(2S,5R,6R)-6-Amino-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester | 37880-26-5

• 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: (2S,5R,6R)-6-Amino-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,5R,6R)-6-amino-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate；methyl (2S,5R,6R)-6-amino-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 37880-26-5
• 化学式: C₉H₁₄N₂O₄S
• 分子量: 246.287
• InChiKey: BRCRNHKQRKSZDG-RCASYBAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,5R,6R)-6-Amino-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (2S,5R,6R)-6-((E)-3-Furan-2-yl-acryloylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Domino functionalizations of the amino terminus of 6-aminopenicillanates with Ph3PCCO

  摘要：

  6-Aminopenicillanates, or the sulfoxides or the sulfones thereof, were N-acylated in a three-component reaction with an aldehyde and Ph3PCCO to give the corresponding 6-(E-2'-alkenoyl)amides. This domino addition-Wittig alkenation sequence was extended by an additional Claisen rearrangement step in the side-chain in the case of 5g. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.083
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成 (2S,5R,6R)-6-Amino-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Domino functionalizations of the amino terminus of 6-aminopenicillanates with Ph3PCCO

  摘要：

  6-Aminopenicillanates, or the sulfoxides or the sulfones thereof, were N-acylated in a three-component reaction with an aldehyde and Ph3PCCO to give the corresponding 6-(E-2'-alkenoyl)amides. This domino addition-Wittig alkenation sequence was extended by an additional Claisen rearrangement step in the side-chain in the case of 5g. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.083

文献信息

• Synthesis of New β-Lactam Analogs and Evaluation of Their Histone Deacetylase (HDAC) Activity
  作者：Seikwan Oh、Jae-Chul Jung、Mitchell A. Avery

  DOI：10.1515/znb-2007-1116

  日期：2007.11.1

  A simple synthesis of the β -lactams 11 - 13 and 16 - 17 as novel histone deacetylase (HDAC) inhibitors is described. The key synthetic strategies involved the O-alkylation of 6-APA and the coupling reactions of freshly prepared N-carbobenzyloxy-L-prolines 5 and 6 and 6-aminopenicillanates 8 - 10 and 15 in high yields. It was found that all compounds show potent growth inhibitory activity on human tumor cell lines, the most potent compound 16 exhibiting an IC₅₀ = 2.1 μM in vitro.

  本文介绍了一种简单的合成方法，用于合成β-内酰胺11-13和16-17，作为新型组蛋白去乙酰化酶（HDAC）抑制剂。关键的合成策略包括6-APA的O-烷基化和新鲜制备的N-碳苄氧基-L-脯氨酸5和6以及6-氨基青霉素酸盐8-10和15的偶联反应，产率高。研究发现，所有化合物均对人类肿瘤细胞系具有强大的生长抑制活性，其中最有效的化合物16在体外的IC50为2.1μM。
• Domino functionalizations of the amino terminus of 6-aminopenicillanates with Ph3PCCO
  作者：Rainer Schobert、Andreas Stangl

  DOI：10.1016/j.tetlet.2004.12.083

  日期：2005.2

  6-Aminopenicillanates, or the sulfoxides or the sulfones thereof, were N-acylated in a three-component reaction with an aldehyde and Ph3PCCO to give the corresponding 6-(E-2'-alkenoyl)amides. This domino addition-Wittig alkenation sequence was extended by an additional Claisen rearrangement step in the side-chain in the case of 5g. (C) 2004 Elsevier Ltd. All rights reserved.