16-hydroxyverrucarin A | 74516-64-6

• 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: 16-hydroxyverrucarin A
• 英文别名: (1R,3R,8R,18E,20Z,24R,25S)-12-hydroxy-5-(hydroxymethyl)-13,25-dimethylspiro[2,10,16,23-tetraoxatetracyclo[22.2.1.03,8.08,25]heptacosa-4,18,20-triene-26,2'-oxirane]-11,17,22-trione
• CAS: 74516-64-6
• 化学式: C₂₇H₃₄O₁₀
• 分子量: 518.561
• InChiKey: CHWMTSYJQGXKSR-KCKQQGKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  37
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  16-hydroxyverrucarin A 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以63%的产率得到16-oxoverrucarin A
  参考文献：
  名称：

  Antileukemic compounds derived from the chemical modification of macrocyclic trichothecenes. 1. Derivatives of verrucarin A

  摘要：

  Verrucarin A (2) was epoxidized to give the beta-9,10-epoxide 7 (major product) and alpha-9,10-epoxide 9 (minor product). The beta-epoxide 7 and its acetate 8 exhibit high in vivo antileukemic activity against P-388 mouse leukemia, whereas 2 and 9 are inactive. Epoxidation of verrucarin B (3) and roridin A (1) to their respective beta-9,10-epoxides (11 and 12, respectively) also yields compounds with substantially increased activity. Allylic alcohols derived from 2, alpha-C8 (20), beta-C8 (14), and C16 (15), were synthesized and tested; only 15 exhibited substantial in vivo activity.

  DOI：

  10.1021/jm00183a018
• 作为产物：
  描述：

  verrucarin A 在 selenium(IV) oxide 、 乙酸酐 、 溶剂黄146 作用下， 反应 0.75h， 以48%的产率得到8β-hydroxyverrucarin A
  参考文献：
  名称：

  Antileukemic compounds derived from the chemical modification of macrocyclic trichothecenes. 1. Derivatives of verrucarin A

  摘要：

  Verrucarin A (2) was epoxidized to give the beta-9,10-epoxide 7 (major product) and alpha-9,10-epoxide 9 (minor product). The beta-epoxide 7 and its acetate 8 exhibit high in vivo antileukemic activity against P-388 mouse leukemia, whereas 2 and 9 are inactive. Epoxidation of verrucarin B (3) and roridin A (1) to their respective beta-9,10-epoxides (11 and 12, respectively) also yields compounds with substantially increased activity. Allylic alcohols derived from 2, alpha-C8 (20), beta-C8 (14), and C16 (15), were synthesized and tested; only 15 exhibited substantial in vivo activity.

  DOI：

  10.1021/jm00183a018

文献信息

• Antileukemic compounds derived by chemical modification of macrocyclic trichothecenes. 2. Derivatives of roridins A and H and verrucarins A and J
  作者：Bruce B. Jarvis、Jacob O. Midiwo、Eugene P. Mazzola

  DOI：10.1021/jm00368a025

  日期：1984.2

  beta,10 beta-epoxy derivatives of roridins A and H and verrucarins A and J have been prepared and tested in vivo against P388 mouse leukemia. The 9 beta,10 beta-epoxy derivatives and 16-hydroxy derivatives consistently exhibit very high activity. The 8 beta-hydroxy-9 beta,10 beta-epoxy and 16-hydroxy-9 beta,10 beta-epoxy derivatives of verrucarin A and roridin A exhibit extraordinary activity against

  制备了鸟苷A和H以及维鲁卡林A和J的多种8β-羟基，16-羟基和9β，10β-环氧衍生物，并在体内针对P388小鼠白血病进行了测试。9 beta，10 beta-环氧衍生物和16-羟基衍生物始终显示出很高的活性。Verrucarin A和roridin A的8 beta-hydroxy-9 beta，10 beta-epoxy和16-hydroxy-9 beta，10 beta-epoxy衍生物对P388具有非凡的活性。Verrucarin A和roridin A的8 beta-hydroxy-9 beta，10 beta-epoxy和16-hydroxy-9 beta，10 beta-epoxy衍生物对P388具有非凡的表现。
• Antileukemic compounds derived from the chemical modification of macrocyclic trichothecenes. 1. Derivatives of verrucarin A
  作者：Bruce B. Jarvis、G. Patrick Stahly、Gowsala Pavanasasivam、Eugene P. Mazzola

  DOI：10.1021/jm00183a018

  日期：1980.9

  Verrucarin A (2) was epoxidized to give the beta-9,10-epoxide 7 (major product) and alpha-9,10-epoxide 9 (minor product). The beta-epoxide 7 and its acetate 8 exhibit high in vivo antileukemic activity against P-388 mouse leukemia, whereas 2 and 9 are inactive. Epoxidation of verrucarin B (3) and roridin A (1) to their respective beta-9,10-epoxides (11 and 12, respectively) also yields compounds with substantially increased activity. Allylic alcohols derived from 2, alpha-C8 (20), beta-C8 (14), and C16 (15), were synthesized and tested; only 15 exhibited substantial in vivo activity.