tert-butyl N-[(2S)-4-(benzylamino)-1-phenylbutan-2-yl]carbamate | 1169870-13-6

• 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: tert-butyl N-[(2S)-4-(benzylamino)-1-phenylbutan-2-yl]carbamate
• CAS: 1169870-13-6
• 化学式: C₂₂H₃₀N₂O₂
• 分子量: 354.492
• InChiKey: HSBLSCYOXZZRJZ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-4-(benzylamino)-1-phenylbutan-2-yl]carbamate 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 thiazol-5-ylmethyl N-benzyl-N-[(3S)-3-[[(2S)-2-[[(2-isopropylthiazol-4-yl)methyl-methyl-carbamoyl]amino]-4-morpholino-butanoyl]amino]-4-phenyl-butyl]carbamate
  参考文献：
  名称：

  INHIBITORS OF CYTOCHROME P450

  摘要：

  公开号：

  EP2231628B1
• 作为产物：
  描述：

  (S)-3-(Boc-氨基)-4-苯基丁酸 在 吡啶 、 lithium aluminium tetrahydride 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl N-[(2S)-4-(benzylamino)-1-phenylbutan-2-yl]carbamate
  参考文献：
  名称：

  Structure–activity relationships of diamine inhibitors of cytochrome P450 (CYP) 3A as novel pharmacoenhancers, part I: Core region

  摘要：

  Ritonavir (RTV), an HIV-1 protease inhibitor (PI), is also a potent mechanism-based inhibitor of human cytochrome P450 3A (CYP3A) and has been widely prescribed as a pharmacoenhancer. As a boosting agent for marketed PIs, it reduces pill burden, and improves compliance. Removal of the hydroxyl group from RTV reduces, but does not eliminate HIV PI activity and does not affect CYP3A inhibition. Herein we report the discovery of a novel series of CYP3A inhibitors that are devoid of antiviral activity. The synthesis and evaluation of analogs with extensive modifications of the 1,4-diamine core along with the structure activity relationships with respect to anti-HIV activity, CYP3A inhibitory activity, selectivity against other CYP enzymes and the human pregnane X receptor (PXR) will be discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.058

文献信息

• US8759379B2
  申请人：——

  公开号：US8759379B2

  公开（公告）日：2014-06-24
• [EN] INHIBITORS OF CYTOCHROME P450<br/>[FR] INHIBITEURS DU CYTROCHROME P450
  申请人：GILEAD SCIENCES INC

  公开号：WO2009088719A1

  公开（公告）日：2009-07-16

  The present application provides for a compound of Formula (I), or a pharmaceutically acceptable salt solvate, and/or ester thereof, compositions containing such compounds, therapeutic methods that include the administration of such compounds, and therapeutic methods and include the administration of such compounds with at least one additional therapeutic agent.
• INHIBITORS OF CYTOCHROME P450
  申请人：Gilead Sciences, Inc.

  公开号：EP2231628B1

  公开（公告）日：2015-10-28
• Structure–activity relationships of diamine inhibitors of cytochrome P450 (CYP) 3A as novel pharmacoenhancers, part I: Core region
  作者：Hongtao Liu、Lianhong Xu、Hon Hui、Randy Vivian、Christian Callebaut、Bernard P. Murray、Allen Hong、Melody S. Lee、Luong K. Tsai、Jennifer K. Chau、Kirsten M. Stray、Carina Cannizzaro、You-Chul Choi、Gerry R. Rhodes、Manoj C. Desai

  DOI：10.1016/j.bmcl.2013.12.058

  日期：2014.2

  Ritonavir (RTV), an HIV-1 protease inhibitor (PI), is also a potent mechanism-based inhibitor of human cytochrome P450 3A (CYP3A) and has been widely prescribed as a pharmacoenhancer. As a boosting agent for marketed PIs, it reduces pill burden, and improves compliance. Removal of the hydroxyl group from RTV reduces, but does not eliminate HIV PI activity and does not affect CYP3A inhibition. Herein we report the discovery of a novel series of CYP3A inhibitors that are devoid of antiviral activity. The synthesis and evaluation of analogs with extensive modifications of the 1,4-diamine core along with the structure activity relationships with respect to anti-HIV activity, CYP3A inhibitory activity, selectivity against other CYP enzymes and the human pregnane X receptor (PXR) will be discussed. (C) 2013 Elsevier Ltd. All rights reserved.