N-(3-morpholin-4-ylpropyl)-1-(3-nitrophenyl)methanimine | 413572-66-4

• 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-morpholin-4-ylpropyl)-1-(3-nitrophenyl)methanimine
• CAS: 413572-66-4
• 化学式: C₁₄H₁₉N₃O₃
• 分子量: 277.323
• InChiKey: LUKLGKXKJUOUJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-morpholin-4-ylpropyl)-1-(3-nitrophenyl)methanimine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 3-morpholin-4-yl-N-[(3-nitrophenyl)methyl]propan-1-amine
  参考文献：
  名称：

  Design, synthesis and structure–activity relationships of antiproliferative 1,3-disubstituted urea derivatives

  摘要：

  Twenty-four new 1,3-disubstituted urea derivatives (compounds 1-24) were synthesized and reported for the first time. The antiproliferative activities of these compounds were evaluated against a panel of one human liver cell line (L02) and two human tumor cell lines (KB and K562) by applying the MTT colorimetric assay. The series of 1,3-disubstituted urea derivatives show good antiproliferative activity against human cancer cell lines (KB and K562) and no antiproliferative activity against liver cell line (L02). The potent in vitro antiproliferative activity of these derivatives and their selectivity for L02 are quite important points for an anticancer drug candidate with fewer side effects. Structure-activity relationships were also discussed based on the obtained experimental data. The hydroxyl groups on the phenyl ring reduced the antiproliferative activities of 1,3-disubstituted urea derivatives. The OH groups could be responsible for a reduction in the permeability of the cell membrane. Generally, an aromatic ring on N-3 seems to be in favor of enhancing the inhibitory activity, compounds introduced a nitro group substituent at C-3 position on the aromatic ring approved to generally decrease activity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.011
• 作为产物：
  描述：

  N-(3-氨丙基)吗啉 、 间硝基苯甲醛 以 乙醇 为溶剂， 反应 1.0h， 生成 N-(3-morpholin-4-ylpropyl)-1-(3-nitrophenyl)methanimine
  参考文献：
  名称：

  Design, synthesis and structure–activity relationships of antiproliferative 1,3-disubstituted urea derivatives

  摘要：

  Twenty-four new 1,3-disubstituted urea derivatives (compounds 1-24) were synthesized and reported for the first time. The antiproliferative activities of these compounds were evaluated against a panel of one human liver cell line (L02) and two human tumor cell lines (KB and K562) by applying the MTT colorimetric assay. The series of 1,3-disubstituted urea derivatives show good antiproliferative activity against human cancer cell lines (KB and K562) and no antiproliferative activity against liver cell line (L02). The potent in vitro antiproliferative activity of these derivatives and their selectivity for L02 are quite important points for an anticancer drug candidate with fewer side effects. Structure-activity relationships were also discussed based on the obtained experimental data. The hydroxyl groups on the phenyl ring reduced the antiproliferative activities of 1,3-disubstituted urea derivatives. The OH groups could be responsible for a reduction in the permeability of the cell membrane. Generally, an aromatic ring on N-3 seems to be in favor of enhancing the inhibitory activity, compounds introduced a nitro group substituent at C-3 position on the aromatic ring approved to generally decrease activity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.011

文献信息

• Synthesis, docking and evaluation of in vitro anti-inflammatory activity of novel morpholine capped β-lactam derivatives
  作者：Roghayeh Heiran、Saghi Sepehri、Aliasghar Jarrahpour、Carole Digiorgio、Hana Douafer、Jean Michel Brunel、Ahmad Gholami、Elham Riazimontazer、Edward Turos

  DOI：10.1016/j.bioorg.2020.104091

  日期：2020.9

  the synthesis and biological investigation of three series of novel monocyclic β-lactam derivatives bearing a morpholine ring substituent on the nitrogen. The resulting β-lactam adducts were synthesized via Staudinger's [2 + 2]-ketene-imine cycloaddition reaction. New synthesized products were fully characterized by spectral data and elemental analyses, and then evaluated for anti-inflammatory activity

  该研究报道了在氮上带有吗啉环取代基的三系列新型单环β-内酰胺衍生物的合成和生物学研究。通过Staudinger's [2 + 2]-乙烯酮-亚胺环加成反应合成所得的β-内酰胺加成物。通过光谱数据和元素分析充分表征了新合成的产物，然后评估了对人诱导型一氧化氮合酶（iNOS）的抗炎活性和对HepG2细胞系的细胞毒性。化合物3e，3h，3k，5c，5f，6c，6d和6f与参考化合物地塞米松的消炎比值为32相比，抗炎比值分别为38、62、51、72、51、35、55和99时显示出更高的活性。因此，这些化合物可以被认为是有效的iNOS抑制剂。相比之下，它们的IC50值分别为0.48±0.04 mM，0.51±0.01 mM，0.22±0.02 mM，0.12±0.00 mM，0.25±0.05 mM，0.82±0.07 mM，0.44±0.04 mM和0.60±0.04 mM。与阿霉素（IC50 <0