m-(diethylaminomethyl)benzylamine | 84227-69-0

• 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: m-(diethylaminomethyl)benzylamine
• 英文别名: {3-[(Diethylamino)methyl]phenyl}methanamine；N-[[3-(aminomethyl)phenyl]methyl]-N-ethylethanamine
• CAS: 84227-69-0
• 化学式: C₁₂H₂₀N₂
• mdl: MFCD08444591
• 分子量: 192.304
• InChiKey: VMRIINWHXFWDNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  m-(diethylaminomethyl)benzylamine 在 盐酸 、 铁粉 、 potassium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.0h， 生成 N,N-Diethyl 3-(p-aminobenzamidomethyl)-benzylamine
  参考文献：
  名称：

  普鲁卡因酰胺的环乙烯基化合物

  摘要：

  描述了普鲁卡因酰胺的三种异构环乙烯基化合物，其中苯环插入在基本链的亚甲基之间。局部麻醉剂和抗心律失常活性之间已经实现了明显的分离。

  DOI：

  10.1002/ardp.19823151205
• 作为产物：
  描述：

  m-(diethylaminomethyl)benzonitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以81%的产率得到m-(diethylaminomethyl)benzylamine
  参考文献：
  名称：

  Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum

  摘要：

  氯喹曾是抗击恶性疟原虫的首选药物，但由于抗药性广泛存在，其疗效现已受到严重限制。阿莫地喹是已知最有效的 4-氨基喹啉类抗疟药物之一，对耐氯喹的寄生虫仍然有效，但与醌-亚胺代谢物有关的毒性问题限制了它在临床上的使用。为了寻找既能保留阿莫地喹的抗疟活性，又能避免醌-亚胺代谢物毒性的新化合物，我们合成了五种 4-氨基喹啉类化合物，这些化合物的分子侧链中缺少羟基环，因此无法生成有毒的醌-亚胺。这些新化合物对氯喹敏感和抗氯喹的恶性疟原虫菌株显示出较高的体外效力（低纳摩尔 IC50），明显优于氯喹，与阿莫地喹相当，同时对 L6 大鼠成纤维细胞和 MRC5 人类肺细胞毒性较低，代谢稳定性与阿莫地喹相当或高于阿莫地喹。计算研究表明，化合物 4 通过位于联苯态的 HOMO 与血红素结合，具有独特的模式，这可能是该化合物具有较高抗疟活性的部分原因。

  DOI：

  10.1371/journal.pone.0140878

文献信息

• Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum
  作者：Chandima S. K. Rajapakse、Maryna Lisai、Christiane Deregnaucourt、Véronique Sinou、Christine Latour、Dipankar Roy、Joseph Schrével、Roberto A. Sánchez-Delgado

  DOI：10.1371/journal.pone.0140878

  日期：——

  The efficacy of chloroquine, once the drug of choice in the fight against Plasmodium falciparum, is now severely limited due to widespread resistance. Amodiaquine is one of the most potent antimalarial 4-aminoquinolines known and remains effective against chloroquine-resistant parasites, but toxicity issues linked to a quinone-imine metabolite limit its clinical use. In search of new compounds able to retain the antimalarial activity of amodiaquine while circumventing quinone-imine metabolite toxicity, we have synthesized five 4-aminoquinolines that feature rings lacking hydroxyl groups in the side chain of the molecules and are thus incapable of generating toxic quinone-imines. The new compounds displayed high in vitro potency (low nanomolar IC50), markedly superior to chloroquine and comparable to amodiaquine, against chloroquine-sensitive and chloroquine-resistant strains of P. falciparum, accompanied by low toxicity to L6 rat fibroblasts and MRC5 human lung cells, and metabolic stability comparable or higher than that of amodiaquine. Computational studies indicate a unique mode of binding of compound 4 to heme through the HOMO located on a biphenyl moeity, which may partly explain the high antiplasmodial activity observed for this compound.

  氯喹曾是抗击恶性疟原虫的首选药物，但由于抗药性广泛存在，其疗效现已受到严重限制。阿莫地喹是已知最有效的 4-氨基喹啉类抗疟药物之一，对耐氯喹的寄生虫仍然有效，但与醌-亚胺代谢物有关的毒性问题限制了它在临床上的使用。为了寻找既能保留阿莫地喹的抗疟活性，又能避免醌-亚胺代谢物毒性的新化合物，我们合成了五种 4-氨基喹啉类化合物，这些化合物的分子侧链中缺少羟基环，因此无法生成有毒的醌-亚胺。这些新化合物对氯喹敏感和抗氯喹的恶性疟原虫菌株显示出较高的体外效力（低纳摩尔 IC50），明显优于氯喹，与阿莫地喹相当，同时对 L6 大鼠成纤维细胞和 MRC5 人类肺细胞毒性较低，代谢稳定性与阿莫地喹相当或高于阿莫地喹。计算研究表明，化合物 4 通过位于联苯态的 HOMO 与血红素结合，具有独特的模式，这可能是该化合物具有较高抗疟活性的部分原因。
• [EN] CLASS OF HETEROAROMATIC COMPOUND, PREPARATION METHOD THEREFOR AND USE THEREOF<br/>[FR] CLASSE D'UN COMPOSÉ HÉTÉROAROMATIQUE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 一类芳杂环类化合物及其制备方法和用途
  申请人：INNOVSTONE THERAPEUTICS LTD

  公开号：WO2022161420A1

  公开（公告）日：2022-08-04

  提供了一种作为TLR7激活剂的式I所示的化合物、该化合物的制备方法及其治疗由TLR7激活剂介导的疾病的用途。人源受体TLR7激动活性研究显示，这些化合物对人源受体TLR7具有较强的激动作用，可作为治疗TLR7激动剂介导的疾病的前景化合物。此外，研究了特定的合成方法，该合成方法工艺简单，操作便捷，利于规模化工业生产和应用。
• [EN] SELECTIVE BUTYRYLCHOLINESTERASE INHIBITOR OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF<br/>[FR] INHIBITEUR SÉLECTIF DE LA BUTYRYLCHOLINESTÉRASE OU SEL PHARMACEUTIQUEMENT ACCEPTABLE DE CELUI-CI, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 选择性丁酰胆碱酯酶抑制剂或其可药用的盐、其制备方法及用途
  申请人：UNIV CHINA PHARMA

  公开号：WO2021042410A1

  公开（公告）日：2021-03-11

  公开了具有通式(I)的选择性丁酰胆碱酯酶抑制剂或其可药用的盐、其制备方法及用途。以丁酰胆碱酯酶抑制活性、选择性的筛选以及对神经细胞的毒性为载体来检验治疗阿尔茨海默氏病的疗效，尤其是中重度阿尔茨海默氏病，发现其具有良好的体外靶标活性、极高的选择性以及药物安全性，可作为进一步开发通过选择性抑制丁酰胆碱酯酶来发挥治疗阿尔茨海默氏病作用的先导物质。
• Determination of Macronutrients, by Chemical Analysis, of Home-Prepared Milk Feeding Bottles and their Contribution to the Energy and Protein Requirements of Infants from High and Low Socioeconomic Classes
  作者：Tania Beninga Morais、Dirce Maria Sigulem

  DOI：10.1080/07315724.2002.10719222

  日期：2002.6

  Objectives: To determine the macronutrients composition of home-prepared milk feeding bottles, by chemical analysis, and assess their contribution to the energy and protein requirements of children under two years of age from high (HSE) and low (LSE) socioeconomic classes.Methods: 72 samples were analyzed for energy density and protein, fat and carbohydrate content: 41 from the LSE group and 31 from the HSE group. The assessment of the percentages of the energy and protein requirements met by the consumption of the milk bottles was calculated as follows: the energy and protein per 100 mL obtained through chemical analysis were multiplied by the volume consumed at each feeding, then by the number of feedings per day, the results divided by the energy and protein requirements and multiplied by 100. Energy and protein requirements were those recommended by the FAO/WHO/UNU Committee and the Food and Nutrition Board. The children's weight-for-age index was assessed.Results: Unmodified cow's milk was largely consumed by both groups. The addition of sugar and other ingredients to the milk was significantly higher in the LSE group. Moisture, protein and fat content were lower in the LSE group. whereas carbohydrate and energy content were higher. The percentages of energy and protein requirements provided by feeding bottles were higher in the LSE group. Children in the LSE group had lower z-scores for weight-for-age.Conclusions: Differences in the preparation practices led to differences in the chemical results. The feeding bottles in the LSE group were high in energy, due to the addition of sugar and cereals to the milk in the bottle. The milk feeding bottles were an important weaning food providing more than 50% and 100% of the children's energy and protein requirements, respectively. The children's weight-for-age index was within the normal Lb-aits.
• VALENTI, P.;MAZZOTTI, M.;RAMPA, A.;MAGISTRETTI, M. J., ARCH. PHARM., 1982, 315, N 12, 1003-1007
  作者：VALENTI, P.、MAZZOTTI, M.、RAMPA, A.、MAGISTRETTI, M. J.

  DOI：——

  日期：——