nocathiacin acid | 952409-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: nocathiacin acid
• 英文别名: 2-[(1S,18S,21E,28S,29S,30S)-30-[(2S,4S,5R,6S)-5-(dimethylamino)-4-hydroxy-4,6-dimethyloxan-2-yl]oxy-9,52-dihydroxy-18-[(1R)-1-hydroxyethyl]-21-(1-methoxyethylidene)-16,19,26,31,42,46-hexaoxo-32,43,54-trioxa-3,13,23,49-tetrathia-7,17,20,27,45,51,52,55,56,57-decazadecacyclo[26.16.6.229,40.12,5.112,15.122,25.138,41.147,50.06,11.034,39]heptapentaconta-2(57),4,6,8,10,12(56),14,22(55),24,34(39),35,37,40,47,50-pentadecaen-8-yl]-1,3-thiazole-4-carboxylic acid
• CAS: 952409-24-4
• 化学式: C₅₈H₅₆N₁₂O₁₈S₅
• 分子量: 1369.48
• InChiKey: ABFLENNUCCPFIK-PYICNBCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  93
• 可旋转键数：
  7
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  551
• 氢给体数：
  9
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  1-(2-羟乙基)-4-甲基哌嗪 、 nocathiacin acid 在 4-二甲氨基吡啶 异丙烯基氯甲酸酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 生成 2-(4-methylpiperazin-1-yl)ethyl 2-[(1S,18S,21E,28S,29S,30S)-30-[(2S,4S,5R,6S)-5-(dimethylamino)-4-hydroxy-4,6-dimethyloxan-2-yl]oxy-9,52-dihydroxy-18-[(1R)-1-hydroxyethyl]-21-(1-methoxyethylidene)-16,19,26,31,42,46-hexaoxo-32,43,54-trioxa-3,13,23,49-tetrathia-7,17,20,27,45,51,52,55,56,57-decazadecacyclo[26.16.6.229,40.12,5.112,15.122,25.138,41.147,50.06,11.034,39]heptapentaconta-2(57),4,6,8,10,12(56),14,22(55),24,34(39),35,37,40,47,50-pentadecaen-8-yl]-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  WO2007/127136

  摘要：

  公开号：
• 作为产物：
  描述：

  N-(1-cyanoethenyl)-2-[(1S,18S,21E,28S,29S,30S)-30-[(2S,4S,5R,6S)-5-(dimethylamino)-4-hydroxy-4,6-dimethyloxan-2-yl]oxy-9,52-dihydroxy-18-[(1R)-1-hydroxyethyl]-21-(1-methoxyethylidene)-16,19,26,31,42,46-hexaoxo-32,43,54-trioxa-3,13,23,49-tetrathia-7,17,20,27,45,51,52,55,56,57-decazadecacyclo[26.16.6.229,40.12,5.112,15.122,25.138,41.147,50.06,11.034,39]heptapentaconta-2(57),4,6,8,10,12(56),14,22(55),24,34(39),35,37,40,47,50-pentadecaen-8-yl]-1,3-thiazole-4-carboxamide 在 吡啶 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 生成 nocathiacin acid
  参考文献：
  名称：

  Conversion of Nocathiacin I to Nocathiacin Acid by a Mild and Selective Cleavage of Dehydroalanine

  摘要：

  [GRAPHICS]Thiazolyl peptide antibiotic: nocathiacin 1 (1) was converted to nocathiacin acid (4) in high yield by treatment with trifluoroacetic anhydride and pyridine in THF at room temperature. Two equipotent water-soluble amide analogues of nocathiacin I were readily prepared from this important and versatile carboxylic acid intermediate under mild peptide coupling conditions. The present method is useful for chemical derivatization of complex natural products that contain C-terminal dehydroalanine.

  DOI：

  10.1021/jo071115p

文献信息

• WO2007/127135
  申请人：——

  公开号：——

  公开（公告）日：——
• Nocathiacin analogs: Synthesis and antibacterial activity of novel water-soluble amides
  作者：Libo Xu、Amy K. Farthing、James F. Dropinski、Peter T. Meinke、Christine McCallum、Penny S. Leavitt、Emily J. Hickey、Lawrence Colwell、John Barrett、Kun Liu

  DOI：10.1016/j.bmcl.2009.04.144

  日期：2009.7

  Novel water-soluble amide analogs were synthesized from nocathiacin I (1) through the formation of the carboxylic acid intermediate followed by coupling to primary or secondary amines. Several compounds with potent antibacterial activity and adequate water solubility were identified. Of these, compound 19 was selected for more extensive evaluation because of its excellent in vitro antibacterial activity and in vivo efficacy, as well as clean off-target screening. (C) 2009 Elsevier Ltd. All rights reserved.
• WO2007/127136
  申请人：——

  公开号：——

  公开（公告）日：——
• Conversion of Nocathiacin I to Nocathiacin Acid by a Mild and Selective Cleavage of Dehydroalanine
  作者：Libo Xu、Amy K. Farthing、Yao-Jun Shi、Peter T. Meinke、Kun Liu

  DOI：10.1021/jo071115p

  日期：2007.9.1

  [GRAPHICS]Thiazolyl peptide antibiotic: nocathiacin 1 (1) was converted to nocathiacin acid (4) in high yield by treatment with trifluoroacetic anhydride and pyridine in THF at room temperature. Two equipotent water-soluble amide analogues of nocathiacin I were readily prepared from this important and versatile carboxylic acid intermediate under mild peptide coupling conditions. The present method is useful for chemical derivatization of complex natural products that contain C-terminal dehydroalanine.