6-羟基-1,4-二甲基咔唑 | 69902-43-8

• 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: 6-羟基-1,4-二甲基咔唑
• 英文名称: 1,4-dimethyl-6-hydroxy-9H-carbazole
• 英文别名: 1,4-Dimethyl-6-hydroxycarbazole；5,8-dimethyl-9H-carbazole-3-ol；5,8-dimethyl-carbazol-3-ol；6-hydroxy-1,4-dimethylcarbazole；5,8-dimethyl-9H-carbazol-3-ol
• CAS: 69902-43-8
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: UERYKPVBQQUNJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-羟基-1,4-二甲基咔唑 在 sodium tetrahydroborate 、 硝酸 、 乙酸酐 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 9.5h， 生成 1,4-dimethyl-6-methoxy-3-nitro-9H-carbazole
  参考文献：
  名称：

  Lancelot, Jean-Charles; Letois, Bertrand; Rault, Sylvain, Heterocycles, 1990, vol. 31, # 2, p. 241 - 246

  摘要：

  DOI：
• 作为产物：
  描述：

  9-tert-butoxycarbonyl-5,8-dimethyl-9H-carbazole-3-boronic acid 在 sodium hydroxide 、 双氧水 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以75%的产率得到6-羟基-1,4-二甲基咔唑
  参考文献：
  名称：

  Novel and efficient synthesis of 5,8-dimethyl-9H-carbazol-3-ol via a hydroxydeboronation reaction

  摘要：

  N-Protected carbazol-3-yl-boronic acid derivatives have been efficiently hydroxydeboronated under mild conditions by employing hydrogen peroxide. The method allows to easily obtain 3-hydroxycarbazoles as precursors of new analogs of the anticancer agent 9-hydroxyellipticine.

  DOI：

  10.1016/s0385-5414(07)81095-1

文献信息

• New Trimethoxybenzamides and Trimethoxyphenylureas Derived from Dimethylcarbazole as Cytotoxic Agents. Part I
  作者：Antonella Panno、Maria Stefania Sinicropi、Anna Caruso、Hussein El-Kashef、Jean-Charles Lancelot、Geneviève Aubert、Aurélien Lesnard、Thierry Cresteil、Sylvain Rault

  DOI：10.1002/jhet.1951

  日期：2014.8

  A convenient synthesis of novel functionalized 1,4-dimethylcarbazole derivatives containing 3,4,5-trimethoxybenzamido-ureido or N-(3,4,5-trimethoxyphenyl)ureido group starting from their corresponding indole derivatives is reported. Three derivatives prepared (, , and ) were active against leukemia cell lines HL60. Both and showed potent antiproliferative activity against KB cell lines, likely associated

  据报道，从它们相应的吲哚衍生物开始，方便地合成了含有3,4,5-三甲氧基苯甲酰胺基-脲基或N-（3,4,5-三甲氧基苯基）脲基的新型功能化的1,4-二甲基咔唑衍生物。准备了三种衍生物（， ， 和 ）对白血病细胞系HL60具有活性。两个都 和 对KB细胞系显示出有效的抗增殖活性，可能与微管蛋白聚合的抑制有关。
• The reactions of α-monosubstituted primary amines with 1,4-dimethyl-6-hydroxycarbazole and 9-hydroxyellipticine under oxidative conditions: formation of a novel series of annulated oxazoles
  作者：Rajeswari Sundaramoorthi、Vinod K. Kansal、Bhupesh C. Das、Pierre Potier

  DOI：10.1039/c39860000371

  日期：——

  The oxidative nucleophilic addition reactions of α-monosubstituted primary amines (RCH2NH2) with a 5-hydroxyindole-containing molecular framework such as 1,4-dimethyl-6-hydroxycarbazole and 9-hydroxyelli-pticine in the presence of manganese dioxide led to the formation of a new series of annulated oxazoles (6)–(11).

  在二氧化锰的存在下，α-单取代的伯胺（RCH 2 NH 2）与含5-羟基吲哚的分子骨架（如1,4-二甲基-6-羟基咔唑和9-羟基苯丙氨酸）的氧化亲核加成反应形成一系列新的环恶唑（6）–（11）。
• Nucleophilic addition of aliphatic amino acids to N-2-methyl-9-hydroxy-ellipticinium acetate under peroxidase-catalysed oxidative conditions : a reinvestigation and structural revision of the adducts
  作者：V.K. Kansal、R. Sundaramoorthi、B.C. Das、P. Potier

  DOI：10.1016/s0040-4039(00)94989-x

  日期：1985.1

  A reinvestigation of the adducts resulting from a peroxidase-catalysed reaction of N-2-methyl-9-hydroxyellipticinium acetate 1 with some aliphatic amino acids led to their structural revision from 3 to 4.

  对过氧化物酶催化的N-2-甲基-9-羟基椭圆乙酸乙酸盐1与某些脂肪族氨基酸反应产生的加合物的重新研究导致其结构从3变为4。
• Identification of Lead Compounds as Inhibitors of STAT3: Design, Synthesis and Bioactivity
  作者：Antonio Botta、Esther Sirignano、Ada Popolo、Carmela Saturnino、Stefania Terracciano、Antonio Foglia、Maria Stefania Sinicropi、Pasquale Longo、Simone Di Micco

  DOI：10.1002/minf.201500043

  日期：2015.10

  the STAT3 protein. Moreover, MTT assay performed on A375 and HeLa, showed significant antiproliferative activity of some of synthesized compounds (3–5). The same compounds (3–5) considerably reduced STAT3 expression, as demonstrated by Western blot analysis. Our multidisciplinary approach shows that 1,4‐dimethyl‐carbazoles are potential building blocks to develop more affinity ligands of STAT3.

  STAT3属于信号转导子和转录激活子（STAT）家族。已经证明STAT3在许多肿瘤中被组成性激活，在致癌和肿瘤进展中起作用。因此，它被认为是癌症治疗的潜在靶标。在这种情况下，我们设计，合成和评估了针对STAT3蛋白的1,4-二甲基咔唑衍生物。此外，MTT法对A375执行和HeLa，显示的一些合成的化合物（的显著抗增殖活性3 - 5）。相同的化合物（3 – 5如WeSTern blot分析所示，STAT3表达大大降低。我们的多学科方法表明，1,4-二甲基咔唑是开发更多STAT3亲和配体的潜在基础。
• 2-N Quaternary ammonium salt derivatives of 9-hydroxy ellipticine
  申请人：Agence Nationale de Valorisation de la Recherche (ANVAR)

  公开号：US04310667A1

  公开（公告）日：1982-01-12

  Derivatives of 9-hydroxy ellipticine, preparation thereof, and use thereof for the treatment of leukemias and solid tumors.

  9-羟基椭圆素的衍生物，其制备方法，以及用于治疗白血病和实体肿瘤的用途。