N'-(2-Amino-4,5-difluoro-benzoyl)-hydrazinecarboxylic acid tert-butyl ester | 897014-45-8

• 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: N'-(2-Amino-4,5-difluoro-benzoyl)-hydrazinecarboxylic acid tert-butyl ester
• CAS: 897014-45-8
• 化学式: C₁₂H₁₅F₂N₃O₃
• 分子量: 287.266
• InChiKey: LNZFZQHIHIJMLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  93.45
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N'-(2-Amino-4,5-difluoro-benzoyl)-hydrazinecarboxylic acid tert-butyl ester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 73.5h， 生成
  参考文献：
  名称：

  Correlation of the acid-sensitivity of polyethylene glycol daunorubicin conjugates with their in vitro antiproliferative activity

  摘要：

  Polyethylene glycol conjugates with linkers of varying acid-sensitivity were prepared by reacting five maleimide derivatives of daunorubicin containing an amide bond (1) or acid-sensitive carboxylic hydrazone bonds (2-5) with of-methoxy-poly(ethylene glycol)-thiopropionic acid amide (MW 20000) or alpha,omega-bis-thiopropionic acid amide poly(ethylene glycol) (MW 20000). The polymer drug derivatives were designed to release daunorubicin inside the tumor cell by acid-cleavage of the hydrazone bond after uptake of the conjugate by endocytosis. In subsequent cell culture experiments, the order of antitumor activity of the PEG daunorubicin conjugates correlated with their acid-sensitivity as determined by HPLC (cell lines: BXF T24 bladder carcinoma and LXFL 529L lung cancer cell line; assay: propidium iodide fluorescence assay). The acid-sensitivity of the link between PEG and daunorubicin is therefore an important parameter for in vitro efficacy. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.007
• 作为产物：
  描述：

  肼基甲酸叔丁酯 、 2-氨基-4,5-二氟苯甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 13.5h， 以78%的产率得到N'-(2-Amino-4,5-difluoro-benzoyl)-hydrazinecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Correlation of the acid-sensitivity of polyethylene glycol daunorubicin conjugates with their in vitro antiproliferative activity

  摘要：

  Polyethylene glycol conjugates with linkers of varying acid-sensitivity were prepared by reacting five maleimide derivatives of daunorubicin containing an amide bond (1) or acid-sensitive carboxylic hydrazone bonds (2-5) with of-methoxy-poly(ethylene glycol)-thiopropionic acid amide (MW 20000) or alpha,omega-bis-thiopropionic acid amide poly(ethylene glycol) (MW 20000). The polymer drug derivatives were designed to release daunorubicin inside the tumor cell by acid-cleavage of the hydrazone bond after uptake of the conjugate by endocytosis. In subsequent cell culture experiments, the order of antitumor activity of the PEG daunorubicin conjugates correlated with their acid-sensitivity as determined by HPLC (cell lines: BXF T24 bladder carcinoma and LXFL 529L lung cancer cell line; assay: propidium iodide fluorescence assay). The acid-sensitivity of the link between PEG and daunorubicin is therefore an important parameter for in vitro efficacy. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.007