methyl (2S,5S)-2-allyl-9-[3'-allyl-2,2'-dimethoxy-1,1'-(RSa)-binaphthalen-3-yl]-(8RS)-acetamido-3,6-diaza-4,7-dioxo-5(3-[3-(2,2,5,7,8-pentamethylchroman-6-ylsulfonyl)guanidino]propyl)nonanoate | 1313497-71-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: methyl (2S,5S)-2-allyl-9-[3'-allyl-2,2'-dimethoxy-1,1'-(RSa)-binaphthalen-3-yl]-(8RS)-acetamido-3,6-diaza-4,7-dioxo-5(3-[3-(2,2,5,7,8-pentamethylchroman-6-ylsulfonyl)guanidino]propyl)nonanoate
• CAS: 1313497-71-0
• 化学式: C₅₆H₆₈N₆O₁₀S
• 分子量: 1017.26
• InChiKey: DPQANCAHWQIAOO-SPOITGTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.48
• 重原子数：
  73.0
• 可旋转键数：
  21.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  223.34
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,5S)-2-allyl-9-[3'-allyl-2,2'-dimethoxy-1,1'-(RSa)-binaphthalen-3-yl]-(8RS)-acetamido-3,6-diaza-4,7-dioxo-5(3-[3-(2,2,5,7,8-pentamethylchroman-6-ylsulfonyl)guanidino]propyl)nonanoate 在 三氟乙酸 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 以79%的产率得到methyl (2S,5R)-2-allyl-9-[3'-allyl-2,2'-dimethoxy-(RSa)-1,1'-binaphthalen-3-yl]-(8RS)-acetamido-3,6-diaza-5-(3-guanidinopropyl)-4,7-dioxononanoate hydrochloride
  参考文献：
  名称：

  Synthesis and antibacterial activity of some binaphthyl-supported macrocycles containing a cationic amino acid

  摘要：

  As part of a programme investigating antibacterial cyclic macrocycles containing a cationic amino acid with an internal aromatic hydrophobic scaffold, we previously reported a macrocycle anchored at the 3,3'-positions of a 1,1'-binaphthyl unit. This was prepared via key intermediates containing an internal allylglycine and an allyl-substituted binaphthyl unit for a subsequent ring-closing metathesis reaction. This paper presents some structure-activity relationship studies with additional macrocycles based on this lead compound against Staphylococcus aureus together with the antibacterial activity of two related acyclic compounds. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.013
• 作为产物：
  描述：

  ethyl (RS)-2-amino-3-[2,2'-dimethoxy-3'-iodo-1,1'-binaphth-3-yl]propanoate hydrochloride 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 magnesium sulfate 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 palladium dichloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 methyl (2S,5S)-2-allyl-9-[3'-allyl-2,2'-dimethoxy-1,1'-(RSa)-binaphthalen-3-yl]-(8RS)-acetamido-3,6-diaza-4,7-dioxo-5(3-[3-(2,2,5,7,8-pentamethylchroman-6-ylsulfonyl)guanidino]propyl)nonanoate
  参考文献：
  名称：

  Synthesis and antibacterial activity of some binaphthyl-supported macrocycles containing a cationic amino acid

  摘要：

  As part of a programme investigating antibacterial cyclic macrocycles containing a cationic amino acid with an internal aromatic hydrophobic scaffold, we previously reported a macrocycle anchored at the 3,3'-positions of a 1,1'-binaphthyl unit. This was prepared via key intermediates containing an internal allylglycine and an allyl-substituted binaphthyl unit for a subsequent ring-closing metathesis reaction. This paper presents some structure-activity relationship studies with additional macrocycles based on this lead compound against Staphylococcus aureus together with the antibacterial activity of two related acyclic compounds. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.013