methyl (1'R) 4-[(1-phenylethyl)amino]-5,6-dihydro-2H-pyran-3-carboxylate | 362490-22-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl (1'R) 4-[(1-phenylethyl)amino]-5,6-dihydro-2H-pyran-3-carboxylate
• 英文别名: methyl 4-[[(1R)-1-phenylethyl]amino]-3,6-dihydro-2H-pyran-5-carboxylate
• CAS: 362490-22-0
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: HVLWFNQWIHSBHX-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1'R) 4-[(1-phenylethyl)amino]-5,6-dihydro-2H-pyran-3-carboxylate 在 盐酸 、 10% Pd(OH)₂ on C 、 盐酸羟胺 、 氢气 、 三乙酰氧基硼氢化钠 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 89.0h， 生成 N-[(3R,4R)-3-(hydroxycarbamoyl)tetrahydro-2H-pyran-4-yl]-6-[(2-trifluoromethyl-1H-benzimidazol-1-yl)methyl]nicotinamide
  参考文献：
  名称：

  Synthesis, preliminary biological evaluation and molecular modeling of some new heterocyclic inhibitors of TACE

  摘要：

  Central heteroaryl ring analogues belonging to a series of potent hydroxamate TACE inhibitors were synthesized. The TACE inhibitory activities of these compounds were evaluated by in vitro WBA and in silico molecular modeling studies using crystal structure of human TACE. Compound 14 showed very good in vitro inhibition, supported by the in silico docking studies. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.018
• 作为产物：
  描述：

  四氢吡喃酮 在 lithium hexamethyldisilazane 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.17h， 生成 methyl (1'R) 4-[(1-phenylethyl)amino]-5,6-dihydro-2H-pyran-3-carboxylate
  参考文献：
  名称：

  Synthesis, preliminary biological evaluation and molecular modeling of some new heterocyclic inhibitors of TACE

  摘要：

  Central heteroaryl ring analogues belonging to a series of potent hydroxamate TACE inhibitors were synthesized. The TACE inhibitory activities of these compounds were evaluated by in vitro WBA and in silico molecular modeling studies using crystal structure of human TACE. Compound 14 showed very good in vitro inhibition, supported by the in silico docking studies. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.018

文献信息

• Asymmetric catalytic hydrogenation process for preparation of chiral cyclic beta-aminoesters
  申请人：——

  公开号：US20040082795A1

  公开（公告）日：2004-04-29

  A novel process for the asymmetric synthesis of substituted cyclic &bgr;-amino-carboxylates of the type shown in the specification from appropriate &bgr;-enamino-ester starting materials is described. These compounds are useful as intermediates for MMP and TACE inhibitors.

  本文介绍了一种新颖的方法，用于从适当的β-烯酰胺酯起始材料不对称合成规范中所示的取代环状β-氨基羧酸酯。这些化合物可用作MMP和TACE抑制剂的中间体。
• Synthesis, preliminary biological evaluation and molecular modeling of some new heterocyclic inhibitors of TACE
  作者：Prabal Sengupta、Chetan S. Puri、Hemant A. Chokshi、Chetana K. Sheth、Ajay S. Midha、Trinadha Rao Chitturi、Rajamannar Thennati、Prashant R. Murumkar、Mange Ram Yadav

  DOI：10.1016/j.ejmech.2011.09.018

  日期：2011.11

  Central heteroaryl ring analogues belonging to a series of potent hydroxamate TACE inhibitors were synthesized. The TACE inhibitory activities of these compounds were evaluated by in vitro WBA and in silico molecular modeling studies using crystal structure of human TACE. Compound 14 showed very good in vitro inhibition, supported by the in silico docking studies. (C) 2011 Elsevier Masson SAS. All rights reserved.