靛红乙烯硫代缩酮 | 38168-18-2

• 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
• 中文名称: 靛红乙烯硫代缩酮
• 英文名称: isatin ethylene thioketal
• 英文别名: spiro[[1,3]dithiolane-2,3'-indolin]-2'-one；1'H-spiro[[1,3]dithiolane-2,3'-indol]-2'-one；Spiro([1,3]dithiolan-2,3'-indolin)-2'-on；Spiro[1,3-dithiolane-2,3'-[3H]indol]-2'(1'H)-one；spiro[1,3-dithiolane-2,3'-1H-indole]-2'-one
• CAS: 38168-18-2
• 化学式: C₁₀H₉NOS₂
• 分子量: 223.32
• InChiKey: QAYGJICGCHGPFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  靛红乙烯硫代缩酮 在 镍 作用下， 以 苯 为溶剂， 反应 76.0h， 生成 3-乙基-1,3-二氢-2H-吲哚-2-酮
  参考文献：
  名称：

  Wenkert, Ernest; Bringi, N. V.; Choulett, Harry E., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 5, p. 348 - 350

  摘要：

  DOI：
• 作为产物：
  描述：

  靛红 、 1,2-乙二硫醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以67%的产率得到靛红乙烯硫代缩酮
  参考文献：
  名称：

  螺二硫杂环戊二烯-吲哚酮对映选择性钌催化的硫氧化中的协同立体控制

  摘要：

  开发了手性钌催化剂用于标题化合物的对映选择性磺氧化。该催化剂结合了两个手性元素，一个手性pybox配体和一个与该配体连接的手性双环内酰胺单元。后者被证明可以通过氢键介导的配位作用将两个对映体硫原子之一暴露于活性位点，从而显着提高催化剂的性能。十个不同取代的底物转化成相应的亚砜中的52-71％的产率和以≥90％ee值。

  DOI：

  10.1002/chem.201501780

文献信息

• 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.
• A NEW PROCEDURE FOR FORMING CARBON-CARBON BONDS¹
  作者：Ernest Wenkert、N. V. Bringi

  DOI：10.1021/ja01553a071

  日期：1958.10
• Baker,J.T.; Duke,C.C., Australian Journal of Chemistry, 1972, vol. 25, p. 2467 - 2475
  作者：Baker,J.T.、Duke,C.C.

  DOI：——

  日期：——
• WENKERT, E.;BRINGI, N. V.;CHOULETT, H. E., ACTA CHEM. SCAND., 1982, 36, N 5, 348-350
  作者：WENKERT, E.、BRINGI, N. V.、CHOULETT, H. E.

  DOI：——

  日期：——