N-(2-oxoindolin-5-yl)methanesulfonamide | 310441-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-oxoindolin-5-yl)methanesulfonamide
• 英文别名: N-(2-oxo-2,3-dihydro-1H-indol-5-yl)methanesulfonamide；N-(2-oxo-1,3-dihydroindol-5-yl)methanesulfonamide
• CAS: 310441-30-6
• 化学式: C₉H₁₀N₂O₃S
• mdl: MFCD08932214
• 分子量: 226.256
• InChiKey: QQUIQJNTCPMFRT-UHFFFAOYSA-N

物化性质

• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-噻吩甲醛 、 N-(2-oxoindolin-5-yl)methanesulfonamide 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以38%的产率得到(3Z)-N-(2-oxo-(3-(thiophen-2-ylmethylene)indolin-5-yl))methanesulfonamide
  参考文献：
  名称：

  Design and synthesis of 2-oxindole based multi-targeted inhibitors of PDK1/Akt signaling pathway for the treatment of glioblastoma multiforme

  摘要：

  Aggressive behavior and diffuse infiltrative growth are the main features of Glioblastoma multiforme (GBM), together with the high degree of resistance and recurrence. Evidence indicate that GBM-derived stem cells (GSCs), endowed with unlimited proliferative potential, play a critical role in tumor development and maintenance. Among the many signaling pathways involved in maintaining GSC sternness, tumorigenic potential, and anti-apoptotic properties, the PDK1/Akt pathway is a challenging target to develop new potential agents able to affect GBM resistance to chemotherapy. In an effort to find new PDK1/Akt inhibitors, we rationally designed and synthesized a small family of 2-oxindole derivatives. Among them, compound 3 inhibited PDK1 kinase and downstream effectors such as CHK1, GS3K alpha and GS3K beta, which contribute to GCS survival. Compound 3 appeared to be a good tool for studying the role of the PDK1/Akt pathway in GCS self-renewal and tumorigenicity, and might represent the starting point for the development of more potent and focused multi-target therapies for GBM. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.020
• 作为产物：
  描述：

  5-硝基-1,3-二氢-2H-吲哚-2-酮 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 N-(2-oxoindolin-5-yl)methanesulfonamide
  参考文献：
  名称：

  Design and synthesis of 2-oxindole based multi-targeted inhibitors of PDK1/Akt signaling pathway for the treatment of glioblastoma multiforme

  摘要：

  Aggressive behavior and diffuse infiltrative growth are the main features of Glioblastoma multiforme (GBM), together with the high degree of resistance and recurrence. Evidence indicate that GBM-derived stem cells (GSCs), endowed with unlimited proliferative potential, play a critical role in tumor development and maintenance. Among the many signaling pathways involved in maintaining GSC sternness, tumorigenic potential, and anti-apoptotic properties, the PDK1/Akt pathway is a challenging target to develop new potential agents able to affect GBM resistance to chemotherapy. In an effort to find new PDK1/Akt inhibitors, we rationally designed and synthesized a small family of 2-oxindole derivatives. Among them, compound 3 inhibited PDK1 kinase and downstream effectors such as CHK1, GS3K alpha and GS3K beta, which contribute to GCS survival. Compound 3 appeared to be a good tool for studying the role of the PDK1/Akt pathway in GCS self-renewal and tumorigenicity, and might represent the starting point for the development of more potent and focused multi-target therapies for GBM. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.020

文献信息

• Pyrrolo [3,2-C] Pyridine-4-One 2-Indolinone Protein Kinase Inhibitors
  申请人：Tang Peng Cho

  公开号：US20100004239A1

  公开（公告）日：2010-01-07

  The present invention relates to pyrrolo[3,2-c]pyridine-4-one 2-indolinone compounds of Formula (I) and their pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 X, Y and have the meaning cited in the specification. Also disclosed are the pharmaceutical compositions containing the foregoing compounds, methods for the preparation and pharmaceutical use thereof, particularly as protein kinase inhibitors. Formula (I).

  本发明涉及Formula(I)中的吡咯[3,2-c]吡啶-4-酮-2-吲哚酮化合物及其在药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8X、Y等在说明书中有所描述。还披露了含有上述化合物的药物组合物、其制备方法和药用方法，特别是作为蛋白激酶抑制剂。Formula(I)。
• [EN] PHARMACEUTICAL COMBINATION FOR THE TREATMENT OF TUMORS<br/>[FR] COMBINAISON PHARMACEUTIQUE POUR LE TRAITEMENT DE TUMEURS
  申请人：INTERNAT SOC FOR DRUG DEV S R L

  公开号：WO2016055454A1

  公开（公告）日：2016-04-14

  The invention concerns a combination comprising at least one 2-oxo-indole derivative of formula (I) in which R1 is selected from the group consisting of thienyl, imidazolyl and pyridyl, optionally substituted by (C1-C3) alkyl, A is a -CH2CO- o -SO2- group; R is selected from the group consisting of 6,7-dimethoxy-1,2,3,4- tetrahydroisoquinolinyl, 3,4-dimethoxy-benzylamino, (C1-C3)alkyl, benzyl or a pharmaceutically acceptable salt thereof and at least one antitumor drug. The combination is for use in the treatment of tumors, in particular glioblastoma multiforme (GBM), breast tumor and pancreatic tumor. The combination is effective in the treatment of resistant tumor forms.

  该发明涉及一种组合物，其中至少包括一个式（I）的2-氧代吲哚衍生物，其中R1从噻吩基团、咪唑基团和吡啶基团中选择，可选地被（C1-C3）烷基取代，A是-CH2CO-或-SO2-基团；R从6,7-二甲氧基-1,2,3,4-四氢异喹啉基团、3,4-二甲氧基苄胺基团、（C1-C3）烷基、苄基或其药学上可接受的盐中选择，并且至少包括一种抗肿瘤药物。该组合物用于治疗肿瘤，特别是胶质母细胞瘤（GBM）、乳腺肿瘤和胰腺肿瘤。该组合物对治疗耐药肿瘤形式有效。
• 3-methylidenyl-2-indolinone modulators of protein kinase
  申请人：Sugen, Inc.

  公开号：US20040024010A1

  公开（公告）日：2004-02-05

  The present invention relates to novel 3-methylidenyl-2-indolinone compounds and physiologically acceptable salts and prodrugs thereof which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

  本发明涉及新型的3-甲基亚烯基-2-吲哚酮化合物及其生理上可接受的盐和前药，这些化合物可调节蛋白激酶的活性，因此预计在预防和治疗蛋白激酶相关的细胞疾病，如癌症方面具有用途。
• INDAZOLYL, BENZIMIDAZOLYL, BENZOTRIAZOLYL SUBSTITUTED INDOLINONE DERIVATIVES AS KINASE INHIBITORS USEFUL IN THE TREATMENT OF CANCER
  申请人：Pauls Heinz W.

  公开号：US20110065702A1

  公开（公告）日：2011-03-17

  The present invention is directed to a compound is represented by Structural Formula (A):or a pharmaceutically acceptable salt therof. The present invention is also directed to a pharmaceutical composition comprising a compound represented by Structural Formula (A) described above or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent. Also disclosed is a method of treating a subject having cancer, wherein the method comprises administering a therapeutically effective amount of a compound represented by Structural Formula (A) described above or a pharmaceutically acceptable salt thereof.

  本发明涉及一种化合物，其结构式表示为(A)或其药学上可接受的盐。本发明还涉及一种药物组合物，包括上述结构式(A)所表示的化合物或其药学上可接受的盐，以及药学上可接受的载体或稀释剂。本发明还揭示了一种治疗患有癌症的受试者的方法，其中该方法包括给予上述结构式(A)所表示的化合物或其药学上可接受的盐的治疗有效量。
• PYRROLO [3,2-C] PYRIDINE-4-ONE 2-INDOLINONE PROTEIN KINASE INHIBITORS
  申请人：TANG Peng Cho

  公开号：US20120058107A1

  公开（公告）日：2012-03-08

  The present invention relates to pyrrolo[3,2-c]pyridine-4-one 2-indolinone compounds of Formula (I) and their pharmaceutically acceptable salts thereof, wherein R 1 , R2, R3, R4, R5, R6, R7, R8 X, Y and have the meaning cited in the specification. Also disclosed are the pharmaceutical compositions containing the foregoing compounds, methods for the preparation and pharmaceutical use thereof, particularly as protein kinase inhibitors. Formula (I).

  本发明涉及公式(I)中的吡咯并[3,2-c]吡啶-4-酮2-吲哚酮化合物及其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8、X、Y具有规范中所述的含义。还公开了含有上述化合物的制药组合物、其制备方法和药物用途，特别是作为蛋白激酶抑制剂。公式(I)。