20-cyano-2,2-dimethyl-4-oxo-3-oxa-5,9,14,18-tetraazaeicosane-9,14-dicarboxylic acid bis(1,1-dimethylethyl) ester | 128550-04-9

• 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: 20-cyano-2,2-dimethyl-4-oxo-3-oxa-5,9,14,18-tetraazaeicosane-9,14-dicarboxylic acid bis(1,1-dimethylethyl) ester
• 英文别名: tert-butyl N-[3-(2-cyanoethylamino)propyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]carbamate
• CAS: 128550-04-9
• 化学式: C₂₈H₅₃N₅O₆
• 分子量: 555.759
• InChiKey: CWHVEEIGNPGBPP-UHFFFAOYSA-N

物化性质

• 沸点：
  661.0±55.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  39.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  133.23
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  20-cyano-2,2-dimethyl-4-oxo-3-oxa-5,9,14,18-tetraazaeicosane-9,14-dicarboxylic acid bis(1,1-dimethylethyl) ester 在 palladium dihydroxide 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 生成 (N¹,N⁴,N⁹,N¹³-tetra-tert-butoxycarbonyl)-1,16-diamino-4,9,13-triazahexadecane
  参考文献：
  名称：

  Polycationic Sulfonamides for the Sequestration of Endotoxin

  摘要：

  Lipopolysaccharides (LPS) play a key role in the pathogenesis of septic shock, a major cause of mortality in the critically ill patient. We had previously shown that monoacylated polyamine compounds specifically bind to and neutralize the activity of LPS with high in vitro potency and afford complete protection in a murine model of endotoxic shock. Fatty acid amides of polyamines may be rapidly cleared from systemic circulation due to their susceptibility to nonspecific serum amidases and, thus, would be predicted to have a short duration of action. In a systematic effort to increase the likelihood of better bioavailability properties together with structural modifications that may result in gains in activity, we now report structure-activity relationships pertaining to endotoxin-binding and -neutralizing activities of homologated polyamine sulfonamides.

  DOI：

  10.1021/jm061198m
• 作为产物：
  描述：

  N-Boc-3-氨基丙基溴 在 palladium dihydroxide potassium fluoride 、 Celite 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 25.0~70.0 ℃ 、344.73 kPa 条件下， 反应 122.0h， 生成 20-cyano-2,2-dimethyl-4-oxo-3-oxa-5,9,14,18-tetraazaeicosane-9,14-dicarboxylic acid bis(1,1-dimethylethyl) ester
  参考文献：
  名称：

  Jasys, V. John; Kelbaugh, Paul B.; Nason, Deane M., Journal of the American Chemical Society, 1990, vol. 112, # 18, p. 6696 - 6704

  摘要：

  DOI：

文献信息

• Polyamines and their use as antibacterial and sensitizing agents
  申请人：David Sunil A.

  公开号：US20070197658A1

  公开（公告）日：2007-08-23

  Polyamines with varying chain-lengths were evaluated for antimicrobial activity in order to test the hypothesis that these bis-cationic amphipathic compounds may also bind to and permeabilize intact Gram negative bacterial membranes. The compounds were found to possess significant antimicrobial activity and mediated via permeabilization of bacterial membranes. Homologated spermine, bis-acylated with C 8 or C 9 chains was found to profoundly sensitize E. coli to hydrophobic antibiotics such as rifampicin.

  多种链长的多胺被评估其抗微生物活性，以验证这些双阳离子两性化合物可能也结合并使革兰氏阴性细菌膜通透的假设。发现这些化合物具有显著的抗微生物活性，并通过细菌膜通透介导。经过烷基化的精胺，与C8或C9链双酰化，被发现能显著增加大肠杆菌对亲脂性抗生素如利福平的敏感性。
• JASYS, V. JOHN;KELBAUGH, PAUL R.;NASON, DEANE M.;PHILLIPS, DOUGLAS;ROSNAC+, J. AMER. CHEM. SOC., 112,(1990) N8, C. 6696-6704
  作者：JASYS, V. JOHN、KELBAUGH, PAUL R.、NASON, DEANE M.、PHILLIPS, DOUGLAS、ROSNAC+

  DOI：——

  日期：——