1--3--propenon-(1) | 22883-41-6

• 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: 1--3--propenon-(1)
• 英文别名: 3-indol-3-yl-1-pyridin-3-yl-propenone；3-(1H-indol-3-yl)-1-pyridin-3-ylprop-2-en-1-one
• CAS: 22883-41-6
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: AWMLUEGACRWOBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.75
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1--3--propenon-(1) 在 copper(l) iodide 、 potassium carbonate 作用下， 以 水 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 54.0h， 生成 (E)-2-(acetoxymethyl)-6-(4-((3-(3-oxo-3-(pyridin-3-yl)prop-1-en-1-yl)-1H-indol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  三唑连接的吲哚和吲哚酮糖缀合物作为潜在抗癌剂的调查：新颖的Akt / PKB信号通路抑制剂†往最‡

  摘要：

  为了继续进行新型生物活性剂的合成，我们从吲哚/羟吲哚（29种化合物）合成了两组三唑连接的糖缀合物，并通过IR（红外光谱），1 H NMR（核磁共振）进行了进一步表征，13 C NMR和质谱分析。评估了新合成的目标化合物对DU145（前列腺癌），HeLa（宫颈癌），A549（肺癌）和MCF-7（乳腺癌）细胞系的初步体外抗癌活性。在磺基罗丹明B（SRB）分析中，结果表明化合物5f（吲哚衍生物）和E -9b（羟吲哚衍生物）对DU145细胞显示出显着的细胞毒活性。此外，集落形成测定法（软琼脂测定法）表明化合物5f和E -9b可以抑制DU145细胞的生长和增殖。在DU145细胞中评估了活性最高的细胞毒性化合物5f和E -9b对细胞周期分布的影响，该细胞在亚G1期表现出细胞周期停滞。接下来，化合物5f和E -9b对DU145细胞中的半胱天冬酶激活进行了测试，结果表明这些化合物具有通过内在途径诱导细胞凋

  DOI：

  10.1039/c5md00513b
• 作为产物：
  描述：

  3-乙酰基吡啶 、 3-吲哚甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 1--3--propenon-(1)
  参考文献：
  名称：

  First‐in‐class pyrido[2,3‐ d ]pyrimidine‐2,4(1 H ,3 H )‐diones against leishmaniasis and tuberculosis: Rationale, in vitro, ex vivo studies and mechanistic insights

  摘要：

  AbstractPyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones were synthesized, for the first time, from indole chalcones and 6‐aminouracil, and their ability to inhibit leishmaniasis and tuberculosis (Tb) infections was evaluated. The in vitro antileishmanial activity against promastigotes of Leishmania donovani revealed exceptional activities of compounds 3, 12 and 13, with IC50 values ranging from 10.23 ± 1.50 to 15.58 ± 1.67 µg/ml, which is better than the IC50 value of the standard drug pentostam of 500 μg/ml. The selectivity of the compounds towards Leishmania parasites was evaluated via ex vivo studies in Swiss albino mice. The efficiency of these compounds against Tb infection was then evaluated using the in vitro anti‐Tb microplate Alamar Blue assay. Five compounds, 3, 7, 8, 9 and 12, showed MIC100 values against the Mycobacterium tuberculosis H37Rv strain at 25 µg/ml, and compound 20 yielded an MIC100 value of 50 µg/ml. Molecular modelling of these compounds highlighted interactions with binding sites of dihydrofolate reductase, pteridine reductase and thymidylate kinase, thus establishing the rationale of their pharmacological activity against both pathogens, which is consistent with the in vitro results. From the above results, it is clear that compounds 3 and 12 are promising lead candidates for Leishmania and Mycobacterium infections and may be promising for coinfections.

  DOI：

  10.1002/ardp.202100440

文献信息

• Materials And Methods Useful To Induce Vacuolization, Cell Death, Or A Combination Thereof
  申请人：The University of Toledo

  公开号：US20150152049A1

  公开（公告）日：2015-06-04

  The present invention provides materials and methods to induce cell death by methuosis, a non-apoptotic cell death mechanism, to induce vacuolization without cell death, or to induce cell death without vacuolization. Small molecules herein are useful for treating cell proliferation disorders or anomalies, particularly, but not exclusively, cancer. Methods related to the research and pharmaceutical use of the small molecules are also provided herein.

  本发明提供了诱导细胞通过非凋亡性细胞死亡机制methuosis死亡、诱导产生空泡而不导致细胞死亡，或诱导细胞死亡而不产生空泡的材料和方法。本文中的小分子可用于治疗细胞增殖异常或疾病，尤其是癌症。本文还提供了与小分子相关的研究和制药方法。
• Materials and Methods Useful to Induce Cell Death via Methuosis
  申请人：Maltese William A.

  公开号：US20140322128A1

  公开（公告）日：2014-10-30

  The present invention provides materials and methods to induce cell death by methuosis, a non-apoptotic cell death mechanism. Small molecules herein are useful for treating cell proliferation disorders or anomalies, particularly, but not exclusively, cancer. Methods related to the research and pharmaceutical use of the small molecules are also provided herein.

  本发明提供了诱导细胞死亡的材料和方法，其中使用了一种非凋亡性细胞死亡机制——甲烷作用。本文提供的小分子化合物对于治疗细胞增殖异常或疾病特别是癌症等方面具有用途。同时，还提供了与小分子化合物相关的研究和药物使用方法。
• Materials and Methods Useful to Induce Vacuolization, Cell Death, or a Combination Thereof
  申请人：THE UNIVERSITY OF TOLEDO

  公开号：US20140213615A1

  公开（公告）日：2014-07-31

  The present invention provides materials and methods to induce cell death by methuosis, a non-apoptotic cell death mechanism, to induce vacuolization without cell death, or to induce cell death without vacuolization. Small molecules herein are useful for treating cell proliferation disorders or anomalies, particularly, but not exclusively, cancer. Methods related to the research and pharmaceutical use of the small molecules are also provided herein.

  本发明提供了诱导细胞死亡的材料和方法，其中包括非凋亡性细胞死亡机制methuosis，诱导出现空泡而不导致细胞死亡，或者诱导细胞死亡而不出现空泡。此处的小分子化合物可用于治疗细胞增殖障碍或异常，特别是但不限于癌症。本文还提供了与小分子化合物的研究和制药使用相关的方法。
• DIANHYDROGALACTITOL TOGETHER WITH RADIATION TO TREAT NON-SMALL-CELL CARCINOMA OF THE LUNG AND GLIOBLASTOMA MULTIFORME
  申请人：Del Mar Pharmaceuticals

  公开号：EP3217970A1

  公开（公告）日：2017-09-20
• USE OF DIANHYDROGALACTITOL AND ANALOGS AND DERIVATIVES THEREOF, TOGETHER WITH RADIATION, TO TREAT NON-SMALL-CELL CARCINOMA OF THE LUNG AND GLIOBLASTOMA MULTIFORME AND SUPPRESS PROLIFERATION OF CANCER STEM CELLS
  申请人：DelMar Pharmaceuticals, Inc.

  公开号：US20190015379A1

  公开（公告）日：2019-01-17

  The use of dianhydrogalactitol provides a novel therapeutic modality for the treatment of non-small-cell lung carcinoma (NSCLC) and for the treatment of glioblastoma multiforme (GBM). Dianhydrogalactitol acts as an alkylating agent on DNA that creates N7 methylation. Dianhydrogalactitol is effective in suppressing the growth of cancer stem cells and is active against tumors that are refractory to temozolomide; the drug acts independently of the MGMT repair mechanism.