<3>-Phalyliden-essigsaeure-aethylester | 13141-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: <3>-Phalyliden-essigsaeure-aethylester
• 英文别名: ethyl 2-(3-oxo-1,3-dihydro-1-isobenzofuranyliden)acetate；(3-oxo-3H-isobenzofuran-1-ylidene)-acetic acid ethyl ester；phthalidyliden-acetic acid ethyl ester；Phthalidyliden-essigsaeure-aethylester；Ethyl 2-(3-oxo-2-benzofuran-1-ylidene)acetate
• CAS: 13141-32-7
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: YUYJWUQIKNLSPN-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  358.9±42.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <3>-Phalyliden-essigsaeure-aethylester 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以100%的产率得到(4-氧代-3,4-二氢二氮杂萘-1-基)-乙酸乙酯
  参考文献：
  名称：

  靶向白细胞介素15蛋白的N-取代酞嗪酮衍生物的合理修饰、合成和生物学评价

  摘要：

  白细胞介素 (IL)-15 是一种多效性细胞因子，在结构上与 IL-2 接近，并与 IL-2Rβ 和 γc 受体 (R) 亚基共享。IL-15 在先天性和适应性免疫中发挥重要作用，支持 NK、NK-T 和 CD8 +的激活和增殖T细胞。IL-15 的过度表达已被证明参与炎症和自身免疫性疾病以及多种 T 细胞恶性肿瘤的发展。这项研究延续了我们之前的工作，通过基于药效团的虚拟筛选和命中优化方法，已经确定了一系列阻碍 IL-15/IL-2Rβ 与亚微摩尔活性相互作用的小分子抑制剂。为了提高我们先导抑制剂的功效和选择性，在优化的 SAR 和建模的基础上引入了特定的修改。已经评估了产生的新系列化合物抑制 IL-15 依赖性细胞的增殖和下游信号传导以及与 IL-15 结合的能力。

  DOI：

  10.1016/j.bmc.2021.116161
• 作为产物：
  描述：

  苯酐 、 乙氧甲酰基亚甲基三苯基膦 以 二氯甲烷 为溶剂， 反应 3.0h， 以84%的产率得到<3>-Phalyliden-essigsaeure-aethylester
  参考文献：
  名称：

  Synthesis and Antimycobacterial Evaluation of Novel Phthalazin-4-ylacetamides Against log- and Starved Phase Cultures

  摘要：

  Twenty four novel 2‐[3‐(4‐bromo‐2‐fluorobenzyl)‐4‐oxo‐3,4‐dihydro‐1‐phthalazinyl]acetic acid amides were synthesized from phthalic anhydride and were subjected to in vitro and in vivo evaluation against log‐ and starved phase of mycobacterial species and Mycobacterium tuberculosis isocitrate lyase enzyme inhibition studies. Among the compounds screened, 2‐(2‐(4‐bromo‐2‐fluorobenzyl)‐1,2‐dihydro‐1‐oxophthalazin‐4‐yl)‐N‐(2,6‐dimethylphenyl)acetamide (5j) inhibited all eight mycobacterial species with MIC’s ranging from 0.08 to 5.05 μm and was non‐toxic to Vero cells till 126.43 μm. Four compounds were tested against starved culture of Mycobacterium tuberculosis and they inhibited with MIC’s ranging from 3.78 to 23.2 μm. Some compounds showed 40–66% inhibition against Mycobacterium tuberculosis isocitrate lyase enzyme at 10 μm. The docking studies also confirmed the binding potential of the compounds at the isocitrate lyase active site. In the in vivo animal model, 5j reduced the mycobacterial load in lung and spleen tissues with 1.38 and 2.9‐log10 protections, respectively, at 25 mg/kg body weight dose.

  DOI：

  10.1111/j.1747-0285.2010.00947.x

文献信息

• [EN] COMPOUNDS AND METHODS FOR TREATING MAMMALIAN GASTROINTESTINAL MICROBIAL INFECTIONS<br/>[FR] COMPOSÉS ET PROCÉDÉS DE TRAITEMENT D'INFECTIONS MICROBIENNES GASTRO-INTESTINALES DE MAMMIFÈRE
  申请人：UNIV BRANDEIS

  公开号：WO2014028931A3

  公开（公告）日：2014-10-09
• [EN] METHODS AND COMPOSITIONS FOR INHIBITING CNKSR1<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR L'INHIBITION DE CNKSR1
  申请人：PHUSIS THERAPEUTICS INC

  公开号：WO2014093988A3

  公开（公告）日：2014-08-07
• WO2008/93920
  申请人：——

  公开号：——

  公开（公告）日：——
• Evaluation of anti-depressant effects of phthalazinone-based triple-acting small molecules against 5-HT2A, 5-HT2C, and the serotonin transporter
  作者：Jihye Kim、Eunji Cha、Woo Kyu Park、Hye Yeon Lee、Sang Min Lim、Hak Joong Kim、Ae Nim Pae

  DOI：10.1016/j.bmcl.2019.126882

  日期：2020.2

  Development of highly effective, safe, and fast-acting anti-depressants is urgently required for the treatment of major depressive disorder. It has been suggested that targeting 5-HT2A and 5-HT2C in addition to inhibition of serotonin reuptake may be beneficial in generating anti-depressant agents with better pharmacology and less adverse effects. We have developed phthalazinone-based compounds that potently bind to 5-HT2A, 5-HT2C, and the serotonin transporter. The representative compounds 11j and 11l displayed strong binding affinities against these targets, and showed favorable toxicity profiles as determined by hERG binding and CYP inhibition assays. Furthermore, these compounds presented promising anti-depressant effects comparable to fluoxetine and also synergistic effects with fluoxetine in forced swimming test, which implicates these compounds can be developed to help the treatment of major depressive disorder.