6-benzyloxycarbonylamino-(2S)-trifluoromethanesulfonyloxyhexanoic acid benzyl ester | 250383-22-3

• 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: 6-benzyloxycarbonylamino-(2S)-trifluoromethanesulfonyloxyhexanoic acid benzyl ester
• 英文别名: benzyl (2S)-6-(phenylmethoxycarbonylamino)-2-(trifluoromethylsulfonyloxy)hexanoate
• CAS: 250383-22-3
• 化学式: C₂₂H₂₄F₃NO₇S
• 分子量: 503.496
• InChiKey: GZMDINHOJWJGJC-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  氨基乙醛缩二乙醇 、 6-benzyloxycarbonylamino-(2S)-trifluoromethanesulfonyloxyhexanoic acid benzyl ester 以 二氯甲烷 为溶剂， 反应 6.0h， 以86%的产率得到
  参考文献：
  名称：

  Triflates as synthons for the synthesis of lysine analogues

  摘要：

  A simple synthesis of various 6-amino-2-substituted hexanoic acids has been developed starting from lysine via the triflate of 6-amino-2-hydroxy hexanoic acid. The same reactions have also been successfully applied starting from the lysyl-proline sequence. The lysine analogues have been introduced in pseudopeptide sequences by the acylfluoride methodology. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01445-8
• 作为产物：
  描述：

  N(epsilon)-苄氧羰基-L-氧基赖氨酸 在 lutidine 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 6-benzyloxycarbonylamino-(2S)-trifluoromethanesulfonyloxyhexanoic acid benzyl ester
  参考文献：
  名称：

  Triflates as synthons for the synthesis of lysine analogues

  摘要：

  A simple synthesis of various 6-amino-2-substituted hexanoic acids has been developed starting from lysine via the triflate of 6-amino-2-hydroxy hexanoic acid. The same reactions have also been successfully applied starting from the lysyl-proline sequence. The lysine analogues have been introduced in pseudopeptide sequences by the acylfluoride methodology. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01445-8

文献信息

• Potent and Fully Noncompetitive Peptidomimetic Inhibitor of Multidrug Resistance P-Glycoprotein
  作者：Ophélie Arnaud、Ali Koubeissi、Laurent Ettouati、Raphaël Terreux、Ghina Alamé、Catherine Grenot、Charles Dumontet、Attilio Di Pietro、Joëlle Paris、Pierre Falson

  DOI：10.1021/jm100839w

  日期：2010.9.23

  N-alpha-Boc-L-Asp(OBn)-L-Lys(Z)-OtBu (reversin 121, I), an inhibitor of the P-gp ABC transporter, was used to conceive compounds inhibiting the drug efflux occurring through the Hoechst 33342 and daunorubicin transport sites of P-gp, respectively H and R sites. Replacement of the aspartyl residue by trans-4-hydroxy-L-proline (4(R)Hyp) gave compounds 11 and 15 characterized by half-maximal inhibitory concentrations (1050) of 0.6 and 0.2 mu M, which are 2- and 7-fold lower than that of the parent molecule. The difference in IC50 between 11 and 15 rests on the carbonyl group of the peptidyl bond, reduced in 15. Those compounds are rather specific of P-gp, having no or limited activity on MRP1 and BCRP. 15 displayed no marked cytotoxicity up to 10-fold its IC50. Importantly, 15 equally inhibited the Hoechst 33342 and daunorubicin effluxes through a typical noncompetitive inhibition mechanism, suggesting its binding to a site different from the and R drug-transport sites.
• Triflates as synthons for the synthesis of lysine analogues
  作者：Ingo Weber、Pierre Potier、Josiane Thierry

  DOI：10.1016/s0040-4039(99)01445-8

  日期：1999.9

  A simple synthesis of various 6-amino-2-substituted hexanoic acids has been developed starting from lysine via the triflate of 6-amino-2-hydroxy hexanoic acid. The same reactions have also been successfully applied starting from the lysyl-proline sequence. The lysine analogues have been introduced in pseudopeptide sequences by the acylfluoride methodology. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.