N-(2-adamantyl)-3-nitrophthalimide | 1372875-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(2-adamantyl)-3-nitrophthalimide
• 英文别名: 2-(2-Adamantyl)-4-nitro-isoindoline-1,3-dione；2-(2-adamantyl)-4-nitroisoindole-1,3-dione
• CAS: 1372875-03-0
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: YSKNJKPXSDYPJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-adamantyl)-3-nitrophthalimide 在 锌 作用下， 生成 N-(2-adamantyl)-3-aminophthalimide
  参考文献：
  名称：

  三个金刚烷衍生物文库的抗增殖和抗病毒活性

  摘要：

  合成了三个金刚烷衍生物文库，并评估了针对多种 DNA 和 RNA 病毒的抗病毒和抗增殖活性。虽然这些化合物在亚毒浓度下均不表现出抗病毒活性，但在 4、8 和 10 年中发现对鼠白血病细胞 (L1210)、人 T 淋巴细胞 (CEM) 和宫颈癌细胞 (HeLa) 具有抗增殖活性。

  DOI：

  10.1002/ardp.201300345
• 作为产物：
  描述：

  3-硝基邻苯二甲酸酐 、 2-氨基金刚烷 以 二氯甲烷 为溶剂， 反应 0.33h， 以58%的产率得到N-(2-adamantyl)-3-nitrophthalimide
  参考文献：
  名称：

  Evaluation of Antiproliferative Effect of N-(alkyladamantyl)phthalimides In vitro

  摘要：

  A series of (1‐adamantyl)phthalimides, 1–4, and (2‐adamantyl)phthalimides, 5–8, characterized by different chain length between the adamantyl and the phthalimide moiety were synthesized, as well as 1‐ and 2‐adamantylphthalimides substituted by nitro 9, 10, and amino group 11, 12, and phthalimides bearing homoadamantyl 13 and protoadamantyl substituent 14 and 15. The compounds were tested for antiproliferative activity in vitro on a series of five human cancer lines: MCF‐7 (breast carcinoma), SW 620 (colon carcinoma), HCT 116 (colon carcinoma), MOLT‐4 (acute lymphoblastic leukemia), H 460 (lung carcinoma), and a non‐tumor cell line HaCaT (human keratinocytes). All compounds except nitro derivatives 9 and 10 exhibited antiproliferative activity. The activity was generally better in the 2‐adamantyl series 5–8 and in the compounds having the longest alkyl spacers as in 4 and 8, or with an amino group as in 9 and 10. The most active compounds with the propylene spacer 4 and 8 showed the highest selectivity toward tumor cells. The activity was found to be due to a delay in the progress through the cell cycle at G1/S phase.

  DOI：

  10.1111/j.1747-0285.2011.01305.x

文献信息

• Evaluation of Antiproliferative Effect of N-(alkyladamantyl)phthalimides In vitro
  作者：Margareta Horvat、Lidija Uzelac、Marko Marjanović、Nikola Cindro、Oliver Franković、Kata Mlinarić-Majerski、Marijeta Kralj、Nikola Basarić

  DOI：10.1111/j.1747-0285.2011.01305.x

  日期：2012.4

  A series of (1‐adamantyl)phthalimides, 1–4, and (2‐adamantyl)phthalimides, 5–8, characterized by different chain length between the adamantyl and the phthalimide moiety were synthesized, as well as 1‐ and 2‐adamantylphthalimides substituted by nitro 9, 10, and amino group 11, 12, and phthalimides bearing homoadamantyl 13 and protoadamantyl substituent 14 and 15. The compounds were tested for antiproliferative activity in vitro on a series of five human cancer lines: MCF‐7 (breast carcinoma), SW 620 (colon carcinoma), HCT 116 (colon carcinoma), MOLT‐4 (acute lymphoblastic leukemia), H 460 (lung carcinoma), and a non‐tumor cell line HaCaT (human keratinocytes). All compounds except nitro derivatives 9 and 10 exhibited antiproliferative activity. The activity was generally better in the 2‐adamantyl series 5–8 and in the compounds having the longest alkyl spacers as in 4 and 8, or with an amino group as in 9 and 10. The most active compounds with the propylene spacer 4 and 8 showed the highest selectivity toward tumor cells. The activity was found to be due to a delay in the progress through the cell cycle at G1/S phase.
• Antiproliferative and Antiviral Activity of Three Libraries of Adamantane Derivatives
  作者：Nikola Basarić、Margareta Sohora、Nikola Cindro、Kata Mlinarić-Majerski、Erik De Clercq、Jan Balzarini

  DOI：10.1002/ardp.201300345

  日期：2014.5

  Three libraries of adamantane derivatives were synthesized and evaluated for antiviral and antiproliferative activities against a broad variety of DNA and RNA viruses. Whereas none of the compounds exhibit antiviral activity at subtoxic concentrations, antiproliferative activity was found against murine leukemia cells (L1210), human T‐lymphocyte cells (CEM), and cervix carcinoma cells (HeLa) for 4

  合成了三个金刚烷衍生物文库，并评估了针对多种 DNA 和 RNA 病毒的抗病毒和抗增殖活性。虽然这些化合物在亚毒浓度下均不表现出抗病毒活性，但在 4、8 和 10 年中发现对鼠白血病细胞 (L1210)、人 T 淋巴细胞 (CEM) 和宫颈癌细胞 (HeLa) 具有抗增殖活性。