N-(3-phenoxybenzyl)ethane-1,2-diamine

• 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: N-(3-phenoxybenzyl)ethane-1,2-diamine
• 英文别名: N'-[(3-phenoxyphenyl)methyl]ethane-1,2-diamine
• 化学式: C₁₅H₁₈N₂O
• mdl: MFCD04365379
• 分子量: 242.321
• InChiKey: LTHKBGCUHYIUOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-phenoxybenzyl)ethane-1,2-diamine 在 三氟乙酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 2-(2-oxo-3-(3-phenoxybenzyl)imidazolidin-1-yl)acetic acid
  参考文献：
  名称：

  Design and synthesis of inhibitors of noroviruses by scaffold hopping

  摘要：

  A scaffold hopping strategy was employed to identify new chemotypes that inhibit noroviruses. The replacement of the cyclosulfamide scaffold by an array of heterocyclic scaffolds lead to the identification of additional series of compounds that possessed anti-norovirus activity in a cell-based replicon system. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.032
• 作为产物：
  描述：

  3-苯氧基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 四溴化碳 、 过氧化苯甲酰 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 N-(3-phenoxybenzyl)ethane-1,2-diamine
  参考文献：
  名称：

  Binding activity of substituted benzyl derivatives of chloronicotinyl insecticides to housefly-head membranes, and its relationship to insecticidal activity against the houseflyMusca domestica

  摘要：

  Variously substituted benzyl derivatives of chloronicotinyl insecticides were synthesized with a wide range of substituents including halogens, NO2, CN, CF, and small alkyl and alkoxy groups at the ortho, meta and para positions, as well as multiple-substituted benzyl analogues. Their binding activity to the alpha-bungarotoxin binding site in housefly (Musca domestica) head membrane preparations was measured. Among the compounds tested, the activity of the meta-CN derivative was the highest, being 20-100 times higher than those of imidacloprid, acetamiprid and nitenpyram. The synergized insecticidal activity against houseflies was also measured for selected compounds with the metabolic inhibitor, NIA16388 (propargyl propyl phenylphosphonate). For the nitromethylene analogues, including both benzyl and pyridylmethyl analogues, higher binding activity usually resulted in higher insecticidal activity. (C) 2000 Society of Chemical Industry.

  DOI：

  10.1002/1526-4998(200010)56:10<875::aid-ps220>3.0.co;2-a

文献信息

• Potent inhibition of Norwalk virus by cyclic sulfamide derivatives
  作者：Dengfeng Dou、Kok-Chuan Tiew、Guijia He、Sivakoteswara Rao Mandadapu、Sridhar Aravapalli、Kevin R. Alliston、Yunjeong Kim、Kyeong-Ok Chang、William C. Groutas

  DOI：10.1016/j.bmc.2011.08.054

  日期：2011.10

  A new class of compounds that exhibit anti-norovirus activity in a cell-based system and embody in their structure a cyclosulfamide scaffold has been identified. The structure of the initial hit (compound 2a, ED50 4 μM, TD50 50 μM) has been prospected by exploiting multiple points of diversity and generating appropriate structure–activity relationships.

  已鉴定出一类在基于细胞的系统中表现出抗诺如病毒活性并在其结构中包含环磺酰胺支架的新化合物。初始命中的结构（化合物2a，ED 50 4 μM，TD 50 50 μM）已通过利用多个多样性点并生成适当的结构-活性关系进行了展望。
• Synthesis and structure–activity relationship study of phenoxybenzylpiperazine analogues as CCR8 agonists
  作者：Qifei Li、Sandra Claes、Yenthel Verhaegen、Stijn Anthonissen、Tom Van Loy、Dominique Schols、Wim Dehaen、Steven De Jonghe

  DOI：10.1016/j.bioorg.2023.106755

  日期：2023.10

  are known to be endowed with CCR8 agonistic activity, systematic structure-activity relationship studies have not been reported. In this study, ZK756326, a previously disclosed CCR8 agonist, was divided in various fragments and each subunit was subjected to structural modifications. All newly synthesized analogues were evaluated in a CCR8 calcium mobilization assay, revealing that only limited structural

  CCR8 激动剂有望治疗各种自身免疫性疾病。尽管已知苯氧基苄基哌嗪衍生物具有CCR8激动活性，但系统的构效关系研究尚未见报道。在这项研究中，ZK756326，一种先前公开的CCR8激动剂，被分成不同的片段，并且每个亚基都进行了结构修饰。所有新合成的类似物均在 CCR8 钙动员测定中进行了评估，结果表明苯环和苄位仅允许有限的结构变化。相比之下，各种接头给出的类似物具有良好的 CCR8 激动效力。此外，哌嗪基部分上小取代基的存在或哌嗪基与哌啶基的交换提供了具有前景的CCR8激动剂的化合物，其中最有效的同系物比ZK756326强10倍。
• Binding activity of substituted benzyl derivatives of chloronicotinyl insecticides to housefly-head membranes, and its relationship to insecticidal activity against the houseflyMusca domestica
  作者：Hisashi Nishiwaki、Yoshiaki Nakagawa、David Y Takeda、Atsushi Okazawa、Miki Akamatsu、Hisashi Miyagawa、Tamio Ueno、Keiichiro Nishimura

  DOI：10.1002/1526-4998(200010)56:10<875::aid-ps220>3.0.co;2-a

  日期：2000.10

  Variously substituted benzyl derivatives of chloronicotinyl insecticides were synthesized with a wide range of substituents including halogens, NO2, CN, CF, and small alkyl and alkoxy groups at the ortho, meta and para positions, as well as multiple-substituted benzyl analogues. Their binding activity to the alpha-bungarotoxin binding site in housefly (Musca domestica) head membrane preparations was measured. Among the compounds tested, the activity of the meta-CN derivative was the highest, being 20-100 times higher than those of imidacloprid, acetamiprid and nitenpyram. The synergized insecticidal activity against houseflies was also measured for selected compounds with the metabolic inhibitor, NIA16388 (propargyl propyl phenylphosphonate). For the nitromethylene analogues, including both benzyl and pyridylmethyl analogues, higher binding activity usually resulted in higher insecticidal activity. (C) 2000 Society of Chemical Industry.
• Design and synthesis of inhibitors of noroviruses by scaffold hopping
  作者：Dengfeng Dou、Sivakoteswara Rao Mandadapu、Kevin R. Alliston、Yunjeong Kim、Kyeong-Ok Chang、William C. Groutas

  DOI：10.1016/j.bmc.2011.08.032

  日期：2011.10

  A scaffold hopping strategy was employed to identify new chemotypes that inhibit noroviruses. The replacement of the cyclosulfamide scaffold by an array of heterocyclic scaffolds lead to the identification of additional series of compounds that possessed anti-norovirus activity in a cell-based replicon system. (C) 2011 Elsevier Ltd. All rights reserved.