5-chloro-1-(p-fluorobenzyl)indoline-2,3-dione | 898925-13-8

• 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: 5-chloro-1-(p-fluorobenzyl)indoline-2,3-dione
• 英文别名: 5-chloro-1-(4-fluorobenzyl)-1H-indole-2,3-dione；5-chloro-1-[(4-fluorophenyl)methyl]indole-2,3-dione
• CAS: 898925-13-8
• 化学式: C₁₅H₉ClFNO₂
• 分子量: 289.693
• InChiKey: PCBYGEHDFLFTNB-UHFFFAOYSA-N

物化性质

• 沸点：
  461.9±55.0 °C(Predicted)
• 密度：
  1.470±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-1-(p-fluorobenzyl)indoline-2,3-dione 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 2-(5-chloro-1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  Synthesis, characterization, antitumor, and cytotoxic activity of mononuclear Ru(II) complexes

  摘要：

  In the search for antitumor active metal complexes several ruthenium complexes have been reported to be promising. A series of mononuclear Ru(II) complexes, [Ru(T)2(S)]2+, where T = 2,2'-bipyridine/1,10-phenanthroline and S = CH3-bitsz, Cl-bitsz, Br-bitsz, tmtsz, dmtsz, have been prepared and characterized by UV-Vis, IR, 1H-NMR, FAB-mass spectroscopy, and elemental analysis. The complexes were subjected to invivo anticancer activity against a transplantable murine tumor cell line Ehrlich's ascitic carcinoma (EAC) and invitro cytotoxic activity against human cancer cell line Molt 4/C8, CEM, and murine tumor cell line L1210. Ruthenium complexes showed promising biological activity especially in decreasing tumor volume and viable ascitic cell counts. Treatment with these complexes prolonged the life span of EAC-tumor-bearing mice by 10-48%. Invitro evaluation of these ruthenium complexes revealed cytotoxic activity from 0.21 to 24 mu mol L-1 against Molt 4/C8, 0.16-19 mu mol L-1 against CEM, and 0.75-32 mu mol L-1 against L1210 cell proliferation, depending on the nature of the compound.

  DOI：

  10.1080/00958972.2010.534140
• 作为产物：
  描述：

  N-(4-氯苯基)-2-(羟基亚胺)乙酰胺 在 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-chloro-1-(p-fluorobenzyl)indoline-2,3-dione
  参考文献：
  名称：

  Synthesis, characterization, antitumor, and cytotoxic activity of mononuclear Ru(II) complexes

  摘要：

  In the search for antitumor active metal complexes several ruthenium complexes have been reported to be promising. A series of mononuclear Ru(II) complexes, [Ru(T)2(S)]2+, where T = 2,2'-bipyridine/1,10-phenanthroline and S = CH3-bitsz, Cl-bitsz, Br-bitsz, tmtsz, dmtsz, have been prepared and characterized by UV-Vis, IR, 1H-NMR, FAB-mass spectroscopy, and elemental analysis. The complexes were subjected to invivo anticancer activity against a transplantable murine tumor cell line Ehrlich's ascitic carcinoma (EAC) and invitro cytotoxic activity against human cancer cell line Molt 4/C8, CEM, and murine tumor cell line L1210. Ruthenium complexes showed promising biological activity especially in decreasing tumor volume and viable ascitic cell counts. Treatment with these complexes prolonged the life span of EAC-tumor-bearing mice by 10-48%. Invitro evaluation of these ruthenium complexes revealed cytotoxic activity from 0.21 to 24 mu mol L-1 against Molt 4/C8, 0.16-19 mu mol L-1 against CEM, and 0.75-32 mu mol L-1 against L1210 cell proliferation, depending on the nature of the compound.

  DOI：

  10.1080/00958972.2010.534140

文献信息

• Experimental and Computational Evaluation of Piperonylic Acid Derived Hydrazones Bearing Isatin Moieties as Dual Inhibitors of Cholinesterases and Monoamine Oxidases
  作者：M. S. Vishnu、V. Pavankumar、Sandeep Kumar、A. Senthil Raja

  DOI：10.1002/cmdc.201900277

  日期：2019.7.17

  for their inhibitory activity against the enzymes acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and monoamine oxidases A and B (MAO‐A/B). The results of in vitro studies revealed IC50 values in the micromolar range, with the majority of the compounds showing selectivity for the MAO‐B isoform. N‐[2‐Oxo‐1‐(prop‐2‐ynyl)indolin‐3‐ylidene]benzo[d][1,3]dioxole‐5‐carbohydrazide (3) was identified

  合成了一组具有可变的isatin部分的胡椒基，并评估了它们对乙酰胆碱酯酶（AChE），丁酰胆碱酯酶（BChE）以及单胺氧化酶A和B（MAO-A / B）的抑制活性。体外研究结果表明，IC 50值在微摩尔范围内，大多数化合物对MAO-B同工型具有选择性。N- [2-氧代-1-（丙-2-炔基）吲哚-3-基]苯并[ d ] [1,3]二恶唑-5-碳酰肼（3）被鉴定为铅AChE抑制剂，IC 50 = 0.052±0.006μ米。N -[（3 E）-5-氯-2-氧-2,3-二氢-1 H-吲哚-3-亚基] -2- ħ -1,3-苯并二氧杂环戊-5-碳酰肼（2）为引MAO-B抑制剂，IC 50 = 0.034±0.007μ米，并表现出对MAO-B的50倍更大的选择性通过MAO-A。动力学研究表明，化合物2和3分别显示出对AChE和MAO-B的竞争性和可逆性抑制。分子对接研究揭示了在所研究的酶的活性位点口
• Synthesis of isatin based N1-alkylated 3-β-C-glycoconjugated-oxopropylidene oxindoles as potent antiplasmodial agents
  作者：Ravi Kumar Thakur、Prince Joshi、Kapil Upadhyaya、Kartikey Singh、Gaurav Sharma、Sanjeev K. Shukla、Renu Tripathi、Rama Pati Tripathi

  DOI：10.1016/j.ejmech.2018.11.008

  日期：2019.1

  In an attempt to develop new antimalarial drugs, we have synthesized a new class of N-alkylated 3-glycoconjugated-oxopropylidene oxindoles starting from substituted isatins and glucopyranosyl propanone via a well-known cross-aldol reaction followed by dehydration. The newly synthesized compounds were screened for their in vitro antiplasmodial activity, and among all the compounds 9g, 9f, 9b, 8d, 9d

  为了开发新的抗疟疾药物，我们已经合成了新的一类N-烷基化的3-糖基共轭-氧亚丙基氧吲哚，它是由取代的靛红和葡萄糖基吡喃糖基丙酮通过众所周知的交叉羟醛反应然后脱水而合成的。筛选了新合成的化合物的体外抗血浆活性，在所有化合物9g，9f，9b，8d，9d，9c和9e中显示出有效的活性，对氯喹的IC 50值在0.1–0.3μM范围内（CQ）敏感的Pf 3D7菌株，而化合物9d，9b，9e，8c，8f，9c和9a显示出对CQ耐药的Pf K1菌株的IC 50值在0.1-0.4μM范围内的有希望的活性，甚至比标准药物氯喹的IC 50值为0.5更好。微米
• Synthesis, spectroscopic investigations, DFT studies, molecular docking and antimicrobial potential of certain new indole-isatin molecular hybrids: Experimental and theoretical approaches
  作者：Maha S. Almutairi、Azza S. Zakaria、P. Primsa Ignasius、Reem I. Al-Wabli、Isaac Hubert Joe、Mohamed I. Attia

  DOI：10.1016/j.molstruc.2017.10.025

  日期：2018.2

  using FT-IR and FT-Raman with the aid of density functional theory approach. The natural bond orbital analysis as well as HOMO and LUMO molecular orbitals investigations of compound 5h were carried out to explore its possible intermolecular delocalization or hyperconjugation and its possible interactions with the target protein. Molecular docking of compound 5h predicted its binding mode with the fungal

  摘要 吲哚-靛红分子杂化物 5a-i 已被合成并通过不同的光谱方法表征，以作为针对一组革兰氏阳性菌、革兰氏阴性菌和霉菌的新型抗菌剂进行评估。选择化合物 5h 作为制备的化合物 5a-i 的代表性实例进行计算研究。借助密度泛函理论方法，使用 FT-IR 和 FT-Raman 研究了其振动特性。进行了化合物5h的自然键轨道分析以及HOMO和LUMO分子轨道研究，以探索其可能的分子间离域或超共轭及其与靶蛋白可能的相互作用。化合物 5h 的分子对接预测了其与真菌靶蛋白的结合模式。
• Me-BIPAM for the Synthesis of Optically Active 3-Aryl-3-hydroxy-2-oxindoles by Ruthenium-catalyzed Addition of Arylboronic Acids to Isatins
  作者：Yasunori Yamamoto、Masaaki Yohda、Tomohiko Shirai、Hajime Ito、Norio Miyaura

  DOI：10.1002/asia.201200481

  日期：2012.10

  arylboronic acids to isatins. Asymmetric synthesis of 3‐aryl‐3‐hydroxy‐2‐oxindoles by 1,2‐addition of arylboronic acids to isatins was carried out in the presence of [RuCl2(PPh3)3]/(R,R)‐Me‐BIPAM and KF, resulting in an enantioselectivity as high as 90 % ee. It was found that the reaction with N‐protected isatins proceeds with high yields and good enantioselectivities. The best protective groups on the

  一个手性的O-连接的C 2-对称的二齿亚磷酰胺（Me-BIPAM）被发现对于钌催化的芳基硼酸到靛红的加成反应是有效的。在[RuCl 2（PPh 3）3 ] /（R，R）-Me-的存在下，通过将芳基硼酸1,2-加成到靛红中进行3-芳基-3-羟基-2-氧吲哚的不对称合成。BIPAM和KF，对映选择性高达90％ee。发现与N保护的靛红的反应以高收率和良好的对映选择性进行。氮原子上的最佳保护基根据芳环上的取代基而不同。使用一个与其他基团相比，N-苄基在许多底物中均具有出色的对映选择性。
• One Pot Synthesis and Biological Activity Studies of New Spirooxindoles
  作者：Amir Reza Omidvar、Sakineh Asghari、Leila Ghasempour、Mojtaba Mohseni

  DOI：10.1002/cbdv.202301942

  日期：2024.6

  data, the synthesized compounds show more activity against Gram-positive bacteria than Gram-negative bacteria. Also, the antioxidant activity of these compounds was measured using the DPPH radical scavenging test method, which showed good to excellent activity (59.65–94.03 %). Among them, the chlorinated derivatives (4 f–j) exhibited more antioxidant activity (84.85–94.03 %) than the other compounds

  本文报道了使用 5-甲基-2-硫代乙内酰脲、靛红衍生物和丙二腈以良好到高产率 (65-90%) 的一锅法合成了 10 种新型螺吲哚。通过1 H-NMR、 13 C NMR、FT-IR 和质谱数据推导了合成化合物的结构。基于Kirby-Bauer法，评估了化合物对两种革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）和两种革兰氏阴性菌（大肠杆菌和铜绿假单胞菌）的抗菌活性。根据获得的数据，合成的化合物对革兰氏阳性菌的活性高于对革兰氏阴性菌的活性。此外，使用DPPH自由基清除测试方法测量了这些化合物的抗氧化活性，结果显示出良好至优异的活性（59.65-94.03%）。其中，氯化衍生物（ 4f - j）比其他化合物（ 4a - e ）（56.65-74.4％）表现出更高的抗氧化活性（84.85-94.03％），甚至比抗坏血酸作为标准抗氧化化合物（82.3％） ）。