3-ethoxycarbonyl-1-(3-methoxyphenyl)-1,4-pentanedione | 94195-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ethoxycarbonyl-1-(3-methoxyphenyl)-1,4-pentanedione
• 英文别名: (+/-)-ethyl 2-acetyl-4-(3-methoxyphenyl)-4-oxobutanoate；2-[2-(3-methoxy-phenyl)-2-oxo-ethyl]-3-oxo-butyric acid ethyl ester；ethyl 2-acetyl-4-(3-methoxyphenyl)-4-oxobutanoate
• CAS: 94195-90-1
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: WASNGNOCYWVARI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonyl-1-(3-methoxyphenyl)-1,4-pentanedione 在 盐酸 、 ammonium hydroxide 、 氯化亚砜 、 水 、 三溴化硼 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 31.67h， 生成 (3-(4-carbamoyl-5-methylfuran-2-yl)phenoxycarbonyl)(butyl)amine
  参考文献：
  名称：

  Discovery of Potent Inhibitors of Human and Mouse Fatty Acid Amide Hydrolases

  摘要：

  Fatty acid amide hydrolase (FAAH, EC 3.5.1.99) is the main enzyme catabolizing endocannabinoid fatty acid amides. FAAH inactivation promotes beneficial effects upon pain and anxiety without the side effects accompanying agonists of type-1 cannabinoid receptors. Aiming at discovering new selective FAAH inhibitors, we developed a series of compounds (5a-u) characterized by a functionalized heteroaromatic scaffold. Particularly, 5c and 5d were identified as extremely potent, noncompetitive, and reversible FAAH inhibitors endowed with a remarkable selectivity profile and lacking interaction with the hERG channels. In vivo antinociceptive activity was demonstrated for 5c, 5d, and 5n at a dose much lower than that able to induce either striatal and limbic stereotypies or anxiolytic activity, thus outlining their potential to turn into optimum preclinical candidates. Aiming at improving pharmacokinetic properties and metabolic stability of 5d, we developed a subset of nanomolar dialyzable FAAH inhibitors (5v-z), functionalized by specific polyethereal lateral chains and fluorinated aromatic rings.

  DOI：

  10.1021/jm300689c
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2-溴-3‘-甲氧基苯乙酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-ethoxycarbonyl-1-(3-methoxyphenyl)-1,4-pentanedione
  参考文献：
  名称：

  通过 C(sp2 或 sp3)-H 系列活化和荧光研究合成 C8-氨基吡咯-菲啶或-吲哚

  摘要：

  本报告开发了一种通过系列邻C(sp 2 )-H 胺化/同样C(sp 2 )-H 或 C(sp 3 )-H 芳基化合成 C8-胺化吡咯并菲啶或 -吲哚的方法。N-苯甲酰氧基胺作为亲电胺化试剂，不与吡咯侧发生亲电取代反应，但通过 Pd/NBE 催化与苯侧发生位点选择性 C-H 胺化反应。C8-胺化的吡咯并菲啶在溶液和固态都具有强荧光。X射线单晶衍射表明氨基和邻苯环的空间位阻可能抑制聚集引起的猝灭(ACQ)。

  DOI：

  10.1021/acs.orglett.2c00318

文献信息

• [EN] CARBAMATE DERIVATIVES IN PARTICULAR FOR THE TREATMENT OF NEUROLOGICAL DISORDERS<br/>[FR] DÉRIVÉS CARBAMATES EN PARTICULIER POUR LE TRAITEMENT DE TROUBLES NEUROLOGIQUES
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2010105930A1

  公开（公告）日：2010-09-23

  The present invention relates to new carbamate derivatives of formula I, processes for their preparation, and to pharmaceutical compositions containing them for the treatment of neurological disorders, such as neuropathic pain and anxiety.

  本发明涉及一类新的氨基甲酸衍生物，其化学式为I，包括它们的制备方法，以及包含这些化合物的药物组合物，用于治疗神经系统疾病，如神经性疼痛和焦虑。
• Enantioselective Synthesis of Nitrogen–Nitrogen Biaryl Atropisomers via Copper-Catalyzed Friedel–Crafts Alkylation Reaction
  作者：Xiao-Mei Wang、Peng Zhang、Qi Xu、Chang-Qiu Guo、De-Bing Zhang、Chuan-Jun Lu、Ren-Rong Liu

  DOI：10.1021/jacs.1c07741

  日期：2021.9.22

  bioactive compounds. However, the atropisomerism arising from a restricted rotation around an N–N bond is largely overlooked. Here, we describe a method to access the first enantioselective synthesis of N–N biaryl atropisomers via a Cu-bisoxazoline-catalyzed Friedel–Crafts alkylation reaction. A wide range of axially chiral N–N bisazaheterocycle compounds were efficiently prepared in high yields with

  含有基序的氮-氮键在天然产物和生物活性化合物中无处不在。然而，由围绕 N-N 键的受限旋转引起的阻转异构在很大程度上被忽视了。在这里，我们描述了一种通过 Cu-双恶唑啉催化的 Friedel-Crafts 烷基化反应对 N-N 联芳基阻转异构体进行首次对映选择性合成的方法。通过去对称化和动力学拆分，以高产率高效制备了多种轴向手性 N-N 双氮杂杂环化合物，并具有优异的对映选择性。加热实验表明轴向手性双氮杂杂环产物具有高旋转势垒。
• Atroposelective Synthesis of 1,1′‐Bipyrroles Bearing a Chiral N−N Axis: Chiral Phosphoric Acid Catalysis with Lewis Acid Induced Enantiodivergence
  作者：Yaru Gao、Luo‐Yu Wang、Tao Zhang、Bin‐Miao Yang、Yu Zhao

  DOI：10.1002/anie.202200371

  日期：2022.4.11

  A highly efficient atroposelective synthesis of axially chiral 1,1′-bipyrroles bearing an N−N linkage from simple hydrazine and 1,4-diones is presented. Further product derivatizations led to axially chiral bifunctional compounds with high potential in asymmetric catalysis. For this chiral phosphoric acid (CPA)-catalyzed double Paal–Knorr reaction, an intriguing Fe(OTf)3-induced enantiodivergence was

  提出了由简单的肼和 1,4-二酮高效选择性合成带有 N-N 键的轴向手性 1,1'-联吡咯。进一步的产物衍生导致了在不对称催化中具有高潜力的轴向手性双功能化合物。对于这种手性磷酸 (CPA) 催化的双 Paal-Knorr 反应，还观察到了有趣的 Fe(OTf) 3诱导的对映发散。
• CARBAMATE DERIVATIVES IN PARTICULAR FOR THE TREATMENT OF NEUROLOGICAL DISORDERS
  申请人：Cabri Walter

  公开号：US20120252865A1

  公开（公告）日：2012-10-04

  The present invention relates to new carbamate derivatives of formula I, processes for their preparation, and to pharmaceutical compositions containing them for the treatment of neurological disorders, such as neuropathic pain and anxiety.

  本发明涉及一种新的I式碳酸酯衍生物，其制备方法以及含有该衍生物的制药组合物，用于治疗神经系统疾病，如神经病性疼痛和焦虑症。
• Synthesis and biological evaluation of panaxadiol ester derivatives possessing pyrazole and pyrrole moiety as HIF-1α inibitors
  作者：Ye-Fang Lu、Chuang Liu、Juan Ma、Hu-Ri Piao、Changhao Zhang、Xuejun Jin、Cheng-Hua Jin

  DOI：10.1016/j.fitote.2024.106052

  日期：2024.9

  hypoxia response in tumor cells. Therefore, its inhibitors have become one of the targets for the treatment of a variety of cancers. Two series of panaxadiol (PD) ester derivatives containing pyrazole () and pyrrole () moiety were synthesized and their HIF-1α inhibitory activities were evaluated. Among all the target compouds, compounds , , and (IC = 8.7010.44 μM) showed better HIF-1α inhibitory activity

  缺氧诱导因子1α（HIF-1α）在多种肿瘤患者中过度表达，在调节肿瘤细胞缺氧反应中发挥重要作用。因此，其抑制剂已成为多种癌症的治疗靶点之一。合成了两个系列含有吡唑()和吡咯()结构的人参二醇(PD)酯衍生物，并评价了它们的HIF-1α抑制活性。在所有目标化合物中，化合物 、 和 (IC = 8.7010.44 μM) 显示出比 PD (IC = 13.35 μM) 更好的 HIF-1α 抑制活性。这些化合物均未表现出高于 100 μM 的细胞毒性，并以剂量​​依赖性方式抑制 HIF-1α 转录。这些化合物表现出良好的抗肿瘤活性，为PD酯衍生物的进一步设计和活性研究提供了先导化合物。