methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate | 314728-05-7

• 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: methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate
• CAS: 314728-05-7
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: OXHYTNGGZUWBPN-GFUIURDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate 在 9-borabicyclo[3.3.1]nonane dimer 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-bromohex-4-enoate
  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-(benzyloxy)carbonyl-homoserine methyl ester 在 碳酸氢钠 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium bromide 作用下， 以 水 、 甲苯 为溶剂， 反应 7.5h， 生成 methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate
  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