(R)-2-{3'-[di-(tert-butyloxycarbonyl)amino]-1'-keto-4'-methylpentyl}-4-carboxylate-thiazole | 1017624-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (R)-2-{3'-[di-(tert-butyloxycarbonyl)amino]-1'-keto-4'-methylpentyl}-4-carboxylate-thiazole
• 英文别名: 2-[(3R)-3-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-4-methylpentanoyl]-1,3-thiazole-4-carboxylic acid
• CAS: 1017624-82-6
• 化学式: C₂₀H₃₀N₂O₇S
• 分子量: 442.533
• InChiKey: RIVMOPWWCZOCEF-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  9

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(R)-2-{3'-[di-(tert-butyloxycarbonyl)amino]-1'-keto-4'-methylpentyl}-4-formylthiazole	1017624-81-5	C20H30N2O6S	426.534

反应信息

• 作为反应物：
  描述：

  (R)-2-{3'-[di-(tert-butyloxycarbonyl)amino]-1'-keto-4'-methylpentyl}-4-carboxylate-thiazole 、 在 五氟苯酚 、 N,N'-二环己基碳二亚胺 作用下， 生成
  参考文献：
  名称：

  Tubulysin analogs incorporating desmethyl and dimethyl tubuphenylalanine derivatives

  摘要：

  A series of tubulysin analogs in which one of the stereogenic centers of tubuphenylalanine was eliminated were synthesized. All compounds were tested for antiproliferative activity towards ovarian cancer cells and for inhibition of tubulin polymerization. The dimethyl analogs were generally more active than the desmethyl analogs, and four analogs have tubulin polymerization IC50 values similar to combretastatin A4 and the hemiasterlin analog HTI-286. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.046
• 作为产物：
  描述：

  (R)-2-{3'-[di-(tert-butyloxycarbonyl)amino]-1'-keto-4'-methylpentyl}-4-formylthiazole 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 1.0h， 以48%的产率得到(R)-2-{3'-[di-(tert-butyloxycarbonyl)amino]-1'-keto-4'-methylpentyl}-4-carboxylate-thiazole
  参考文献：
  名称：

  细胞毒性简化的微管溶素类似物。

  摘要：

  开发了合成抗有丝分裂肽微管溶素家族的有效途径。合成了简化的微管溶素类似物以定义细胞毒性所需的最小药效基团。简化的微管溶素类似物保留了明显的细胞毒性，并显示出重要的初步构效关系。

  DOI：

  10.1021/jm701321p

文献信息

• Cytotoxic Simplified Tubulysin Analogues
  作者：Bhooma Raghavan、Ranganathan Balasubramanian、Jaeson C. Steele、Dan L. Sackett、Robert A. Fecik

  DOI：10.1021/jm701321p

  日期：2008.3.1

  An efficient route for the synthesis of the tubulysin family of antimitotic peptides was developed. Simplified tubulysin analogues were synthesized to define the minimum pharmacophore required for cytotoxicity. Simplified tubulysin analogues retain significant cytotoxicity and reveal important preliminary structure-activity relationships.

  开发了合成抗有丝分裂肽微管溶素家族的有效途径。合成了简化的微管溶素类似物以定义细胞毒性所需的最小药效基团。简化的微管溶素类似物保留了明显的细胞毒性，并显示出重要的初步构效关系。
• Tubulysin analogs incorporating desmethyl and dimethyl tubuphenylalanine derivatives
  作者：Ranganathan Balasubramanian、Bhooma Raghavan、Jaeson C. Steele、Dan L. Sackett、Robert A. Fecik

  DOI：10.1016/j.bmcl.2008.03.046

  日期：2008.5

  A series of tubulysin analogs in which one of the stereogenic centers of tubuphenylalanine was eliminated were synthesized. All compounds were tested for antiproliferative activity towards ovarian cancer cells and for inhibition of tubulin polymerization. The dimethyl analogs were generally more active than the desmethyl analogs, and four analogs have tubulin polymerization IC50 values similar to combretastatin A4 and the hemiasterlin analog HTI-286. (C) 2008 Elsevier Ltd. All rights reserved.