N,N-bis[2-(4-methyl(phenylsulfonamido))ethyl]-N-[2-(5-(dimethylamino)-1-naphthalenesulfonamido)ethyl]amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-bis[2-(4-methyl(phenylsulfonamido))ethyl]-N-[2-(5-(dimethylamino)-1-naphthalenesulfonamido)ethyl]amine
• 英文别名: N-[2-[bis[2-[(4-methylphenyl)sulfonylamino]ethyl]amino]ethyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• 化学式: C₃₂H₄₁N₅O₆S₃
• 分子量: 687.905
• InChiKey: GIZAJUTVFWVYTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  丹酰氯 、 N,N-bis[2-(4-methyl(phenylsulfonamido))ethyl]-N-(2-aminoethyl)amine bis(trifluoroacetate) 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 19.0h， 以84%的产率得到N,N-bis[2-(4-methyl(phenylsulfonamido))ethyl]-N-[2-(5-(dimethylamino)-1-naphthalenesulfonamido)ethyl]amine
  参考文献：
  名称：

  Structure/Activity Study of Tris(2-aminoethyl)amine-Derived Translocases for Phosphatidylcholine

  摘要：

  Sulfonamide and amide derivatives of tris(aminoethyl)amine (TREN) are known to facilitate phospholipid translocation across vesicle and erythrocyte membranes; that is, they act as synthetic translocases. In this report, a number of new TREN-based translocases are evaluated for their abilities to bind phosphatidylcholine and translocate a fluorescent phosphatidylcholine probe. Association constants were determined from H-1 NMR titration experiments, and translocation half-lives were determined via 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD)/dithionite quenching assays. A rough correlation exists between translocase/phosphatidylcholine association constants and translocation half-lives. The tris-sulfonamide translocases are superior to the tris-amide versions because they associate more strongly with the phospholipid headgroup. The stronger association is due to the increased acidity of the sulfonamide NHs as well as a molecular geometry (as shown by X-ray crystallography) that is able to form tridentate complexes with one of the phosphate oxygens. Two fluorescent translocase analogues were synthesized and used to characterize membrane partitioning properties. The results indicate that the facilitated translocation of phospholipids by TREN-derived translocases is due to the formation of hydrogen-bonded complexes with the phospholipid headgroups. In the case of zwitterionic phosphatidylcholine, it is the neutral form of the translocases that rapidly associates with the phosphate portion of the phosphocholine headgroup. Complexation masks the headgroup polarity and promotes diffusion of the phospholipid-translocase complex across the lipophilic interior of the membrane.

  DOI：

  10.1021/jo016416s