N-[1-hydroxy-4-(4-octylphenyl)-2-(phenylmethoxymethyl)butan-2-yl]hexadecanamide | 903894-70-2

• 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-[1-hydroxy-4-(4-octylphenyl)-2-(phenylmethoxymethyl)butan-2-yl]hexadecanamide
• CAS: 903894-70-2
• 化学式: C₄₂H₆₉NO₃
• 分子量: 636.015
• InChiKey: AHIIICDBIJITLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  46
• 可旋转键数：
  30
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[1-hydroxy-4-(4-octylphenyl)-2-(phenylmethoxymethyl)butan-2-yl]hexadecanamide 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 生成 N-[1-hydroxy-4-(4-octylphenyl)-2-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]butan-2-yl]hexadecanamide
  参考文献：
  名称：

  Induction of promotive rather than suppressive immune responses from a novel NKT cell repertoire Vα19 NKT cell with α-mannosyl ceramide analogues consisting of the immunosuppressant ISP-I as the sphingosine unit

  摘要：

  A 2-substituted 2-aminopropane-1,3-diol or 2-aminoethanol is the minimum structure required for the immunosuppressive activity of ISP-I, an antibiotic isolated from the culture broth of Isaria sinclairil. A series of alpha-mannosyl ceramide (alpha-ManCer) analogues was derived from 2-substituted 2-aminopropane-1,3-diols or 2-aminoethanols in place of sphingosine. The newly synthesized glycosides were evaluated for their effects on immune responses. In contrast to the immunosuppressive activity of the precursors, the a-ManCer analogues induced immunopromotive responses from invariant V alpha N-J alpha 26 transgenic mouse lymphocytes more effectively than the original a-ManCer. Collectively, it is strongly suggested that the 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols mimic sphingosine in the alpha-ManCer analogues so that they potentially acquire specific antigenicity toward V alpha 19 NKT cell, a novel NKT cell subset. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.11.013
• 作为产物：
  描述：

  2-氨基-2-[2-(4-辛基苯基)乙基]-1,3-丙二醇 在 吡啶 、 盐酸 、 三甲基氯硅烷 、 二乙基异丙基胺 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-[1-hydroxy-4-(4-octylphenyl)-2-(phenylmethoxymethyl)butan-2-yl]hexadecanamide
  参考文献：
  名称：

  Induction of promotive rather than suppressive immune responses from a novel NKT cell repertoire Vα19 NKT cell with α-mannosyl ceramide analogues consisting of the immunosuppressant ISP-I as the sphingosine unit

  摘要：

  A 2-substituted 2-aminopropane-1,3-diol or 2-aminoethanol is the minimum structure required for the immunosuppressive activity of ISP-I, an antibiotic isolated from the culture broth of Isaria sinclairil. A series of alpha-mannosyl ceramide (alpha-ManCer) analogues was derived from 2-substituted 2-aminopropane-1,3-diols or 2-aminoethanols in place of sphingosine. The newly synthesized glycosides were evaluated for their effects on immune responses. In contrast to the immunosuppressive activity of the precursors, the a-ManCer analogues induced immunopromotive responses from invariant V alpha N-J alpha 26 transgenic mouse lymphocytes more effectively than the original a-ManCer. Collectively, it is strongly suggested that the 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols mimic sphingosine in the alpha-ManCer analogues so that they potentially acquire specific antigenicity toward V alpha 19 NKT cell, a novel NKT cell subset. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.11.013

文献信息

• Induction of promotive rather than suppressive immune responses from a novel NKT cell repertoire Vα19 NKT cell with α-mannosyl ceramide analogues consisting of the immunosuppressant ISP-I as the sphingosine unit
  作者：Michio Shimamura、Naoki Okamoto、Yi-Ying Huang、Jouji Yasuoka、Kenji Morita、Akira Nishiyama、Yuusuke Amano、Tadashi Mishina

  DOI：10.1016/j.ejmech.2005.11.013

  日期：2006.5

  A 2-substituted 2-aminopropane-1,3-diol or 2-aminoethanol is the minimum structure required for the immunosuppressive activity of ISP-I, an antibiotic isolated from the culture broth of Isaria sinclairil. A series of alpha-mannosyl ceramide (alpha-ManCer) analogues was derived from 2-substituted 2-aminopropane-1,3-diols or 2-aminoethanols in place of sphingosine. The newly synthesized glycosides were evaluated for their effects on immune responses. In contrast to the immunosuppressive activity of the precursors, the a-ManCer analogues induced immunopromotive responses from invariant V alpha N-J alpha 26 transgenic mouse lymphocytes more effectively than the original a-ManCer. Collectively, it is strongly suggested that the 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols mimic sphingosine in the alpha-ManCer analogues so that they potentially acquire specific antigenicity toward V alpha 19 NKT cell, a novel NKT cell subset. (c) 2006 Elsevier SAS. All rights reserved.