benzyl N-[4-amino-1-bis(4-methoxyphenoxy)phosphoryl-4-oxobutyl]carbamate | 1394940-75-0

• 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-[4-amino-1-bis(4-methoxyphenoxy)phosphoryl-4-oxobutyl]carbamate
• CAS: 1394940-75-0
• 化学式: C₂₆H₂₉N₂O₈P
• 分子量: 528.499
• InChiKey: ASUIJKTZGCPWMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  benzyl N-[1-bis(4-methoxyphenoxy)phosphoryl-4-oxo-4-(tritylamino)butyl]carbamate 在 三异丙基硅烷 、 三氟乙酸 作用下， 反应 2.0h， 以40%的产率得到benzyl N-[4-amino-1-bis(4-methoxyphenoxy)phosphoryl-4-oxobutyl]carbamate
  参考文献：
  名称：

  The development of first Staphylococcus aureus SplB protease inhibitors: Phosphonic analogues of glutamine

  摘要：

  Produced by Staphylococcus aureus, SplB belongs to the chymotrypsin-like serine protease family. Since the biological role of SplB protease is unknown, the design and application of its specific inhibitors may help to reveal the function of this enzyme. Until now no SplB inhibitors have been reported. Herein, we present the design and synthesis of novel a-aminophosphonic analogues of glutamine, as well as their peptidyl derivatives. The inhibitory effects of these compounds towards the newly discovered SplB serine protease from S. aureus are characterized. We have also investigated the influence of aromatic ester substituents on inhibitory potency towards SplB. One of the compounds-Cbz-Glu-Leu-Gln(P)(OC6H4-4-O-CH3)(2)-displayed an apparent second-order inhibition rate value of 1400 M(-1)s(-1). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.011

文献信息

• The development of first Staphylococcus aureus SplB protease inhibitors: Phosphonic analogues of glutamine
  作者：Burchacka Ewa、Walczak Maciej、Sieńczyk Marcin、Dubin Grzegorz、Zdżalik Michał、Potempa Jan、Oleksyszyn Józef

  DOI：10.1016/j.bmcl.2012.07.011

  日期：2012.9

  Produced by Staphylococcus aureus, SplB belongs to the chymotrypsin-like serine protease family. Since the biological role of SplB protease is unknown, the design and application of its specific inhibitors may help to reveal the function of this enzyme. Until now no SplB inhibitors have been reported. Herein, we present the design and synthesis of novel a-aminophosphonic analogues of glutamine, as well as their peptidyl derivatives. The inhibitory effects of these compounds towards the newly discovered SplB serine protease from S. aureus are characterized. We have also investigated the influence of aromatic ester substituents on inhibitory potency towards SplB. One of the compounds-Cbz-Glu-Leu-Gln(P)(OC6H4-4-O-CH3)(2)-displayed an apparent second-order inhibition rate value of 1400 M(-1)s(-1). (C) 2012 Elsevier Ltd. All rights reserved.