N-(β-carbolin-3-yl)-2-phenylacetamide | 122137-51-3

• 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: N-(β-carbolin-3-yl)-2-phenylacetamide
• 英文别名: (β-carbolin-3-yl)-2-phenylacetamide；N-(9H-beta-Carbolin-3-yl)-2-phenyl-acetamide；2-phenyl-N-(9H-pyrido[3,4-b]indol-3-yl)acetamide
• CAS: 122137-51-3
• 化学式: C₁₉H₁₅N₃O
• 分子量: 301.348
• InChiKey: UMSGMQIUOLLKQV-UHFFFAOYSA-N

物化性质

• 熔点：
  137.8-139.0 °C
• 沸点：
  643.9±45.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(β-carbolin-3-yl)-2-phenylacetamide 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以50%的产率得到3-(2-phenylethyl)amino-β-carboline
  参考文献：
  名称：

  3-Benzylamino-β-carboline derivatives induce apoptosis through G2/M arrest in human carcinoma cells HeLa S-3

  摘要：

  beta-Carboline derivatives are known as the lead compounds for anti-tumor agents. To examine an optimal structure for anti-tumor activity, we synthesized a variety of beta-carboline derivatives, possessing a variety of substituents on the nitrogen atom of the amino group of 3-amino-beta-carboline, and evaluated their anti-tumor activity for HeLa S-3 cell line. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MU) assay showed that an optimal structure for anti-tumor activity was 3-cyclohexylmethylamino (le) or 3-benzylamino-beta-carboline (le. An optimal counter anion of 2-methyl-3-benzylamino-beta-carbolinium salts was a triflate anion 2c. In addition, the introduction of a hydroxyl group on the meta-position of the benzyl group of 3-benzylamino-beta-carboline (3e) enhanced its anti-tumor activity. Hoechst 33342 staining and DNA fragmentation assay suggested that 1f, 2c and 3e induced cell death by apoptosis unlike le. Flow cytometry analysis showed that if, 2c and 3e induced cell apoptosis through arrest of the cell cycle in the G(2)/M phase. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.044
• 作为产物：
  描述：

  2,3,4,9-四氢-1H-beta-咔啉-3-甲酸 在 吡啶 、 盐酸 、 氯化亚砜 、 三氯异氰尿酸 、 水 、 一水合肼 、 三乙胺 、 potassium hydroxide 、 sodium nitrite 作用下， 以 乙醇 、 戊醇 、 邻二甲苯 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 N-(β-carbolin-3-yl)-2-phenylacetamide
  参考文献：
  名称：

  3-Benzylamino-β-carboline derivatives induce apoptosis through G2/M arrest in human carcinoma cells HeLa S-3

  摘要：

  beta-Carboline derivatives are known as the lead compounds for anti-tumor agents. To examine an optimal structure for anti-tumor activity, we synthesized a variety of beta-carboline derivatives, possessing a variety of substituents on the nitrogen atom of the amino group of 3-amino-beta-carboline, and evaluated their anti-tumor activity for HeLa S-3 cell line. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MU) assay showed that an optimal structure for anti-tumor activity was 3-cyclohexylmethylamino (le) or 3-benzylamino-beta-carboline (le. An optimal counter anion of 2-methyl-3-benzylamino-beta-carbolinium salts was a triflate anion 2c. In addition, the introduction of a hydroxyl group on the meta-position of the benzyl group of 3-benzylamino-beta-carboline (3e) enhanced its anti-tumor activity. Hoechst 33342 staining and DNA fragmentation assay suggested that 1f, 2c and 3e induced cell death by apoptosis unlike le. Flow cytometry analysis showed that if, 2c and 3e induced cell apoptosis through arrest of the cell cycle in the G(2)/M phase. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.044

文献信息

• US5223509A
  申请人：——

  公开号：US5223509A

  公开（公告）日：1993-06-29
• 3-Benzylamino-β-carboline derivatives induce apoptosis through G2/M arrest in human carcinoma cells HeLa S-3
  作者：Reiko Ikeda、Toshie Iwaki、Tomoko Iida、Takasumi Okabayashi、Eishiro Nishi、Masaki Kurosawa、Norio Sakai、Takeo Konakahara

  DOI：10.1016/j.ejmech.2010.11.044

  日期：2011.2

  beta-Carboline derivatives are known as the lead compounds for anti-tumor agents. To examine an optimal structure for anti-tumor activity, we synthesized a variety of beta-carboline derivatives, possessing a variety of substituents on the nitrogen atom of the amino group of 3-amino-beta-carboline, and evaluated their anti-tumor activity for HeLa S-3 cell line. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MU) assay showed that an optimal structure for anti-tumor activity was 3-cyclohexylmethylamino (le) or 3-benzylamino-beta-carboline (le. An optimal counter anion of 2-methyl-3-benzylamino-beta-carbolinium salts was a triflate anion 2c. In addition, the introduction of a hydroxyl group on the meta-position of the benzyl group of 3-benzylamino-beta-carboline (3e) enhanced its anti-tumor activity. Hoechst 33342 staining and DNA fragmentation assay suggested that 1f, 2c and 3e induced cell death by apoptosis unlike le. Flow cytometry analysis showed that if, 2c and 3e induced cell apoptosis through arrest of the cell cycle in the G(2)/M phase. (C) 2010 Elsevier Masson SAS. All rights reserved.