N-乙酰基氨萘非特 | 69409-02-5

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: N-乙酰基氨萘非特
• 英文名称: 2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5-ylacetamide
• 英文别名: N-acetylamonafide；N-Acetyl Amonafide；N-[2-[2-(dimethylamino)ethyl]-1,3-dioxobenzo[de]isoquinolin-5-yl]acetamide
• CAS: 69409-02-5
• 化学式: C₁₈H₁₉N₃O₃
• 分子量: 325.367
• InChiKey: VQQUFGOEIGXAOM-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212°C
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  米托萘胺 在 palladium on activated charcoal 吡啶 、 甲酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.67h， 生成 N-乙酰基氨萘非特
  参考文献：
  名称：

  2,2,2-Trichloro-N-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin- 5-yl}carbamoyl)acetamide (UNBS3157), a Novel Nonhematotoxic Naphthalimide Derivative with Potent Antitumor Activity

  摘要：

  Amonafide (1), a naphthalimide which binds to DNA by intercalation and poisons topoisomerase II alpha, has demonstrated activity in phase II breast cancer trials, but has failed thus far to enter clinical phase III because of dose-limiting bone marrow toxicity. Compound 17 (one of 41 new compounds synthesized) is a novel anticancer naphthalimide with a distinct mechanism of action, notably inducing autophagy and senescence in cancer cells. Compound 17 (2,2,2-trichloro-N-({2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-5-yl}carbamoyl)acetamide (UNBS3157)) was found to have a 3-4-fold higher maximum tolerated dose compared to amonafide and not to provoke hematotoxicity in mice at doses that display significant antitumor effects. Furthermore, 17 has shown itself to be superior to amonafide in vivo in models of (i) L1210 murine leukemia, (ii) MXT-HI murine mammary adenocarcinoma, and (iii) orthotopic models of human A549 NSCLC and BxPC3 pancreatic cancer. Compound 17, therefore, merits further investigation as a potential anticancer agent.

  DOI：

  10.1021/jm070315q

文献信息

• Cancer cell-targeted two-photon fluorescence probe for the real-time ratiometric imaging of DNA damage
  作者：Hua Zhang、Kui Wang、Xiaopeng Xuan、Qingzhang Lv、Yamin Nie、Haiming Guo

  DOI：10.1039/c6cc02290a

  日期：——

  Real-time imaging of DNA damage in cancer cells could provide much valuable information for the formation and development of cancer. Herein, a two-photon fluorescence probe (ANF-Glu) was designed based on...

  癌细胞中DNA损伤的实时成像可以为癌症的形成和发展提供许多有价值的信息。在此，基于...设计了双光子荧光探针（ANF-Glu）。
• Selective and sensitive detection and quantification of arylamine N-acetyltransferase 2 by a ratiometric fluorescence probe
  作者：Lei Cui、Ye Zhong、Weiping Zhu、Yufang Xu、Xuhong Qian

  DOI：10.1039/c0cc01000f

  日期：——

  A novel NAT2 specific probe has been developed for sensitive detection of the activity of NAT2. Upon NAT2 catalyzed acetylation of the molecule to N-acetyl-amonafide, the ratiometric response of fluorescence with significant changes in wavelength and intensity is observed. Its significant application potential has been successfully demonstrated in cellular systems.

  一种新型 NAT2 特异性探针已被开发用于灵敏检测 NAT2 的活动。在 NAT2 催化分子乙酰化为 N-乙酰基-amonafide 后，观察到荧光的比率响应，波长和强度发生显着变化。其巨大的应用潜力已在蜂窝系统中得到成功证明。
• Fernandez Brana; Martinez Sanz; Castellano, European Journal of Medicinal Chemistry, 1981, vol. 16, # 3, p. 207 - 212
  作者：Fernandez Brana、Martinez Sanz、Castellano、et al.

  DOI：——

  日期：——
• BRANA M. F.; SANZ A. M.; CASTELLANO J. M.; ROLDAN C. M.; ROLDAN C., EUR. J. MED. CHEM.-CHIM. THER., 1981, 16, NO 3, 207-212,
  作者：BRANA M. F.、 SANZ A. M.、 CASTELLANO J. M.、 ROLDAN C. M.、 ROLDAN C.

  DOI：——

  日期：——
• US4204063A
  申请人：——

  公开号：US4204063A

  公开（公告）日：1980-05-20