ethyl 4-(5-oxopentyl)benzoate | 76865-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-(5-oxopentyl)benzoate
• CAS: 76865-48-0
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: JIVLMGLEHMMRHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  ethyl 4-(5-oxopentyl)benzoate 在 lithium hydroxide monohydrate 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 生成
  参考文献：
  名称：

  一类作为蛋白降解剂的化合物及其制备方法和医药用途

  摘要：

  本发明公开了一类作为蛋白降解剂的化合物及其制备方法和医药用途，具体地，本发明公开了式(Ⅰ)所示化合物及其药效上可接受的盐，以及该化合物作为雄激素受体(AR)、雌激素受体(ER)、含溴结构域蛋白质、TANK结合激酶等降解的应用。

  公开号：

  CN113582974B
• 作为产物：
  描述：

  4-戊炔-1-醇 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 ethyl 4-(5-oxopentyl)benzoate
  参考文献：
  名称：

  一类作为蛋白降解剂的化合物及其制备方法和医药用途

  摘要：

  本发明公开了一类作为蛋白降解剂的化合物及其制备方法和医药用途，具体地，本发明公开了式(Ⅰ)所示化合物及其药效上可接受的盐，以及该化合物作为雄激素受体(AR)、雌激素受体(ER)、含溴结构域蛋白质、TANK结合激酶等降解的应用。

  公开号：

  CN113582974B

文献信息

• Interphenylene 9-thia-11-oxo-12-aza-prostanoic acids
  申请人：Merck & Co., Inc.

  公开号：US04225609A1

  公开（公告）日：1980-09-30

  This invention relates to novel interphenylene 9-thia-11-oxo-12-azaprostanoic acid compounds, salts, and derivatives thereof. These compounds are exceptionally potent renal vasodilators and antihypertensives which are active when administered orally but which have a more specific type of biological activity than that of many of the natural prostaglandins and their synthetic analogs or derivatives.

  这项发明涉及新型的间苯二酚9-硫-11-酮-12-氮代前列腺酸化合物、盐和衍生物。这些化合物在口服后表现出异常强大的肾脏扩血管作用和降压作用，但其生物活性比许多天然前列腺素及其合成类似物或衍生物具有更特定的类型。
• Synthesis of aryl-substituted aldehydes and ketones via palladium-catalyzed coupling of aryl halides and non-allylic unsaturated alcohols
  作者：Richard C. Larock、Wai-Yee Leung、Sandra Stolz-Dunn

  DOI：10.1016/s0040-4039(00)70636-8

  日期：——

  The palladium-catalyzed coupling of aryl halides and non-allylic unsaturated alcohols affords excellent yields of aryl-substituted aldehydes and ketones.

  芳基卤化物和非烯丙基不饱和醇的钯催化偶联提供了芳基取代的醛和酮的优异收率。
• Synthesis and Biological Activity of a Novel Series of 6-Substituted Thieno[2,3-<i>d</i>]pyrimidine Antifolate Inhibitors of Purine Biosynthesis with Selectivity for High Affinity Folate Receptors over the Reduced Folate Carrier and Proton-Coupled Folate Transporter for Cellular Entry^†
  作者：Yijun Deng、Xilin Zhou、Sita Kugel Desmoulin、Jianmei Wu、Christina Cherian、Zhanjun Hou、Larry H. Matherly、Aleem Gangjee

  DOI：10.1021/jm8011323

  日期：2009.5.14

  A series of seven 2-amino4-oxo-6-substituted thieno[2,3-d]pyrimidines with bridge length variations (from 2 to 8 carbon atoms) were synthesized as selective folate receptor (FR) alpha and beta substrates and as antitumor agents. The syntheses were accomplished from appropriate allylalcohols and 4-iodobenzoate to afford the aldehydes, which were converted to the appropriate 2-amino-4-carbethoxy-5-substituted thiophenes 23-29. Cyclization with chloroformamidine afforded the thieno[2,3-d]pyrimidines 30-36, which were hydrolyzed and coupled with diethyl-L-glutamate, followed by saponification, to give the target compounds 2-8. Compounds 3-6 were potent growth inhibitors (IC50 4.7-334 nM) of human tumor cells (KB and IGROV1) that express FRs. In addition, compounds 3-6 inhibited the growth of Chinese hamster ovary (CHO) cells that expressed FRs but not the reduced folate carrier (RFC) or proton-coupled folate transporter (PCFT). However, the compounds were inactive toward CHO cells that lacked FRs but contained either the RFC or PCFT. By nucleoside and 5-amino-imidazole carboxamide (AICA) protection studies, along with in vitro and in situ enzyme activity assays, the mechanism of antitumor activity was identified as the dual inhibition of glycinamide ribonucleotide formyltransferase and, likely, AICA ribonucleotide formyltransferase. The dual inhibitory activity of the active thieno[2,3-d]pyrimidine antifolates and the FR specificity represent unique mechanistic features for these compounds distinct from all other known antifolates. The potent inhibitory effects of compounds 3-6 toward cells expressing FRs but not PCFT provide direct evidence that cellular uptake of this series of compounds by FRs does not depend on the presence of PCFT and argues that direct coupling between these transporters is not obligatory.
• Discovery of 5-Substituted Pyrrolo[2,3-<i>d</i>]pyrimidine Antifolates as Dual-Acting Inhibitors of Glycinamide Ribonucleotide Formyltransferase and 5-Aminoimidazole-4-carboxamide Ribonucleotide Formyltransferase in De Novo Purine Nucleotide Biosynthesis: Implications of Inhibiting 5-Aminoimidazole-4-carboxamide Ribonucleotide Formyltransferase to AMPK Activation and Antitumor Activity
  作者：Shermaine Mitchell-Ryan、Yiqiang Wang、Sudhir Raghavan、Manasa Punaha Ravindra、Eric Hales、Steven Orr、Christina Cherian、Zhanjun Hou、Larry H. Matherly、Aleem Gangjee

  DOI：10.1021/jm401328u

  日期：2013.12.27

  We synthesized 5-substituted pyrrolo[2,3-d]pyrimidine antifolates (compounds 5-10) with one-to-six bridge carbons and a benozyl ring in the side chain as antitumor agents. Compound 8 with a 4-carbon bridge was the most active analogue and potently inhibited proliferation of folate receptor (FR) alpha-expressing Chinese hamster ovary and KB human tumor cells. Growth inhibition was reversed completely or in part by excess folic acid, indicating that FR alpha is involved in cellular uptake, and resulted in S-phase accumulation and apoptosis. Antiproliferative effects of compound 8 toward KB cells were protected by excess adenosine but not thymidine, establishing de novo purine nucleotide biosynthesis as the targeted pathway. However, 5-aminoimidazole-4-carboxamide (AICA) protection was incomplete, suggesting inhibition of both AICA ribonucleotide formyltransferase (AICARFTase) and glycinamide ribonucleotide formyltransferase (GARFTase). Inhibition of GARFTase and AICARFTase by compound 8 was confirmed by cellular metabolic assays and resulted in ATP pool depletion. To our knowledge, this is the first example of an antifolate that acts as a dual inhibitor of GARFTase and AICARFTase as its principal mechanism of action.
• LAROCK, RICHARD C.;LAUND, WAI-YEE;STOLZ-DUNN, SANDRA, TETRAHEDRON LETT., 30,(1989) N8, C. 6629-6632
  作者：LAROCK, RICHARD C.、LAUND, WAI-YEE、STOLZ-DUNN, SANDRA

  DOI：——

  日期：——