10-溴-9-氧代癸酸甲酯 | 85060-82-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 10-溴-9-氧代癸酸甲酯
• 英文名称: 10-bromo-9-ketodecanoic acid methyl ester
• 英文别名: methyl 10-bromo-9-oxodecanoate
• CAS: 85060-82-8
• 化学式: C₁₁H₁₉BrO₃
• 分子量: 279.174
• InChiKey: GLRDTVHBIZVRND-UHFFFAOYSA-N

物化性质

• 沸点：
  339.4±22.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  10-溴-9-氧代癸酸甲酯 在 盐酸 、 sodium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 4-氧代十二烷二酸
  参考文献：
  名称：

  Synthesis of 4-oxododecanoic and 4-oxododecanedioic acids

  摘要：

  DOI：

  10.1007/bf00962129
• 作为产物：
  描述：

  9-氧代癸酸甲酯 在 溴 、 尿素 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 10-溴-9-氧代癸酸甲酯
  参考文献：
  名称：

  Synthesis of 4-oxododecanoic and 4-oxododecanedioic acids

  摘要：

  DOI：

  10.1007/bf00962129

文献信息

• Identification of Novel Triazole-Based Nicotinamide Phosphoribosyltransferase (NAMPT) Inhibitors Endowed with Antiproliferative and Antiinflammatory Activity
  作者：Cristina Travelli、Silvio Aprile、Reza Rahimian、Ambra A. Grolla、Federica Rogati、Mattia Bertolotti、Floriana Malagnino、Rosanna di Paola、Daniela Impellizzeri、Roberta Fusco、Valentina Mercalli、Alberto Massarotti、Giorgio Stortini、Salvatore Terrazzino、Erika Del Grosso、Gohar Fakhfouri、Maria Pia Troiani、Maria Alessandra Alisi、Giorgio Grosa、Giovanni Sorba、Pier Luigi Canonico、Giuseppe Orsomando、Salvatore Cuzzocrea、Armando A. Genazzani、Ubaldina Galli、Gian Cesare Tron

  DOI：10.1021/acs.jmedchem.6b01392

  日期：2017.3.9

  inflammatory diseases. We describe the synthesis and characterization of a novel class of one-digit nanomolar NAMPT inhibitors based on in vitro characterization. The most active compound tested, 30c, displayed activity in xenograft and allograft models, strengthening the potential of NAMPT inhibitors as antitumoral drugs. Furthermore, in the present contribution we describe the ability of 30c to significantly

  烟酰胺磷酸核糖基转移酶（NAMPT）是参与烟酰胺再循环以维持细胞内足够NAD水平的关键酶。由于它在癌细胞和炎性疾病中过表达，因此已假定它是药理学靶标。我们描述了基于体外表征的一类新型一位数纳摩尔NAMPT抑制剂的合成和表征。测试的活性最高的化合物30c在异种移植和同种异体移植模型中均显示出活性，从而增强了NAMPT抑制剂作为抗肿瘤药物的潜力。此外，在本文稿中，我们描述了30c的能力显着改善小鼠结肠炎的预后。鉴于这是NAMPT抑制剂在结肠炎中作用的首次报道，该结果为此类化合物的新应用铺平了道路。
• Effect of amides on the bromination of methyl alkyl ketones
  作者：S. I. Zav'yalov、N. E. Kravchenko

  DOI：10.1007/bf00951090

  日期：1984.2
• Influence of urea on the bromination of methyl alkyl ketones
  作者：S. I. Zav'yalov、N. E. Kravchenko

  DOI：10.1007/bf00953198

  日期：1983.6
• Synthesis of dimethyl ester of 4-ketododecanedioic acid
  作者：S. I. Zav'yalov、N. E. Knyaz'kova

  DOI：10.1007/bf01167792

  日期：1983.1
• 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.