methyl (2S,4R)-4-[[2-[(1R,3R)-3-[[1-(butylamino)-1-oxopropan-2-yl]-[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]-1-hydroxy-4-methylpentyl]-1,3-thiazole-4-carbonyl]amino]-2-methyl-5-phenylpentanoate | 1303556-61-7

• 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: methyl (2S,4R)-4-[[2-[(1R,3R)-3-[[1-(butylamino)-1-oxopropan-2-yl]-[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]-1-hydroxy-4-methylpentyl]-1,3-thiazole-4-carbonyl]amino]-2-methyl-5-phenylpentanoate
• CAS: 1303556-61-7
• 化学式: C₄₃H₆₈N₆O₇S
• 分子量: 813.115
• InChiKey: VJVWXMJSFQCZNW-CFSIITNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  57
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  199
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (2S,4R)-4-[[2-[(1R,3R)-3-[[1-(butylamino)-1-oxopropan-2-yl]-[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]-1-hydroxy-4-methylpentyl]-1,3-thiazole-4-carbonyl]amino]-2-methyl-5-phenylpentanoate 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 120.0h， 生成 (2S,4R)-4-[[2-[(1R,3R)-1-acetyloxy-3-[[1-(butylamino)-1-oxopropan-2-yl]-[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]-4-methylpentyl]-1,3-thiazole-4-carbonyl]amino]-2-methyl-5-phenylpentanoic acid
  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：

  (R)-Mep-(S)-Ile-OH*HCl 在 五氟苯酚 、 三氟乙酸 、 lithium hydroxide 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 59.17h， 生成 methyl (2S,4R)-4-[[2-[(1R,3R)-3-[[1-(butylamino)-1-oxopropan-2-yl]-[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]-1-hydroxy-4-methylpentyl]-1,3-thiazole-4-carbonyl]amino]-2-methyl-5-phenylpentanoate
  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

• The Multiple Multicomponent Approach to Natural Product Mimics: Tubugis, N-Substituted Anticancer Peptides with Picomolar Activity
  作者：Orlando Pando、Sebastian Stark、Annika Denkert、Andrea Porzel、Rainer Preusentanz、Ludger A. Wessjohann

  DOI：10.1021/ja2022027

  日期：2011.5.25

  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.