3-[(4-methylphenylimino)methyl]indole | 105850-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[(4-methylphenylimino)methyl]indole
• 英文别名: ZINC00499454；ZINC48090221；Benzenamine, N-(1H-indol-3-ylmethylene)-4-methyl-；1-(1H-indol-3-yl)-N-(4-methylphenyl)methanimine
• CAS: 105850-59-7
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: OPUZFNDUUCKCHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  449.2±28.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-[(4-methylphenylimino)methyl]indole 、 硫代乳酸 在 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以59%的产率得到2-(1H-indol-3-yl)-5-methyl-3-p-tolylthiazolidin-4-one
  参考文献：
  名称：

  Indole-Appended Thiazolidin-4-ones 的超声辅助合成、抗惊厥活性和对接研究

  摘要：

  通过使用巯基乙酸或硫代乳酸（0.01 mol）和无水氯化锌处理希夫碱（0.01 mol）的混合物，通过环保合成方案获得了两个系列的新型吲哚基噻唑烷-4-one 衍生物 4a-j 和 5a-j使用带有合成固体探针的超声合成仪，在超声辐照下以催化量的 DMF 作为溶剂。合成化合物的结构经IR、1H NMR、13C NMR、MS和元素分析确证。新合成化合物的抗惊厥活性和神经毒性分别通过 MES 和 sc-PTZ 模型以及旋转棒试验在小鼠模型体内建立。光度计用于行为活动的筛选。这些化合物表现出有希望的抗惊厥活性；尤其，这些化合物在 MES 模型中以 100 mg/kg 的剂量显示出最大的保护作用。此外，针对钠通道受体进行了合成化合物的对接研究，并显示出与受体的良好结合相互作用。进行了计算研究以突出药效团距离映射、log p 测定和药代动力学参数。

  DOI：

  10.1002/ardp.201400148
• 作为产物：
  描述：

  吲哚 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 3-[(4-methylphenylimino)methyl]indole
  参考文献：
  名称：

  Indole-Appended Thiazolidin-4-ones 的超声辅助合成、抗惊厥活性和对接研究

  摘要：

  通过使用巯基乙酸或硫代乳酸（0.01 mol）和无水氯化锌处理希夫碱（0.01 mol）的混合物，通过环保合成方案获得了两个系列的新型吲哚基噻唑烷-4-one 衍生物 4a-j 和 5a-j使用带有合成固体探针的超声合成仪，在超声辐照下以催化量的 DMF 作为溶剂。合成化合物的结构经IR、1H NMR、13C NMR、MS和元素分析确证。新合成化合物的抗惊厥活性和神经毒性分别通过 MES 和 sc-PTZ 模型以及旋转棒试验在小鼠模型体内建立。光度计用于行为活动的筛选。这些化合物表现出有希望的抗惊厥活性；尤其，这些化合物在 MES 模型中以 100 mg/kg 的剂量显示出最大的保护作用。此外，针对钠通道受体进行了合成化合物的对接研究，并显示出与受体的良好结合相互作用。进行了计算研究以突出药效团距离映射、log p 测定和药代动力学参数。

  DOI：

  10.1002/ardp.201400148

文献信息

• Facile synthesis of indole heterocyclic compounds based micellar nano anti-cancer drugs
  作者：Imran Ali、Sofi Danish Mukhtar、Ming Fa Hsieh、Zeid A. Alothman、Abdulrahman Alwarthan

  DOI：10.1039/c8ra07060a

  日期：——

  Facile synthesis of micellar “nano” indole heterocyclic anti-cancer compounds is described. The synthesized compounds (11–23) were characterized by UV-VIS, 1H NMR, FT-IR and mass spectroscopy. The binding energies of DNA–compound adducts varied from −20.08 to −23.85 kJ mol−1, and they were stabilized by hydrophobic interactions and H-bonding. The synthesized compounds enter into minor grooves of DNA

  描述了胶束“纳米”吲哚杂环抗癌化合物的简便合成。合成的化合物( 11-23 ) 用UV-VIS、1 H NMR、FT-IR和质谱进行了表征。DNA-化合物加合物的结合能从-20.08 到-23.85 kJ mol -1不等，它们通过疏水相互作用和氢键来稳定。合成的化合物在加合物形成过程中进入 DNA 的小沟。化合物11-23的 DNA 结合常数为 1.00 至 2.00 × 10 5 M -1。记录其胶束形式的载药效率和载药含量。化合物11 , 12 , 1419和19在 670 μL mL -1的胶束浓度下显示出对 HepG2/C3A 系的优异抗癌活性（25-50%）。使用 Lipinski 的“五法则”通过药物相似性预测纳米抗癌药物的效力。总之，化合物11-23可用于治疗癌症。
• Schiff Bases of Indole-3-Carbaldehyde: Synthesis and Evaluation as Antimicrobial Agents
  作者：B. Priya、D. Utreja、A. Kalia

  DOI：10.1134/s1068162022060188

  日期：2022.12

  Abstract A series of Schiff bases of indole-3-carbaldehyde were synthesized by the condensation reaction of indole-3-carbaldehyde with different aryl amines. The reaction of indole-3-carbaldehyde with different aryl amines was carried out in the presence of glacial acetic acid. All the synthesized compounds were characterized with microanalytical data 1H and 13C NMR, FT-IR spectroscopy and Mass spectrometry

  摘要 通过吲哚-3-甲醛与不同的芳基胺的缩合反应合成了一系列的吲哚-3-甲醛席夫碱。吲哚-3-甲醛与不同芳基胺的反应是在冰醋酸存在下进行的。用微量分析数据1 H 和13 C NMR、FT-IR 光谱和质谱对所有合成的化合物进行了表征，并筛选了它们对细菌菌株Dickeya和真菌培养尖孢镰刀菌的体外微生物活性。采用琼脂井扩散法。用于细菌和真菌培养的标准分别是多菌灵和庆大霉素。结果表明，合成的席夫碱N -((indol-1 H -3-yl)methylene)-4-nitrobenzenamine 对细菌 (MIC = 2000 µg/mL) 和真菌 (MFC = 5000) 均表现出最大活性。 µg/mL) 培养物与所有其他合成化合物相比。
• N-1 and C-3 substituted indole Schiff bases as selective COX-2 inhibitors: Synthesis and biological evaluation
  作者：Jatinder Kaur、Atul Bhardwaj、Zhangjian Huang、Edward E. Knaus

  DOI：10.1016/j.bmcl.2012.01.130

  日期：2012.3

  A group of N-1 and C-3 disubstituted-indole Schiff bases bearing an indole N-1 (R' = H, CH2Ph, COPh) substituent in conjunction with a C-3-CH=N-C6H4-4-X (X = F, Me, CF3, Cl) substituent were synthesized and evaluated as inhibitors of cyclooxygenase (COX) isozymes (COX-1/COX-2). Within this group of Schiff bases, compounds 15 (R-1 = CH2Ph, X = F), 17 (R-1 = CH2Ph, X = CF3), 18 (R-1 = COPh, X = F) and 20 (R-1 = COPh, X = CF3) were identified as effective and selective COX-2 inhibitors (COX-2 IC50's = 0.32-0.84 mu M range; COX-2 selectivity index (SI) = 113 to > 312 range). 1-Benzoyl-3-[(4-trifluoromethylphenylimino) methyl]indole (20) emerged as the most potent (COX-1 IC50 > 100 mu M; COX-2 IC50 = 0.32 mu M) and selective (SI >312) COX-2 inhibitor. Furthermore, compound 20 is a selective COX-2 inhibitor in contrast to the reference drug indomethacin that is a potent and selective COX-1 inhibitor (COX-1 IC50 = 0.13 mu M; COX-2 IC50 = 6.9 mu M, COX-2 SI = 0.02). Molecular modeling studies employing compound 20 showed that the phenyl CF3 substituent attached to the C=N spacer is positioned near the secondary pocket of the COX-2 active site, the C=N nitrogen atom is hydrogen bonded (N center dot center dot center dot NH = 2.85 angstrom) to the H90 residue, and the indole N-1 benzoyl is positioned in a hydrophobic pocket of the COX-2 active site near W387. (C) 2012 Elsevier Ltd. All rights reserved.
• Reactivity of 3-Imino-Functionalized Indoles with Rare-Earth-Metal Amides: Unexpected Substituent Effects on C–H Activation Pathways and Assembly of Rare-Earth-Metal Complexes
  作者：Xiancui Zhu、Yang Li、Yun Wei、Shaowu Wang、Shuangliu Zhou、Lijun Zhang

  DOI：10.1021/acs.organomet.6b00221

  日期：2016.6.13

  The reactivities of different 3-imino-fiinctionalized indoles with rare -earth -metal amides [(Me3Si)(2)N](3)RE(mu-Cl)Li(THF)(3) were studied to reveal unexpected substituent effects on C H bond activation pathways, leading to the formation of unusual rare -earth -metal complexes. The reactions of 3-(tert-butylimino)indole with [(Me3Si)(2)N](3)RE(mu-ClLi(THF)(3) produced tetranuclear rare -earth -metal complexes eta(1):mu(2)eta(1):eta(1)):eta(1)-3-(tBuN=CH)C8H4N]RE,(mu(2)-Cl-2)HF)[N(SiMe3)(2)](eta(1):eta 1(7)[mu(3)(tBuN=-CH)C8H5NbLi)}(2) (RE = Ho (la), Er (lb)), incorporating a unique indoly1-1,2-dianion through sp2 C H activation bonded with the central metal in eta(1) :(mu(2)-eta(1) :eta(1)) ions of 3,(phenylimino)indole with [(Me3Si)(2)N](3)RE(mu-Cl)Li(THF)(3) afforded novel binuclear complexes formulated as 3-[PhNCH(CH2SiMe2)N(SiMe3)]C8H5NRE(THF)(t(2)-COLi(THF)(2)](2) (RE = Y (2a), Sm (2b), Dy (2c), Yb (2d)) through an unexpected sp3 C H bond activation with subsequent C C bond coupling reactions. Treatment of 3-(2-methylphenylimino)indole or 3-(4methylphenylimino)indole with [(Me3Si)(2)N](3)Yb(y-Cl)Li(THF)(3) generated the corresponding dinuclear rare -earth -metal amido complexes (3-[(2-MePh)NCH(CH2SiMe2)N(SiMe3)]C8H5NYb(THF)(y(2)-COLi(THF)(2)}(2) (3) and 3-[(4-MePh)NCH(CH2SiMe2)N(SiMe3)]C8H5NYb(THF)(eta(2)-COLi(THF)(2)](2) (4), following the same pathway for the formation of complexes 2a d. Treatment of 3-(4-tert-butylphenylimino)indole with [(Me3SO2N](3)RE(eta-COLi(THF)(3) afforded new hexanuclear rareearth -metal complexes 3-[(4-tBu-Ph)NHCH(CH2SiMe2)N(SiMe3)]C8H5NREN(SiIVIe(3))(2)}(6) (RE = Dy (5a), Ho (5b), Er (5c)) via sp3 C-H bond activation followed by C-C bond coupling reactions. In contrast, under the same conditions as those for the preparation of 5, the reaction with the corresponding yttrium complex provided the new heterohexayttrium complex 3-[(4-tBuPh)NCH(CH2SiMe2)N(SiMe3)]C8H5NYN(SiMe3)21i(THF)}(6) (6), having a 4-tBu-anilido moiety. All of these complexes were fully characterized by elemental analysis, spectroscopic methods, and X-ray structure analysis. Plausible pathways for the formation of these different rare -earth -metal complexes were proposed.
• Ultrasound-Assisted Synthesis, Anticonvulsant Activity, and Docking Study of Indole-Appended Thiazolidin-4-ones
  作者：Anna Pratima G. Nikalje、Sameer I. Shaikh、Abhineet Mulay、Firoz A. K. Khan、Jaiprakash N. Sangshetti、Shoaib Shaikh

  DOI：10.1002/ardp.201400148

  日期：2014.10

  NMR, 13C NMR, MS, and elemental analysis. The anticonvulsant activity and neurotoxicity of the newly synthesized compounds were established by MES and sc‐PTZ model and by rotarod test, respectively, in vivo using mouse models. The actophotometer was used for the screening of behavioral activity. The compounds exhibited promising anticonvulsant activity; especially, the compounds showed maximum protection

  通过使用巯基乙酸或硫代乳酸（0.01 mol）和无水氯化锌处理希夫碱（0.01 mol）的混合物，通过环保合成方案获得了两个系列的新型吲哚基噻唑烷-4-one 衍生物 4a-j 和 5a-j使用带有合成固体探针的超声合成仪，在超声辐照下以催化量的 DMF 作为溶剂。合成化合物的结构经IR、1H NMR、13C NMR、MS和元素分析确证。新合成化合物的抗惊厥活性和神经毒性分别通过 MES 和 sc-PTZ 模型以及旋转棒试验在小鼠模型体内建立。光度计用于行为活动的筛选。这些化合物表现出有希望的抗惊厥活性；尤其，这些化合物在 MES 模型中以 100 mg/kg 的剂量显示出最大的保护作用。此外，针对钠通道受体进行了合成化合物的对接研究，并显示出与受体的良好结合相互作用。进行了计算研究以突出药效团距离映射、log p 测定和药代动力学参数。