4-oxo-1-methyl-2-methyl-4,5,6,7-tetrahydroindole | 111141-07-2

• 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
• 英文名称: 4-oxo-1-methyl-2-methyl-4,5,6,7-tetrahydroindole
• 英文别名: 6,7-dihydro-1,2-dimethylindol-4(5H)-one；1,2-dimethyl-1,5,6,7-tetrahydro-4H-indol-4-one；4-Oxo-1,2-dimethyl-4,5,6,7-tetrahydro-indol；1,2-dimethyl-1,5,6,7-tetrahydro-indol-4-one；1,2-dimethyl-6,7-dihydro-5H-indol-4-one
• CAS: 111141-07-2
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: FIPFCYAIMHXQSX-UHFFFAOYSA-N

物化性质

• 沸点：
  308.3±21.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-oxo-1-methyl-2-methyl-4,5,6,7-tetrahydroindole 、 氰化钾 在 碳酸氢铵 作用下， 以 乙醇 为溶剂， 以52%的产率得到1,2-dimethylspiro[6,7-dihydro-5H-indole-4,5'-imidazolidine]-2',4'-dione
  参考文献：
  名称：

  螺旋乙内酰脲醛糖还原酶抑制剂。

  摘要：

  据信由醛糖还原酶催化的葡萄糖形成山梨醇在糖尿病的某些慢性并发症的发生中起作用。源自与芳香族环或环系统融合的五元和六元酮的螺乙内酰脲抑制从小牛晶状体分离的醛糖还原酶。在体内，这些化合物是链脲佐剂化大鼠坐骨神经中山梨醇形成的有效抑制剂。在衍生自6-卤代的2,3-二氢-4H-1-苯并吡喃-4-酮（4-苯并二氢吡喃酮）的螺旋乙内酰脲中可达到最佳的体内活性。在2,4-二氢-6-氟螺[4H-1-苯并吡喃-4,4'-咪唑烷] -2'，5'-二酮中，活性仅存在于4S异构体化合物115（CP-45,634，USAN ：山梨醇）。该化合物目前正用于测试人体，

  DOI：

  10.1021/jm00396a037
• 作为产物：
  描述：

  N-methyl-N-<7-(trimethylsilyl)-5-oxohept-6-yn-1-oyl>alanine 以 乙酸乙酯 为溶剂， 生成 4-oxo-1-methyl-2-methyl-4,5,6,7-tetrahydroindole
  参考文献：
  名称：

  通过新颖的分子内1,3-偶极环加成方法轻松合成4-氧代-4,5,6,7-四氢吲哚

  摘要：

  使用新的分子内1,3-偶极环加成方法可分两步实现4-酮-4,5,6,7-四氢吲哚6-12的一般合成，产率中等（45-60％）。这种方法的潜力通过丝裂霉素骨架（15）和拓扑异构酶-1抑制剂骨架（17）的合成得到证明。

  DOI：

  10.1016/0040-4039(96)00426-1

文献信息

• Pyrrolo[2,3-h]quinolinones: A new ring system with potent photoantiproliferative activity
  作者：Paola Barraja、Patrizia Diana、Alessandra Montalbano、Gaetano Dattolo、Girolamo Cirrincione、Giampietro Viola、Daniela Vedaldi、Francesco Dall’Acqua

  DOI：10.1016/j.bmc.2006.07.061

  日期：2006.12

  A new class of compounds, the pyrrolo[2,3-h]quinolin-2-ones, nitrogen isosters of the angular furocoumarin Angelicin, was synthesized with the aim of obtaining new photochemotherapeutic agents with increased antiproliferative activity and lower undesired toxic effects than the lead compound. Two synthetic pathways were approached to allow the isolation both of the dihydroderivatives 10-17 and of the

  合成了新型化合物，即角呋喃香豆素Anglicin的吡咯并[2,3-h]喹啉-2-酮，氮等价物，目的是获得新的光化学治疗药物，该药物具有比抗肿瘤活性更高的抗增殖活性和更低的不良毒性作用。铅化合物。接近两个合成途径以分离二氢衍生物10-17和芳环系统23。化合物10-17显示出显着的光毒性和很大的UVA剂量依赖性，在亚微摩尔水平达到IC（50）值。这些化合物的细胞内定位已经通过使用四甲基若丹明甲酯和a啶橙的荧光显微镜法进行了评估，它们分别是线粒体和溶酶体的特异性荧光探针。线粒体染色观察到弱共染色，而在溶酶体中观察到了特定的定位。旨在阐明该系列化合物作用方式的研究表明，它们不嵌入DNA，也不会诱导对大分子的光损伤。相反，它们诱导对脂质和蛋白质的显着光损伤。
• Thiopyrano[2,3-e]indol-2-ones: Angelicin heteroanalogues with potent photoantiproliferative activity
  作者：Paola Barraja、Patrizia Diana、Alessandra Montalbano、Anna Carbone、Girolamo Cirrincione、Giampietro Viola、Alessia Salvador、Daniela Vedaldi、Francesco Dall’Acqua

  DOI：10.1016/j.bmc.2008.10.002

  日期：2008.11

  A new class of compounds, the thiopyrano[2,3-e]indol-2-ones, bioisosters of the angular furocoumarin angelicin, was synthesized with the aim of obtaining new photochemotherapeutic agents. In particular 7,8-dimethyl-thiopyranoindolone 6c s showed a remarkable phototoxicity and a great dose UVA dependence reaching IC(50) values at submicromolar level. This latter photoinduced a massive apoptosis and

  为了获得新的光化学治疗剂，合成了一类新的化合物，即角呋喃香豆素当归的生物等位基因thiopyrano [2,3-e] indol-2-ones。特别是7,8-二甲基-硫代吡喃并吲哚酮6c s表现出了显着的光毒性，并且在亚微摩尔水平上对UVA的依赖性很大，达到了IC（50）值。后者光诱导大量的细胞凋亡，并对脂质和蛋白质产生显着的光损伤。尽管它不插入DNA，但它能够引起DNA碱基的光氧化。
• New Approach for the General Synthesis of Oxotetrahydroindoles via Intramolecular Cycloadditions of Azomethine Ylides with Tethered Alkynes
  作者：Naresh K. Nayyar、Darrell R. Hutchison、Michael J. Martinelli

  DOI：10.1021/jo9614598

  日期：1997.2.1

  A new method for the synthesis of oxotetrahydroindoles has been achieved employing an intramolecular dipolar cycloaddition approach involving mesoionic species (munchnones) with electron-deficient alkynes. The methodology is quite general and convergent as shown by the synthesis of a variety of tri- and tetrasubstituted oxotetrahydroindoles 18, 21, 24, 27, 30, and 34. LiI-based ester cleavage in the presence of an electrophilic acetylenic ketone was critical for formation of the requisite cycloaddition substrates. The cycloaddition is virtually unaffected by the presence of gem-dimethyl groups in the side chain (cf. 38). The presence of a substituted benzyl or a phenethyl moiety on nitrogen, a polarized acetylene, and an appropriate tether between dipole and dipolarophile are essential for obtaining optimal efficiency.
• Pyrrolo[2,3-h]quinolinones: synthesis and photochemotherapic activity
  作者：Paola Barraja、Patrizia Diana、Antonino Lauria、Alessandra Montalbano、Anna Maria Almerico、Gaetano Dattolo、Girolamo Cirrincione、Giampietro Viola、Francesco Dall'Acqua

  DOI：10.1016/s0960-894x(03)00529-8

  日期：2003.8

  A series of derivatives of the new ring system pyrrolo[2,3-h]quinoline-2-one was synthesized and evaluated as photoreagents toward cultured human tumor cells. Remarkable phototoxycity resulted for some derivatives, especially those bearing the phenyl group at the 7-position. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and photochemotherapeutic activity of thiopyrano[2,3-e]indol-2-ones
  作者：Paola Barraja、Laura Sciabica、Patrizia Diana、Antonino Lauria、Alessandra Montalbano、Anna Maria Almerico、Gaetano Dattolo、Girolamo Cirrincione、Silvia Disarò、Giuseppe Basso、Giampietro Viola、Francesco Dall’Acqua

  DOI：10.1016/j.bmcl.2005.03.016

  日期：2005.5

  A series of derivatives of the new ring system thiopyrano[2,3-e]indol-2-one was prepared with the aim of obtaining new photochemotherapeutic drugs. Biological screenings were performed on this new class of photoactivable drugs and a strong anti-proliferative effect was observed upon irradiation with UVA light. The compound bearing a methyl substituent at the pyrrole nitrogen resulted as the most interesting showing IC50 in the nanomolar range. (c) 2005 Elsevier Ltd. All rights reserved.