(4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-(cyclohexanecarboxamido)-3-methylbutanoate | 1325236-02-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-(cyclohexanecarboxamido)-3-methylbutanoate
• CAS: 1325236-02-9
• 化学式: C₃₉H₆₀N₂O₅
• 分子量: 636.916
• InChiKey: KPZKASXDVUNXEW-GQJKSIIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.03
• 重原子数：
  46.0
• 可旋转键数：
  22.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-(cyclohexanecarboxamido)-3-methylbutanoate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以83%的产率得到[(13R,16E)-22-methoxy-16-methyl-3-oxo-2-azabicyclo[18.3.1]tetracosa-1(23),10,16,20(24),21-pentaen-13-yl] (2R)-2-(cyclohexanecarbonylamino)-3-methylbutanoate
  参考文献：
  名称：

  Monoenomycin: A Simplified Trienomycin A Analogue That Manifests Anticancer Activity

  摘要：

  Macrocydic natural products are a powerful class of leadlike chemical entities. Despite commonly violating Lipinski's "rule of 5", these compounds often demonstrate superior druglike physicochemical and pharmacokinetic attributes when compared to their acyclic counterparts. However, the elaborate structural architectures of such molecules require rigorous synthetic investigation that complicates analogue development and their application to drug discovery programs. To circumvent these limitations, a conformation-based approach using limited structure-activity relationships and molecular modeling was implemented to design simplified analogues of trienomycin A, in which the corresponding analogues could be prepared in a succinct manner to rapidly identify essential structural components necessary for biological activity. Trienomycin A is a member of the ansamycin family of natural products that possesses potent anticancer activity. These studies revealed a novel trienomycin A analogue, rnonoenomycin, which manifests potent anticancer activity.

  DOI：

  10.1021/ml200108y
• 作为产物：
  描述：

  3-甲氧基-4-硝基苯甲醛 在 咪唑 、 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 碘 、 sodium hydride 、 二异丁基氢化铝 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 64.0h， 生成 (4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-(cyclohexanecarboxamido)-3-methylbutanoate
  参考文献：
  名称：

  Monoenomycin: A Simplified Trienomycin A Analogue That Manifests Anticancer Activity

  摘要：

  Macrocydic natural products are a powerful class of leadlike chemical entities. Despite commonly violating Lipinski's "rule of 5", these compounds often demonstrate superior druglike physicochemical and pharmacokinetic attributes when compared to their acyclic counterparts. However, the elaborate structural architectures of such molecules require rigorous synthetic investigation that complicates analogue development and their application to drug discovery programs. To circumvent these limitations, a conformation-based approach using limited structure-activity relationships and molecular modeling was implemented to design simplified analogues of trienomycin A, in which the corresponding analogues could be prepared in a succinct manner to rapidly identify essential structural components necessary for biological activity. Trienomycin A is a member of the ansamycin family of natural products that possesses potent anticancer activity. These studies revealed a novel trienomycin A analogue, rnonoenomycin, which manifests potent anticancer activity.

  DOI：

  10.1021/ml200108y