(S)-2-(1-oxo-3-phenyl-1-(piperidin-1-yl)propan-2-yl)isoindoline-1,3-dione | 1217836-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (S)-2-(1-oxo-3-phenyl-1-(piperidin-1-yl)propan-2-yl)isoindoline-1,3-dione
• 英文别名: 2-[(1S)-1-benzyl-2-oxo-2-(1-piperidyl)ethyl]isoindoline-1,3-dione；2-[(2S)-1-oxo-3-phenyl-1-piperidin-1-ylpropan-2-yl]isoindole-1,3-dione
• CAS: 1217836-72-0
• 化学式: C₂₂H₂₂N₂O₃
• mdl: MFCD00226081
• 分子量: 362.428
• InChiKey: NUJZCVFNMNJUHO-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-邻苯二甲酰基-L-苯丙氨酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (S)-2-(1-oxo-3-phenyl-1-(piperidin-1-yl)propan-2-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  Design, synthesis and biological evaluation of functionalized phthalimides: A new class of antimalarials and inhibitors of falcipain-2, a major hemoglobinase of malaria parasite

  摘要：

  Phthalimides functionalized with cyclic amines were synthesized, characterized and screened for their in vitro antimalarial efficacy against Plasmodium falciparum (Pf3D7). Of all the listed phthalimides evaluated, 14 and 24 were identified as potent antimalarial agents as advocated by assessment of their ability to inhibit [H-3] hypoxanthine incorporation in the nucleic acid of parasites. In addition, phthalimides 14 and 24 were incubated for 60 and 90 h and an enhanced antimalarial effect was noticed with increase in time to great extent. A reduction in IC50 values was observed with increase in exposure time of the parasite to the compounds. A symmetric phthalimide, 24 possessing piperazine as linker unit was identified as the most potent antimalarial agent with IC50 values of 5.97 +/- 0.78, 2.0 +/- 1.09 and 1.1 +/- 0.75 mu M on incubation period of 42, 60 and 90 h, respectively. The abnormal morphologies such as delay in developmental stages, growth arrest and condensed nuclei of parasite were observed with the aid of microscopic studies upon exposure with 14 and 24. The evaluation of 14 and 24 against chloroquine resistant strain, (Pf7GB) of P. falciparum afforded IC50 values, 13.29 +/- 1.20 and 7.21 +/- 0.98 mu M, respectively. The combination of 24 with artemisinin (ART) showed enhanced killing of parasite against Pf3D7. Further, all phthalimides were evaluated for their activity against falcipain-2 (FP2), a major hemoglobinase of malarial parasite. The enzymatic assay afforded 6 as most active member against FP2. To the best of our knowledge this is the initial study represents phthalimide protected amino acids functionalized with cyclic amines as potent antimalarial agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.029

文献信息

• Entry of chiral phthalimides with significant second order nonlinear optical and piezoelectric properties
  作者：Anil K. Singh、Ram Kishan、N. Vijayan、V. Balachandran、Taruna Singh、Hemandra K. Tiwari、Brajendra K. Singh、Brijesh Rathi

  DOI：10.1039/c3ra41089g

  日期：——

  Three new chiral phthalimides have been synthesized and characterized. Phthalimides (1–3) possess an acentric structure as revealed by structural investigation. Compounds 1 and 2 crystallize in an orthorhombic system with the space group P212121, however the monoclinic system with the chiral space group P21 is observed for 3. The presence of C–H⋯O hydrogen bonds in 1–3 facilitates the construction of several supramolecular structures. Helical structural motifs are also observed. The maximum value of hyperpolarizability (β), 159.9446 × 10−30 esu calculated for compound 3 is several times greater than that of urea. On the other hand 1 and 2 have hyperpolarizabilities of 10.8063 × 10−30 and 121.9519 × 10−30 esu, respectively. The polycrystalline samples of 1–3 were assessed for a second-harmonic generation response, which was found to be 8.8, 10.2 and 9.7 mV respectively. Further, compounds 1–3 showed d33 values of 0.93, 1.97 and 1.88 pC N−1 respectively. The present investigation demonstrates chiral phthalimides as effective contenders for nonlinear optical and piezoelectric properties.

  三种新的手性邻苯二甲酰亚胺已被合成并表征。结构研究表明，邻苯二甲酰亚胺 (1-3) 具有无中心结构。化合物 1 和 2 在具有空间群 P212121 的斜方晶系中结晶，但是在 3 中观察到具有手性空间群 P21 的单斜晶系。1-3 中 C–H⋯O 氢键的存在促进了几种超分子的构建结构。还观察到螺旋结构图案。化合物 3 的超极化率 (β) 最大值为 159.9446 × 10−30 esu，是尿素的几倍。另一方面，1 和 2 的超极化率分别为 10.8063 × 10−30 和 121.9519 × 10−30 esu。对 1-3 的多晶样品的二次谐波产生响应进行了评估，结果分别为 8.8、10.2 和 9.7 mV。此外，化合物 1-3 的 d33 值分别为 0.93、1.97 和 1.88 pC N−1。目前的研究表明手性邻苯二甲酰亚胺是非线性光学和压电特性的有效竞争者。
• Design, synthesis and biological evaluation of functionalized phthalimides: A new class of antimalarials and inhibitors of falcipain-2, a major hemoglobinase of malaria parasite
  作者：Anil K. Singh、Vinoth Rajendran、Akansha Pant、Prahlad C. Ghosh、Neelu Singh、N. Latha、Sandeep Garg、Kailash C. Pandey、Brajendra K. Singh、Brijesh Rathi

  DOI：10.1016/j.bmc.2015.02.029

  日期：2015.4

  Phthalimides functionalized with cyclic amines were synthesized, characterized and screened for their in vitro antimalarial efficacy against Plasmodium falciparum (Pf3D7). Of all the listed phthalimides evaluated, 14 and 24 were identified as potent antimalarial agents as advocated by assessment of their ability to inhibit [H-3] hypoxanthine incorporation in the nucleic acid of parasites. In addition, phthalimides 14 and 24 were incubated for 60 and 90 h and an enhanced antimalarial effect was noticed with increase in time to great extent. A reduction in IC50 values was observed with increase in exposure time of the parasite to the compounds. A symmetric phthalimide, 24 possessing piperazine as linker unit was identified as the most potent antimalarial agent with IC50 values of 5.97 +/- 0.78, 2.0 +/- 1.09 and 1.1 +/- 0.75 mu M on incubation period of 42, 60 and 90 h, respectively. The abnormal morphologies such as delay in developmental stages, growth arrest and condensed nuclei of parasite were observed with the aid of microscopic studies upon exposure with 14 and 24. The evaluation of 14 and 24 against chloroquine resistant strain, (Pf7GB) of P. falciparum afforded IC50 values, 13.29 +/- 1.20 and 7.21 +/- 0.98 mu M, respectively. The combination of 24 with artemisinin (ART) showed enhanced killing of parasite against Pf3D7. Further, all phthalimides were evaluated for their activity against falcipain-2 (FP2), a major hemoglobinase of malarial parasite. The enzymatic assay afforded 6 as most active member against FP2. To the best of our knowledge this is the initial study represents phthalimide protected amino acids functionalized with cyclic amines as potent antimalarial agents. (C) 2015 Elsevier Ltd. All rights reserved.