lasalocid | 1195438-33-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: lasalocid
• 英文别名: 6-[(3R,4S,5S,7R)-7-[(3S,5S)-5-ethyl-5-[(5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-3-methyloxolan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid
• CAS: 1195438-33-5
• 化学式: C₃₄H₅₄O₈
• 分子量: 590.798
• InChiKey: BBMULGJBVDDDNI-GTRJCNPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  lasalocid 、 烯丙基羟乙基醚 在 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以77%的产率得到lasalocid ester with 2-allyloxyethanol
  参考文献：
  名称：

  Spectroscopic and PM5 semiempirical study of a new lasalocid ester with 2-allyloxyethanol and its complexes with monovalent cations

  摘要：

  A new ester of lasalocid with 2-allyloxyethanol (Las9) has been synthesised and its ability to form complexes with Li+, Na+, K+, Rb+ and Cs+ cations has been studied by ESI mass spectrometry as well as H-1, C-13 NMR and Fr-IR spectroscopic methods. The ESI-MS spectra indicate that Las9 forms stable 1: 1 complexes with all cations studied. The Fr-IR spectra of Las9 in acetonitrile solution have evidenced the existence of an equilibrium between keto and enol forms, with the predominance of the keto form. No effect of the kind of cations on this keto-enol equilibrium has been found. The results of the PM5 semiempirical calculations show that the keto form of Las9 is more favourable than the enol form. In the Las9 molecule two parts can be distinguished, stabilised by hydrogen bonds. In the structure of the complexes these two parts are no longer observed. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2005.12.007

文献信息

• One-pot synthesis and cytotoxicity studies of new Mannich base derivatives of polyether antibiotic—Lasalocid acid
  作者：Adam Huczyński、Jacek Rutkowski、Izabela Borowicz、Joanna Wietrzyk、Ewa Maj、Bogumil Brzezinski

  DOI：10.1016/j.bmcl.2013.07.040

  日期：2013.9

  Seven Mannich base derivatives of polyether antibiotic Lasalocid acid (2a–2g) were synthesized and screened for their antiproliferative activity against various human cancer cell lines. A novel chemoselective one-pot synthesis of these Mannich bases was developed. Compounds 2a–2c and 2g with sterically smaller dialkylamine substituent, displayed potent antiproliferative activity (IC50: 3.2–7.3 μM)

  合成了7种聚醚抗生素拉沙酸（2a – 2g）的曼尼希碱衍生物，并筛选了它们对多种人类癌细胞系的抗增殖活性。开发了这些曼尼希碱的新型化学选择性一锅法合成。具有更小的二烷基胺取代基的化合物2a – 2c和2g，显示出强大的抗增殖活性（IC 50：3.2–7.3μM），并且对特定类型的癌症具有超过两倍的选择性。在寻找对特定癌细胞的选择性中，芳环上C-2原子上的曼尼希碱基取代基的性质可能至关重要。
• Spectroscopic and PM5 semiempirical study of a new lasalocid ester with 2-allyloxyethanol and its complexes with monovalent cations
  作者：Radosław Pankiewicz、Grzegorz Schroeder、Bogumil Brzezinski

  DOI：10.1016/j.molstruc.2005.12.007

  日期：2006.5

  A new ester of lasalocid with 2-allyloxyethanol (Las9) has been synthesised and its ability to form complexes with Li+, Na+, K+, Rb+ and Cs+ cations has been studied by ESI mass spectrometry as well as H-1, C-13 NMR and Fr-IR spectroscopic methods. The ESI-MS spectra indicate that Las9 forms stable 1: 1 complexes with all cations studied. The Fr-IR spectra of Las9 in acetonitrile solution have evidenced the existence of an equilibrium between keto and enol forms, with the predominance of the keto form. No effect of the kind of cations on this keto-enol equilibrium has been found. The results of the PM5 semiempirical calculations show that the keto form of Las9 is more favourable than the enol form. In the Las9 molecule two parts can be distinguished, stabilised by hydrogen bonds. In the structure of the complexes these two parts are no longer observed. (c) 2005 Elsevier B.V. All rights reserved.