semduramicin sodium salt | 119068-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: semduramicin sodium salt
• 英文别名: Semduramicin Sodium；sodium;2-[(2R,3S,4S,5R,6S)-2,4-dihydroxy-6-[(1R)-1-[(2S,5R,7S,8R,9S)-7-hydroxy-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxyoxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-5-methoxy-3-methyloxan-2-yl]acetate
• CAS: 119068-77-8
• 化学式: C₄₅H₇₅O₁₆*Na
• 分子量: 895.071
• InChiKey: JXRFTGPGWGUBQB-LHOUOPCDSA-M

物化性质

• 熔点：
  175-176°
• 比旋光度：
  D25 +19.3° (c = 0.5 in methanol)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  62
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  213
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  semduramicin sodium salt 在 potassium perchlorate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  2D NMR, FT-IR, ESI MS studies and DFT, PM5 semiempirical calculations of new benzoic semduramicin anhydride and their complexes with selected monovalent cations

  摘要：

  A new benzoic semduramicin anhydride (SemBz) was obtained. The new compound and its ability to form complexes with monovalent cations was studied by the ESI mass spectrometry, DFT, 2D NMR and FT-IR spectroscopic methods. The FT-IR spectra indicate that the K+ cation in SemBz complex is localised. However, Li+ and Na+ cations in SemBz complexes undergoes fast fluctuations between oxygen atoms inside the cavity of the molecule. These observations were compared to the behavior of semduramicin salts with these cations. The structures of all salts and complexes obtained were calculated by the PM5 semiempirical method. All results are in agreement with the spectroscopic data and allow visualisation of SemBz structure and its complexes with monovalent cations. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.12.021
• 作为产物：
  描述：

  2-[(2R,3S,4S,5S,6S)-2-hydroxy-6-[(1R)-1-[(2S,5R,7S,8R,9S)-7-hydroxy-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxyoxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-5-methoxy-4-[(2R,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-3-methyloxan-2-yl]acetic acid 以32%的产率得到
  参考文献：
  名称：

  GOUDIE, ALEXANDER CROSSAN;WALSHE, NIGEL DEREK ARTHUR

  摘要：

  DOI：

文献信息

• Synthetic modification of a novel microbial ionophore: exploration of anticoccidial structure-activity relationships
  作者：E. A. Glazer、D. A. Koss、J. A. Olson、A. P. Ricketts、T. K. Schaaf、R. J. Wiscount

  DOI：10.1021/jm00088a020

  日期：1992.5

  While fermentation-derived polyether ionophores such as salinomycin are the dominant class of anticoccidial feed additives, there is little information concerning the structural features which confer optimal potency/efficacy in this important series. The recently discovered microbial polyether 1a, featuring potent, broad-spectrum anticoccidial activity, was employed as a template to explore structure-activity relationships. A number of single-step synthetic modifications targeted structural changes in both the lipophilic carbon backbone and the ion-binding cavity of 1a. Although previous semisynthetic transformations among the polyether ionophores almost always resulted in a substantial loss of anticoccidial activity, we obtained several analogues, altered on the periphery of the ionophore-ion complex, which retain good potency and efficacy. Monoglycone 7 (semduramicin sodium) has the most impressive anticoccidial profile of this series, and is undergoing further biological testing under field conditions.