010294e

  日期：2001.12.1

  The synthesis and biological activities of biarylamide-substituted diaminoindanes as microsomal triglyceride transfer protein (MTP) inhibitors are described. One of the more potent compounds, 8aR, inhibited both the secretion of apoB from Hep G2 cells and the MTP-mediated transfer of triglycerides between synthetic acceptor and donor liposomes with IC50 values of 0.7 and 70 nM, respectively. In normolipidemic rats and dogs, oral administration of 8aR dose-dependently reduced both plasma triglycerides and total cholesterol. Moreover, in rats and dogs, 8aR also prevented the postprandial rise in plasma triglycerides following a bolus administration of a fat load. Because MTP inhibitors decrease very low density lipoprotein assembly in the liver, the potential for hepatic lipid accumulation was evaluated. In normolipidemic rats, hepatic cholesterol and triglyceride contents were dose-dependently increased by 8aR. However, hepatic lipid accumulation resulted in negligible change in total liver weight and was reversible after withdrawal of the compound.