tert-butyl N-[(1S)-5-[[(2S)-2,6-bis(tert-butoxycarbonylamino)hexanoyl]amino]-1-[[4-[2-(2,3,5,6-tetrafluoro-4-pyridyl)ethynyl]phenyl]carbamoyl]pentyl]carbamate | 1350811-88-9

• 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: tert-butyl N-[(1S)-5-[[(2S)-2,6-bis(tert-butoxycarbonylamino)hexanoyl]amino]-1-[[4-[2-(2,3,5,6-tetrafluoro-4-pyridyl)ethynyl]phenyl]carbamoyl]pentyl]carbamate
• 英文别名: tert-butyl N-[(2S)-6-[[(2S)-2,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]-1-oxo-1-[4-[2-(2,3,5,6-tetrafluoropyridin-4-yl)ethynyl]anilino]hexan-2-yl]carbamate
• CAS: 1350811-88-9
• 化学式: C₄₀H₅₄F₄N₆O₈
• 分子量: 822.898
• InChiKey: JRKJXOVNEFSAMQ-NSOVKSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  58
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  186
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-5-[[(2S)-2,6-bis(tert-butoxycarbonylamino)hexanoyl]amino]-1-[[4-[2-(2,3,5,6-tetrafluoro-4-pyridyl)ethynyl]phenyl]carbamoyl]pentyl]carbamate 、 三氟乙酸 以 二氯甲烷 为溶剂， 生成 (S)-2,6-diamino-N-((S)-5-amino-6-oxo-6-((4-((perfluoropyridin-4-yl)ethynyl)phenyl)amino)hexyl)hexanamide tritrifluoroacetic acid
  参考文献：
  名称：

  DIPEPTIDE ACETYLENE CONJUGATES AND A METHOD FOR PHOTOCLEAVAGE OF DOUBLE STRAND DNA BY DIPEPTIDE ACETYLENE CONJUGATES

  摘要：

  提供了光反应性DNA切割共轭化合物，其中包含一个含有芳基炔基团的DNA切割部分和一个含有至少一个或两个氨基团的多功能pH调节DNA结合部分。

  公开号：

  US20120288940A1
• 作为产物：
  描述：

  N-α-(tert-butoxycarbonyl)-L-lysine methyl ester 在 4-二甲氨基吡啶 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 tert-butyl N-[(1S)-5-[[(2S)-2,6-bis(tert-butoxycarbonylamino)hexanoyl]amino]-1-[[4-[2-(2,3,5,6-tetrafluoro-4-pyridyl)ethynyl]phenyl]carbamoyl]pentyl]carbamate
  参考文献：
  名称：

  DIPEPTIDE ACETYLENE CONJUGATES AND A METHOD FOR PHOTOCLEAVAGE OF DOUBLE STRAND DNA BY DIPEPTIDE ACETYLENE CONJUGATES

  摘要：

  提供了光反应性DNA切割共轭化合物，其中包含一个含有芳基炔基团的DNA切割部分和一个含有至少一个或两个氨基团的多功能pH调节DNA结合部分。

  公开号：

  US20120288940A1

文献信息

• DIPEPTIDE ACETYLENE CONJUGATES AND A METHOD FOR PHOTOCLEAVAGE OF DOUBLE STRAND DNA BY DIPEPTIDE ACETYLENE CONJUGATES
  申请人：Alabugin Igor

  公开号：US20120288940A1

  公开（公告）日：2012-11-15

  Photoreactive DNA cleaving conjugate compounds are provided comprising a DNA cleaving moiety which comprises an aryl alkyne group and a polyfunctional pH-regulated DNA-binding moiety which comprises at least one or two amino groups.

  提供了光反应性DNA切割共轭化合物，其中包含一个含有芳基炔基团的DNA切割部分和一个含有至少一个或两个氨基团的多功能pH调节DNA结合部分。
• Engineering pH-Gated Transitions for Selective and Efficient Double-Strand DNA Photocleavage in Hypoxic Tumors
  作者：Wang-Yong Yang、Saumya Roy、Boondaniwon Phrathep、Zach Rengert、Rachael Kenworthy、Diego A. R. Zorio、Igor V. Alabugin

  DOI：10.1021/jm2010282

  日期：2011.12.22

  We describe a family of hybrid compounds for the most efficient light-activated double-strand (ds) DNA cleavage known to date. This family represents the second generation of "switchable" molecular systems for pH-gated ds DNA-cleavage which combine a potent DNA-photocleaver and a pH-regulated part derived from a dipeptide. Design of the pH-switchable part utilizes amino groups of different basicity. Whereas the basic amino groups are protonated throughout the biologically relevant pH range, the pH-gating amines undergo protonation at the pH threshold which separates cancer and normal cells. Control over the reactivity and selectivity is achieved via transformation of the initial protonation state (a monocation or a dication) into a trication at the acidic pH. This change leads to an extraordinary increase in the efficiency of ds DNA cleavage leading to the ds:ss ratios comparable with the most efficient nonenzymatic ds DNA cleavers. Statistical analysis reveals that these high ds:ss ratios result from the combination of several factors: (a) true double-stranded cleavage, and (b) conversion of single-stranded (ss)-scission into ds cleavage. Considerable part of ds cleavage is also produced via the combination of ss cleavage events.