N1,N3-二[3-(乙基氨基)丙基]-1,3-丙烷二胺 | 121749-39-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N1,N3-二[3-(乙基氨基)丙基]-1,3-丙烷二胺
• 英文名称: DENSPM
• 英文别名: N¹,N¹¹-diethylnorspermine；(N¹, N¹¹)-bisethylnorspermine；BENSpm；Diethylnorspermine；N1,N11-Bis(ethyl)norspermine；N-ethyl-N'-[3-[3-(ethylamino)propylamino]propyl]propane-1,3-diamine
• CAS: 121749-39-1
• 化学式: C₁₃H₃₂N₄
• 分子量: 244.424
• InChiKey: UMJJGDUYVQCBMC-UHFFFAOYSA-N

物化性质

• 沸点：
  357.1±10.0 °C(Predicted)
• 密度：
  0.877±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N¹,N⁴,N⁸,N¹¹-tetrakis(mesitylenesulfonyl)-N¹,N¹¹-diethylnorspermine 在 氢溴酸 、 溶剂黄146 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 N1,N3-二[3-(乙基氨基)丙基]-1,3-丙烷二胺
  参考文献：
  名称：

  Antiproliferative Properties of Polyamine Analogs: A Structure-Activity Study

  摘要：

  A basis set of polyamine analogues was designed and synthesized. These compounds were used to initiate a systematic investigation of the role of chain length, terminal nitrogen alkyl group size, and symmetry of the methylene backbone in the antineoplastic properties of polyamine analogues. New synthetic methods predicated on our earlier polyamine fragment synthesis are described for accessing the tetraamines of interest. An unsymmetrically substituted diamine reagent, N-(tert-butoxycarbonyl)-N,N'-bis(mesitylene sulfonyl)-1,4- di-aminobutane, was developed for entry into unsymmetrical tetraamines. All of the tetraamines synthesized were first evaluated in a murine leukemia L1210 cell IC50 assay at 48 and 96 h. In an attempt to correlate this behavior with some aspect of polyamine metabolism, each compound was tested for its ability to compete with spermidine for the polyamine uptake apparatus, its impact on the polyamine biosynthetic enzymes ornithine decarboxylase (ODC) and S-adenosylmethionine decarboxylase (AdoMetDC), and its effect on the polyamine-catabolizing enzyme spermidine/spermine N-1-acetyltransferase (SSAT) and on polyamine pools. While there was no obvious correlation between the 48 and 96 h IC50'S and the impact of the analogues on polyamine metabolism, there were other structure-activity relationships. Correlations were observed to exist between chain length and IC50'S and between terminal alkyl substituents and impact on K-i, ODC, and AdoMetDC. Also, preliminary studies suggest a relationship may exist between the 48 and 96 h IC50's activities and the analogue's chronic toxicity in vivo. Finally, when the overall length of the polyamine backbone was held constant, the symmetry of the methylene chains of the polyamine fragments was shown to be unimportant to the compound's activity.

  DOI：

  10.1021/jm00047a004

文献信息

• AMINOQUINOLINE DERIVATIVES AND USES THEREOF
  申请人：THE MCLEAN HOSPITAL CORPORATION

  公开号：US20150023930A1

  公开（公告）日：2015-01-22

  Described herein are aminoquinoline and aminoacridine based hybrids, pharmaceutical compositions and medicaments that include such aminoquinoline and aminoacridine based hybrids, and methods of using such compounds for diagnosing and/or treating infections, neurodegerative diseases or disorders, inflammation, inflammation associated diseases and disorders, and/or diseases or disorders that are treatable with dopamine agonists such as the restless leg syndrome.

  本文描述了基于氨基喹啉和氨基蒽醌的混合物，包括含有这种基于氨基喹啉和氨基蒽醌的混合物的制药组合物和药物，以及使用这种化合物诊断和/或治疗感染、神经退行性疾病或障碍、炎症、与炎症相关的疾病和障碍以及可用多巴胺激动剂治疗的疾病或障碍（如不宁腿综合征）的方法。
• Novel polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases
  申请人：SLIL Biomedical Corporation

  公开号：US20040006049A1

  公开（公告）日：2004-01-08

  Peptide conjugates in which cytocidal and cytostatic agents, such as polyamine analogs or naphthoquinones, are conjugated to a polypeptide recognized and cleaved by enzymes such as prostate-specific antigen (PSA) and cathepsin B are provided, as well as compositions comprising these conjugates. Methods of using these conjugates in the treatment of prostate diseases are also provided.

  本发明提供了肽共轭物，其中将细胞毒性和细胞增殖抑制剂，如多胺类似物或萘醌类化合物，与被酶如前列腺特异性抗原（PSA）和半胱氨酸蛋白酶B识别和切割的多肽共轭。同时提供了包含这些共轭物的组合物。本发明还提供了使用这些共轭物治疗前列腺疾病的方法。
• NOVEL POLYAMINE ANALOG CONJUGATES AND QUINONE CONJUGATES AS THERAPIES FOR CANCERS AND PROSTATE DISEASES
  申请人：Frydman Benjamin

  公开号：US20080194697A1

  公开（公告）日：2008-08-14

  Peptide conjugates in which cytostatic and cytostatic agents, such as polyamine analogs or naphthoquinones, are conjugated to a polypeptide recognized and cleaved by enzymes such as prostate-specific antigen (PSA) and cathepsin B are provided, as well as compositions comprising these conjugates. Methods of using these conjugates in the treatment of prostate diseases are also provided.

  提供了肽共轭物，其中细胞生长抑制剂和细胞毒剂，如多胺类似物或萘醌，与多肽共轭，并被酶如前列腺特异性抗原（PSA）和半胱氨酸蛋白酶B识别和剪切，以及包含这些共轭物的组合物。还提供了使用这些共轭物治疗前列腺疾病的方法。
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• Polyamine Analogs as Modulators of Cell Migration and Cell Motility
  申请人：Marton Laurence J.

  公开号：US20090143456A1

  公开（公告）日：2009-06-04

  This disclosure relates to methods of inhibiting cell motility or cell migration, and of treating diseases involving cell migration or cell motility, using polyamine analogs, such as conformationally restricted polyamine analogs. The diseases to be treated include immune disorders, inflammatory conditions, infection, abnormal immune responses, undesired angiogenesis, tumor cell metastasis or invasion, atherosclerosis, vascular graft occlusion, transplant rejection, other complications of transplants, glomerulonephritis, arthritis, inflammatory responses subsequent to stroke or ischemia, and asthma.

  本披露涉及使用聚胺类似物，如构象限制聚胺类似物，抑制细胞运动或细胞迁移的方法，以及治疗涉及细胞迁移或细胞运动的疾病。要治疗的疾病包括免疫障碍，炎症状况，感染，异常免疫反应，不良血管生成，肿瘤细胞转移或侵袭，动脉硬化，血管移植闭塞，移植排斥，移植其他并发症，肾小球肾炎，关节炎，中风或缺血后的炎症反应以及哮喘。