methyl 11-bromo-10-oxoundecanoate | 173411-46-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 11-bromo-10-oxoundecanoate
• CAS: 173411-46-6
• 化学式: C₁₂H₂₁BrO₃
• 分子量: 293.201
• InChiKey: RMTUAQIOBWIRGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 11-bromo-10-oxoundecanoate 在 吡啶 、 4-二甲氨基吡啶 、 氢溴酸 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 三氯乙酰氯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.75h， 生成 methyl 9-[2-[(E)-3-[(3aS,4S,7S,7aR)-7-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]-2-methoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]-2-methylprop-1-enyl]-1,3-oxazol-5-yl]nonanoate
  参考文献：
  名称：

  假单宁酸的化学。15.一系列5-烷基，5-烯基和5-杂取代的恶唑的合成和抗菌活性。

  摘要：

  描述了一系列5-烷基，5-烯基和5-杂取代的2-（1-正丙基-2-基）恶唑的合成。使用标准琼脂稀释程序，将抗菌活性确定为对一系列革兰氏阳性和革兰氏阴性生物的最小抑制浓度。发现在环上直接或靠近环具有酸官能度的化合物的效力大大降低，而亲脂性随着链长的增加而增加，导致这些衍生物的效力增加。

  DOI：

  10.1021/jm9503862
• 作为产物：
  描述：

  癸二酸单甲酯 在 草酰氯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 methyl 11-bromo-10-oxoundecanoate
  参考文献：
  名称：

  Tumor-Targeting with Novel Non-Benzoyl 6-Substituted Straight Chain Pyrrolo[2,3-d]pyrimidine Antifolates via Cellular Uptake by Folate Receptor α and Inhibition of de Novo Purine Nucleotide Biosynthesis

  摘要：

  A new series of 6-substituted straight side chain pyrrolo[2,3-d]pyrimidines 3a-d with varying chain lengths (n = 5-8) was designed and synthesized as part of our program to provide targeted antitumor agents with folate receptor (FR) cellular uptake specificity and glycinamide ribonucleotide formyltransferase (GARFTase) inhibition. Carboxylic acids 4a-d were converted to the acid chlorides and reacted with diazomethane, followed by 48% HBr to generate the alpha-bromomethylketones 5a-d. Condensation of 2,4-diamino-6-hydroxypyrimidine 6 with 5a-d afforded the 6-substituted pyrrolo[2,3-d]pyrimidines 7a-d. Hydrolysis and subsequent coupling with diethyl L-glutamate and saponification afforded target compounds 3a-d. Compounds 3b-d showed selective cellular uptake via FR alpha and -beta, associated with high affinity binding and inhibition of de novo purine nucleotide biosynthesis via GARFTase, resulting in potent inhibition against FR-expressing Chinese hamster cells and human KB tumor cells in culture. Our studies establish, for the first time, that a side chain benzoyl group is not essential for tumor-selective drug uptake by FR alpha.

  DOI：

  10.1021/jm401139z

文献信息

• The Chemistry of Pseudomonic Acid. 15. Synthesis and Antibacterial Activity of a Series of 5-Alkyl, 5-Alkenyl, and 5-Heterosubstituted Oxazoles
  作者：Pamela Brown、David T. Davies、Peter J. O'Hanlo、Jennifer M. Wilson

  DOI：10.1021/jm9503862

  日期：1996.1.1

  antibacterial activity was determined as the minimum inhibitory concentration against a range of Gram-positive and Gram-negative organisms using a standard Agar dilution procedure. Compounds possessing an acid functionality directly on, or close to, the ring were found to be of greatly decreased potency, while increasing lipophilicity with greater chain length led to increased potency of these derivatives

  描述了一系列5-烷基，5-烯基和5-杂取代的2-（1-正丙基-2-基）恶唑的合成。使用标准琼脂稀释程序，将抗菌活性确定为对一系列革兰氏阳性和革兰氏阴性生物的最小抑制浓度。发现在环上直接或靠近环具有酸官能度的化合物的效力大大降低，而亲脂性随着链长的增加而增加，导致这些衍生物的效力增加。
• Tumor-Targeting with Novel Non-Benzoyl 6-Substituted Straight Chain Pyrrolo[2,3-<i>d</i>]pyrimidine Antifolates via Cellular Uptake by Folate Receptor α and Inhibition of de Novo Purine Nucleotide Biosynthesis
  作者：Yiqiang Wang、Christina Cherian、Steven Orr、Shermaine Mitchell-Ryan、Zhanjun Hou、Sudhir Raghavan、Larry H. Matherly、Aleem Gangjee

  DOI：10.1021/jm401139z

  日期：2013.11.14

  A new series of 6-substituted straight side chain pyrrolo[2,3-d]pyrimidines 3a-d with varying chain lengths (n = 5-8) was designed and synthesized as part of our program to provide targeted antitumor agents with folate receptor (FR) cellular uptake specificity and glycinamide ribonucleotide formyltransferase (GARFTase) inhibition. Carboxylic acids 4a-d were converted to the acid chlorides and reacted with diazomethane, followed by 48% HBr to generate the alpha-bromomethylketones 5a-d. Condensation of 2,4-diamino-6-hydroxypyrimidine 6 with 5a-d afforded the 6-substituted pyrrolo[2,3-d]pyrimidines 7a-d. Hydrolysis and subsequent coupling with diethyl L-glutamate and saponification afforded target compounds 3a-d. Compounds 3b-d showed selective cellular uptake via FR alpha and -beta, associated with high affinity binding and inhibition of de novo purine nucleotide biosynthesis via GARFTase, resulting in potent inhibition against FR-expressing Chinese hamster cells and human KB tumor cells in culture. Our studies establish, for the first time, that a side chain benzoyl group is not essential for tumor-selective drug uptake by FR alpha.