benzyl N-[(E,2S,7S)-1,8-bis[[2-[3-(dimethylamino)propylamino]-2-oxoethyl]amino]-1,8-dioxo-7-(phenylmethoxycarbonylamino)oct-4-en-2-yl]carbamate | 314728-14-8

• 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: benzyl N-[(E,2S,7S)-1,8-bis[[2-[3-(dimethylamino)propylamino]-2-oxoethyl]amino]-1,8-dioxo-7-(phenylmethoxycarbonylamino)oct-4-en-2-yl]carbamate
• CAS: 314728-14-8
• 化学式: C₃₈H₅₆N₈O₈
• 分子量: 752.911
• InChiKey: FESDPHHBKNKGLQ-JIKQTTLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  54
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  200
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl N-[(E,2S,7S)-1,8-bis[[2-[3-(dimethylamino)propylamino]-2-oxoethyl]amino]-1,8-dioxo-7-(phenylmethoxycarbonylamino)oct-4-en-2-yl]carbamate 在 Wilkinson's catalyst 氢气 作用下， 以 乙醇 、 苯 为溶剂， 反应 120.0h， 以78%的产率得到benzyl N-[(2S,7S)-1,8-bis[[2-[3-(dimethylamino)propylamino]-2-oxoethyl]amino]-1,8-dioxo-7-(phenylmethoxycarbonylamino)octan-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：

  N-Cbz-L-天冬氨酸 1-甲酯 在 碳酸氢钠 盐酸 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 lithium hydroxide 、 sodium hypochlorite 、 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 四溴化碳 、 硼烷 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 sodium bromide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 57.67h， 生成 benzyl N-[(E,2S,7S)-1,8-bis[[2-[3-(dimethylamino)propylamino]-2-oxoethyl]amino]-1,8-dioxo-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

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.