1-(3,4-dimethoxyphenyl)-3-(1-phenylethyl)urea

• 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: 1-(3,4-dimethoxyphenyl)-3-(1-phenylethyl)urea
• 英文别名: 1-(3,4-dimethoxyphenyl)-3-[(1S)-1-phenylethyl]urea
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: HLBPRWKSAIZDLO-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-3-(1-phenylethyl)urea 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.25h， 以1.18 g的产率得到1-(3,4-dimethoxyphenyl)-1,3-dimethyl-3-((S)-1-phenylethyl)urea
  参考文献：
  名称：

  锂化脲的立体特异性分子内亲电芳基化取代二芳基甲胺

  摘要：

  在锂化时，N-苄基脲随着 N'-芳基取代基发生变化，芳环迁移到 N-苄基的 α 碳上。使用手性、对映体纯的 N-α-甲基苄基脲，重排是立体定向的，并产生一个新的、完全取代的立体中心 α 到 N。通过 N-亚硝化和水解去除脲功能允许在高对映体中合成手性叔卡宾胺纯度。

  DOI：

  10.1021/ja071523a
• 作为产物：
  描述：

  藜芦酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 5.17h， 生成 1-(3,4-dimethoxyphenyl)-3-(1-phenylethyl)urea
  参考文献：
  名称：

  Discovery and Structural Modification of 1-Phenyl-3-(1-phenylethyl)urea Derivatives as Inhibitors of Complement

  摘要：

  A series of 1-phenyl-3-(1-phenylethyl)urea derivatives were identified as novel and potent complement inhibitors through structural modification of the original compound from high-throughput screening. Various analogues (7 and 13-15) were synthesized and identified as complement inhibitors, with the introduction of a five- or six-carbon chain (7c, 7d, 7k, 7I, and 7o) greatly improving their activity. Optimized compound 7I has an excellent inhibition activity with IC50 values as low as 13 nM. We demonstrated that the compound 7I inhibited C9 deposition through the classical, the lectin, and the alternative pathways but had no influence on C3 and C4 depositions.

  DOI：

  10.1021/ml300005w

文献信息

• Discovery and Structural Modification of 1-Phenyl-3-(1-phenylethyl)urea Derivatives as Inhibitors of Complement
  作者：Mei Zhang、Xiao-Ying Yang、Wei Tang、Tom W. L. Groeneveld、Pei-Lan He、Feng-Hua Zhu、Jia Li、Wei Lu、Anna M. Blom、Jian-Ping Zuo、Fa-Jun Nan

  DOI：10.1021/ml300005w

  日期：2012.4.12

  A series of 1-phenyl-3-(1-phenylethyl)urea derivatives were identified as novel and potent complement inhibitors through structural modification of the original compound from high-throughput screening. Various analogues (7 and 13-15) were synthesized and identified as complement inhibitors, with the introduction of a five- or six-carbon chain (7c, 7d, 7k, 7I, and 7o) greatly improving their activity. Optimized compound 7I has an excellent inhibition activity with IC50 values as low as 13 nM. We demonstrated that the compound 7I inhibited C9 deposition through the classical, the lectin, and the alternative pathways but had no influence on C3 and C4 depositions.
• Substituted Diarylmethylamines by Stereospecific Intramolecular Electrophilic Arylation of Lithiated Ureas
  作者：Jonathan Clayden、Jérémy Dufour、Damian M. Grainger、Madeleine Helliwell

  DOI：10.1021/ja071523a

  日期：2007.6.1

  On lithiation, N-benzyl ureas varying N‘-aryl substituents undergo a migration of the aryl ring to the α carbon of the N-benzyl group. With chiral, enantiomerically pure N-α-methylbenzyl ureas, the rearrangement is stereospecific and creates a new, fully substituted stereogenic center α to N. Removal of the urea function by N-nitrosation and hydrolysis allows the synthesis of chiral tertiary carbinamines

  在锂化时，N-苄基脲随着 N'-芳基取代基发生变化，芳环迁移到 N-苄基的 α 碳上。使用手性、对映体纯的 N-α-甲基苄基脲，重排是立体定向的，并产生一个新的、完全取代的立体中心 α 到 N。通过 N-亚硝化和水解去除脲功能允许在高对映体中合成手性叔卡宾胺纯度。