N-Cbz-Phe-Lys(ε-Alloc)OH | 159857-88-2

• 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: N-Cbz-Phe-Lys(ε-Alloc)OH
• 英文别名: N-Cbz-Phe-Lys(Alloc)OH；(2S)-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]-6-(prop-2-enoxycarbonylamino)hexanoic acid
• CAS: 159857-88-2
• 化学式: C₂₇H₃₃N₃O₇
• 分子量: 511.575
• InChiKey: KLHMRFYTBWVQOJ-GOTSBHOMSA-N

物化性质

• 沸点：
  789.5±60.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-Cbz-Phe-Lys(ε-Alloc)OH 在 N-甲基吗啉 、 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 生成 4-((S)-6-(((allyloxy)carbonyl)amino)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)hexanamido)benzyl ((S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)carbamate
  参考文献：
  名称：

  Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B

  摘要：

  Novel colchicine derivatives possessing various substituents at the C4 position were prepared. Among them, 4-halo derivatives 3-6 were found to exhibit higher activity against cancer cell lines (A549, HT29, HCT116) as well as on mice transplanted with the HCT116 human colorectal carcinoma cell line than colchicine (1). Further, utilizing the 4-substituted colchicines, we prepared pro-drugs having a dipeptide side chain and demonstrated that these pro-drugs were activated by cathepsin B, an enzyme overexpressed in tumor cells, and exhibited selective toxicity to the tumor cells.

  DOI：

  10.1021/ml100287y
• 作为产物：
  描述：

  L-赖氨酸 在 碳酸氢钠 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 N-Cbz-Phe-Lys(ε-Alloc)OH
  参考文献：
  名称：

  Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B

  摘要：

  Novel colchicine derivatives possessing various substituents at the C4 position were prepared. Among them, 4-halo derivatives 3-6 were found to exhibit higher activity against cancer cell lines (A549, HT29, HCT116) as well as on mice transplanted with the HCT116 human colorectal carcinoma cell line than colchicine (1). Further, utilizing the 4-substituted colchicines, we prepared pro-drugs having a dipeptide side chain and demonstrated that these pro-drugs were activated by cathepsin B, an enzyme overexpressed in tumor cells, and exhibited selective toxicity to the tumor cells.

  DOI：

  10.1021/ml100287y

文献信息

• [EN] CONJUGATE COMPOUNDS<br/>[FR] COMPOSÉS CONJUGUÉS
  申请人：CALLAGHAN INNOVATION RES LTD

  公开号：WO2014088432A1

  公开（公告）日：2014-06-12

  The invention relates to sphingoglycolipid analogues and peptide derivatives thereof, which are useful in treating or preventing diseases or such as those relating to infection, atopic disorders, autoimmune diseases or cancer.

  这项发明涉及鞘氨醇糖脂类似物及其肽衍生物，可用于治疗或预防与感染、特应性疾病、自身免疫疾病或癌症相关的疾病。
• CONJUGATE COMPOUNDS
  申请人：ANDERSON Regan James

  公开号：US20150352219A1

  公开（公告）日：2015-12-10

  The invention relates to sphingoglycolipid analogues and peptide derivatives thereof, which are useful in treating or preventing diseases or such as those relating to infection, atopic disorders, autoimmune diseases or cancer.

  该发明涉及鞘氨醇糖脂类似物及其肽衍生物，可用于治疗或预防感染、特应性疾病、自身免疫疾病或癌症等疾病。
• Dubowchik, Gene M.; Firestone, Raymond A., Bioorganic and medicinal chemistry letters, 1998, vol. 8, # 23, p. 3343 - 3346
  作者：Dubowchik, Gene M.、Firestone, Raymond A.

  DOI：——

  日期：——
• Inhibitory prodrug mechanism for cysteine cathepsin-targeted self-controlled drug release
  作者：Floris J. van Dalen、Martijn Verdoes

  DOI：10.1080/14756366.2022.2122961

  日期：2022.12.31
• Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B
  作者：Naoko Yasobu、Mariko Kitajima、Noriyuki Kogure、Yoshiyuki Shishido、Takeshi Matsuzaki、Masato Nagaoka、Hiromitsu Takayama

  DOI：10.1021/ml100287y

  日期：2011.5.12

  Novel colchicine derivatives possessing various substituents at the C4 position were prepared. Among them, 4-halo derivatives 3-6 were found to exhibit higher activity against cancer cell lines (A549, HT29, HCT116) as well as on mice transplanted with the HCT116 human colorectal carcinoma cell line than colchicine (1). Further, utilizing the 4-substituted colchicines, we prepared pro-drugs having a dipeptide side chain and demonstrated that these pro-drugs were activated by cathepsin B, an enzyme overexpressed in tumor cells, and exhibited selective toxicity to the tumor cells.