methyl (2S)-6-isothiocyanato-2-(phenylmethoxycarbonylamino)hexanoate | 88576-94-7

• 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)-6-isothiocyanato-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 88576-94-7
• 化学式: C₁₆H₂₀N₂O₄S
• 分子量: 336.412
• InChiKey: OPSCLZGJGQVTNA-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-6-isothiocyanato-2-(phenylmethoxycarbonylamino)hexanoate 在 氨 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以59%的产率得到methyl (2S)-6-(carbamothioylamino)-2-(phenylmethoxycarbonylamino)hexanoate
  参考文献：
  名称：

  Time-dependence and preliminary SAR studies in inhibition of nitric oxide synthase isoforms by homologues of thiocitrulline

  摘要：

  Treatment of N-alpha-Cbz-N-epsilon-(2-hydroxyethylaminothiocarbonyl)-L-lysine N-(2-hydroxyethyl)amide with boiling hydrochloric acid gave N-epsilon-(4,5-dihydrothiazol-2-yl)-L-lysine. This was a weak and non-isoform selective inhibitor of NOS, whereas N-epsilon-aminothiocarbonyl-L-lysine and its methyl ester were potent, with IC50 = 13 and 18 muM, respectively, against human iNOS and IC50 = 3 and 8 muM, respectively, against rat nNOS. Time dependence was observed for inhibition of nNOS by the ester. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.018
• 作为产物：
  描述：

  N-alpha-Cbz-L-赖氨酸 在 氯化亚砜 、 calcium carbonate 作用下， 以 氯仿 、 水 为溶剂， 反应 112.0h， 生成 methyl (2S)-6-isothiocyanato-2-(phenylmethoxycarbonylamino)hexanoate
  参考文献：
  名称：

  Time-dependence and preliminary SAR studies in inhibition of nitric oxide synthase isoforms by homologues of thiocitrulline

  摘要：

  Treatment of N-alpha-Cbz-N-epsilon-(2-hydroxyethylaminothiocarbonyl)-L-lysine N-(2-hydroxyethyl)amide with boiling hydrochloric acid gave N-epsilon-(4,5-dihydrothiazol-2-yl)-L-lysine. This was a weak and non-isoform selective inhibitor of NOS, whereas N-epsilon-aminothiocarbonyl-L-lysine and its methyl ester were potent, with IC50 = 13 and 18 muM, respectively, against human iNOS and IC50 = 3 and 8 muM, respectively, against rat nNOS. Time dependence was observed for inhibition of nNOS by the ester. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.018