NSC13480 | 69760-27-6

• 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: NSC13480
• 英文别名: (2-phenylbenzo[h]quinolin-4-yl)(piperidin-2-yl)methanol；(2-phenylbenzo[h]quinolin-4-yl)-piperidin-2-ylmethanol
• CAS: 69760-27-6
• 化学式: C₂₅H₂₄N₂O
• 分子量: 368.478
• InChiKey: QEFWYSWSVVMRHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  NSC13480 在 盐酸 作用下， 以 乙醚 为溶剂， 以60%的产率得到2-(hydroxy(2-phenylbenzo[h]quinolin-4-yl)methyl)piperidin-1-ium chloride
  参考文献：
  名称：

  Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5′-phosphatase (SHIP)

  摘要：

  Recently, inhibition of the SH2-containing inositol 5'-phosphatase 1 (SHIP1) has become an attractive strategy for facilitating engraftment of MHC-I mismatched bone marrow grafts, increasing the number of adult stem cells in vivo, and inducing mobilization of hematopoietic stem cells. Utilizing high-throughput screening, two quinoline small molecules (NSC13480 and NSC305787) that inhibit SHIP1 enzymatic activity were discovered. New syntheses of these inhibitors have been developed which verified the relative stereochemistry of these structures. Utilizing this synthetic route, some analogs of these quinolines have been prepared and tested for their ability to inhibit SHIP. These structure activity studies determined that an amine tethered to the quinoline core is required for SHIP inhibition. SHIP inhibition may explain the antitumor effects of similar quinoline amino alcohols and provides an impetus for further synthetic studies in this class of compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.034
• 作为产物：
  描述：

  2-phenylbenzo[h]quinoline-4-carboxylic acid 在 氯化亚砜 、 硼烷四氢呋喃络合物 、 一水合肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 146.0h， 生成 NSC13480
  参考文献：
  名称：

  Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5′-phosphatase (SHIP)

  摘要：

  Recently, inhibition of the SH2-containing inositol 5'-phosphatase 1 (SHIP1) has become an attractive strategy for facilitating engraftment of MHC-I mismatched bone marrow grafts, increasing the number of adult stem cells in vivo, and inducing mobilization of hematopoietic stem cells. Utilizing high-throughput screening, two quinoline small molecules (NSC13480 and NSC305787) that inhibit SHIP1 enzymatic activity were discovered. New syntheses of these inhibitors have been developed which verified the relative stereochemistry of these structures. Utilizing this synthetic route, some analogs of these quinolines have been prepared and tested for their ability to inhibit SHIP. These structure activity studies determined that an amine tethered to the quinoline core is required for SHIP inhibition. SHIP inhibition may explain the antitumor effects of similar quinoline amino alcohols and provides an impetus for further synthetic studies in this class of compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.034

文献信息

• COMPOUNDS AND USE FOR TREATING CANCER
  申请人：GLIONOVA AB

  公开号：US20160214958A1

  公开（公告）日：2016-07-28

  The present invention relates to certain 2,4-disubstituted quinoline derivatives, to their therapy, as well as to pharmaceutical compositions comprising said compounds. More specifically the invention relates to certain 2,4-disubstituted quinoline derivatives or pharmaceutical compositions comprising said compounds for the treatment of cancers characterized by overactive Ras and/or Rac or signalling pathway.

  本发明涉及某些2,4-二取代喹啉衍生物及其治疗方法，以及包含该化合物的制药组合物。更具体地说，本发明涉及某些2,4-二取代喹啉衍生物或包含该化合物的制药组合物，用于治疗由过度活跃的Ras和/或Rac或信号通路所特征的癌症。
• POTENTIAL ANTIMALARIALS. (2-PHENYL-7,8-BENZOQUINOLYL-4)-α-PIPERIDYLCARBINOLS¹
  作者：E. R. BUCHMAN、D. R. HOWTON

  DOI：10.1021/jo01157a025

  日期：1949.9
• REPROGRAMMING EFFECTOR PROTEIN INTERACTIONS TO CORRECT EPIGENETIC DEFECTS IN CANCER
  申请人：British Columbia Cancer Agency Branch

  公开号：EP2819662B1

  公开（公告）日：2019-04-10
• ANTIANGIOGENIC SMALL MOLECULES AND METHODS OF USE
  申请人：Zudaire Enrique

  公开号：US20120129775A1

  公开（公告）日：2012-05-24

  Methods of inhibiting undesired angiogenesis are provided, which methods include administering to a subject a therapeutically effective amount of at least one of the compounds described herein, or a pharmaceutically acceptable salt thereof.
• METHOD OF MODULATING SHIP ACTIVITY
  申请人：Kerr William G.

  公开号：US20120178725A1

  公开（公告）日：2012-07-12

  A method of treating or preventing an immune disorder, such as graft versus host disease, in a subject. The method includes the administering a SHIP1 inhibitor, such as 3α-aminocholestane, to a subject in need of treatment. Thus, SHIP1 inhibitors taught herein represent a novel class of small molecules that have the potential to enhance allogeneic transplantation, boost innate immunity and improve the treatment of hematologic malignancies.