2-indol-3-yl-thioacetamide | 59108-91-7

• 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: 2-indol-3-yl-thioacetamide
• 英文别名: 2-(1H-indol-3-yl)-thioacetamide；3-Indolyl-thioacetamid；3-Indolylthioacetamid；2-(1H-indol-3-yl)ethanethioamide
• CAS: 59108-91-7
• 化学式: C₁₀H₁₀N₂S
• 分子量: 190.269
• InChiKey: WMUAHAJSNVMGRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  73.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-indol-3-yl-thioacetamide 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到3,5-bis((indol-3-yl)methyl)-1,2,4-thiadiazole
  参考文献：
  名称：

  Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles

  摘要：

  A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-thiocarboxamide 3 with iodobenzene diacetate underwent oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles 4a-n. Among the synthesized bis(indoly)-1,2,4-thiadiazoles, the compound 4h with 4-chlorobenzyl and methoxy substituents showed the most potent activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.089
• 作为产物：
  描述：

  3-吲哚乙酰胺 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 生成 2-indol-3-yl-thioacetamide
  参考文献：
  名称：

  Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles

  摘要：

  A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-thiocarboxamide 3 with iodobenzene diacetate underwent oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles 4a-n. Among the synthesized bis(indoly)-1,2,4-thiadiazoles, the compound 4h with 4-chlorobenzyl and methoxy substituents showed the most potent activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.089

文献信息

• Influence of the structures of α-halo ketones and thioamides on the Hantzsch synthesis of thiazoles and thiazolo[5,4-b]indoles. A new approach to 4-acetyl-2-methyl-4H-thiazolo[5,4-b]indole
  作者：A. Yu. Lepeshkin、K. F. Turchin、A. L. Sedov、V. S. Velezheva

  DOI：10.1007/s11172-007-0219-5

  日期：2007.7

  into thiazoles (the expected Hantzsch reaction products). To the contrary, thiazoles are produced in the reactions of the same α-halo ketones with thioamides of phenylacetic, diphenylacetic, 3-indolylacetic, or cyanoacetic acids. The abnormal course of the Hantzsch reaction in the former case results from the fact that 4-hydroxy-Δ2-thiazolines, which are intermediates in the thiazole synthesis, undergo

  在与一些 α-卤代酮（3-bromo-1,1,1-trifluoropropan-2-one、1-acetyl-2-bromoindolin-3-one 和 α-bromoacetophenone）、硫代乙酰胺和一系列硫代酰胺的反应中芳族和杂芳族酸转化为 4-羟基-Δ2-噻唑啉而不是噻唑（预期的 Hantzsch 反应产物）。相反，噻唑是在相同的 α-卤代酮与苯乙酸、二苯乙酸、3-吲哚乙酸或氰基乙酸的硫代酰胺反应中产生的。前一种情况下 Hantzsch 反应的异常过程是由于作为噻唑合成中间体的 4-羟基-Δ2-噻唑啉在 Hantzsch 反应条件下几乎不发生脱水的事实。在噻唑合成条件下羟基噻唑啉脱水的容易程度和噻唑自发合成的可能性取决于2位取代基的性质，因此取决于起始硫代酰胺的结构。Me、Ar 和 Het 取代基会阻止脱水，而在噻唑啉部分的 C(2) 原子上包含 α-亚甲基（次甲基）单元的
• Pyrrolidinone, pyrrolidine-2,5-dione, pyrrolidine and thiosuccinimide derivatives, compositions and methods for treatment of cancer
  申请人：ArQule, Inc.

  公开号：US08304425B2

  公开（公告）日：2012-11-06

  The present invention relates to pyrrolidin-2-one, pyrrolidin-2,5-dione, pyrrolidine and thiosucciniroide compounds of formulae (I)-(IV), and methods of preparation of these compounds. The present invention also relates to pharmaceutical compositions comprising pyrrolidin-2-one, pyrrolidin-2,5-dione, pyrrolidine and thiosuccinimide compounds. The present invention provides methods of treating a cell proliferative disorder, such as a cancer, by administering to a subject in need thereof a therapeutically effective amount of a compound of pyrrolidin-2-one, pyrrolidin-2,5-dione, pyrrolidine and thiosuccinimide compound of the present invention.

  本发明涉及式(I)-(IV)的吡咯烷-2-酮、吡咯烷-2,5-二酮、吡咯烷和硫代琥珀酰亚胺化合物以及这些化合物的制备方法。本发明还涉及包含吡咯烷-2-酮、吡咯烷-2,5-二酮、吡咯烷和硫代琥珀酰亚胺化合物的药物组合物。本发明提供了通过向需要治疗细胞增殖性疾病（如癌症）的受试者投与本发明的吡咯烷-2-酮、吡咯烷-2,5-二酮、吡咯烷和硫代琥珀酰亚胺化合物的治疗有效量的方法。
• Pyrrolidinone, Pyrrolidine-2, 5-Dione, Pyrrolidine and Thiosuccinimide Derivatives, Compositions and Methods for Treatment of Cancer
  申请人：Wang Jianqiang

  公开号：US20100178291A1

  公开（公告）日：2010-07-15

  The present invention relates to pyrrolidin-2-one, pyrrolidin-2,5-dione, pyrrolidine and thiosucciniroide compounds of formulae (I)-(IV), and methods of preparation of these compounds. The present invention also relates to pharmaceutical compositions comprising pyrrolidin-2-one, pyrrolidin-2,5-dione, pyrrolidine and thiosuccinimide compounds. The present invention provides methods of treating a cell proliferative disorder, such as a cancer, by administering to a subject in need thereof a therapeutically effective amount of a compound of pyrrolidin-2-one, pyrrolidin-2,5-dione, pyrrolidine and thiosuccinimide compound of the present invention.

  本发明涉及式(I)-(IV)的吡咯烷-2-酮、吡咯烷-2,5-二酮、吡咯烷和硫代琥珀酰亚胺化合物，以及这些化合物的制备方法。本发明还涉及包括吡咯烷-2-酮、吡咯烷-2,5-二酮、吡咯烷和硫代琥珀酰亚胺化合物的药物组合物。本发明提供了一种通过向需要治疗细胞增殖性疾病（如癌症）的受试者施用本发明的吡咯烷-2-酮、吡咯烷-2,5-二酮、吡咯烷和硫代琥珀酰亚胺化合物的治疗有效量来治疗该疾病的方法。
• 一种同时合成硫醚类化合物和腈类化合物的方法
  申请人：石河子大学

  公开号：CN117567332A

  公开（公告）日：2024-02-20

  本发明提供了一种同时合成硫醚类化合物和腈类化合物的方法，属于有机合成技术领域；本发明将硫代酰胺类化合物、氟化物和乙腈混合，然后向其中加入苯炔前体，从而实现在室温条件下同时合成硫醚类化合物和腈类化合物；所述方法简便快捷、无需过渡金属催化，底物范围广，所用氟源廉价易得，不会造成环境污染；所述方法具有工艺简单，反应条件温和、普适性好等优点，并且所合成的硫醚类化合物和腈类化合物产率都很高，硫醚类化合物和腈类化合物最高可达98％，具有极高的工业推广价值。
• WO2009/2806
  申请人：——

  公开号：——

  公开（公告）日：——