1-(4-fluorobenzyl)-5-bromoindolin-2,3-dione | 312589-90-5

• 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: 1-(4-fluorobenzyl)-5-bromoindolin-2,3-dione
• 英文别名: Cambridge id 6060523；5-bromo-1-[(4-fluorophenyl)methyl]indole-2,3-dione
• CAS: 312589-90-5
• 化学式: C₁₅H₉BrFNO₂
• mdl: MFCD00736170
• 分子量: 334.144
• InChiKey: ANBXQIMDYMEMAX-UHFFFAOYSA-N

物化性质

• 沸点：
  476.5±55.0 °C(Predicted)
• 密度：
  1.660±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：

  1-(4-fluorobenzyl)-5-bromoindolin-2,3-dione 、 4-4-甲苯基-3-胺基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以80%的产率得到2-(5-bromo-1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-N-p-tolylhydrazine carbothioamide
  参考文献：
  名称：

  Synthesis and cytostatic evaluation of some 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide

  摘要：

  Various substituted 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide 4a-g and 2-(5-substituted-1-(4-substituted benzyl)-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide 5a-k were synthesized. The compounds were evaluated for their cytostatic activity against human Molt4/C8 and CEM T-lymphocytes as well as murine L1210 leukemia cells. Several of these compounds were endowed with low micromolar 50%-inhibitory concentration (IC50) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells were also most inhibitory against human T-lymphocyte tumor cells. 2-(5-fluoro-1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-N-p-tolylhydrazine carbothioamide (5b) emerged as the most potent cytostatic compound among the tested compounds. The encouraging cytostatic data provide an adequate rationale for further modification of these molecular scaffolds.

  DOI：

  10.1007/s00044-010-9458-3
• 作为产物：
  描述：

  4-溴苯胺 在 硫酸 、 potassium carbonate 、 sodium sulfate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-fluorobenzyl)-5-bromoindolin-2,3-dione
  参考文献：
  名称：

  Synthesis and cytostatic evaluation of some 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide

  摘要：

  Various substituted 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide 4a-g and 2-(5-substituted-1-(4-substituted benzyl)-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide 5a-k were synthesized. The compounds were evaluated for their cytostatic activity against human Molt4/C8 and CEM T-lymphocytes as well as murine L1210 leukemia cells. Several of these compounds were endowed with low micromolar 50%-inhibitory concentration (IC50) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells were also most inhibitory against human T-lymphocyte tumor cells. 2-(5-fluoro-1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-N-p-tolylhydrazine carbothioamide (5b) emerged as the most potent cytostatic compound among the tested compounds. The encouraging cytostatic data provide an adequate rationale for further modification of these molecular scaffolds.

  DOI：

  10.1007/s00044-010-9458-3

文献信息

• Marine-Inspired Bis-indoles Possessing Antiproliferative Activity against Breast Cancer; Design, Synthesis, and Biological Evaluation
  作者：Wagdy M. Eldehna、Ghada S. Hassan、Sara T. Al-Rashood、Hamad M. Alkahtani、Abdulrahman A. Almehizia、Ghada H. Al-Ansary

  DOI：10.3390/md18040190

  日期：——

  level of caspase-3 (11.7- and 9.5-fold) and p53 (15.4- and 11.75-fold). Both compounds arrested the cell cycle mainly in the G2/M phase. Furthermore, 7e and 9a displayed good selectivity toward tumor cells (S.I. = 38.7 and 18.3), upon testing of their cytotoxicity toward non-tumorigenic breast MCF-10A cells. Finally, compounds 7a, 7b, 7d, 7e, and 9a were examined for their plausible CDK2 inhibitory action

  从海洋中提取的多种吲哚和双吲哚已被确定为有前景的抗癌药物。在此，我们设计并合成了新型双吲哚系列 7a-f 和 9a-h 作为 Topsentin 和 Nortopsentin 类似物。我们的设计基于用更灵活的酰肼连接基取代天然引线中的杂环间隔基，同时保留两个外围吲哚环。检查所有合成的双吲哚对人乳腺癌（MCF-7 和 MDA-MB-231）细胞系的抗增殖作用。针对 MCF-7 细胞最有效的同源物 7e 和 9a（IC50 分别为 0.44 ± 0.01 和 1.28 ± 0.04 μM）可诱导 MCF-7 细胞凋亡（总凋亡百分比增加 23.7 倍和 16.8 倍），这一点显而易见通过膜联蛋白 V-FITC/PI 测定检测质膜磷脂酰丝氨酸的外化。这一证据得到了 Bax/Bcl-2 比率增加（与对照相比，18.65 倍和 11.1 倍）以及 caspase-3 水平（11.7 倍和 9.5 倍）和
• 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。
• Development of novel benzofuran-isatin conjugates as potential antiproliferative agents with apoptosis inducing mechanism in Colon cancer
  作者：Wagdy M. Eldehna、Rofaida Salem、Zainab M. Elsayed、Tarfah Al-Warhi、Hamada R. Knany、Rezk R. Ayyad、Thamer Bin Traiki、Maha-Hamadien Abdulla、Rehan Ahmad、Hatem A. Abdel-Aziz、Radwan El-Haggar

  DOI：10.1080/14756366.2021.1944127

  日期：2021.1.1
• <p>Antiproliferative activity and possible mechanism of action of certain 5-methoxyindole tethered C-5 functionalized isatins</p>
  作者：Maha S. Almutairi、Eman S. Hassan、Adam B. Keeton、Gary A. Piazza、Ali S. Abdelhameed、Mohamed I. Attia

  DOI：10.2147/dddt.s208241

  日期：——

  Background: Cancer is one of the most dreaded human diseases, that has become an ever-increasing health problem and is a prime cause of death globally. The potential antiproliferative activity of certain indole-isatin molecular hybrids 5a-w was evaluated in vitro against three human cancer cell lines.Methods: Standard protocols were adopted to examine the antiproliferative potential and mechanisms of compounds 5a-w. Western blot analysis was carried out on compound 5o.Results: Compounds 5a-w demonstrated in vitro antiproliferative activity in the range of 22.6-97.8%, with compounds 5o and 5w being the most active antiproliferative compounds with IC50 values of 1.69 and 1.91 mu M, which is fivefold and fourfold more potent than sunitinib (IC50 =8.11 mu M), respectively. Compound 5o was selected for in-depth pharmacological testing to understand its possible mechanism of antiproliferative activity. It caused a lengthening of the G1 phase and a reduction in the S and G2/M phases of the cell cycle and had an IC50 value of 10.4 pM with the resistant NCI-H69AR cancer cell line. Moreover, compound 5o significantly decreased the amount of phosphorylated Rb protein in a dose-dependent fashion, which was confirmed via Western blot analysis.Conclusion: The current investigation highlighted the potential antiproliferative activity of compounds 5a-w as well as the antiproliferative profile of compound 5o. These compounds can be harnessed as new lead antiproliferatives in the preclinical studies of cancer chemotherapy.
• Synthesis, characterization, antitumor, and cytotoxic activity of mononuclear Ru(II) complexes
  作者：Sreekanth Thota、Subhas Somalingappa Karki、K.N. Jayaveera、Jan Balzarini、Erik De Clercq

  DOI：10.1080/00958972.2010.534140

  日期：2010.12.20

  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.