N-(tert-butoxycarbonyl)glycine 3-[N-(9-fluorenylmethoxycarbonyl)propylamino]propylamide | 314728-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(tert-butoxycarbonyl)glycine 3-[N-(9-fluorenylmethoxycarbonyl)propylamino]propylamide
• 英文别名: 9H-fluoren-9-ylmethyl N-[3-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]propyl]-N-propylcarbamate
• CAS: 314728-17-1
• 化学式: C₂₈H₃₇N₃O₅
• 分子量: 495.619
• InChiKey: YMOXOLFGSDZHMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)glycine 3-[N-(9-fluorenylmethoxycarbonyl)propylamino]propylamide 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 38.0h， 生成 benzyl N-[(E,2S,7S)-1,8-dioxo-1,8-bis[[2-oxo-2-[3-(propylamino)propylamino]ethyl]amino]-7-(phenylmethoxycarbonylamino)oct-4-en-2-yl]carbamate
  参考文献：
  名称：

  Inhibition of Trypanothione Reductase by Substrate Analogues

  摘要：

  [GRAPHICS]Trypanothione reductase (TR) catalyzes the NAPDH-dependent reduction of the spermidine-glutathione conjugate trypanothione, an antioxidant found in Trypanosomatid parasites. TR plays an essential role in the parasite's defense against oxidative stress and has emerged as a prime target for drug development. Here we report the synthesis of several trypanothione analogues and their inhibitory effects on T. cruzi TR. All are competitive inhibitors with K-i values ranging from 30 to 91 muM.

  DOI：

  10.1021/ol0065423
• 作为产物：
  描述：

  BOC-甘氨酸-N-羟基琥柏酰亚胺酯 、 N-丙基-1,3-丙二胺 、 氯甲酸-9-芴基甲酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以72%的产率得到N-(tert-butoxycarbonyl)glycine 3-[N-(9-fluorenylmethoxycarbonyl)propylamino]propylamide
  参考文献：
  名称：

  Inhibition of Trypanothione Reductase by Substrate Analogues

  摘要：

  [GRAPHICS]Trypanothione reductase (TR) catalyzes the NAPDH-dependent reduction of the spermidine-glutathione conjugate trypanothione, an antioxidant found in Trypanosomatid parasites. TR plays an essential role in the parasite's defense against oxidative stress and has emerged as a prime target for drug development. Here we report the synthesis of several trypanothione analogues and their inhibitory effects on T. cruzi TR. All are competitive inhibitors with K-i values ranging from 30 to 91 muM.

  DOI：

  10.1021/ol0065423

文献信息

• Inhibition of Trypanothione Reductase by Substrate Analogues
  作者：Elizabeth A. Garrard、Emily C. Borman、Brian N. Cook、Emily J. Pike、David G. Alberg

  DOI：10.1021/ol0065423

  日期：2000.11.1

  [GRAPHICS]Trypanothione reductase (TR) catalyzes the NAPDH-dependent reduction of the spermidine-glutathione conjugate trypanothione, an antioxidant found in Trypanosomatid parasites. TR plays an essential role in the parasite's defense against oxidative stress and has emerged as a prime target for drug development. Here we report the synthesis of several trypanothione analogues and their inhibitory effects on T. cruzi TR. All are competitive inhibitors with K-i values ranging from 30 to 91 muM.