1-(4-chlorobenzyl)indolin-2-one | 34998-70-4

• 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-chlorobenzyl)indolin-2-one
• 英文别名: 1-[(4-chlorophenyl)methyl]-3H-indol-2-one
• CAS: 34998-70-4
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: WQPUQUMINADXQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-chlorobenzyl)indolin-2-one 、 3,4,5-三甲氧基苯甲醛 在 哌啶 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (3Z)-1-[(4-chlorophenyl)methyl]-3-[(3,4,5-trimethoxyphenyl)methylidene]indol-2-one
  参考文献：
  名称：

  Cytotoxic activities of substituted 3-(3,4,5-trimethoxybenzylidene)-1,3-dihydroindol-2-ones and studies on their mechanisms of action

  摘要：

  The synthesis of new trimethoxybenzylidene-indolinones is reported. Their cytotoxic activity was evaluated according to Developmental Therapeutics Program, National Cancer Institute, Bethesda, MD, drug screen protocols. The study of the mechanism of action suggests that inhibition of Nox4 in B1647 cells (acute myeloid leukemia) could contribute to the antiproliferative effect of some compounds. Moreover, inhibition of tubulin assembly was observed for the most cytotoxic compound, and the structural basis for this activity was delineated by binding models. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.033
• 作为产物：
  描述：

  N-phenyl-C-(4-chlorophenyl)nitrone 在 sodium cyanoborohydride 、 platinum(II) chloride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 1.83h， 生成 1-(4-chlorobenzyl)indolin-2-one
  参考文献：
  名称：

  Platinum-Catalyzed Oxoarylations of Ynamides with Nitrones

  摘要：

  A new platinum-catalyzed oxoarylation of ynamides with nitrones is reported. Cascade sequences for the synthesis of indolin-2-ones via NaBH3CN reduction in situ of the initially formed oxoarylation products are also developed.

  DOI：

  10.1021/ol302621z

文献信息

• Iron-catalyzed cross-dehydrogenative coupling of indolin-2-ones with active methylenes for direct carbon–carbon double bond formation
  作者：Zhi-Yu Tan、Ke-Xin Wu、Lu-Shan Huang、Run-Shi Wu、Zheng-Yu Du、Da-Zhen Xu

  DOI：10.1039/c9gc03639c

  日期：——

  The iron-catalyzed cross-dehydrogenative coupling (CDC) of C(sp3)–H/C(sp3)–H bonds to afford olefins by 4H elimination is described. This method employs air (molecular oxygen) as an ideal oxidant, and is performed under mild, ligand-free and base-free conditions. H2O is the only byproduct. Good tolerance of functional groups and high yields have also been achieved. Preliminary mechanistic investigations

  描述了铁催化的C（sp 3）–H / C（sp 3）–H键的交叉脱氢偶联（CDC），可通过4H消除得到烯烃。该方法使用空气（分子氧）作为理想的氧化剂，并且在温和，无配体和无碱的条件下进行。H 2 O是唯一的副产物。还获得了对官能团的良好耐受性和高产率。初步的机械研究表明，目前的转变涉及一个根本过程。
• Microwave-Assisted Sequential Amide Bond Formation and Intramolecular Amidation:  A Rapid Entry to Functionalized Oxindoles
  作者：Rajamohan R. Poondra、Nicholas J. Turner

  DOI：10.1021/ol0473804

  日期：2005.3.1

  two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueous conditions. In the case of alkylamines, the procedure can be carried out as a one-pot process without isolation of the intermediate amide. [structure: see text]

  已经开发了用于合成N-取代的羟吲哚的通用方法。此两步过程涉及在2-卤代芳酸与各种烷基胺和苯胺之间首先形成微波辅助的酰胺键，然后在水性条件下进行钯催化的分子内酰胺化反应。在烷基胺的情况下，该过程可以一锅法进行，而无需分离中间体酰胺。[结构：见文字]
• Identification of a new bisindolinone arresting IGROV1 cells proliferation
  作者：Rita Morigi、Chiara Zalambani、Giovanna Farruggia、Laura Verardi、Daniele Esposito、Alberto Leoni、Francesca Borsetti、Manuela Voltattorni、Laura Zambonin、Luca Pincigher、Natalia Calonghi、Alessandra Locatelli

  DOI：10.1016/j.ejmech.2024.116365

  日期：2024.5

  were submitted to the National Cancer Institute for evaluation of antitumor activity in human cell lines. In particular, compound showed remarkable selectivity against IGROV1, an ovarian cancer cell line, without affecting healthy human fibroblast cells. Analyses of cytotoxicity, cell proliferation, cell migration, epigenetic changes, gene expression, and DNA damage were performed to obtain detailed

  在初步筛选中，一系列新型 Knoevenagel 加合物被提交给国家癌症研究所，用于评估人类细胞系的抗肿瘤活性。特别是，该化合物对 IGROV1（一种卵巢癌细胞系）表现出显着的选择性，而不影响健康的人类成纤维细胞。对细胞毒性、细胞增殖、细胞迁移、表观遗传变化、基因表达和 DNA 损伤进行分析，以获得有关其抗肿瘤特性的详细信息。我们的结果表明，它会导致增殖停滞、运动性降低、组蛋白过度乙酰化、细胞周期蛋白 D1 和整合素 β1 基因转录的 α5 亚基下调。此外，治疗会降低细胞周期蛋白 D1 的转录物和蛋白水平，从而增加对电离辐射的敏感性，并导致与细胞周期蛋白 D1 基因沉默相当的 DNA 损伤。
• Platinum-Catalyzed Oxoarylations of Ynamides with Nitrones
  作者：Sabyasachi Bhunia、Chin-Jung Chang、Rai-Shung Liu

  DOI：10.1021/ol302621z

  日期：2012.11.2

  A new platinum-catalyzed oxoarylation of ynamides with nitrones is reported. Cascade sequences for the synthesis of indolin-2-ones via NaBH3CN reduction in situ of the initially formed oxoarylation products are also developed.
• Cytotoxic activities of substituted 3-(3,4,5-trimethoxybenzylidene)-1,3-dihydroindol-2-ones and studies on their mechanisms of action
  作者：Aldo Andreani、Massimiliano Granaiola、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Francesco Vieceli Dalla Sega、Cecilia Prata、Tam L. Nguyen、Ruoli Bai、Ernest Hamel

  DOI：10.1016/j.ejmech.2013.03.033

  日期：2013.6

  The synthesis of new trimethoxybenzylidene-indolinones is reported. Their cytotoxic activity was evaluated according to Developmental Therapeutics Program, National Cancer Institute, Bethesda, MD, drug screen protocols. The study of the mechanism of action suggests that inhibition of Nox4 in B1647 cells (acute myeloid leukemia) could contribute to the antiproliferative effect of some compounds. Moreover, inhibition of tubulin assembly was observed for the most cytotoxic compound, and the structural basis for this activity was delineated by binding models. (C) 2013 Elsevier Masson SAS. All rights reserved.