(2S,2′S)-2,2′-((2,2′-diselanediylbis(benzoyl))bis(azanediyl))dipropanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,2′S)-2,2′-((2,2′-diselanediylbis(benzoyl))bis(azanediyl))dipropanoic acid
• 英文别名: (2S)-2-[[2-[[2-[[(1S)-1-carboxyethyl]carbamoyl]phenyl]diselanyl]benzoyl]amino]propanoic acid
• 化学式: C₂₀H₂₀N₂O₆Se₂
• 分子量: 542.309
• InChiKey: ZEHWFHKNRVVIGV-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.63
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  双（2-羧基苯基）二硒化物 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,2′S)-2,2′-((2,2′-diselanediylbis(benzoyl))bis(azanediyl))dipropanoic acid
  参考文献：
  名称：

  1,2-Benzisoselenazol-3（2 H）-一衍生物作为一类新的细菌脲酶抑制剂

  摘要：

  脲酶抑制剂被认为是用于治疗尿素分解细菌感染，特别是由胃管中的幽门螺杆菌引起的感染的有前途的化合物。在本文中，我们介绍了新型高效的有机硒化合物的合成和抑菌活性，这些化合物作为巴斯德氏菌和幽门螺杆菌脲酶的抑制剂。这些研究的化合物代表了一类竞争性可逆脲​​酶抑制剂。活性最高的化合物2-phenyl-1,2-benzisoselenazol-3（2 H）-one（ebselen）对S. Pasturii和H. pylori的K i值分别为2.11和226 nM 。这两种酶分别表示依布硒仑是迄今为止报道的最有效的细菌脲酶低分子量抑制剂之一。这些分子大多数在体外穿透革兰氏阴性细菌大肠杆菌（pGEM :: ureOP）的细胞膜。此外，对幽门螺杆菌J99参考菌株的全细胞研究证实了所检查的有机硒化合物作为尿素酶抑制剂对致病菌的高效性。

  DOI：

  10.1021/acs.jmedchem.6b00986

文献信息

• Design and Synthesis of DiselenoBisBenzamides (DISeBAs) as Nucleocapsid Protein 7 (NCp7) Inhibitors with anti-HIV Activity
  作者：Luca Sancineto、Alice Mariotti、Luana Bagnoli、Francesca Marini、Jenny Desantis、Nunzio Iraci、Claudio Santi、Christophe Pannecouque、Oriana Tabarrini

  DOI：10.1021/acs.jmedchem.5b01183

  日期：2015.12.24

  The interest in the synthesis of Se-containing compounds is growing with the discovery of derivatives exhibiting various biological activities. In this manuscript, we have identified a series of 2,2'-diselenobisbenzamides (DISeBAs) as novel HIV retroviral nucleocapsid protein 7 (NCp7) inhibitors. Because of its pleiotropic functions in the whole viral life cycle and its mutation intolerant nature, NCp7 represents a target of great interest which is not reached by any anti-HIV agent in clinical use. Using the diselenobisbenzoic scaffold, amino acid, and benzenesulfonamide derivatives were prepared and biologically profiled against different models of HIV infection. The incorporation of amino acids such as glycine and glutamate into DISeBAs 7 and 8 resulted in selective anti-HIV activity against both acutely and chronically infected cells as well as an interesting virucidal effect. DISeBAs demonstrated broad antiretroviral activity, encompassing HIV-1 drug-resistant strains including clinical isolates, as well as simian immunodeficiency virus (SW). Time of addition experiments, along with the observed dose dependent inhibition of the Gag precursor proper processing, confirmed that their mechanism of action is based on NCp7 inhibition.