(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(tosylamido)hexanoic acid | 105751-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(tosylamido)hexanoic acid
• 英文别名: Fmoc-Lyz(Tos)；Nε-(4-Methylbenzenesulfonyl)-Nα-(9-fluorenylmethoxycarbonyl)-L-lysine；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(p-tolylsulfonylamino)hexanoic acid；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(4-methylphenyl)sulfonylamino]hexanoic acid
• CAS: 105751-17-5
• 化学式: C₂₈H₃₀N₂O₆S
• 分子量: 522.622
• InChiKey: WIACKTUQKMCUJV-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(tosylamido)hexanoic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 N-(4-((6S,9S,12S,15S,20aR)-6-benzyl-15-isobutyl-12-methyl-1,4,7,10,13,16-hexaoxoicosahydropyrrolo[1,2-a][1,4,7,10,13,16]hexaazacyclooctadecin-9-yl)butyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Post-Assembly Modification of Head-to-Tail Cyclic Peptides by Methionine-Directed β-C(sp³)–H Arylation

  摘要：

  DOI：

  10.1021/acs.orglett.2c02253
• 作为产物：
  描述：

  (S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(tosylamido)hexanoate 在 水 、 calcium chloride 、 sodium hydroxide 、 溶剂黄146 作用下， 以 异丙醇 、 水 为溶剂， 反应 6.0h， 以100%的产率得到(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(tosylamido)hexanoic acid
  参考文献：
  名称：

  Nε-Modified lysine containing inhibitors for SIRT1 and SIRT2

  摘要：

  Sirtuins catalyze the NAD(+) dependent deacetylation of N-epsilon-acetyl lysine residues to nicotinamide, O '-acetyl- ADP-ribose (OAADPR) and N-epsilon-deacetylated lysine. Here, an easy-to-synthesize Ac-Ala-Lys-Ala sequence has been used as a probe for the screening of novel N-epsilon-modified lysine containing inhibitors against SIRT1 and SIRT2. N-epsilon-Selenoacetyl and N-epsilon-isothiovaleryl were the most potent moieties found in this study, comparable to the widely studied N-epsilon-thioacetyl group. The N-epsilon-3,3-dimethylacryl and N-epsilon-isovaleryl moieties gave significant inhibition in comparison to the N-epsilon-acetyl group present in the substrates. In addition, the studied N-epsilon-alkanoyl, N-epsilon-alpha,beta-unsaturated carbonyl and N-epsilon-aroyl moieties showed that the acetyl binding pocket can accept rather large groups, but is sensitive to even small changes in electronic and steric properties of the N-epsilon-modification. These results are applicable for further screening of Ne-acetyl analogues. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.035

文献信息

• Amino acid derivatives as HIV aspartyl protease inhibitors
  申请人：Pharmacor Inc.

  公开号：US06455587B1

  公开（公告）日：2002-09-24

  The present invention relates to a class of amino acid derivatives with HIV aspartyl protease inhibitory properties.

  本发明涉及一类具有HIV天冬氨酸蛋白酶抑制性能的氨基酸衍生物。
• 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。
• Schoen, Istvan; Kisfaludy, Lajos, Synthesis, 1986, # 4, p. 303 - 305
  作者：Schoen, Istvan、Kisfaludy, Lajos

  DOI：——

  日期：——
• SCHOEN, I.;KISFALUDY, L., SYNTHESIS, BRD, 1986, N 4, 303-305
  作者：SCHOEN, I.、KISFALUDY, L.

  DOI：——

  日期：——
• AMINO ACID DERIVATIVES USEFUL FOR THE TREATMENT OF ALZHEIMER'S DISEASE
  申请人：Elan Pharmaceuticals, Inc.

  公开号：EP1458378A1

  公开（公告）日：2004-09-22