2-[(5-acetyl-3-(4-bromophenyl)-1,3,4-thiadiazol-2(3H)-ylidene)]-3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile | 1447699-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(5-acetyl-3-(4-bromophenyl)-1,3,4-thiadiazol-2(3H)-ylidene)]-3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile
• CAS: 1447699-55-9
• 化学式: C₁₈H₁₃BrN₄O₂S
• 分子量: 429.297
• InChiKey: ILYXRXAXGYYFQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.46
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3-(1-甲基-1H-丙基-2-基)-3-氧丙腈 在 potassium hydroxide 、 chitosan 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 150.0~160.0 ℃ 、1.12 MPa 条件下， 反应 0.5h， 生成 2-[(5-acetyl-3-(4-bromophenyl)-1,3,4-thiadiazol-2(3H)-ylidene)]-3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile
  参考文献：
  名称：

  A Facile Green Synthesis and Anti-Cancer Activity of bis-Arylhydrazononitriles, Triazolo[5,1-c][1,2,4]triazine, and 1,3,4-Thiadiazolines

  摘要：

  Coupling of 2-cyanoacetyl-1-methyl-1H-pyrrole (1) with diazonium salts of 1,4-benzenediamine (2), 2,6-dichlorobenzene-1,4-diamine (4), and benzidine (6) afforded bis-arylhydrazononitriles 3, 5, and 7, respectively. Also, coupling of 1 with [1,2,4]triazole-3-diazonium sulfate (8) gave the respective [1,2,4]triazolo [5,1-c] [1,2,4]triazine derivative 11. On the other hands, treatment of 2-[(1-methyl-1H-pyrrol-2-yl)carbonyl]-3-mercapto-3-(phenylamino)acrylonitrile (12) with hydrazonoyl chlorides 13a-h in dioxane, in the presence of chitosan as eco-friendly heterogeneous basic catalyst, under microwave irradiation furnished 1,3,4-thiadiazolines 16a-h, incorporating pyrrole moiety. The anti-cancer activities of the synthesized products were determined against the colon carcinoma (HCT), human laryngeal carcinoma (Hep-2), human medulloblastoma (Daoy), human breast adenocarcinoma (MCF-7), and human colon adenocarcinoma (WiDr) cell lines.

  DOI：

  10.3987/com-13-12696