10,11,12,13-tetrahydrotylosin | 120090-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10,11,12,13-tetrahydrotylosin
• 英文别名: 10,11,12,13-tetrahydro-tylosin A；2-[(4R,5S,6S,7R,9R,15R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-oxacyclohexadec-7-yl]acetaldehyde
• CAS: 120090-76-8
• 化学式: C₄₆H₈₁NO₁₇
• 分子量: 920.146
• InChiKey: MXLPAVFBCXCDSH-YGTYELNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  64
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  239
• 氢给体数：
  5
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  10,11,12,13-tetrahydrotylosin 在 甲醇 、 四丁基碘化铵 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 50.5h， 生成
  参考文献：
  名称：

  TYLOSIN A ANALOGS AND DERIVATIVES

  摘要：

  本发明涉及霉素A的衍生物。具体而言，本发明涉及具有式（I）结构的化合物。本发明还涉及包含霉素A衍生物的组合物以及使用这些化合物和组合物治疗或预防疾病或疾病的方法。

  公开号：

  US20150259374A1
• 作为产物：
  描述：

  泰乐菌素 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以93.5%的产率得到10,11,12,13-tetrahydrotylosin
  参考文献：
  名称：

  Structure-activity relationship among polyhydro derivatives of tylosin.

  摘要：

  通过还原共轭双键和羰基，制备了泰乐菌素的四氢、六氢和八氢衍生物。二烯的氢化不会改变化合物的体外抗菌活性，而羰基的还原则会导致活性的少量或完全丧失。

  DOI：

  10.7164/antibiotics.47.581

文献信息

• Semisynthetic Macrolide Antibacterials Derived from Tylosin. Synthesis and Structure−Activity Relationships of Novel Desmycosin Analogues
  作者：Stjepan Mutak、Nataša Maršić、Miroslava Dominis Kramarić、Dražen Pavlović

  DOI：10.1021/jm0308951

  日期：2004.1.1

  proceeded smoothly to give corresponding esters in yields ranging from 70 to 80%. Base- and acid-catalyzed rearrangement products including desmycosin 8,20-aldols (24a and 24b) and desmycosin 3,19-aldol (25) are also described. Parallel array synthesis and purification techniques allowed for the rapid exploration of structure-activity relationships within this class and for the improvement in potency. In vitro

  合成了一系列脱麦角菌素的20-O-取代的和3,20-di-O-取代的衍生物，并评估了它们的生物学特性。特别地，我们已经合成了脱麦角菌素的许多侧链修饰的类似物，以及一些具有修饰的侧链和可替代的C-3取代基的类似物。因此，通过维蒂希（Wittig）从相应的醛制备了脱麦考菌素（2），泰乐菌素（1），10,11,12,13-四氢泰乐菌素（11）和2,3-二氢脱氢麦芽素（13）的α，β-不饱和类似物。与稳定的乙炔（ad）反应，生成反式双键，然后对C-3羟基进行修饰的Pfitzner-Moffat氧化。要评估去麦草素C-3位置对生物活性的重要性，C-3取代的衍生物是按照标准的保护基化学顺序合成的，然后进行Wittig反应和酯化反应是关键步骤。为了连接C-3酯官能团，采用了混合酸酐方案。反应平稳进行，得到相应的酯，产率为70-80％。还描述了碱和酸催化的重排产物，包括除麦草素8,20-醛醇（24a和24b）和除麦草素3
• Treatment of filarial diseases
  申请人：AbbVie Inc.

  公开号：US10238677B2

  公开（公告）日：2019-03-26

  The present invention pertains to prevention of and/or treatment for filariasis. In particular, the present invention pertains to the use of tylosin A and its analogs and derivatives to prevent or treat filarial worm infection and/or diseases associated with filarial worm infection. The present invention also pertains to pharmaceutical compositions comprising tylosin A or an analog or derivative thereof for use in preventing or treating filarial worm infection and/or diseases associated with filarial worm infection.

  本发明涉及丝虫病的预防和/或治疗。特别是，本发明涉及使用泰乐菌素 A 及其类似物和衍生物来预防或治疗丝虫感染和/或与丝虫感染相关的疾病。本发明还涉及包含泰乐菌素A或其类似物或衍生物的药物组合物，用于预防或治疗丝虫感染和/或与丝虫感染相关的疾病。
• TREATMENT OF FILARIAL DISEASES
  申请人：AbbVie Inc.

  公开号：US20170368088A1

  公开（公告）日：2017-12-28

  The present invention pertains to prevention of and/or treatment for filariasis. In particular, the present invention pertains to the use of tylosin A and its analogs and derivatives to prevent or treat filarial worm infection and/or diseases associated with filarial worm infection. The present invention also pertains to pharmaceutical compositions comprising tylosin A or an analog or derivative thereof for use in preventing or treating filarial worm infection and/or diseases associated with filarial worm infection.
• [EN] 4"-0-SUBSTITUTED TYLOSIN A DERIVATIVES<br/>[FR] DÉRIVÉS DE TYLOSINE A 4"-0-SUBSTITUÉS
  申请人：ABBVIE INC

  公开号：WO2015138458A1

  公开（公告）日：2015-09-17

  The present invention pertains to derivatives of tylosin A. In particular, the present invention pertains to compounds having a structure of Formula (I). The present invention also pertains to compositions comprising derivatives of tylosin A and methods of treating or preventing conditions or disorders using such compounds and compositions.
• [EN] TREATMENT OF FILARIAL DISEASES<br/>[FR] TRAITEMENT DE MALADIES FILARIENNES
  申请人：ABBVIE INC

  公开号：WO2016112317A1

  公开（公告）日：2016-07-14

  The present invention pertains to prevention of and/or treatment for filariasis. In particular, the present invention pertains to the use of tylosin A and its analogs and derivatives to prevent or treat filarial worm infection and/or diseases associated with filarial worm infection. The present invention also pertains to pharmaceutical compositions comprising tylosin A or an analog or derivative thereof for use in preventing or treating filarial worm infection and/or diseases associated with filarial worm infection.