16-phenylthiodidemnimide C | 259752-97-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 16-phenylthiodidemnimide C
• 英文别名: 3-(1H-indol-3-yl)-4-(3-methyl-2-phenylsulfanylimidazol-4-yl)pyrrole-2,5-dione
• CAS: 259752-97-1
• 化学式: C₂₂H₁₆N₄O₂S
• 分子量: 400.461
• InChiKey: ICMKLWKMEURHRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  16-phenylthiodidemnimide C 在 镍 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以77%的产率得到didemnimide C
  参考文献：
  名称：

  Improved Synthesis of Isogranulatimide, a G2 Checkpoint Inhibitor. Syntheses of Didemnimide C, Isodidemnimide A, Neodidemnimide A, 17-Methylgranulatimide, and Isogranulatimides A−C

  摘要：

  A concise, improved synthesis of isogranulatimide (6), a naturally occurring substance with G2 checkpoint inhibition activity, is described. Also reported are the syntheses of didemnimide C (18), isodidemnimide A (24), neodidemnimide A (36), 17-methylgranulatimide (9), and isogranulatimides A (10), B (11), and C (12). Compounds 9-12, congeners of isogranulatimide (6), are now available for biological evaluation.

  DOI：

  10.1021/jo9914723
• 作为产物：
  描述：

  1-methyl-2-phenylsulfanyl-1H-imidazole 在 4 A molecular sieve 、 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 乙二醇二甲醚 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.25h， 生成 16-phenylthiodidemnimide C
  参考文献：
  名称：

  Improved Synthesis of Isogranulatimide, a G2 Checkpoint Inhibitor. Syntheses of Didemnimide C, Isodidemnimide A, Neodidemnimide A, 17-Methylgranulatimide, and Isogranulatimides A−C

  摘要：

  A concise, improved synthesis of isogranulatimide (6), a naturally occurring substance with G2 checkpoint inhibition activity, is described. Also reported are the syntheses of didemnimide C (18), isodidemnimide A (24), neodidemnimide A (36), 17-methylgranulatimide (9), and isogranulatimides A (10), B (11), and C (12). Compounds 9-12, congeners of isogranulatimide (6), are now available for biological evaluation.

  DOI：

  10.1021/jo9914723

文献信息

• US6291447B1
  申请人：——

  公开号：US6291447B1

  公开（公告）日：2001-09-18
• Improved Synthesis of Isogranulatimide, a G2 Checkpoint Inhibitor. Syntheses of Didemnimide C, Isodidemnimide A, Neodidemnimide A, 17-Methylgranulatimide, and Isogranulatimides A−C
  作者：Edward Piers、Robert Britton、Raymond J. Andersen

  DOI：10.1021/jo9914723

  日期：2000.1.1

  A concise, improved synthesis of isogranulatimide (6), a naturally occurring substance with G2 checkpoint inhibition activity, is described. Also reported are the syntheses of didemnimide C (18), isodidemnimide A (24), neodidemnimide A (36), 17-methylgranulatimide (9), and isogranulatimides A (10), B (11), and C (12). Compounds 9-12, congeners of isogranulatimide (6), are now available for biological evaluation.