1-Benzyl-5-(3,4-dichlorophenyl)-5-(3-hydroxypropyl)piperidin-2-one | 210545-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Benzyl-5-(3,4-dichlorophenyl)-5-(3-hydroxypropyl)piperidin-2-one
• CAS: 210545-36-1
• 化学式: C₂₁H₂₃Cl₂NO₂
• 分子量: 392.325
• InChiKey: OMLHZRHURNQREK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 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：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Benzyl-5-(3,4-dichlorophenyl)-5-(3-hydroxypropyl)piperidin-2-one 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-benzyl-5-(3,4-dichlorophenyl)-5-[3-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)propyl]piperidin-2-one
  参考文献：
  名称：

  High affinity, selective neurokinin 2 and neurokinin 3 receptor antagonists from a common structural template

  摘要：

  High affinity, selective hNK(2) or hNK(3) ligands can be prepared from the common template 1 in a few simple chemical operations. The hNK(3) ligands 3 antagonise the calcium mobilisation caused by activation of hNK(3) receptors expressed in CHO cells as measured using fura-2 microspectrofluorimetry. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00215-7
• 作为产物：
  描述：

  3,4-二氯苯乙腈 在 镍 盐酸 、 甲醇 、 氢气 、 苄基三甲基氢氧化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 生成 1-Benzyl-5-(3,4-dichlorophenyl)-5-(3-hydroxypropyl)piperidin-2-one
  参考文献：
  名称：

  High affinity, selective neurokinin 2 and neurokinin 3 receptor antagonists from a common structural template

  摘要：

  High affinity, selective hNK(2) or hNK(3) ligands can be prepared from the common template 1 in a few simple chemical operations. The hNK(3) ligands 3 antagonise the calcium mobilisation caused by activation of hNK(3) receptors expressed in CHO cells as measured using fura-2 microspectrofluorimetry. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00215-7

文献信息

• Discovery of Bioavailable 4,4-Disubstituted Piperidines as Potent Ligands of the Chemokine Receptor 5 and Inhibitors of the Human Immunodeficiency Virus-1
  作者：Wieslaw M. Kazmierski、Christopher Aquino、Brian A. Chauder、Felix Deanda、Robert Ferris、Deborah K. Jones-Hertzog、Terrence Kenakin、Cecilia S. Koble、Christian Watson、Pat Wheelan、Hanbiao Yang、Michael Youngman

  DOI：10.1021/jm800598a

  日期：2008.10.23

  We describe robust chemical approaches toward putative CCR5 scaffolds designed in our laboratories. Evaluation of analogues in the (125)I-[MIP-1 beta] binding and Ba-L-HOS antiviral assays resulted in the discovery of 64 and 68 in the 4,4-disubstitited piperidine class H, both potent CCR5 ligands (pIC(50) = 8.30 and 9.00, respectively) and HIV-1 inhibitors (pIC(50) = 7.80 and 7.84, respectively, in Ba-L-HOS assay). In addition, 64 and 68 were bioavailable in rodents, establishing them as lead molecules for further optimization toward CCR5 clinical candidates.
• US6124319A
  申请人：——

  公开号：US6124319A

  公开（公告）日：2000-09-26
• High affinity, selective neurokinin 2 and neurokinin 3 receptor antagonists from a common structural template
  作者：T Harrison、M.P.G Korsgaard、C.J Swain、M.A Cascieri、S Sadowski、G.R Seabrook

  DOI：10.1016/s0960-894x(98)00215-7

  日期：1998.6

  High affinity, selective hNK(2) or hNK(3) ligands can be prepared from the common template 1 in a few simple chemical operations. The hNK(3) ligands 3 antagonise the calcium mobilisation caused by activation of hNK(3) receptors expressed in CHO cells as measured using fura-2 microspectrofluorimetry. (C) 1998 Elsevier Science Ltd. All rights reserved.