methyl 2-(5'-bromo-2'-oxospiro[[1,3]dioxolane-2,3'-indoline]-1'-yl)acetate | 133189-11-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(5'-bromo-2'-oxospiro[[1,3]dioxolane-2,3'-indoline]-1'-yl)acetate
• 英文别名: Methyl 2-(5'-bromo-2'-oxospiro[1,3-dioxolane-2,3'-indole]-1'-yl)acetate
• CAS: 133189-11-4
• 化学式: C₁₃H₁₂BrNO₅
• 分子量: 342.146
• InChiKey: XXWJKZJQLIWGGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(5'-bromo-2'-oxospiro[[1,3]dioxolane-2,3'-indoline]-1'-yl)acetate 在 N-甲基吗啉 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 13.5h， 生成 methyl (S)-2-(2-(5-bromo-2-oxospiro[indoline-3,2'-[1,3]dioxolan]-1-yl)acetamido)-2-phenylacetate
  参考文献：
  名称：

  Novel indoline-2,3-dione derivatives as inhibitors of aminopeptidase N (APN)

  摘要：

  Aminopeptidase N (APN/CD13), as a zinc-containing ectoenzyme, plays a critical role in the process of tumor angiogenesis, invasion and metastasis. Through the docking-based virtual screening of chemical databases and the further activity assay, we discovered that compound 10c exhibits potent and selective inhibitory ability towards APN. In addition, a series of indoline-2,3-dione derivates have been designed and synthesized as APN inhibitors. The results of preliminary activity evaluation showed that compound 12a (IC50 = 0.074 +/- 0.0026 mu M) exhibited the best inhibitory activity against APN, which could be used for further anticancer agent research. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.06.024
• 作为产物：
  描述：

  N-(4-bromophenyl)-2-(hydroxyimino) acetamide 在 硫酸 、 四丁基溴化铵 、 potassium carbonate 、 对甲苯磺酸 、 potassium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 11.5h， 生成 methyl 2-(5'-bromo-2'-oxospiro[[1,3]dioxolane-2,3'-indoline]-1'-yl)acetate
  参考文献：
  名称：

  Novel indoline-2,3-dione derivatives as inhibitors of aminopeptidase N (APN)

  摘要：

  Aminopeptidase N (APN/CD13), as a zinc-containing ectoenzyme, plays a critical role in the process of tumor angiogenesis, invasion and metastasis. Through the docking-based virtual screening of chemical databases and the further activity assay, we discovered that compound 10c exhibits potent and selective inhibitory ability towards APN. In addition, a series of indoline-2,3-dione derivates have been designed and synthesized as APN inhibitors. The results of preliminary activity evaluation showed that compound 12a (IC50 = 0.074 +/- 0.0026 mu M) exhibited the best inhibitory activity against APN, which could be used for further anticancer agent research. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.06.024

文献信息

• Design, synthesis and anti-tumor activity study of novel histone deacetylase inhibitors containing isatin-based caps and o -phenylenediamine-based zinc binding groups
  作者：Shuai Gao、Jie Zang、Qianwen Gao、Xuewu Liang、Qinge Ding、Xiaoyang Li、Wenfang Xu、C. James Chou、Yingjie Zhang

  DOI：10.1016/j.bmc.2017.03.036

  日期：2017.6

  As a hot topic of epigenetic studies, histone deacetylases (HDACs) are related to lots of diseases, especially cancer. Further researches indicated that different HDAC isoforms played various roles in a wide range of tumor types. Herein a novel series of HDAC inhibitors with isatin-based caps and o-phenylenediamine-based zinc binding groups have been designed and synthesized through scaffold hopping

  作为表观遗传学研究的热门话题，组蛋白脱乙酰基酶（HDAC）与许多疾病，尤其是癌症有关。进一步的研究表明，不同的HDAC亚型在多种肿瘤类型中起着不同的作用。在本文中，已经设计并通过支架跳跃策略合成了一系列具有基于靛红的帽和基于邻苯二胺的锌结合基团的HDAC抑制剂。在这些化合物中，与阳性对照恩替司他（MS-275）相比，最有效的化合物9n对多种肿瘤细胞系表现出相似的，甚至不是更好的HDAC抑制作用和抗增殖活性。此外，与MS-275（HDAC1、2和3的IC50值分别为0.163、0.396和0.605µM）相比，化合物9n的HDAC1、2和3的IC50值分别为0.032、0.256和0.311µM，
• Isatin derivatives as a new class of aldose reductase inhibitors with antioxidant activity
  作者：Wenchao Liu、Huan Chen、Xiaonan Zhang、Xin Zhang、Long Xu、Yanqi Lei、Changjin Zhu、Bing Ma

  DOI：10.1007/s00044-021-02751-4

  日期：2021.8

  showed potent antioxidant activity. Particularly, the phenolic compound 9h demonstrated similar antioxidant activity with the well-known antioxidant Trolox. Structure-activity relationship and molecular docking studies showed that the acetic acid group at N1 and C5 p-hydroxystyryl side chain were the key structures to increase the aldose reductase inhibitory activity and antioxidant activity.

  在这项工作中，靛红被用作支架来设计具有抗氧化活性的醛糖还原酶抑制剂。大多数靛红衍生物在抑制醛糖还原酶 (ALR2) 方面表现出色，IC 50值在亚微摩尔水平，( E )-2-(5-(4-甲氧基苯乙烯基)-2,3-二氧吲哚-1 -yl) 乙酸(9g ) 被鉴定为最有效，IC 50值为 0.015 μM。此外，在靛红 C5 位具有苯乙烯基侧链的化合物9a - h显示出有效的抗氧化活性。特别是酚类化合物9h表现出与众所周知的抗氧化剂 Trolox 相似的抗氧化活性。构效关系和分子对接研究表明，N1和C5对羟基苯乙烯基侧链的乙酸基团是提高醛糖还原酶抑制活性和抗氧化活性的关键结构。
• Design, synthesis and preliminary biological evaluation of indoline-2,3-dione derivatives as novel HDAC inhibitors
  作者：Kang Jin、Shanshan Li、Xiaoguang Li、Jian Zhang、Wenfang Xu、Xuechen Li

  DOI：10.1016/j.bmc.2015.05.048

  日期：2015.8

  Histone deacetylases (HDACs) are zinc-dependent or NAD+ dependent enzymes and play a critical role in the process of tumor development. Herein a series of indoline-2,3-dione derivatives have been designed and synthesized as potential HDACs inhibitors. The preliminary biological evaluation showed that most compounds synthesized have exhibited moderate Hela cell nuclear extract inhibitory activities, among which compound 25a (IC50 = 10.13 nM) has shown the best efficacy. The anti-proliferative activities of some of these compounds were also discussed. (C) 2015 Published by Elsevier Ltd.
• Novel indoline-2,3-dione derivatives as inhibitors of aminopeptidase N (APN)
  作者：Kang Jin、Xiaopan Zhang、Chunhua Ma、Yingying Xu、Yumei Yuan、Wenfang Xu

  DOI：10.1016/j.bmc.2012.06.024

  日期：2013.5

  Aminopeptidase N (APN/CD13), as a zinc-containing ectoenzyme, plays a critical role in the process of tumor angiogenesis, invasion and metastasis. Through the docking-based virtual screening of chemical databases and the further activity assay, we discovered that compound 10c exhibits potent and selective inhibitory ability towards APN. In addition, a series of indoline-2,3-dione derivates have been designed and synthesized as APN inhibitors. The results of preliminary activity evaluation showed that compound 12a (IC50 = 0.074 +/- 0.0026 mu M) exhibited the best inhibitory activity against APN, which could be used for further anticancer agent research. (C) 2012 Published by Elsevier Ltd.