N,N-bis[2-(4-methyl(phenylsulfonamido))ethyl]-N-[2-(tert-butylcarbamoyl)ethyl]amine | 426833-33-2

• 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: N,N-bis[2-(4-methyl(phenylsulfonamido))ethyl]-N-[2-(tert-butylcarbamoyl)ethyl]amine
• 英文别名: tert-butyl N-[2-[bis[2-[(4-methylphenyl)sulfonylamino]ethyl]amino]ethyl]carbamate
• CAS: 426833-33-2
• 化学式: C₂₅H₃₈N₄O₆S₂
• 分子量: 554.732
• InChiKey: PDIZBDPWWQYAPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N,N-bis[2-(4-methyl(phenylsulfonamido))ethyl]-N-[2-(tert-butylcarbamoyl)ethyl]amine 在 三氟乙酸 作用下， 生成 N,N′-(((2-aminoethyl)azanediyl)bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide)
  参考文献：
  名称：

  使用尿素衍生的合成转位酶促进囊泡和细胞膜上的磷脂酰丝氨酸翻转。

  摘要：

  具有附加的尿素和磺酰胺基团的三（2-氨基乙基）胺衍生物显示出促进荧光磷脂探针和内源性磷脂酰丝氨酸跨囊泡和红细胞细胞膜的转运。合成的转位酶似乎是通过与磷脂的头基结合并形成亲脂性超分子复合物而起作用的，所述亲脂性超分子复合物扩散通过双层膜的非极性内部。

  DOI：

  10.1039/b314006g
• 作为产物：
  描述：

  三(2-氨基乙基)胺 在 三乙胺 作用下， 生成 N,N-bis[2-(4-methyl(phenylsulfonamido))ethyl]-N-[2-(tert-butylcarbamoyl)ethyl]amine
  参考文献：
  名称：

  使用尿素衍生的合成转位酶促进囊泡和细胞膜上的磷脂酰丝氨酸翻转。

  摘要：

  具有附加的尿素和磺酰胺基团的三（2-氨基乙基）胺衍生物显示出促进荧光磷脂探针和内源性磷脂酰丝氨酸跨囊泡和红细胞细胞膜的转运。合成的转位酶似乎是通过与磷脂的头基结合并形成亲脂性超分子复合物而起作用的，所述亲脂性超分子复合物扩散通过双层膜的非极性内部。

  DOI：

  10.1039/b314006g

文献信息

• Structure/Activity Study of Tris(2-aminoethyl)amine-Derived Translocases for Phosphatidylcholine
  作者：J. Middleton Boon、Timothy N. Lambert、Bradley D. Smith、Alicia M. Beatty、Vesela Ugrinova、Seth N. Brown

  DOI：10.1021/jo016416s

  日期：2002.4.1

  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.
• Facilitated phospholipid translocation in vesicles and nucleated cells using synthetic small molecule scramblases
  作者：Kristy M. DiVittorio、Frank T. Hofmann、James R. Johnson、Lica Abu-Esba、Bradley D. Smith

  DOI：10.1016/j.bmc.2008.11.011

  日期：2009.1

  of 16 synthetic scramblase candidates were prepared from a tris(aminoethyl)amine (TREN) scaffold and evaluated for ability to facilitate translocation of fluorescent phospholipid probes across vesicle membranes and endogenous phosphatidylserine across the plasma membrane of nucleated cells. More than half of the compounds were found to greatly accelerate phospholipid translocation in vesicles. However

  从三（氨基乙基）胺 (TREN) 支架中制备了一系列 16 种合成加扰酶候选物，并评估了促进荧光磷脂探针跨囊泡膜和内源性磷脂酰丝氨酸跨有核细胞质膜易位的能力。发现超过一半的化合物极大地加速了囊泡中的磷脂易位。然而，它们通常无法诱导有核哺乳动物细胞表面磷脂酰丝氨酸的量大幅增加，这与之前使用红细胞的结果形成对比。荧光显微镜显示合成的乱序快速从细胞质膜转运到内部细胞器的膜中。
• Facilitated phosphatidylserine flip-flop across vesicle and cell membranes using urea-derived synthetic translocases
  作者：Yoshihiro Sasaki、Rameshwer Shukla、Bradley D. Smith

  DOI：10.1039/b314006g

  日期：——

  sulfonamide groups are shown to facilitate the translocation of fluorescent phospholipid probes and endogenous phosphatidylserine across vesicle and erythrocyte cell membranes. The synthetic translocases appear to operate by binding to the phospholipid head groups and forming lipophilic supramolecular complexes which diffuse through the non-polar interior of the bilayer membrane.

  具有附加的尿素和磺酰胺基团的三（2-氨基乙基）胺衍生物显示出促进荧光磷脂探针和内源性磷脂酰丝氨酸跨囊泡和红细胞细胞膜的转运。合成的转位酶似乎是通过与磷脂的头基结合并形成亲脂性超分子复合物而起作用的，所述亲脂性超分子复合物扩散通过双层膜的非极性内部。