(2-(Acridin-9-ylamino)ethyl)(tert-butoxycarbonyl)glycine | 1404200-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (2-(Acridin-9-ylamino)ethyl)(tert-butoxycarbonyl)glycine
• 英文别名: 2-[2-(acridin-9-ylamino)ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetic acid
• CAS: 1404200-25-4
• 化学式: C₂₂H₂₅N₃O₄
• 分子量: 395.458
• InChiKey: IUJGZJSOSCLIEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2-(Acridin-9-ylamino)ethyl)(tert-butoxycarbonyl)glycine 在 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2-[2-(acridin-9-ylamino)ethylamino]-N-(2-azidoethyl)acetamide
  参考文献：
  名称：

  [EN] TARGETED DELIVERY AND PRODRUG DESIGNS FOR PLATINUM-ACRIDINE ANTI-CANCER COMPOUNDS AND METHODS THEREOF
  [FR] ADMINISTRATION CIBLÉE ET CONCEPTIONS DE PROMÉDICAMENTS POUR COMPOSÉS ANTICANCÉREUX À BASE DE PLATINE ET D'ACRIDINE ET MÉTHODES ASSOCIÉES

  摘要：

  含有环丙啶结构的吖啶类化合物已被披露，显示出比其他顺铂类化合物更有效地对抗癌症。使用一种或多种氨基酸、一种或多种糖、一种或多种聚合醚、C i^aikylene-phenyl-NH-C(0)-R.15、叶酸、av03整合RGD结合肽、他莫昔芬、恩多西芬、表皮生长因子受体、抗体结合物、激酶抑制剂、二唑类化合物、三唑类化合物、噁唑类化合物、厄洛替尼和/或它们的混合物将这些更有效的吖啶类化合物传递到癌细胞核中的方法被披露；其中R]§是一个肽。

  公开号：

  WO2013033430A1
• 作为产物：
  描述：

  9-phenoxyacridine 以 甲醇 为溶剂， 反应 7.0h， 生成 (2-(Acridin-9-ylamino)ethyl)(tert-butoxycarbonyl)glycine
  参考文献：
  名称：

  [EN] TARGETED DELIVERY AND PRODRUG DESIGNS FOR PLATINUM-ACRIDINE ANTI-CANCER COMPOUNDS AND METHODS THEREOF
  [FR] ADMINISTRATION CIBLÉE ET CONCEPTIONS DE PROMÉDICAMENTS POUR COMPOSÉS ANTICANCÉREUX À BASE DE PLATINE ET D'ACRIDINE ET MÉTHODES ASSOCIÉES

  摘要：

  含有环丙啶结构的吖啶类化合物已被披露，显示出比其他顺铂类化合物更有效地对抗癌症。使用一种或多种氨基酸、一种或多种糖、一种或多种聚合醚、C i^aikylene-phenyl-NH-C(0)-R.15、叶酸、av03整合RGD结合肽、他莫昔芬、恩多西芬、表皮生长因子受体、抗体结合物、激酶抑制剂、二唑类化合物、三唑类化合物、噁唑类化合物、厄洛替尼和/或它们的混合物将这些更有效的吖啶类化合物传递到癌细胞核中的方法被披露；其中R]§是一个肽。

  公开号：

  WO2013033430A1

文献信息

• Targeted Delivery and Prodrug Designs for Platinum-Acridine Anti-Cancer Compounds and Methods Thereof
  申请人：Bierbach Ulrich

  公开号：US20140193334A1

  公开（公告）日：2014-07-10

  Acridine containing cisplatin compounds have been disclosed that show greater efficacy against cancer than other cisplatin compounds. Methods of delivery of those more effective cisplatin compounds to the nucleus in cancer cells is disclosed using one or more amino acids, one or more sugars, one or more polymeric ethers, C 1-6 alkylene-phenyl-NH—C(O)—R 15 , folic acid, α v β 3 integrin RGD binding peptide, tamoxifen, endoxifen, epidermal growth factor receptor, antibody conjugates, kinase inhibitors, diazoles, triazoles, oxazoles, erlotinib, and/or mixtures thereof; wherein R 15 is a peptide.

  披萨啤酒含有顺式铂类化合物，其对癌症的疗效比其他顺式铂类化合物更高。披萨啤酒使用一种或多种氨基酸、一种或多种糖、一种或多种聚醚、C1-6烷基苯基-NH—C(O)—R15、叶酸、αvβ3整合素RGD结合肽、他莫昔芬、恩多西芬、表皮生长因子受体、抗体偶联物、激酶抑制剂、咪唑、三唑、噁唑、厄洛替尼和/或其混合物来递送更有效的顺式铂类化合物到癌细胞核中。其中R15是一种肽。
• Targeted delivery and prodrug designs for platinum-acridine anti-cancer compounds and methods thereof
  申请人：Bierbach Ulrich

  公开号：US09090640B2

  公开（公告）日：2015-07-28

  Acridine containing cisplatin compounds have been disclosed that show greater efficacy against cancer than other cisplatin compounds. Methods of delivery of those more effective cisplatin compounds to the nucleus in cancer cells is disclosed using one or more amino acids, one or more sugars, one or more polymeric ethers, C1-6alkylene-phenyl-NH—C(O)—R15, folic acid, αvβ3 integrin RGD binding peptide, tamoxifen, endoxifen, epidermal growth factor receptor, antibody conjugates, kinase inhibitors, diazoles, triazoles, oxazoles, erlotinib, and/or mixtures thereof; wherein R15 is a peptide.

  披萨啤酒含有的顺式铂化合物已经被披露，与其他顺式铂化合物相比，其对癌症的疗效更高。揭示了将这些更有效的顺式铂化合物传递到癌细胞核中的传递方法，使用一个或多个氨基酸，一个或多个糖，一个或多个聚醚，C1-6烷基苯基-NH-C（O）-R15，叶酸，αvβ3整合素RGD结合肽，他莫昔芬，恩多西芬，表皮生长因子受体，抗体结合物，激酶抑制剂，二唑类，三唑类，噁唑类，厄洛替尼和/或其混合物;其中R15是肽。
• Using a Build-and-Click Approach for Producing Structural and Functional Diversity in DNA-Targeted Hybrid Anticancer Agents
  作者：Song Ding、Xin Qiao、Gregory L. Kucera、Ulrich Bierbach

  DOI：10.1021/jm301278c

  日期：2012.11.26

  An efficient screening method was developed for functionalized DNA targeted platinum-containing hybrid anticancer agents based on metal mediated amine-to-nitrile addition, a form of "click" chemistry. The goal of the study was in generate platinum-acridine agents for their use as cytotoxic "warheads" in targeted and multifunctional therapies. This was achieved by introducing hydroxl, carboxylic acid, and azide functionalities in the acridine linker moiety and by varying the nonleaving groups attached to platinum. The assay, which was based on microscale reactions between 6 platinum-nitrile complexes and 10 acridine derivatives, yielded a small library of 60 platinum-acridines. Reactions were monitored, and product mixtures were quantitatively analyzed by automated in-line high-performance liquid chromatography-electrospray mass spectrometry (LC-ESMS) analysis and subjected to cell viability screening using a nonradioactive cell proliferation assay. The new prescreening methodology proves to be a powerful tool for establishing structure-activity relationships and for identifying target compounds.