N(1),N(12)-二乙基精胺 | 61345-84-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N(1),N(12)-二乙基精胺
• 英文名称: N1,N12-diethylspermine
• 英文别名: 1,12-di(ethylamino)-4,9-diazadodecane；(N¹,N¹²)-bis(ethyl)-spermine；N,N'-bis-(3-ethylaminopropyl)butane-1,4-diamine；N¹,N¹²-bis(ethyl)spermine；N¹,N¹²- diethylspermine；N¹,N¹²-diethylspermine；N(1), N(12)-diethylspermine；N,N'-bis[3-(ethylamino)propyl]butane-1,4-diamine
• CAS: 61345-84-4
• 化学式: C₁₄H₃₄N₄
• 分子量: 258.451
• InChiKey: PGMIWVSHZMWSSI-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C (decomp)(Solv: ethanol (64-17-5); ethyl acetate (141-78-6); water (7732-18-5))
• 沸点：
  368.4±10.0 °C(Predicted)
• 密度：
  0.876±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  15
• 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

安全信息

• 海关编码：
  2921290000

反应信息

• 作为反应物：
  描述：

  N(1),N(12)-二乙基精胺 在 recombinant human polyamine oxidase 、 spermine oxidase 作用下， 生成 亚精胺
  参考文献：
  名称：

  Metabolism of N-alkylated spermine analogues by polyamine and spermine oxidases

  摘要：

  N-alkylated polyamine analogues have potential as anticancer and antiparasitic drugs. However, their metabolism in the host has remained incompletely defined thus potentially limiting their utility. Here, we have studied the degradation of three different spermine analogues N,N'-bis-(3-ethylaminopropyl)butane-1,4-diamine (DESPM), N-(3-benzyl-aminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine (BnEtSPM) and N,N'-bis-(3-benzylaminopropyl)butane-1,4-diamine (DBSPM) and related mono-alkylated derivatives as substrates of recombinant human polyamine oxidase (APAO) and spermine oxidase (SMO). APAO and SMO metabolized DESPM to EtSPD [K (m(APAO)) = 10 mu M, k (cat(APAO)) = 1.1 s(-1) and K (m(SMO)) = 28 mu M, k (cat(SMO)) = 0.8 s(-1), respectively], metabolized BnEtSPM to EtSPD [K (m(APAO)) = 0.9 mu M, k (cat(APAO)) = 1.1 s(-1) and K (m(SMO)) = 51 mu M, k (cat(SMO)) = 0.4 s(-1), respectively], and metabolized DBSPM to BnSPD [K (m(APAO)) = 5.4 mu M, k (cat(APAO)) = 2.0 s(-1) and K (m(SMO)) = 33 mu M, k (cat(SMO)) = 0.3 s(-1), respectively]. Interestingly, mono-alkylated spermine derivatives were metabolized by APAO and SMO to SPD [EtSPM K (m(APAO)) = 16 mu M, k (cat(APAO)) = 1.5 s(-1); K (m(SMO)) = 25 mu M, k (cat(SMO)) = 8.2 s(-1); BnSPM K (m(APAO)) = 6.0 mu M, k (cat(APAO)) = 2.8 s(-1); K (m(SMO)) = 19 mu M, k (cat(SMO)) = 0.8 s(-1), respectively]. Surprisingly, EtSPD [K (m(APAO)) = 37 mu M, k (cat(APAO)) = 0.1 s(-1); K (m(SMO)) = 48 mu M, k (cat(SMO)) = 0.05 s(-1)] and BnSPD [K (m(APAO)) = 2.5 mu M, k (cat(APAO)) = 3.5 s(-1); K (m(SMO)) = 60 mu M, k (cat(SMO)) = 0.54 s(-1)] were metabolized to SPD by both the oxidases. Furthermore, we studied the degradation of DESPM, BnEtSPM or DBSPM in the DU145 prostate carcinoma cell line. The same major metabolites EtSPD and/or BnSPD were detected both in the culture medium and intracellularly after 48 h of culture. Moreover, EtSPM and BnSPM were detected from cell samples. Present data shows that inducible SMO parallel with APAO could play an important role in polyamine based drug action, i.e. degradation of parent drug and its metabolites, having significant impact on efficiency of these drugs, and hence for the development of novel N-alkylated polyamine analogues.

  DOI：

  10.1007/s00726-009-0429-2
• 作为产物：
  描述：

  N¹,N⁴,N⁹,N¹²-tetrakis(mesityenesulfonyl)spermine 在 氢溴酸 、 sodium hydride 、 溶剂黄146 、 苯酚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 N(1),N(12)-二乙基精胺
  参考文献：
  名称：

  多胺类似物止泻药：结构活性研究。

  摘要：

  描述了一组精胺多胺类似物的合成及其作为止泻药的评价。在啮齿动物蓖麻油诱发的腹泻模型中评估每种化合物降低粪便量和体重减轻的能力，这些剂量呈剂量依赖性。精胺药效基团被证明是构建止泻药的绝佳平台。化合物的活性非常取决于末端烷基的性质和分隔氮的亚甲基间隔基的几何形状。毒性特征还完全取决于这些相同的结构特征。根据皮下剂量反应数据和毒性概况，将两种化合物N（1），N（12）-二异丙精胺和N（1），N（12）-二乙基精胺进行了更全面的评估。这些测量包括正式的急性和慢性毒性试验，药物和代谢组织分布研究，以及这些类似物对组织多胺库的影响的评估。最后，N，N′-双[3-（乙基氨基）丙基]-反式1，4-环己二胺的显着活性强调需要进一步探索该构架作为构建其他止泻药的药效基团。

  DOI：

  10.1021/jm000277+

文献信息

• Cycloalkyl substituted polyamines for cancer therapy and methods of synthesis therefor
  申请人：Frydman Benjamin

  公开号：US20070287754A1

  公开（公告）日：2007-12-13

  Conformationally restricted polyamine compounds useful in treatment of cancer and other diseases marked by abnormal cell proliferation are disclosed. Improved methods of synthesizing such compounds are also disclosed. In one method of the invention, a carbene-bearing or carbene equivalent-bearing compound is reacted with the double bond of an alkene compound to form a cyclopropyl ring as the first step in the synthesis.

  本发明揭示了在治疗癌症和其他由异常细胞增殖引起的疾病中有用的构象限制的多胺化合物。本发明还揭示了改进的合成这种化合物的方法。在本发明的一种方法中，通过使含有卡宾或卡宾等效物的化合物与烯烃化合物的双键反应，形成环丙基环作为合成的第一步。
• 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。
• RNA POLYMERASE TRANSCRIPTION PROMOTERS AND METHOD FOR DETERMINING BASE SEQUENCE
  申请人：Riken

  公开号：EP1061130A1

  公开（公告）日：2000-12-20

  An RNA polymerase transcription accelerator comprising a compound represented by the following Formula (I) or salts thereof. A method of sequencing DNA in which nucleic acid transcripts are obtained using an RNA polymerase and a DNA fragment as a template, the resulted nucleic acid transcripts are separated, the nucleic acid sequence is determined from the separated fractions wherein the nucleic acid transcription reaction is carried out in the presence of a compound selected from a group of compounds represented by the above formula (I). The polyamine compounds above have outstanding accelerating activity on transcription activity of RNA polymerase. Therefore, use of the polyamine compounds in a DNA sequencing method using RNA polymerase can make a length of DNA sequence that can be determined in one sequencing longer.

  一种 RNA 聚合酶转录促进剂，包括下式 (I) 所代表的化合物或其盐类。 一种 DNA 测序方法，其中使用 RNA 聚合酶和 DNA 片段作为模板获得核酸转录本，分离得到的核酸转录本，从分离的部分确定核酸序列，其中核酸转录反应是在选自上式（I）所代表的一组化合物的存在下进行的。 上述多胺化合物对 RNA 聚合酶的转录活性具有突出的加速活性。因此，在使用 RNA 聚合酶的 DNA 测序方法中使用这些多胺化合物，可使一次测序确定的 DNA 序列长度更长。
• MITOGUAZONE FOR PREVENTING THE RELAPSE OR THE PROGRESSION OF MULTIPLE SCLEROSIS
  申请人：Pathologica LLC

  公开号：EP3831372A1

  公开（公告）日：2021-06-09

  Disclosed herein are new oral pharmaceutical compositions of SAMDC inhibitors, polyamine analogs, and polyamine biosynthesis inhibitors, and their application for the treatment of conditions including demyelinating diseases, autoimmune disorders affecting the nervous system, and other neurodegenerative conditions.

  本文公开了SAMDC抑制剂、多胺类似物和多胺生物合成抑制剂的新型口服药物组合物，以及它们在治疗脱髓鞘疾病、影响神经系统的自身免疫性疾病和其他神经退行性疾病等疾病中的应用。
• Linear polyamine compounds and polyamine anticancer agents
  申请人：——

  公开号：US20020067472A1

  公开（公告）日：2002-06-06

  Nobel polyamine compounds and polyamine compounds having carcinostatic action are provided. There are also provided anticancer agents containing as active ingredient at least one of polyamine compounds represented by the following Formula (I) or (III) and/or pharmaceutically acceptable salts thereof. 1 Specifically, there are provided anticancer agents containing as active ingredient at least one of 1,18-bis(ethylamino)-5,14-diazaoctadecane, 1,16-bis(cyclopropylmethylamino)-5,12-diazahexadecane, 1,17-bis(cyclopropylmethylamino)-5,13-diazaheptadecane and/or pharmaceutically acceptable salts thereof.

  提供了诺贝尔多胺化合物和具有致癌作用的多胺化合物。此外，还提供了含有下式（I）或（III）代表的至少一种多胺化合物和/或其药学上可接受的盐作为活性成分的抗癌剂。 1 具体地说，提供了含有至少一种 1,18-双(乙基氨基)-5,14-二氮杂十八烷、1,16-双(环丙基甲基氨基)-5,12-二氮杂十六烷、1,17-双(环丙基甲基氨基)-5,13-二氮杂十七烷和/或其药学上可接受的盐作为活性成分的抗癌剂。