5'-methylspiro[[1,3]dioxolane-2,3'-indolin]-2'-one | 75822-58-1

• 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'-methylspiro[[1,3]dioxolane-2,3'-indolin]-2'-one
• 英文别名: 5′-methylspiro[[1,3]dioxolane-2,3′-indolin]-2′-one；5'-Methyl-spiro[1,3-dioxolane-2,3'-[3H]indol]-2'(1'H)-one；3-(1',3'-dioxolynyl)-5-methyl-1,3-dihydro-2H-indol-2-one；5'-methylspiro[1,3-dioxolane-2,3'-1H-indole]-2'-one
• CAS: 75822-58-1
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: WEKVUWUYWCGLCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-methylspiro[[1,3]dioxolane-2,3'-indolin]-2'-one 在 4-磺酰杯[4]芳烃 作用下， 以 水 为溶剂， 反应 0.08h， 生成 5-甲基靛红
  参考文献：
  名称：

  Novel Greener Microwave-Assisted Deprotection Methodology for the 1,3-Dioxolane Ketal of Isatin Using Calix[n]arenes

  摘要：

  在这项工作中，评估了p-磺酸基-杯[ n ]芳烃和微波能量的联合使用，以优异的结果水解异喹啉的1,3-二氧兰酮缩合物。这是第一次将p-磺酸基-杯[n]芳烃用作酮缩水解反应的催化剂，并报道了异喹啉酮羰基去保护的结果。在160℃时，加入2.5mol%的p-磺酸基-杯[4,6]芳烃，可以在10分钟内将这种酮缩物转化率达到96%以上，另一个优势是使用水作为溶剂。这种催化体系（含有p-磺酸基-杯[4]芳烃的水相）被重复使用了五个循环，保持了96%以上的转化率。使用p-甲苯磺酸和p-羟基苯磺酸作为催化剂的可重复使用的体系是不可行的，因为两者都会随反应产物被提取到有机相中。还评估了在芳环中具有不同取代基（CH3，I，Br，Cl，F，NO2）的异喹啉的1,3-二氧兰酮缩合物的水解反应。使用2.5mol%的p-磺酸基-杯[4]芳烃，在160℃下，5-甲基异喹啉的保护基在5分钟内转化率为73%。相比之下，使用相同条件，5-硝基异喹啉的酮缩物在40分钟后达到了80%的转化率。

  DOI：

  10.21577/0103-5053.20210165
• 作为产物：
  描述：

  2-hydroxyimino-N-p-tolyl-acetamide 在 硫酸 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.5h， 生成 5'-methylspiro[[1,3]dioxolane-2,3'-indolin]-2'-one
  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

• Enantioselective N-alkylation of isatins and synthesis of chiral N-alkylated indoles
  作者：Xiaowei Dou、Weijun Yao、Chunhui Jiang、Yixin Lu

  DOI：10.1039/c4cc04586f

  日期：——

  Asymmetric N-alkylations of isatins with enals were shown to be feasible via a prolinol-catalyzed iminium activation, and N-alkylated isatins and indoles were obtained in good yields and with excellent enantioselectivity.

  通过脯氨醇催化的亚胺活化，显示了使用烯醛对异喹啉进行不对称N-烷基化是可行的，得到了产率较高且具有优异对映选择性的N-烷基化异喹啉和吲哚。
• Composition containing an oxoindole compound
  申请人：Aktiebolaget Astra

  公开号：US05585378A1

  公开（公告）日：1996-12-17

  The present invention relates to an oxindole compound having the formula 5-cyclohexyl-1,3-dihydro-1-[2-[4-(phenylmethyl)-1-piperazinyl]ethyl]-2H-in dol-2-one for the prevention or treatment of cognitive dysfunctions.

  本发明涉及一种具有下列结构式的氧吲哚化合物，用于预防或治疗认知功能障碍：5-环己基-1,3-二氢-1-[2-[4-(苯甲基)-1-哌嗪基]乙基]-2H-吲哚-2-酮。
• 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.
• Potential anticonvulsants. 11. Synthesis and anticonvulsant activity of spiro[1,3-dioxolane-2,3'-indolin]-2'-ones and structural analogs
  作者：Milind Rajopadhye、Frank D. Popp

  DOI：10.1021/jm00400a018

  日期：1988.5

  A number of spiro[1,3-dioxolane-2,3'-indolin]-2'-ones were synthesized and tested for anticonvulsant activity in the maximal electroshock seizure (MES) and pentylenetetrazole seizure threshold (sc-Met) tests. 5'-Chlorospiro[1,3-dioxolane-2,3'-indolin]-2'-one was the most active compound in the MES test and had ED50 = 27.97 mg/kg. Structural analogues spiro[1,3-dioxane-2,3'-indolin]-2'-one, spiro[1,3-dithiolane-2,3'-indolin]-2'-one, spiro[indoline-3,2'-[1,3]-oxathiolan]-2-one, and 3,3-dimethoxyindolin-2-one were also evaluated for anticonvulsant activity. Almost all compounds submitted for screening exhibited the ability to protect mice against electrically and chemically induced seizures. The ED50 and TD50 values for some of the title compounds are reported. Anticonvulsant screenings were carried out through NINCDS, NIH.
• Novel 2-oxoindoline-based hydroxamic acids: synthesis, cytotoxicity, and inhibition of histone deacetylation
  作者：Tran Thi Lan Huong、Do Thi Mai Dung、Phan Thi Phuong Dung、Phung Thanh Huong、Tran Khac Vu、Hyunggu Hahn、Byung Woo Han、Jisung Kim、Minji Pyo、Sang-Bae Han、Nguyen-Hai Nam

  DOI：10.1016/j.tetlet.2015.09.147

  日期：2015.11

  In a continuation of a research program to discover novel small molecules targeting histone deacetylases, a series of 2'-oxospiro[1,3]dioxolane/dithiolane-2,3'-indoline-based hydroxamic acids have been designed and synthesized. These 2-oxoindoline-based hydroxamic acids displayed potent cytotoxicity against three human cancer cell lines, including SW620 (colon cancer), PC-3 (prostate cancer) and AsPC-1 (pancreatic cancer), with IC50 values as low as 0.05-0.07 mu M, 74-fold lower than that of SAHA (1.64-3.70 mu M). Additionally, compounds in this series exhibited good inhibition against histone-H3 and histone-H4 deacetylation, as evaluated by Western blot assay. These compounds also strongly inhibited HDAC2 with IC50 values as low as 0.03 mu M. Docking studies performed using Autodock Vina showed all compounds bound to HDAC2 with relatively higher affinities (from -7.7 to -8.0 kcal/mol) compared to SAHA (-7.4 kcal/mol). (C) 2015 Elsevier Ltd. All rights reserved.