monensin A benzyl ester | 127648-49-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: monensin A benzyl ester
• 英文别名: Monensin benzyl ester；benzyl (2S,3R,4S)-4-[(2S,5R,7S,8R,9S)-2-[(2R,5S)-5-ethyl-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]oxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-3-methoxy-2-methylpentanoate
• CAS: 127648-49-1
• 化学式: C₄₃H₆₈O₁₁
• 分子量: 761.006
• InChiKey: JMAJAZLXRQBPGT-MHQIPXBZSA-N

物化性质

• 沸点：
  816.0±65.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿；可溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  54
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  莫能菌素 、 溴甲苯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以89%的产率得到monensin A benzyl ester
  参考文献：
  名称：

  Monensin A benzyl ester and its complexes with monovalent metal cations studied by spectroscopic, mass spectrometry and semiempirical methods

  摘要：

  Monensin A benzyl ester (MON3) was synthesized and its ability to form complexes with Li+, Na+ and K+ cations was studied by ESI MS, H-1 and C-13 NMR, FT-IR and PM5 semiempirical methods. MON3 has been found to preferentially form complex with Na+ cations. The formation of stable complexes of 1: 1 stoichiometry up to cv = 70 V is indicated in the electrospray ionisation mass spectra. With increasing cone voltage value, the fragmentation of the respective complexes is detected and is connected primary with the dehydration process. The structures of the complexes are stabilized by intramolecular hydrogen bonds in which the OH groups are always involved. The structures of MON3 and its complexes with Li+, Na+ and K+ cations are visualized and discussed in detail. It is shown that in the structure of MON3 the oxygen atom of this C=O ester group is involved in very weak bifurcated hydrogen bonds with two hydroxyl groups. Within the complexes of MON3 with Li+ and K+ cations, this C=O ester group is not hydrogen bonded, whereas in the structure of MON3 with Na+ it can also coordinate this cation. Such a structure is, however, not dominant in acetonitrile solution. It is demonstrated that the formation of a pseudo-crown ring structure formed by MON3 prefers the complexation of Na+ cations. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2006.03.014

文献信息

• Bis-monensin: Synthesis of new chiral receptor from naturally occurring monensin ionophore
  作者：Hiroshi Tsukube、Hajime Sohmiya

  DOI：10.1016/s0040-4039(00)97234-4

  日期：——

  Bis-monensin derivatives were synthesized and characterized for the first time as chiral receptor molecules. Among them, o-xylene-bridged bis-monensin exhibited particularly excellent chiral recognition ability by the inclusion of chiral ammonium guest cations in its central cavity.

  合成了双-莫能菌素衍生物并将其首次表征为手性受体分子。其中，邻二甲苯桥连的双莫能菌素通过在其中心腔中包含手性铵客体阳离子而表现出特别优异的手性识别能力。
• Methods for controlling gram negative bacteria in mammals
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20010044463A1

  公开（公告）日：2001-11-22

  Methods for controlling growth of gram negative bacteria, such as Helicobacter pylori, which are agents associated with disorders of the gastrointestinal tract of a mammal are described. They include administering a therapeutically effective amount of a polyether ionophore antibiotic to a mammal, such that growth of gram negative bacteria which are agents associated with disorders of the gastrointestinal tract of a mammal is controlled. Packaged pharmaceutical compositions for controlling gram negative bacteria are also described. The packaged compositions include a container holding a therapeutically effective amount of a pharmaceutical composition for controlling gram negative bacteria which are agents associated with disorders of the gastrointestinal tract of a mammal and instructions for using the pharmaceutical composition for control of the gram negative bacteria, such that growth of gram negative bacteria which are agents associated with disorders of the gastrointestinal tract of a mammal is controlled. The pharmaceutical composition includes at least one polyether ionophore antibiotic or a bicyclic spiroether.

  本文描述了控制革兰氏阴性菌的生长方法，例如与哺乳动物胃肠道疾病相关的代理Helicobacter pylori。其中包括向哺乳动物施用治疗有效量的聚醚离子载体抗生素，以控制与哺乳动物胃肠道疾病相关的代理革兰氏阴性菌的生长。此外，还描述了用于控制革兰氏阴性菌的包装药物组合物。该包装组合物包括一个容器，其中装有治疗有效量的药物组合物，用于控制与哺乳动物胃肠道疾病相关的代理革兰氏阴性菌，并包括使用该药物组合物控制革兰氏阴性菌的说明，以控制与哺乳动物胃肠道疾病相关的代理革兰氏阴性菌的生长。该药物组合物包括至少一种聚醚离子载体抗生素或双环螺酚醚。
• Methods for controlling gram negative bacteria in mammals with bicyclo spiroether compounds
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US06271256B1

  公开（公告）日：2001-08-07

  Methods for controlling growth of gram negative bacteria, such as Helicobacter pylori, which are agents associated with disorders of the gastrointestinal tract of a mammal are described. They include administering a therapeutically effective amount of a polyether ionophore antibiotic to a mammal, such that growth of gram negative bacteria which are agents associated with disorders of the gastrointestinal tract of a mammal is controlled. Packaged pharmaceutical compositions for controlling gram negative bacteria are also described. The packaged compositions include a container holding a therapeutically effective amount of a pharmaceutical composition for controlling gram negative bacteria which are agents associated with disorders of the gastrointestinal tract of a mammal and instructions for using the pharmaceutical composition for control of the gram negative bacteria, such that growth of gram negative bacteria which are agents associated with disorders of the gastrointestinal tract of a mammal is controlled. The pharmaceutical composition includes at least one polyether ionophore antibiotic or a bicyclic spiroether.

  本文描述了控制革兰氏阴性菌（如幽门螺杆菌）生长的方法，这些菌是与哺乳动物胃肠道疾病有关的病原体。方法包括向哺乳动物施用治疗有效量的聚醚离子载体抗生素，以控制与哺乳动物胃肠道疾病有关的革兰氏阴性菌的生长。本文还描述了用于控制革兰氏阴性菌的包装药物组合物。该组合物包括一个容器，其中装有治疗有效量的药物组合物，用于控制与哺乳动物胃肠道疾病有关的革兰氏阴性菌，并包括使用该药物组合物控制革兰氏阴性菌的说明，以控制与哺乳动物胃肠道疾病有关的革兰氏阴性菌的生长。药物组合物包括至少一种聚醚离子载体抗生素或一种双环螺醚。
• Monensin A benzyl ester and its complexes with monovalent metal cations studied by spectroscopic, mass spectrometry and semiempirical methods
  作者：Adam Huczyński、Dominik Michalak、Piotr Przybylski、Bogumil Brzezinski、Franz Bartl

  DOI：10.1016/j.molstruc.2006.03.014

  日期：2006.9

  Monensin A benzyl ester (MON3) was synthesized and its ability to form complexes with Li+, Na+ and K+ cations was studied by ESI MS, H-1 and C-13 NMR, FT-IR and PM5 semiempirical methods. MON3 has been found to preferentially form complex with Na+ cations. The formation of stable complexes of 1: 1 stoichiometry up to cv = 70 V is indicated in the electrospray ionisation mass spectra. With increasing cone voltage value, the fragmentation of the respective complexes is detected and is connected primary with the dehydration process. The structures of the complexes are stabilized by intramolecular hydrogen bonds in which the OH groups are always involved. The structures of MON3 and its complexes with Li+, Na+ and K+ cations are visualized and discussed in detail. It is shown that in the structure of MON3 the oxygen atom of this C=O ester group is involved in very weak bifurcated hydrogen bonds with two hydroxyl groups. Within the complexes of MON3 with Li+ and K+ cations, this C=O ester group is not hydrogen bonded, whereas in the structure of MON3 with Na+ it can also coordinate this cation. Such a structure is, however, not dominant in acetonitrile solution. It is demonstrated that the formation of a pseudo-crown ring structure formed by MON3 prefers the complexation of Na+ cations. (c) 2006 Elsevier B.V. All rights reserved.
• Synthesis and antimicrobial properties of Monensin A esters
  作者：Adam Huczyński、Joanna Stefańska、Piotr Przybylski、Bogumil Brzezinski、Franz Bartl

  DOI：10.1016/j.bmcl.2008.03.038

  日期：2008.4

  The esters (2-10) of the ionophore antibiotic Monensin (1) were synthesized by four different methods, which are discussed in detail. These new esters were characterized by various spectroscopic techniques and subsequently tested in the face of their antimicrobial properties. Three derivatives (3, 8 and 10) showed activity against Gram-positive bacteria. Additionally derivative (10) exhibited a relatively low antifungal activity against Candida in contrast to Monensin A. (c) 2008 Elsevier Ltd. All rights reserved.