甘氨酰胺-beta-咔啉-3-羧酸酯甲酯 | 100009-01-6

• 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
• 中文名称: 甘氨酰胺-beta-咔啉-3-羧酸酯甲酯
• 中文别名: 甘氨酸酰胺-β-咔啉-3-羧酸酯甲基酯
• 英文名称: methyl 2-(9H-pyrido[3,4-b]indole-3-carboxamido)acetate
• 英文别名: Glycinamide-beta-carboline-3-carboxylate methyl ester；methyl 2-(9H-pyrido[3,4-b]indole-3-carbonylamino)acetate
• CAS: 100009-01-6
• 化学式: C₁₅H₁₃N₃O₃
• 分子量: 283.287
• InChiKey: KRSQNSNAAQYQQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甘氨酰胺-beta-咔啉-3-羧酸酯甲酯 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 9H-pyrido<3,4-b>indole-3-carbonyl-N-glycine
  参考文献：
  名称：

  β-咔啉-3-羧酸的寡肽 - 苯二氮卓受体的合成和亲和力

  摘要：

  制备了 β-咔啉-3-羧酸的寡肽，并测定了它们对小鼠脑膜中苯二氮卓受体的亲和力。结构 - 报告亲和关系。

  DOI：

  10.1002/ardp.19873200210
• 作为产物：
  描述：

  (S)-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸 在 N-甲基吗啉 、 potassium permanganate 、 氯甲酸乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 甘氨酰胺-beta-咔啉-3-羧酸酯甲酯
  参考文献：
  名称：

  Novel β-Carboline/Hydroxamic Acid Hybrids Targeting Both Histone Deacetylase and DNA Display High Anticancer Activity via Regulation of the p53 Signaling Pathway

  摘要：

  A novel series of hybrids from beta-carboline and hydroxamic acid were designed and synthesized. Several compounds (5m, 11b-d, and 11h) not only exerted significant antiproliferation activity against four human colorectal cancer (CRC) cell lines but also showed histone deacetylase inhibitory effects in vitro. The most potent compound, 11c, exhibited anticancer potency sevenfold higher than that of SAHA. 11c triggered more significant cancer cell apoptosis than did SAHA by cleavage of both PARP and caspase 3 in a dose-dependent manner. Furthermore, 11c simultaneously increased the acetylation of histone H3 and alpha-tubulin, enhanced expression of DNA damage markers histone H2AX phosphorylation and p-p53 (Ser15), and activated p53 signaling pathway in HCT116 cells. Finally, 11c showed low acute toxicity in mice and inhibited the growth of implanted human CRC in mice more potently than did SAHA. Together, 11c possessed potent antitumor activity and may be a promising candidate for the potential treatment of human CRC.

  DOI：

  10.1021/acs.jmedchem.5b01052

文献信息

• β-Carbolines as Benzodiazepine Receptor Ligands II: Synthesis and Benzodiazepine Receptor Affinity of β-Carboline-3-carboxylic Acid Amides
  作者：Klaus P. Lippke、Walter E. Müller、Walter G. Schunack

  DOI：10.1002/jps.2600740620

  日期：1985.6

  Numerous beta-carboline-3-carboxamides were synthesized by amidation of beta-carboline-3-carboxylic acid, with various amino acids and amino acid esters serving as amine components, and tested in respect to their affinity for the benzodiazepine receptor in mouse brain membranes. The title compounds have affinities in the low micromolar range. The results are discussed with respect to their relevance

  通过酰胺化β-咔啉-3-羧酸，将各种氨基酸和氨基酸酯用作胺成分，合成了许多β-咔啉-3-羧酰胺，并测试了它们对小鼠脑膜中苯二氮卓受体的亲和力。 。标题化合物的亲和力在低微摩尔范围内。就其与可能的含有苯二氮杂receptor受体内源性配体的β-咔啉结构的相关性讨论了结果。