methyl (4S)-5-(6-hydroxyhexylamino)-5-oxo-4-(phenylmethoxycarbonylamino)pentanoate | 205252-10-4

• 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: methyl (4S)-5-(6-hydroxyhexylamino)-5-oxo-4-(phenylmethoxycarbonylamino)pentanoate
• CAS: 205252-10-4
• 化学式: C₂₀H₃₀N₂O₆
• 分子量: 394.468
• InChiKey: XZGCUSHPXQULFG-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (4S)-5-(6-hydroxyhexylamino)-5-oxo-4-(phenylmethoxycarbonylamino)pentanoate 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 methyl (4S)-4-amino-5-oxo-5-[6-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyhexylamino]pentanoate
  参考文献：
  名称：

  Synthesis and Activity of Dipeptides, Linked to Targeting Ligands, as Specific NK Cell Enhancers

  摘要：

  Water soluble analogues of the lipophilic immunostimulant, octadecyl D-alanyl-L-glutamine, BCH-527, were synthesized and evaluated for the ability to stimulate natural killer (NK) cells. One of these compounds in which the octadecyl chain of BCH-527 was replaced with a shorter chain alcohol, 6-(D-alanyl-L-glutaminylamino)hexan-1-ol, 9, displayed an in vitro stimulation of NK cells comparable to that of interleukin 2 (IL 2). However, when the hydroxyl of 9 was linked to L-fucose to yield 1-beta-[6-(D-alanyl-L-glutaminylamino)hex-1-yl]-L-fucopyranose (BCH-2537 1), the observed stimulation of NK cells was greater than that observed with IL 2. Further evaluation of these compounds revealed that the improved in vitro activity of BCH-2537 was more pronounced in vivo. That is, while both compounds significantly increased splenic NK cells, only BCH-2537 significantly increased the activity of these cells in vivo. In terms of a structure-activity relationship, NK cell activity was sensitive to minor structural modifications. It was influenced by conservative substitutions within the dipeptide, the length of the hydrocarbon chain, and the functionality at the end of the chain. No other compound enhanced NK cell activity to the extent exhibited by BCH-2537, although a few were equipotent to 9.

  DOI：

  10.1021/jm970734v
• 作为产物：
  描述：

  6-氨基-1-己醇 、 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 氯仿 为溶剂， 以87%的产率得到methyl (4S)-5-(6-hydroxyhexylamino)-5-oxo-4-(phenylmethoxycarbonylamino)pentanoate
  参考文献：
  名称：

  Synthesis and Activity of Dipeptides, Linked to Targeting Ligands, as Specific NK Cell Enhancers

  摘要：

  Water soluble analogues of the lipophilic immunostimulant, octadecyl D-alanyl-L-glutamine, BCH-527, were synthesized and evaluated for the ability to stimulate natural killer (NK) cells. One of these compounds in which the octadecyl chain of BCH-527 was replaced with a shorter chain alcohol, 6-(D-alanyl-L-glutaminylamino)hexan-1-ol, 9, displayed an in vitro stimulation of NK cells comparable to that of interleukin 2 (IL 2). However, when the hydroxyl of 9 was linked to L-fucose to yield 1-beta-[6-(D-alanyl-L-glutaminylamino)hex-1-yl]-L-fucopyranose (BCH-2537 1), the observed stimulation of NK cells was greater than that observed with IL 2. Further evaluation of these compounds revealed that the improved in vitro activity of BCH-2537 was more pronounced in vivo. That is, while both compounds significantly increased splenic NK cells, only BCH-2537 significantly increased the activity of these cells in vivo. In terms of a structure-activity relationship, NK cell activity was sensitive to minor structural modifications. It was influenced by conservative substitutions within the dipeptide, the length of the hydrocarbon chain, and the functionality at the end of the chain. No other compound enhanced NK cell activity to the extent exhibited by BCH-2537, although a few were equipotent to 9.

  DOI：

  10.1021/jm970734v

文献信息

• Synthesis and Activity of Dipeptides, Linked to Targeting Ligands, as Specific NK Cell Enhancers
  作者：Shaun D. Abbott、Lyne Gagnon、Mouna Lagraoui、Salam Kadhim、Giorgio Attardo、Boulos Zacharie、Christopher L. Penney

  DOI：10.1021/jm970734v

  日期：1998.5.1

  Water soluble analogues of the lipophilic immunostimulant, octadecyl D-alanyl-L-glutamine, BCH-527, were synthesized and evaluated for the ability to stimulate natural killer (NK) cells. One of these compounds in which the octadecyl chain of BCH-527 was replaced with a shorter chain alcohol, 6-(D-alanyl-L-glutaminylamino)hexan-1-ol, 9, displayed an in vitro stimulation of NK cells comparable to that of interleukin 2 (IL 2). However, when the hydroxyl of 9 was linked to L-fucose to yield 1-beta-[6-(D-alanyl-L-glutaminylamino)hex-1-yl]-L-fucopyranose (BCH-2537 1), the observed stimulation of NK cells was greater than that observed with IL 2. Further evaluation of these compounds revealed that the improved in vitro activity of BCH-2537 was more pronounced in vivo. That is, while both compounds significantly increased splenic NK cells, only BCH-2537 significantly increased the activity of these cells in vivo. In terms of a structure-activity relationship, NK cell activity was sensitive to minor structural modifications. It was influenced by conservative substitutions within the dipeptide, the length of the hydrocarbon chain, and the functionality at the end of the chain. No other compound enhanced NK cell activity to the extent exhibited by BCH-2537, although a few were equipotent to 9.