N-stearoyl-sulfanilic acid | 101524-15-6

• 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-stearoyl-sulfanilic acid
• 英文别名: N-Stearoyl-sulfanilsaeure；4-(Octadecanoylamino)benzenesulfonic acid
• CAS: 101524-15-6
• 化学式: C₂₄H₄₁NO₄S
• 分子量: 439.66
• InChiKey: LNYRYOZKJZWZCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  30
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  十八烷酰氯 、 对氨基苯磺酸 在 N,N-二异丙基乙胺 作用下， 生成 N-stearoyl-sulfanilic acid
  参考文献：
  名称：

  2,4-Bis(octadecanoylamino)benzenesulfonic acid sodium salt as a novel scavenger receptor inhibitor with low molecular weight

  摘要：

  In order to investigate the effect of the fixation of the orientations of the two long chains, three types of novel derivatives of scavenger receptor inhibitor I were synthesized, and their biological activities were evaluated. Among the novel derivatives, 2,4-bis(octadecanoylamino)benzenesulfonic acid sodium salt (4d) showed the most potent inhibitory activity against the incorporation of 1,1'-dioctadecyl-3,3,3',3'-tetramethylindocarbocyanine perchlorate-labeled acetyl-LDL (DiI-acetyl-LDL) into macrophages. 2,5-Bis(octadecanoylamino)benzenesulfonic acid sodium salt (4c), a regioisomer of 4d, did not exhibit as potent an inhibitory activity as 4d, meaning that the substitution pattern of two long chains on the benzene ring must be important. Compound Q exhibited 10 times more potent inhibitory activity against the binding of 121 I-labeled acetyl-LDL to the surface of macrophages than compound 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.082

文献信息

• Seidel; Engelfried, Chemische Berichte, 1936, vol. 69, p. 2567,2581
  作者：Seidel、Engelfried

  DOI：——

  日期：——
• Uppal; Venkataraman, 1939, vol. 55, p. 125,129
  作者：Uppal、Venkataraman

  DOI：——

  日期：——
• 2,4-Bis(octadecanoylamino)benzenesulfonic acid sodium salt as a novel scavenger receptor inhibitor with low molecular weight
  作者：Kazuya Yoshiizumi、Fumio Nakajima、Rika Dobashi、Noriyasu Nishimura、Shoji Ikeda

  DOI：10.1016/j.bmcl.2004.03.082

  日期：2004.6

  In order to investigate the effect of the fixation of the orientations of the two long chains, three types of novel derivatives of scavenger receptor inhibitor I were synthesized, and their biological activities were evaluated. Among the novel derivatives, 2,4-bis(octadecanoylamino)benzenesulfonic acid sodium salt (4d) showed the most potent inhibitory activity against the incorporation of 1,1'-dioctadecyl-3,3,3',3'-tetramethylindocarbocyanine perchlorate-labeled acetyl-LDL (DiI-acetyl-LDL) into macrophages. 2,5-Bis(octadecanoylamino)benzenesulfonic acid sodium salt (4c), a regioisomer of 4d, did not exhibit as potent an inhibitory activity as 4d, meaning that the substitution pattern of two long chains on the benzene ring must be important. Compound Q exhibited 10 times more potent inhibitory activity against the binding of 121 I-labeled acetyl-LDL to the surface of macrophages than compound 1. (C) 2004 Elsevier Ltd. All rights reserved.