methyl (2S,5R)-8-acetamido-2-allyl-9-[6-allyl-9-tert-butoxycarbonyl-9H-carbazol-3-yl]-3,6-diaza-5-{4-[(fluorenylmethoxycarbonyl)amino]butyl}-4,7-dioxononanoate | 639462-92-3

• 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)-8-acetamido-2-allyl-9-[6-allyl-9-tert-butoxycarbonyl-9H-carbazol-3-yl]-3,6-diaza-5-{4-[(fluorenylmethoxycarbonyl)amino]butyl}-4,7-dioxononanoate
• 英文别名: tert-butyl 3-[2-acetamido-3-[[(2R)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-1-[[(2S)-1-methoxy-1-oxopent-4-en-2-yl]amino]-1-oxohexan-2-yl]amino]-3-oxopropyl]-6-prop-2-enylcarbazole-9-carboxylate
• CAS: 639462-92-3
• 化学式: C₅₂H₅₉N₅O₉
• 分子量: 898.069
• InChiKey: XGLWWVZHDAEHHC-MQPYHFCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  183
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2S,5R)-8-acetamido-2-allyl-9-[6-allyl-9-tert-butoxycarbonyl-9H-carbazol-3-yl]-3,6-diaza-5-{4-[(fluorenylmethoxycarbonyl)amino]butyl}-4,7-dioxononanoate 在 palladium on activated charcoal 、 Grubbs catalyst first generation 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 23.0h， 生成 (9R,12S)-6-acetamido-8,11-diaza-1-tert-butoxycarbonyl-9-{4-[(fluorenylmethoxycarbonyl)amino]butyl}-12-methoxycarbonyl-7,10-dioxo-[12]-(4,17)carbazolophane
  参考文献：
  名称：

  Synthesis of carbazole-linked cyclic and acyclic peptoids with antibacterial activity

  摘要：

  This paper describes the synthesis of several novel cyclic and acyclic peptoids, the former structurally comprising a tripeptide moiety linked through a carbazole scaffold. In a key step, a ring-closing metathesis reaction was used giving efficient access to this new class of cyclic peptoids. The target compounds were tested against Staphylococcus aureus (ATCC 6538P) and their minimum inhibitory concentration (MIC) values were determined. These compounds showed moderate to poor activities with MIC values ranging from 15-250 mug/mL. (C) 2003 Elsevier Ltd. All richts reserved.

  DOI：

  10.1016/j.tet.2003.09.034
• 作为产物：
  描述：

  4-溴苯肼盐酸盐 在 palladium dichloride 4-二甲氨基吡啶 、 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 3 A molecular sieve 、 sodium hydride 、 caesium carbonate 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 环己烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 128.75h， 生成 methyl (2S,5R)-8-acetamido-2-allyl-9-[6-allyl-9-tert-butoxycarbonyl-9H-carbazol-3-yl]-3,6-diaza-5-{4-[(fluorenylmethoxycarbonyl)amino]butyl}-4,7-dioxononanoate
  参考文献：
  名称：

  Synthesis of carbazole-linked cyclic and acyclic peptoids with antibacterial activity

  摘要：

  This paper describes the synthesis of several novel cyclic and acyclic peptoids, the former structurally comprising a tripeptide moiety linked through a carbazole scaffold. In a key step, a ring-closing metathesis reaction was used giving efficient access to this new class of cyclic peptoids. The target compounds were tested against Staphylococcus aureus (ATCC 6538P) and their minimum inhibitory concentration (MIC) values were determined. These compounds showed moderate to poor activities with MIC values ranging from 15-250 mug/mL. (C) 2003 Elsevier Ltd. All richts reserved.

  DOI：

  10.1016/j.tet.2003.09.034

文献信息

• Synthesis of carbazole-linked cyclic and acyclic peptoids with antibacterial activity
  作者：John B. Bremner、Jonathan A. Coates、Paul A. Keller、Stephen G. Pyne、Helen M. Witchard

  DOI：10.1016/j.tet.2003.09.034

  日期：2003.10

  This paper describes the synthesis of several novel cyclic and acyclic peptoids, the former structurally comprising a tripeptide moiety linked through a carbazole scaffold. In a key step, a ring-closing metathesis reaction was used giving efficient access to this new class of cyclic peptoids. The target compounds were tested against Staphylococcus aureus (ATCC 6538P) and their minimum inhibitory concentration (MIC) values were determined. These compounds showed moderate to poor activities with MIC values ranging from 15-250 mug/mL. (C) 2003 Elsevier Ltd. All richts reserved.