| 1303556-56-0

• 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
• CAS: 1303556-56-0
• 化学式: C₃₇H₆₇N₅O₆SSi
• 分子量: 738.12
• InChiKey: IGWLHRGKOSGEPM-LBFQUQHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  50.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  130.17
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  The Multiple Multicomponent Approach to Natural Product Mimics: Tubugis, N-Substituted Anticancer Peptides with Picomolar Activity

  摘要：

  The synthesis of a new generation of highly cytotoxic tubulysin analogues (i.e., tubugis) is described. In the key step, the rare, unstable, and synthetically difficult to introduce tertiary amide-N,O-acetal moiety required for high potency in natural tubulysins is replaced by a dipeptoid element formed in an Ugi four-component reaction. Two of the four components required are themselves produced by other multicomponent reactions (MCRs). Thus, the tubugis represent the first examples of the synthesis of natural-product-inspired compounds using three intertwined isonitrile MCRs.

  DOI：

  10.1021/ja2022027
• 作为产物：
  描述：

  ethyl 2-[(1R,3R)-1-acetyloxy-4-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentyl]-1,3-thiazole-4-carboxylate 在 咪唑 、 sodium ethanolate 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.17h， 生成
  参考文献：
  名称：

  The Multiple Multicomponent Approach to Natural Product Mimics: Tubugis, N-Substituted Anticancer Peptides with Picomolar Activity

  摘要：

  The synthesis of a new generation of highly cytotoxic tubulysin analogues (i.e., tubugis) is described. In the key step, the rare, unstable, and synthetically difficult to introduce tertiary amide-N,O-acetal moiety required for high potency in natural tubulysins is replaced by a dipeptoid element formed in an Ugi four-component reaction. Two of the four components required are themselves produced by other multicomponent reactions (MCRs). Thus, the tubugis represent the first examples of the synthesis of natural-product-inspired compounds using three intertwined isonitrile MCRs.

  DOI：

  10.1021/ja2022027

文献信息

• Tubulysin analogues
  申请人：Wessjohann Ludger A.

  公开号：US09371358B2

  公开（公告）日：2016-06-21

  The present invention relates to novel tubulysin compounds (tubulysin analogs) as well as pharmaceutical formulations thereof. The present invention further relates to the use of such compounds for medicinal, agricultural, biotool or cosmetic applications. In particular, the novel tubulysin analogs show a cytostatic effect and can therefore be used for the treatment of proliferative disorders. The tertiary amide moiety of the tubulysin analogs (so-called tubugis) according to the present invention is generated by an Ugi-type reaction.

  本发明涉及新型的管肽素化合物（管肽素类似物）以及其药物配方。本发明进一步涉及这些化合物在药用、农业、生物工具或化妆品应用中的使用。特别是，这些新型的管肽素类似物显示出细胞静止效应，因此可用于治疗增生性疾病。根据本发明，管肽素类似物（即所谓的管肽）的三级酰胺基团是通过Ugi型反应生成的。