4-((S)-2-{4-[3-[(R)-1-(4-fluorophenyl)ethylcarbamoyl]-5-(methanesulfonyl(methyl)amino)phenylcarbamoyl]-4-hydroxy-5-phenylpentanoylamino}-3-methylbutyrylamino)benzoic acid methyl ester | 1187975-80-9

• 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: 4-((S)-2-{4-[3-[(R)-1-(4-fluorophenyl)ethylcarbamoyl]-5-(methanesulfonyl(methyl)amino)phenylcarbamoyl]-4-hydroxy-5-phenylpentanoylamino}-3-methylbutyrylamino)benzoic acid methyl ester
• 英文别名: 4-((S)-2-{4-[3-[(R)-1-(4-Fluoro-phenyl)-ethylcarbamoyl]-5-(methanesulfonyl-methyl-amino)-phenylcarbamoyl]-4-hydroxy-5-phenyl-pentanoylamino}-3-methyl-butyrylamino)-benzoic acid methyl ester；methyl 4-[[(2S)-2-[[4-benzyl-5-[3-[[(1R)-1-(4-fluorophenyl)ethyl]carbamoyl]-5-[methyl(methylsulfonyl)amino]anilino]-4-hydroxy-5-oxopentanoyl]amino]-3-methylbutanoyl]amino]benzoate
• CAS: 1187975-80-9
• 化学式: C₄₂H₄₈FN₅O₉S
• 分子量: 817.936
• InChiKey: AHTYFIFCTULFRB-ZFHGVCKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  58
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  209
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-((S)-2-{4-[3-[(R)-1-(4-fluorophenyl)ethylcarbamoyl]-5-(methanesulfonyl(methyl)amino)phenylcarbamoyl]-4-hydroxy-5-phenylpentanoylamino}-3-methylbutyrylamino)benzoic acid methyl ester 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以77%的产率得到4-((S)-2-{4-[3-[(R)-1-(4-fluorophenyl)ethylcarbamoyl]-5-(methanesulfonyl(methyl)amino)phenylcarbamoyl]-4-hydroxy-5-phenylpentanoylamino}-3-methylbutyrylamino)benzoic acid
  参考文献：
  名称：

  Design and synthesis of BACE-1 inhibitors utilizing a tertiary hydroxyl motif as the transition state mimic

  摘要：

  Two series of drug-like BACE-1 inhibitors with a shielded tertiary hydroxyl as transition state isostere have been synthesized. The most potent inhibitor exhibited a BACE-1 IC50 value of 0.23 mu M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.065
• 作为产物：
  描述：

  4-((S)-2-amino-3-methylbutyrylamino)benzoic acid methyl ester 、 2-benzyl-5-oxotetrahydrofuran-2-carboxylic acid [3-[(R)-1-(4-fluorophenyl)ethylcarbamoyl]-5-(methanesulfonylmethylamino)phenyl]amide 在 2-羟基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以50%的产率得到4-((S)-2-{4-[3-[(R)-1-(4-fluorophenyl)ethylcarbamoyl]-5-(methanesulfonyl(methyl)amino)phenylcarbamoyl]-4-hydroxy-5-phenylpentanoylamino}-3-methylbutyrylamino)benzoic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of BACE-1 inhibitors utilizing a tertiary hydroxyl motif as the transition state mimic

  摘要：

  Two series of drug-like BACE-1 inhibitors with a shielded tertiary hydroxyl as transition state isostere have been synthesized. The most potent inhibitor exhibited a BACE-1 IC50 value of 0.23 mu M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.065

文献信息

• Design and synthesis of BACE-1 inhibitors utilizing a tertiary hydroxyl motif as the transition state mimic
  作者：Fredrik Wångsell、Francesco Russo、Jonas Sävmarker、Åsa Rosenquist、Bertil Samuelsson、Mats Larhed

  DOI：10.1016/j.bmcl.2009.06.065

  日期：2009.8

  Two series of drug-like BACE-1 inhibitors with a shielded tertiary hydroxyl as transition state isostere have been synthesized. The most potent inhibitor exhibited a BACE-1 IC50 value of 0.23 mu M. (C) 2009 Elsevier Ltd. All rights reserved.