N4-acetyl,N1-methyl-cyclo-Trp-Gly | 221336-86-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N4-acetyl,N1-methyl-cyclo-Trp-Gly
• 英文别名: N⁴-acetyl,N¹-methyl-cyclo-Trp-Gly
• CAS: 221336-86-3
• 化学式: C₁₆H₁₇N₃O₃
• 分子量: 299.329
• InChiKey: MKUUNBCTFAAKLS-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  73.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N4-acetyl,N1-methyl-cyclo-Trp-Gly 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 对硝基苯甲醛 作用下， 以 乙腈 为溶剂， 反应 23.0h， 生成 tert-butyl 3-[[(2S)-1-methyl-3,6-dioxopiperazin-2-yl]methyl]indole-1-carboxylate
  参考文献：
  名称：

  Synthesis of tryptophan-dehydrobutyrine diketopiperazines and analogues

  摘要：

  Condensation of N-1-methyl-cyclo-Trp-Gly and aldehydes in basic media was studied to confirm the structure of the natural product TDD (N-methyl-Tryptophan Dehydrobutyrine Diketopiperazine, 1) and to prepare analogues with potential activity as GST (Glutathione-S-Transferase) inhibitors. This strategy was successful for 1,4-diacetyl-cyclo-Trp-Gly but it did not work for N-4-acetyl, N-1-methyl-cyclo-Trp-Gly derivatives. Pyrolytic cyclization of N-Boc-L-Thr-N-methyl-L-Trp methyl ester gave the Z-isomer of N-methyltryptophan dehydrobutyrine diketopiperazine, which was previously supposed to be the natural product. However, by comparison of melting points and pectroscopic data with those of 1, we conclude that the proposed structure for TDD must be corrected. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01095-3
• 作为产物：
  描述：

  N-甲基色氨酸甲酯 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 反应 16.75h， 生成 N4-acetyl,N1-methyl-cyclo-Trp-Gly
  参考文献：
  名称：

  Synthesis of tryptophan-dehydrobutyrine diketopiperazines and analogues

  摘要：

  Condensation of N-1-methyl-cyclo-Trp-Gly and aldehydes in basic media was studied to confirm the structure of the natural product TDD (N-methyl-Tryptophan Dehydrobutyrine Diketopiperazine, 1) and to prepare analogues with potential activity as GST (Glutathione-S-Transferase) inhibitors. This strategy was successful for 1,4-diacetyl-cyclo-Trp-Gly but it did not work for N-4-acetyl, N-1-methyl-cyclo-Trp-Gly derivatives. Pyrolytic cyclization of N-Boc-L-Thr-N-methyl-L-Trp methyl ester gave the Z-isomer of N-methyltryptophan dehydrobutyrine diketopiperazine, which was previously supposed to be the natural product. However, by comparison of melting points and pectroscopic data with those of 1, we conclude that the proposed structure for TDD must be corrected. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01095-3