1-[(2R)-4-benzoyl-2-methyl-piperazin-1-yl]-2-bromo-propan-1-one | 845654-95-7

• 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: 1-[(2R)-4-benzoyl-2-methyl-piperazin-1-yl]-2-bromo-propan-1-one
• 英文别名: 1-[(2R)-4-benzoyl-2-methylpiperazin-1-yl]-2-bromopropan-1-one
• CAS: 845654-95-7
• 化学式: C₁₅H₁₉BrN₂O₂
• 分子量: 339.232
• InChiKey: DJCBFFSLTRCHLT-JHJMLUEUSA-N

物化性质

• 沸点：
  474.8±40.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基水杨酰胺 、 1-[(2R)-4-benzoyl-2-methyl-piperazin-1-yl]-2-bromo-propan-1-one 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 2-[1-[(2R)-4-benzoyl-2-methylpiperazin-1-yl]-1-oxopropan-2-yl]oxy-N-methylbenzamide
  参考文献：
  名称：

  Discovery of a small molecule inhibitor through interference with the gp120–CD4 interaction

  摘要：

  A series of piperazine derivatives were designed and synthesised as gp120-CD4 inhibitors. SAR studies led to the discovery of potent inhibitors in a cell based anti viral assay represented by compounds 9 and 28. The rat pharmacokinetic and antiviral profiles of selected compounds are also presented. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.080
• 作为产物：
  描述：

  2-溴丙酸 、 (R)-2-甲基-4-苯甲酰基哌嗪 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.92h， 以76%的产率得到1-[(2R)-4-benzoyl-2-methyl-piperazin-1-yl]-2-bromo-propan-1-one
  参考文献：
  名称：

  Piperazine derivatives

  摘要：

  这项发明涉及一种具有化学式(I)的化合物 或其药用可接受的盐、溶剂合物或衍生物，其中R 1 至R 5 在描述中有定义，并涉及其制备方法、制备中使用的中间体、含有它们的组合物以及这些衍生物的用途。 本发明的化合物抑制gp120与CD4的相互作用，因此在治疗HIV、与HIV有遗传关系的逆转录病毒感染或艾滋病方面有用。

  公开号：

  US20050043300A1

文献信息

• Design and optimisation of potent gp120-CD4 inhibitors
  作者：Thien-Duc Tran、Fiona M. Adam、Frederick Calo、David R. Fenwick、Juin Fok-Seang、Iain Gardner、Duncan A. Hay、Manos Perros、Jaiessh Rawal、Donald S. Middleton、Tanya Parkinson、Christopher Pickford、Michelle Platts、Amy Randall、Peter T. Stephenson、Hannah Vuong、David H. Williams

  DOI：10.1016/j.bmcl.2009.06.102

  日期：2009.9

  The synthesis and structure-activity relationship of a series of novel gp120-CD4 inhibitors are described. Pharmacokinetic studies and antiviral spectrum assessment of lead compounds led to the identification of compound 36, a potent gp120-CD4 inhibitor which exhibited antiviral potency across a spectrum of 25 clade B isolates. (C) 2009 Elsevier Ltd. All rights reserved.
• PIPERAZINE DERIVATIVES FOR THE TREATMENT OF HIV INFECTIONS
  申请人：Pfizer Limited

  公开号：EP1663234A1

  公开（公告）日：2006-06-07
• [EN] PIPERAZINE DERIVATIVES FOR THE TREATMENT OF HIV INFECTIONS<br/>[FR] DÉRIVÉS DE PIPÉRAZINE POUR LE TRAITEMENT DES INFECTIONS À VIH
  申请人：PFIZER LTD

  公开号：WO2005016344A1

  公开（公告）日：2005-02-24

  This invention relates to a compound of formula (I) or pharmaceutically acceptable salts, solvates or derivatives thereof, wherein R1 to R5 are defined in the description, and to processes for the preparation thereof, intermediates used in their preparation, compositions containing them and the uses of such derivatives. The compounds of the present invention inhibit the interaction of gp 120 with CD4 and are therefore of use in the treatment of HIV, a retroviral infection genetically related to HIV, or AIDS.
• Piperazine derivatives
  申请人：Middleton Stuart Donald

  公开号：US20050043300A1

  公开（公告）日：2005-02-24

  This invention relates to a compound of formula (I) or pharmaceutically acceptable salts, solvates or derivatives thereof, wherein R 1 to R 5 are defined in the description, and to processes for the preparation thereof, intermediates used in their preparation, compositions containing them and the uses of such derivatives. The compounds of the present invention inhibit the interaction of gp120 with CD4 and are therefore of use in the treatment of HIV, a retroviral infection genetically related to HIV, or AIDS.

  这项发明涉及一种具有化学式(I)的化合物 或其药用可接受的盐、溶剂合物或衍生物，其中R 1 至R 5 在描述中有定义，并涉及其制备方法、制备中使用的中间体、含有它们的组合物以及这些衍生物的用途。 本发明的化合物抑制gp120与CD4的相互作用，因此在治疗HIV、与HIV有遗传关系的逆转录病毒感染或艾滋病方面有用。
• Discovery of a small molecule inhibitor through interference with the gp120–CD4 interaction
  作者：David H. Williams、Fiona Adam、David R. Fenwick、Juin Fok-Seang、Iain Gardner、Duncan Hay、Rawal Jaiessh、Donald S. Middleton、Charles E. Mowbray、Tanya Parkinson、Manos Perros、Christopher Pickford、Michelle Platts、Amy Randall、Daniel Siddle、Peter T. Stephenson、Thien-Duc Tran、Hannah Vuong

  DOI：10.1016/j.bmcl.2009.06.080

  日期：2009.9

  A series of piperazine derivatives were designed and synthesised as gp120-CD4 inhibitors. SAR studies led to the discovery of potent inhibitors in a cell based anti viral assay represented by compounds 9 and 28. The rat pharmacokinetic and antiviral profiles of selected compounds are also presented. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.