5-(1-benzyl-1-methylamino)pentylamine | 34987-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(1-benzyl-1-methylamino)pentylamine
• 英文别名: 5-(N-benzyl-N-methylamino)pentylamine；N¹-benzyl-N¹-methylpentane-1,5-diamine；N-benzyl-N-methylpentane-1,5-diamine；5-Benzylmethylaminopentylamin；N-benzyl-N-methyl-pentanediyldiamine；5--pentylamin；N-Benzyl-N-methyl-pentandiyldiamin；N'-benzyl-N'-methylpentane-1,5-diamine
• CAS: 34987-10-5
• 化学式: C₁₃H₂₂N₂
• 分子量: 206.331
• InChiKey: PPIDOZCBSCCLAU-UHFFFAOYSA-N

物化性质

• 沸点：
  107-109 °C(Press: 0.5 Torr)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(1-benzyl-1-methylamino)pentylamine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 生成
  参考文献：
  名称：

  Tic-乙内酰脲衍生物作为选择性sigma1配体的合成和药理评价。第2部分。

  摘要：

  本文描述了由四氢异喹啉-乙内酰脲（Tic-乙内酰脲）衍生物组成的一类新的选择性sigma1配体。化合物1a对sigma1受体具有高亲和力（IC50 = 16 nM），并且在许多治疗靶标中具有选择性。这项研究提出了tic乙内酰脲核心的侧链上的结构变化。可以鉴定出具有更高亲和力的类似物（IC50约为2-3 nM）。

  DOI：

  10.1016/j.bmcl.2005.07.039
• 作为产物：
  描述：

  5-溴戊腈 在 lithium aluminium tetrahydride 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 123.0h， 生成 5-(1-benzyl-1-methylamino)pentylamine
  参考文献：
  名称：

  改进的N-甲基尸胺的合成。

  摘要：

  生物碱构成一大类天然产物，单甲基化多胺是其生物合成中的常见中间体。为了评估选择性甲基化天然产物的作用，需要合成策略来制备它们。在此，通过三个步骤以37.3％的产率制备N-甲基尸胺。替代文献的两步策略导致还原脱氨作用，得到N-甲基哌啶，由单晶结构确定。展示了一种获得单烷基化脂肪族二胺尸胺的直接方法，该方法避免了潜在的副反应。

  DOI：

  10.3390/molecules23051216

文献信息

• Aminopyridazines as Acetylcholinesterase Inhibitors
  作者：Jean-Marie Contreras、Yveline M. Rival、Said Chayer、Jean-Jacques Bourguignon、Camille G. Wermuth

  DOI：10.1021/jm981101z

  日期：1999.2.1

  Following the discovery of the weak, competitive and reversible acetylcholinesterase (AChE)-inhibiting activity of minaprine (3c) (IC50 = 85 microM on homogenized rat striatum AChE), a series of 3-amino-6-phenylpyridazines was synthesized and tested for inhibition of AChE. A classical structure-activity relationship exploration suggested that, in comparison to minaprine, the critical elements for high

  发现米那匹林（3c）的弱，竞争性和可逆性乙酰胆碱酯酶（AChE）抑制活性（对均质大鼠纹状体AChE的IC50 = 85 microM）后，合成了一系列3-氨基-6-苯基哒嗪并测试了其抑制作用AChE。一项经典的构效关系研究表明，与米萘普林相比，高乙酰胆碱酯酶抑制的关键因素如下：（i）中央哒嗪环的存在；（ii）亲脂性阳离子头的必要性；（iii）改变哒嗪环与阳离子头之间的碳原子数为2至4-5。在研究的所有衍生物中，3- [2-（1-苄基哌啶-4-基）乙基氨基] -6-苯基哒嗪（3y）在纯化的AChE（电鳗）上的IC50为0.12 microM，
• Quinolino[3,4- b ]quinoxalines and pyridazino[4,3- c ]quinoline derivatives: Synthesis, inhibition of topoisomerase IIα, G-quadruplex binding and cytotoxic properties
  作者：Fausta Palluotto、Alice Sosic、Odra Pinato、Grigoris Zoidis、Marco Catto、Claudia Sissi、Barbara Gatto、Angelo Carotti

  DOI：10.1016/j.ejmech.2016.07.063

  日期：2016.11

  with other heterocyclic systems plays an important role in the field of anticancer drug development. An extensive series of tetracyclic quinolino[3,4-b]quinoxalines N-5 or C-6 substituted with basic side chain and a limited number of tricyclic pyridazino[4,3-c]quinolines N-6 substituted were designed, synthesized and evaluated for topoisomerase IIα (Topo IIα) inhibitory activity, ability to bind and

  与其他杂环系统融合的喹啉基序在抗癌药物开发领域中发挥着重要作用。设计，合成并合成了一系列被碱性侧链取代的四环喹啉代[3,4- b ]喹喔啉N -5或C -6和有限数量的三环哒嗪并[4,3- c ]喹啉N -6取代评估拓扑异构酶IIα（TopoIIα）的抑制活性，结合和稳定G-四链体结构的能力以及对两种人类癌细胞系（HeLa和MCF-7）的细胞毒性。几乎所有受试药物均具有TopoIIα抑制剂和G-四链体稳定剂的高活性。在所有研究的衍生物中，喹啉基[3,4- b分别取代的]喹喔啉11和23，N -5和C -6是最有前途的化合物。衍生物11对选定的G-四链体序列具有选择性结合，而衍生物23显示出最有趣的TopoIIα抑制活性（IC 50  = 5.14μM）；两者均显示出高细胞毒性活性（IC 50 HeLa分别为2.04μM和2.32μM）。
• Central Cholinergic Agents. II. Synthesis and Acetylcholinesterase Inhibitory Activities of N-(.OMEGA.-(N-Alkyl-N-(phenylmethyl)amino)alkyl)-3-arylpropenamides.
  作者：Yuji ISIHARA、Koki KATO、Giichi GOTO

  DOI：10.1248/cpb.39.3236

  日期：——

  A series of N-[ω-[N-phenylmethyl)amino]alkyl-3-arylpropenamides was prepared and tested for its inhibitory activities on acetylcholinesterase. Some in the series were found to be potent inhibitors. The structure-activity relationships were discussed in detail.

  制备了一系列 N-[ω-[N-苯基甲基]氨基]烷基-3-芳基丙烯酰胺，并测试了其对乙酰胆碱酯酶的抑制活性。发现该系列中的一些化合物是强效抑制剂。对其结构-活性关系进行了详细讨论。
• Structure-activity relationship study of hypoxia-activated prodrugs for proteoglycan-targeted chemotherapy in chondrosarcoma
  作者：Donia Ghedira、Aurélien Voissière、Caroline Peyrode、Jamil Kraiem、Yvain Gerard、Elise Maubert、Magali Vivier、Elisabeth Miot-Noirault、Jean-Michel Chezal、Farhat Farhat、Valérie Weber

  DOI：10.1016/j.ejmech.2018.08.060

  日期：2018.10

  Due to an abundant chondrogenic, poorly vascularized and particularly hypoxic extracellular matrix, chondrosarcoma, a malignant cartilaginous tumour, is chemo- and radio-resistant. Surgical resection with wide margins remains the mainstay of treatment. To address the lack of therapy, our strategy aims to increase anticancer drugs targeting and delivery in the tumour, by leveraging specific chondrosarcoma hallmarks: an extensive cartilaginous extracellular matrix, namely the high negative fixed charge density and severe chronic hypoxia. A dual targeted therapy for chondrosarcoma was investigated by conjugation of a hypoxia-activated prodrug (HAP) to quaternary ammonium (QA) functions which exhibit a high affinity for polyanionic sites of proteoglycans (PGs), the major components of the chondrosarcoma extracellular matrix. Based on preclinical results, an imidazole prodrug, ICF05016, was identified and provided the basis for a lead optimization study. A series of 27 QA-phosphoramide mustard conjugates, differing by the type of QA function and the length of the alkyl linker, was yielded by a common multistep sequence involving phosphorylation of a key 2-nitroimidazole alcohol. Then, a screening was realized by surface plasmon resonance technology to assess biomolecular interactions between QA derivatives and aggrecan, the most abundant PG in chondrosarcoma. Results revealed that affinity depends more on the type of QA function, than on the linker length. Moreover, the presence of a benzyl group enhanced affinity to aggrecan. Twelve compounds were shortlisted and evaluated for antiproliferative activity (i.e., growth inhibiting concentration 50), under normoxic and hypoxic conditions using the human extraskeletal myeloid chondrosarcoma cell line (HEMC-SS). For all prodrugs, hypoxic selectivity was maintained and even increased, compared with the lead. From this study, compound 31f emerged as the most effective PG-targeted HAPs with a dissociation constant of 2.10 mu M in the SPR experiment, a hypoxia cytotoxicity ratio of 24 and an efficient reductive cleavage under chemical and enzymatic conditions. (C) 2018 Elsevier Masson SAS. All rights reserved.
• The Synthesis of Bis-quaternary Salts of Some 1,7-Phenanthroline Derivatives
  作者：Alexander R. Surrey、Arthur J. Olivet、James O. Hoppe

  DOI：10.1021/ja01648a046

  日期：1954.10