methyl (2S,5R)-2-allyl-9-[3'-allyl-2,2'-dimethoxy-1,1'-(RSa)-binaphthalen-3-yl]-(8RS)-acetamido-3,6-diaza-5-(4-[((9H-fluoren-9-yl)methoxycarbonyl)amino]butyl)-4,7-dioxononanoate | 484023-96-3

• 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 (2S,5R)-2-allyl-9-[3'-allyl-2,2'-dimethoxy-1,1'-(RSa)-binaphthalen-3-yl]-(8RS)-acetamido-3,6-diaza-5-(4-[((9H-fluoren-9-yl)methoxycarbonyl)amino]butyl)-4,7-dioxononanoate
• 英文别名: methyl (2S)-2-[[(2S)-2-[[2-acetamido-3-[3-methoxy-4-(2-methoxy-3-prop-2-enylnaphthalen-1-yl)naphthalen-2-yl]propanoyl]amino]-6-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoyl]amino]pent-4-enoate
• CAS: 484023-96-3
• 化学式: C₅₇H₆₀N₄O₉
• 分子量: 945.125
• InChiKey: XUBNOEKLXKMBIS-PXRUOCAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  70
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  170
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2S,5R)-2-allyl-9-[3'-allyl-2,2'-dimethoxy-1,1'-(RSa)-binaphthalen-3-yl]-(8RS)-acetamido-3,6-diaza-5-(4-[((9H-fluoren-9-yl)methoxycarbonyl)amino]butyl)-4,7-dioxononanoate 在 哌啶 、 Grubbs catalyst first generation 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 61.17h， 生成
  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：

  (S)-(-)-2,2’-二甲氧基-1,1’-联萘 在 盐酸 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 lithium hydroxide monohydrate 、 四甲基乙二胺 、 水 、 magnesium sulfate 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 palladium dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 四氯化碳 、 六甲基磷酰三胺 、 乙醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 19.0h， 生成 methyl (2S,5R)-2-allyl-9-[3'-allyl-2,2'-dimethoxy-1,1'-(RSa)-binaphthalen-3-yl]-(8RS)-acetamido-3,6-diaza-5-(4-[((9H-fluoren-9-yl)methoxycarbonyl)amino]butyl)-4,7-dioxononanoate
  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

文献信息

• Peptoid compounds
  申请人：Bremner John

  公开号：US20070111927A1

  公开（公告）日：2007-05-17

  The invention relates to new peptoid compounds of formula (I), as well as their use in the treatment of bacterial infections, such as those caused by vancomycin resistant microorganisms, and to compositions thereof.

  本发明涉及公式（I）的新型肽酰胺化合物，以及它们在治疗细菌感染方面的用途，例如由万古霉素耐药微生物引起的感染，以及其组成物。
• PEPTOID COMPOUNDS
  申请人：BREMNER John

  公开号：US20120108499A1

  公开（公告）日：2012-05-03

  The invention relates to new peptoid compounds of formula (I), as well as their use in the treatment of bacterial infections, such as those caused by vancomycin resistant microorganisms, and to compositions thereof.

  本发明涉及公式（I）的新型肽状化合物，以及它们在治疗细菌感染方面的应用，例如由万古霉素耐药微生物引起的感染，以及它们的组成物。
• US7160854B2
  申请人：——

  公开号：US7160854B2

  公开（公告）日：2007-01-09
• US7612036B2
  申请人：——

  公开号：US7612036B2

  公开（公告）日：2009-11-03
• Synthesis and antibacterial activity of some binaphthyl-supported macrocycles containing a cationic amino acid
  作者：Daniel R. Coghlan、John B. Bremner、Paul A. Keller、Stephen G. Pyne、Dorothy M. David、Kittiya Somphol、Dean Baylis、Jonathan Coates、John Deadman、David I. Rhodes、Alan D. Robertson

  DOI：10.1016/j.bmc.2011.04.013

  日期：2011.6

  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.