(3S)-3-{[4-(acetyl-tert-butoxycarbonyl-amino)-benzenesulfonyl]-isobutyl-amino}-2-oxo-azepane-1-carboxylic acid tert-butyl ester | 874339-75-0

• 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: (3S)-3-{[4-(acetyl-tert-butoxycarbonyl-amino)-benzenesulfonyl]-isobutyl-amino}-2-oxo-azepane-1-carboxylic acid tert-butyl ester
• 英文别名: (3S)-3-{[4-(acetyl-tert-butoxycarbonyl-amino)-benzenesulfonyl]-isobutyl-amino}-2-oxo-azepane-1-carboxylic acid tert-butylester；tert-butyl (3S)-3-[[4-[acetyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]phenyl]sulfonyl-(2-methylpropyl)amino]-2-oxoazepane-1-carboxylate
• CAS: 874339-75-0
• 化学式: C₂₈H₄₃N₃O₈S
• 分子量: 581.731
• InChiKey: BTZVOTWCJOPCKG-QHCPKHFHSA-N

物化性质

• 沸点：
  685.2±65.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3S)-3-{[4-(acetyl-tert-butoxycarbonyl-amino)-benzenesulfonyl]-isobutyl-amino}-2-oxo-azepane-1-carboxylic acid tert-butyl ester 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (1S)-4-amino-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-benzenesulfonamide
  参考文献：
  名称：

  Lysine sulfonamides as novel HIV-protease inhibitors: Nε-Acyl aromatic α-amino acids

  摘要：

  A series of lysine sulfonamide analogues bearing N epsilon-acyl aromatic amino acids were synthesized using an efficient synthetic route. Evaluation of these novel protease inhibitors revealed compounds with high potency against wild-type and multiple-protease inhibitor-resistant HIV viruses. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.011
• 作为产物：
  描述：

  (S)-3-氨基-2-己内酰胺 在 4-二甲氨基吡啶 、 TEA 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 生成 (3S)-3-{[4-(acetyl-tert-butoxycarbonyl-amino)-benzenesulfonyl]-isobutyl-amino}-2-oxo-azepane-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Lysine sulfonamides as novel HIV-protease inhibitors: Nε-Acyl aromatic α-amino acids

  摘要：

  A series of lysine sulfonamide analogues bearing N epsilon-acyl aromatic amino acids were synthesized using an efficient synthetic route. Evaluation of these novel protease inhibitors revealed compounds with high potency against wild-type and multiple-protease inhibitor-resistant HIV viruses. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.011

文献信息

• Lysine based compounds
  申请人：Stranix Richard Brent

  公开号：US20060025592A1

  公开（公告）日：2006-02-02

  The present invention provides lysine based compounds of the formula; and when the compound of formula I comprises an amino group, pharmaceutically acceptable ammonium salts thereof, wherein R 1 may be, for example, (HO) 2 P(O)—, (NaO) 2 P(O)—, alkyl-CO— or cycloalkyl-CO—, wherein X may be, for example, F, Cl, and Br, and wherein R 2 and R 3 are as defined herein.

  本发明提供了一种式I的赖氨酸基化合物；当式I的化合物包含氨基时，还包括其药学上可接受的铵盐，其中R1可以是例如(HO)2P(O)—、(NaO)2P(O)—、烷基-CO—或环烷基-CO—，其中X可以是例如F、Cl和Br，而R2和R3如本文所定义。
• [EN] LYSINE BASED COMPOUNDS<br/>[FR] COMPOSES A BASE DE LYSINE
  申请人：PROCYON BIOPHARMA INC

  公开号：WO2006012725A1

  公开（公告）日：2006-02-09

  The present invention provides lysine based compounds of the formula (I); and when the compound of formula (I) comprises an amino group, pharmaceutically acceptable ammonium salts thereof, wherein Rl may be, for example, (HO)2P(O)-, (NaO)2P(O)-, alkyl­CO- or cycloalkyl-CO-, wherein X may be, for example, F, Cl, and Br, and wherein R2 and R3 are as defined herein. These lysine based compounds have a physiologically cleavable unit, namely R1 , whereby upon cleavage of the unit, an HIV aspartyl protease inhibitor is released,

  本发明提供了以赖氨酸为基础的化合物的公式（I）；当公式（I）的化合物包含氨基时，其药用可接受的铵盐，其中R1可以是，例如，（HO）2P(O)-，（NaO）2P(O)-，烷基CO-或环烷基CO-，其中X可以是，例如，F，Cl和Br，而R2和R3如本文所定义。这些以赖氨酸为基础的化合物具有一个生理可切割的单元，即R1，通过切割该单元，释放出HIV天冬氨酸蛋白酶抑制剂。
• Protease Inhibitors
  申请人：Stranix Brent Richard

  公开号：US20100184974A1

  公开（公告）日：2010-07-22

  The present invention provides HIV protease inhibitors of formulas I, IA, IB, Ib or II, or pharmaceutically acceptable salts thereof, wherein R 2 may be, for example, 2-pyridyl-CH 2 —, 3-pyridyl-CH 2 —, 4-pyridyl-CH 2 —, a sulfonyl group as described in the formulas herein including benzenesulfonyl or thiophenesulfonyl groups, R 2a —CO)—, R 2a being selected from the group consisting of piperonyl, 2-pyranzinyl (unsubstituted or substituted with H, or an alkyl of 1 to 4 carbon atoms) or a picolylamine group as described herein, wherein R3 may be, for example, a phenyl group or diphenylmethyl group as described herein, and wherein Cx may be, for example, COOH, CONR 5 R 6 , CH 2 OH or CH 2 OR 7 .

  本发明提供了公式I、IA、IB、Ib或II的HIV蛋白酶抑制剂，或其药学上可接受的盐，其中R2可能是，例如，2-吡啶基-CH2—，3-吡啶基-CH2—，4-吡啶基-CH2—，如本文中所述的磺酰基，包括苯磺酰基或噻吩磺酰基，R2a—CO)—，R2a选自由本文中所述的吡哌啶基、2-吡啶基（未取代或取代为H，或1至4个碳原子的烷基）或本文中所述的吡哌啶胺基，其中R3可能是，例如，本文中所述的苯基或二苯甲基基团，Cx可能是，例如，COOH、CONR5R6、CH2OH或CH2OR7。
• Lysine-based prodrugs of aspartyl protease inhibitors and processes for their preparation
  申请人：Milot Guy

  公开号：US20090253926A1

  公开（公告）日：2009-10-08

  The present invention provides processes for synthesizing lysine based compounds of the formula; wherein R 1 may be, for example, (HO) 2 P(O)—, (NaO) 2 P(O)—, wherein X may be, for example, NH 2 , Y may be H, F, Cl, or Br, and wherein n, X′, Y′, R 2 , R 3 , R 4 , R 5 and R 6 are as defined herein.

  本发明提供了合成基于赖氨酸的化合物的方法，其化学式为：其中，R1可以是例如(HO)2P(O)−，(NaO)2P(O)−，其中X可以是例如NH2，Y可以是H，F，Cl或Br，n，X'，Y'，R2，R3，R4，R5和R6如本文所定义。
• METHOD FOR IMPROVING PHARMACOKINETICS OF PROTEASE INHIBITORS AND PROTEASE INHIBITOR PRECURSORS
  申请人：Wu Jinzi Jason

  公开号：US20120053139A1

  公开（公告）日：2012-03-01

  The present invention provides methods for improving the pharmacokinetics of protease inhibitors and protease inhibitor precursors and pharmaceutical composition comprising protease inhibitors or protease inhibitor precursors of formula I and a cytochrome P450 monooxigenase inhibitor; when the compound of formula I comprises an amino group, pharmaceutically acceptable ammonium salts thereof, wherein R 1 may be, for example, (HO) 2 P(O)—, (NaO) 2 P(O)—, alkyl-CO— or cycloalkyl-CO—, wherein X may be, for example, F, Cl, and Br, and wherein R 2 and R 3 are as defined herein.

  本发明提供改善蛋白酶抑制剂和蛋白酶抑制剂前体的药代动力学的方法，以及包含式I的蛋白酶抑制剂或蛋白酶抑制剂前体和细胞色素P450单加氧酶抑制剂的制药组合物；当式I的化合物包含氨基团时，其药学上可接受的铵盐可以是R1，例如（HO）2P（O）—、（NaO）2P（O）—、烷基-CO—或环烷基-CO—，其中X可以是F、Cl和Br，其中R2和R3如本文所定义。