(S)-6-Benzyloxycarbonylamino-2-[isobutyl-(toluene-4-sulfonyl)-amino]-hexanoic acid benzyl ester | 359780-66-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-6-Benzyloxycarbonylamino-2-[isobutyl-(toluene-4-sulfonyl)-amino]-hexanoic acid benzyl ester
• 英文别名: Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-Nepsilon-benzyloxycarbonyl-L-lysine Benzyl Ester；benzyl (2S)-2-[(4-methylphenyl)sulfonyl-(2-methylpropyl)amino]-6-(phenylmethoxycarbonylamino)hexanoate
• CAS: 359780-66-8
• 化学式: C₃₂H₄₀N₂O₆S
• 分子量: 580.745
• InChiKey: RXVDAAQOPZPLLT-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-6-Benzyloxycarbonylamino-2-[isobutyl-(toluene-4-sulfonyl)-amino]-hexanoic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine
  参考文献：
  名称：

  Lysine sulfonamides as novel HIV-Protease inhibitors: optimization of the Nε -acyl-phenyl spacer

  摘要：

  A series of Nalpha-isobutyl-Nalpha-arylsulfonamido-(Nepsilon acyl) lysine and lysinol derivatives were prepared and evaluated as inhibitors of HIV protease and wild type virus. A simple original synthesis was devised to form Nalpha-(arylsulfonamide)-Nalpha-isobutyI lysine, which could be easily acylated with carboxylic acids at the NE position. A two-atom spacer was found to be optimal between this acyl group and a phenyl yielding compounds of sub-nanomolar potency on purified enzyme. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.058
• 作为产物：
  描述：

  N6-[(苯基甲氧基)羰基]-L-赖氨酸苄酯 在 sodium cyanoborohydride 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-6-Benzyloxycarbonylamino-2-[isobutyl-(toluene-4-sulfonyl)-amino]-hexanoic acid benzyl ester
  参考文献：
  名称：

  Lysine sulfonamides as novel HIV-Protease inhibitors: optimization of the Nε -acyl-phenyl spacer

  摘要：

  A series of Nalpha-isobutyl-Nalpha-arylsulfonamido-(Nepsilon acyl) lysine and lysinol derivatives were prepared and evaluated as inhibitors of HIV protease and wild type virus. A simple original synthesis was devised to form Nalpha-(arylsulfonamide)-Nalpha-isobutyI lysine, which could be easily acylated with carboxylic acids at the NE position. A two-atom spacer was found to be optimal between this acyl group and a phenyl yielding compounds of sub-nanomolar potency on purified enzyme. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.058

文献信息

• Amino acid derivatives useful for the treatment of alzheimer's disease
  申请人：John Varghese

  公开号：US20060079550A1

  公开（公告）日：2006-04-13

  The present invention is a method of treating Alzheimer's disease, and other diseases, and/or inhibiting beta-secretase enzyme, and/or inhibiting deposition of A beta peptide in a mammal, by use of known compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , W and C x are herein defined.

  本发明涉及一种治疗阿尔茨海默病和其他疾病，和/或抑制β-分泌酶酶，和/或抑制哺乳动物体内Aβ肽沉积的方法，使用已知的式(I)化合物，其中R1、R2、R3、R4、W和Cx在此定义。
• Lysine derivatives as potent HIV protease inhibitors. Discovery, synthesis and structure–activity relationship studies
  作者：Abderrahim Bouzide、Gilles Sauvé、Jocelyn Yelle

  DOI：10.1016/j.bmcl.2004.12.068

  日期：2005.3

  A screening assay program on HIV-protease was carried out on more than fifty commercially available N-protected amino acids and has revealed that those with a long side chain such as lysine, ornithine and arginine exhibited significant inhibition of HIV protease enzyme. The presence of an Fmoc group was found to be essential to obtain micromolar inhibitors and the addition of an alkyl group at the N alpha-position resulted in the discovery of the lead compound 11 displaying a 5 nM inhibition constant. Although this new inhibitor series is not categorized among those mimicking the substrate with a non-hydrolyzable transition-state isoster, it was found very specific to inhibit HIV protease enzyme in comparison to the mammalian aspartyl proteases pepsin, renin and cathepsin. Furthermore, these inhibitors did not show any cytotoxicity at a concentration below 75 mu M. (c) 2005 Elsevier Ltd. All rights reserved.
• Lysine sulfonamides as novel HIV-Protease inhibitors: optimization of the Nε -acyl-phenyl spacer
  作者：Brent R. Stranix、Gilles Sauvé、Abderrahim Bouzide、Alexandre Coté、Guy Sévigny、Jocelyn Yelle

  DOI：10.1016/j.bmcl.2003.09.058

  日期：2003.12

  A series of Nalpha-isobutyl-Nalpha-arylsulfonamido-(Nepsilon acyl) lysine and lysinol derivatives were prepared and evaluated as inhibitors of HIV protease and wild type virus. A simple original synthesis was devised to form Nalpha-(arylsulfonamide)-Nalpha-isobutyI lysine, which could be easily acylated with carboxylic acids at the NE position. A two-atom spacer was found to be optimal between this acyl group and a phenyl yielding compounds of sub-nanomolar potency on purified enzyme. (C) 2003 Elsevier Ltd. All rights reserved.