(3S,4S)-3-{(1'S)-1'-hydroxyethyl}oxirane-2-carboxylic acid amide | 718627-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (3S,4S)-3-{(1'S)-1'-hydroxyethyl}oxirane-2-carboxylic acid amide
• 英文别名: (2S,3S)-3-[(1S)-1-hydroxyethyl]oxirane-2-carboxamide
• CAS: 718627-56-6
• 化学式: C₅H₉NO₃
• 分子量: 131.131
• InChiKey: MSVWOONKDAYNOM-HZLVTQRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-{(1'S)-1'-hydroxyethyl}oxirane-2-carboxylic acid amide 在 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 、 lithium hydroxide 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 1.34h， 以67%的产率得到(1S,5R)-4-hydroxy-4-methyl-6-oxa-3-aza-bicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Structure–activity relationships of epolactaene analogs as DNA polymerases inhibitors

  摘要：

  Epolactaene, a neuritogenic compound in human neuroblastoma cells, showed inhibitory activities against DNA polymerases alpha and beta. The synthesis and inhibitory activities of epolactaene analogs are described. The alpha,beta-epoxy-gamma-lactam moiety in the core and the length of the side chain greatly influenced the activities. Compound 5 was the strongest inhibitor of DNA polymerase a and 0 of all synthesized compounds with IC50 values of 13 and 78 muM, respectively. N- and O-alkyl derivatives that had modified core moieties showed moderate inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.007
• 作为产物：
  描述：

  (3RS,4RS,5RS)-3,4-Epoxy-5-methyldihydro-2(3H)-furanone 在 氨 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以83%的产率得到(3S,4S)-3-{(1'S)-1'-hydroxyethyl}oxirane-2-carboxylic acid amide
  参考文献：
  名称：

  Structure–activity relationships of epolactaene analogs as DNA polymerases inhibitors

  摘要：

  Epolactaene, a neuritogenic compound in human neuroblastoma cells, showed inhibitory activities against DNA polymerases alpha and beta. The synthesis and inhibitory activities of epolactaene analogs are described. The alpha,beta-epoxy-gamma-lactam moiety in the core and the length of the side chain greatly influenced the activities. Compound 5 was the strongest inhibitor of DNA polymerase a and 0 of all synthesized compounds with IC50 values of 13 and 78 muM, respectively. N- and O-alkyl derivatives that had modified core moieties showed moderate inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.007

文献信息

• Structure–activity relationships of epolactaene analogs as DNA polymerases inhibitors
  作者：Kouji Kuramochi、Yoshiyuki Mizushina、Seigo Nagata、Fumio Sugawara、Kengo Sakaguchi、Susumu Kobayashi

  DOI：10.1016/j.bmc.2004.03.007

  日期：2004.5

  Epolactaene, a neuritogenic compound in human neuroblastoma cells, showed inhibitory activities against DNA polymerases alpha and beta. The synthesis and inhibitory activities of epolactaene analogs are described. The alpha,beta-epoxy-gamma-lactam moiety in the core and the length of the side chain greatly influenced the activities. Compound 5 was the strongest inhibitor of DNA polymerase a and 0 of all synthesized compounds with IC50 values of 13 and 78 muM, respectively. N- and O-alkyl derivatives that had modified core moieties showed moderate inhibition. (C) 2004 Elsevier Ltd. All rights reserved.