Met-Pro-pNA | 99264-69-4

• 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: Met-Pro-pNA
• 英文别名: (L)-Methionyl-(L)-prolyl-P-nitroanilide；(2S)-1-[(2S)-2-amino-4-methylsulfanylbutanoyl]-N-(4-nitrophenyl)pyrrolidine-2-carboxamide
• CAS: 99264-69-4
• 化学式: C₁₆H₂₂N₄O₄S
• 分子量: 366.441
• InChiKey: HQRJJHXKCFABSI-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  Met-Pro-pNA 以 甲苯 为溶剂， 生成 Tfa-Met-Pro-pNA
  参考文献：
  名称：

  Discovery and SAR studies of methionine–proline anilides as dengue virus NS2B-NS3 protease inhibitors

  摘要：

  A series of methionine-proline dipeptide derivatives and their analogues were designed, synthesized and assayed against the serotype 2 dengue virus NS2B-NS3 protease, and methionine-proline anilides 1 and 2 were found to be the most active DENV 2 NS2B-NS3 competitive inhibitors with K-i values of 4.9 and 10.5 mu M. The structure and activity relationship and the molecular docking revealed that L-proline, L-methionine and p-nitroaniline in 1 and 2 are the important characters in blocking the active site of NS2B-NS3 protease. Our current results suggest that the title dipeptidic scaffold represents a promising structural core to discover a new class of active NS2B-NS3 competitive inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.071
• 作为产物：
  描述：

  L-脯氨酰对硝基苯胺 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 Met-Pro-pNA
  参考文献：
  名称：

  Discovery and SAR studies of methionine–proline anilides as dengue virus NS2B-NS3 protease inhibitors

  摘要：

  A series of methionine-proline dipeptide derivatives and their analogues were designed, synthesized and assayed against the serotype 2 dengue virus NS2B-NS3 protease, and methionine-proline anilides 1 and 2 were found to be the most active DENV 2 NS2B-NS3 competitive inhibitors with K-i values of 4.9 and 10.5 mu M. The structure and activity relationship and the molecular docking revealed that L-proline, L-methionine and p-nitroaniline in 1 and 2 are the important characters in blocking the active site of NS2B-NS3 protease. Our current results suggest that the title dipeptidic scaffold represents a promising structural core to discover a new class of active NS2B-NS3 competitive inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.071

文献信息

• Type-I methionyl aminopeptidases inhibitors in antibacterial targeting
  申请人：Holz C. Richard

  公开号：US20050026873A1

  公开（公告）日：2005-02-03

  Novel compounds act as molecular inhibitors to target new enzymatic targets on bacteria and provide a new class of bactericidal compounds. The compounds provide for selective inhibition of Type I methionyl aminopeptidases (MetAPs) in bacteria. Because humans and other animals have both type-I and type-II MetAPs, which are functionally equivalent, the compounds are bactericidal but do not completely inhibit MetAP activity in humans and other animals. The compounds also have anti-microbial activity in microbes other than bacteria provided the targeted microbes have predominately type-I MetAP.

  新型化合物作为分子抑制剂，针对细菌的新酶靶点并提供一类新的细菌杀死化合物。这些化合物对细菌中的I型甲硫氨肽酶（MetAPs）进行选择性抑制。由于人类和其他动物都具有I型和II型MetAPs，它们在功能上是等效的，因此这些化合物具有细菌杀死作用，但不会完全抑制人类和其他动物中的MetAP活性。这些化合物还具有针对除细菌以外的微生物的抗微生物活性，前提是目标微生物主要具有I型MetAP。
• Novel methionine aminopeptidase-2 and uses thereof
  申请人：——

  公开号：US20040077031A1

  公开（公告）日：2004-04-22

  The present invention uses the manganese-dependent physiological form of the enzyme methionine aminopeptidase type 2 to assess inhibition by agents that might be used in the treatment of angiogenesis, cancer, malaria and leishmaniasis. This method has the advantage of using the manganese form of the enzyme and therefore, the advantage of identifying potent inhibitors that might not show activity in cellular systems because the wrong metal cofactor is used. Therefore it is a new tool for the development of agents useful in the therapy of cancer and other angiogenesis-related diseases and, several infectious diseases including malaria, leishmaniais and microsporidiosis.

  本发明利用蛋氨酸氨肽酶 2 型的锰依赖生理形式来评估可能用于治疗血管生成、癌症、疟疾和利什曼病的药物的抑制作用。这种方法的优点是使用了锰形式的酶，因此可以鉴定出有效的抑制剂，而这些抑制剂可能因为使用了错误的金属辅助因子而无法在细胞系统中显示出活性。因此，这是一种新的工具，可用于开发治疗癌症、其他血管生成相关疾病以及包括疟疾、利什曼病和微孢子虫病在内的多种传染病的药物。
• Discovery and SAR studies of methionine–proline anilides as dengue virus NS2B-NS3 protease inhibitors
  作者：Guo-Chun Zhou、Zhibing Weng、Xiaoxia Shao、Fang Liu、Xin Nie、Jinsong Liu、Decai Wang、Chunguang Wang、Kai Guo

  DOI：10.1016/j.bmcl.2013.10.071

  日期：2013.12

  A series of methionine-proline dipeptide derivatives and their analogues were designed, synthesized and assayed against the serotype 2 dengue virus NS2B-NS3 protease, and methionine-proline anilides 1 and 2 were found to be the most active DENV 2 NS2B-NS3 competitive inhibitors with K-i values of 4.9 and 10.5 mu M. The structure and activity relationship and the molecular docking revealed that L-proline, L-methionine and p-nitroaniline in 1 and 2 are the important characters in blocking the active site of NS2B-NS3 protease. Our current results suggest that the title dipeptidic scaffold represents a promising structural core to discover a new class of active NS2B-NS3 competitive inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.