刀豆素 C | 81552-34-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 中文名称: 刀豆素 C
• 中文别名: 刀豆素C
• 英文名称: concanamycin C
• 英文别名: (3Z,5E,7R,8R,9S,10S,11R,13E,15E,17S,18R)-18-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-4-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-2-hydroxy-5-methyl-6-[(E)-prop-1-enyl]oxan-2-yl]-3-hydroxypentan-2-yl]-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyl-1-oxacyclooctadeca-3,5,13,15-tetraen-2-one
• CAS: 81552-34-3
• 化学式: C₄₅H₇₄O₁₃
• 分子量: 823.075
• InChiKey: XKYYLWWOGLVPOR-GKJVGUBMSA-N

物化性质

• 沸点：
  914.2±65.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  58
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  194
• 氢给体数：
  6
• 氢受体数：
  13

安全信息

• 危险品标志：
  T+
• 危险类别码：
  R26/27/28,R36
• 危险品运输编号：
  UN 3462 6.1/PG 1
• WGK Germany：
  3
• RTECS号：
  GK6887000

反应信息

• 作为反应物：
  描述：

  刀豆素 C 在 水 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以56%的产率得到concanamycin F
  参考文献：
  名称：

  Chemistry of unusual macrolides. 1. Preparation of the aglycons of concanamycin A and elaiophylin

  摘要：

  The aglycons of the concanamycins (1, 2) and elaiophylin (11) have been prepared for direct comparison to the vacuolar-type ATPase inhibitor bafilomycin A1 (10). The deglycosylation was achieved by acid hydrolysis in the absence of MeOH, while acid-catalyzed methanolysis proceed ed with unexpected displacement of carbohydrate residues rather than methoxy groups. Structure assignments of the derivatives were made with the help of one- and two-dimensional NMR studies. Especially helpful were the 9-O-acetylated concanamycin derivatives because they showed reduced flexibility of the macrolactone ring. As a result of a detailed analysis of the O-methyl derivatives of elaiolide (15) the structure of an earlier reported aglycon derivative of elaiophylin has to be revised to 12.

  DOI：

  10.1021/jo00072a036

文献信息

• [EN] MACROCYCLIC LACTONE DERIVATIVES FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE LACTONE MACROCYCLIQUE POUR LE TRAITEMENT DU CANCER
  申请人：PIRAMAL LIFE SCIENCES LTD

  公开号：WO2011061666A1

  公开（公告）日：2011-05-26

  The present invention provides compounds represented by formula (1): wherein, R1, R2, R3 and R4 are as defined in the specification, in all their stereoisomeric and tautomeric forms and mixtures thereof in all ratios, and their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable polymorphs and prodrugs. The invention also relates to processes for the manufacture of compounds of formula (1) and pharmaceutical compositions containing them. The compounds and the pharmaceutical compositions of the present invention are useful for the treatment of cancer. The present invention further provides a method of treatment of cancer by administering a therapeutically effective amount of the said compound of formula (1) or its pharmaceutical composition, to a mammal in need thereof.

  本发明提供了由式（1）表示的化合物：其中，R1、R2、R3和R4如规范中定义，在它们的所有立体异构体和互变异构体形式以及所有比例的混合物中，以及它们的药学上可接受的盐、药学上可接受的溶剂合物、药学上可接受的多型体和前药。本发明还涉及制备式（1）化合物的方法和含有它们的药物组合物。本发明的化合物和药物组合物对于治疗癌症是有用的。本发明进一步提供了一种通过向需要的哺乳动物体内给予所述式（1）化合物或其药物组合物的治疗有效量来治疗癌症的方法。
• Boddien, Claudia; Gerber-Nolte, Jutta; Zeeck, Axel, Liebigs Annalen, 1996, # 9, p. 1381 - 1384
  作者：Boddien, Claudia、Gerber-Nolte, Jutta、Zeeck, Axel

  DOI：——

  日期：——
• [EN] INHIBITORS OF NEF DOWNMODULATION<br/>[FR] INHIBITEURS DE LA SOUS-MODULATION DE NEF
  申请人：[en]THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：WO2022133031A1

  公开（公告）日：2022-06-23

  This disclosure relates generally to inhibitors of MHC-I downmodulation, and methods of treating or preventing an HIV infection by administering the inhibitors to a patient in need of treatment thereof.
• Chemistry of unusual macrolides. 1. Preparation of the aglycons of concanamycin A and elaiophylin
  作者：Kai U. Bindseil、Axel Zeeck

  DOI：10.1021/jo00072a036

  日期：1993.9

  The aglycons of the concanamycins (1, 2) and elaiophylin (11) have been prepared for direct comparison to the vacuolar-type ATPase inhibitor bafilomycin A1 (10). The deglycosylation was achieved by acid hydrolysis in the absence of MeOH, while acid-catalyzed methanolysis proceed ed with unexpected displacement of carbohydrate residues rather than methoxy groups. Structure assignments of the derivatives were made with the help of one- and two-dimensional NMR studies. Especially helpful were the 9-O-acetylated concanamycin derivatives because they showed reduced flexibility of the macrolactone ring. As a result of a detailed analysis of the O-methyl derivatives of elaiolide (15) the structure of an earlier reported aglycon derivative of elaiophylin has to be revised to 12.