ethyl β-(5-methoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)-α-oxoacetate | 511533-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: ethyl β-(5-methoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)-α-oxoacetate
• 英文别名: Ethyl 2-(6-methoxy-3-oxo-1,2-dihydroinden-2-yl)-2-oxoacetate；ethyl 2-(6-methoxy-3-oxo-1,2-dihydroinden-2-yl)-2-oxoacetate
• CAS: 511533-37-2
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: LFYZYFJETYNVBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  ethyl β-(5-methoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)-α-oxoacetate 在 双氧水 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 生成 2-(羧甲基)-4-甲氧基苯甲酸
  参考文献：
  名称：

  Synthesis and antitumor activity evaluation of 2-arylisoquinoline-1,3(2H,4H)-diones in vitro and in vivo

  摘要：

  Six 2-(2-acylaminobenzothiazol-6-yl)isoquinoline-1,3(2H,4H)-diones (1a-1f) and five 2-arylisoquinoline-1,3(2H,4H)-diones (1g-1k) were synthesized by refluxing homophthalic anhydrides with 2-acylaminobenzothiazolyl-6-amine or substituted aniline in glacial acetic acid. The cytotoxic activities of 1a-1k were evaluated via MTT method against A431, A549, and PC3. Compound 1b relatively displayed a higher cytotoxic activity than the others. The antitumor effect of 1b were evaluated in established nude mice PANC-1 xenograft model. The results suggest that compound 1b could potentially inhibit tumor growth.

  DOI：

  10.1007/s00044-013-0734-x
• 作为产物：
  描述：

  3-(3-甲氧基苯基)丙酸 在 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.0h， 生成 ethyl β-(5-methoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)-α-oxoacetate
  参考文献：
  名称：

  Synthesis and antitumor activity evaluation of 2-arylisoquinoline-1,3(2H,4H)-diones in vitro and in vivo

  摘要：

  Six 2-(2-acylaminobenzothiazol-6-yl)isoquinoline-1,3(2H,4H)-diones (1a-1f) and five 2-arylisoquinoline-1,3(2H,4H)-diones (1g-1k) were synthesized by refluxing homophthalic anhydrides with 2-acylaminobenzothiazolyl-6-amine or substituted aniline in glacial acetic acid. The cytotoxic activities of 1a-1k were evaluated via MTT method against A431, A549, and PC3. Compound 1b relatively displayed a higher cytotoxic activity than the others. The antitumor effect of 1b were evaluated in established nude mice PANC-1 xenograft model. The results suggest that compound 1b could potentially inhibit tumor growth.

  DOI：

  10.1007/s00044-013-0734-x

文献信息

• Design, synthesis, and antimicrobial evaluation of 1,4-dihydroindeno[1,2-<i>c</i>]pyrazole tethered carbohydrazide hybrids: exploring their<i>in silico</i>ADMET, ergosterol inhibition and ROS inducing potential
  作者：Mohd Adil Shareef、K. Sirisha、Irfan Khan、Ibrahim Bin Sayeed、Surender Singh Jadav、Gopathi Ramu、C. Ganesh Kumar、Ahmed Kamal、Bathini Nagendra Babu

  DOI：10.1039/c9md00155g

  日期：——

  Non-toxic compounds with antifungal activity, ergosterol inhibition and ROS inducing potential.

  具有抗真菌活性、麦角固醇抑制和诱导ROS潜力的无毒化合物。
• New indenopyrazole linked oxadiazole conjugates as anti-pancreatic cancer agents: Design, synthesis, in silico studies including 3D-QSAR analysis
  作者：Irfan Khan、Thipparapu Ganapathi、MD. Muzaffar-ur- Rehman、Mohd Adil Shareef、C. Ganesh Kumar、Ahmed Kamal

  DOI：10.1016/j.bmcl.2021.128094

  日期：2021.7

  herein a novel class of 1,4-Dihydroindenopyrazole linked oxadiazole conjugates 9(a-r) was designed, synthesized and experimented for their anti-proliferative activities against four different cancer cell lines (human) such as MDA MB-231 (breast), PANC-1 (pancreatic), MCF-7 (breast), and Caco-2 (Colorectal) by using MTT assay. Among the series compound 9h and 9 m demonstrated significant potency against

  为了继续探索更新的抗癌剂，本文设计、合成了一类新型的 1,4-二氢茚并吡唑连接的恶二唑缀合物 9(ar) 并对其对四种不同癌细胞系（人类）如 MDA 的抗增殖活性进行了实验MB-231（乳房）、PANC-1（胰腺）、MCF-7（乳房）和 Caco-2（结肠直肠），使用 MTT 检测。在系列化合物中，9h 和 9m 显示出对 PANC-1（人胰腺癌细胞）的显着效力，IC 50值分别为 7.4 μM 和 4.3 μM。虽然发现化合物 9 m 与标准戈米他滨 (IC 50 = 4.2 μM）。详细的生物学分析揭示了 S 期细胞周期停滞及其通过激活半胱天冬酶 3 和 9 酶来传播细胞凋亡的能力，膜联蛋白-FITC 分析和半胱天冬酶分析证实了这一点。此外，对接研究表明它们的结合模式和与 caspase-3 的相互作用。此外，计算机研究表明它们表现出良好的药代动力学和药物相似性。此外，进行 3D-QSAR
• Tricyclic Pyrazoles. Part 1: Synthesis and Biological Evaluation of Novel 1,4-Dihydroindeno[1,2-c]pyrazol-based Ligands for CB1and CB2 Cannabinoid Receptors
  作者：Jean-Mario Mussinu、Stefania Ruiu、Antonio C Mulè、Amedeo Pau、Mauro A.M Carai、Giovanni Loriga、Gabriele Murineddu、Gérard A Pinna

  DOI：10.1016/s0968-0896(02)00319-x

  日期：2003.1

  Cannabinoids receptors, cellular elements of the endocannabinoid system, have been the focus of extensive studies because of their potential functional role in several important physiological and pathological processes. To further evaluate the properties of CB receptors, especially CB1 and CB2 subtypes, we have designed, using SR141716A as a benchmark, a new series of rigid 1-aryl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides. Compounds I were synthesized from substituted 1-aryl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylic acids and requisite amines. The various analogues were assayed for binding both to the brain and peripheral cannabinoid receptors (CB1 and CB2). Seven of the new compounds displayed very high in vitro CB2 binding affinities, especially 1a, 1b, 1c, 1e, 1g, 1h and 1j which showed K-i values of 0.34, 0.225, 0.27, 0.23, 0.385, 0.037 and 0.9 nM, respectively. Compounds 1a, 1b, 1c and 1h showed the highest selectivity for CB2 receptor with K-i(CB1) to K-i(CB2) ratios of 6029, 5635, 5814 and 9810, respectively. Noticeably, 1h exhibited the highest affinity and selectivity for CB2 receptors. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and antitumor activity evaluation of 2-arylisoquinoline-1,3(2H,4H)-diones in vitro and in vivo
  作者：Bo-Rui Kang、Juan Wang、Huan Li、Yan Li、Qi-Bing Mei、San-Qi Zhang

  DOI：10.1007/s00044-013-0734-x

  日期：2014.3

  Six 2-(2-acylaminobenzothiazol-6-yl)isoquinoline-1,3(2H,4H)-diones (1a-1f) and five 2-arylisoquinoline-1,3(2H,4H)-diones (1g-1k) were synthesized by refluxing homophthalic anhydrides with 2-acylaminobenzothiazolyl-6-amine or substituted aniline in glacial acetic acid. The cytotoxic activities of 1a-1k were evaluated via MTT method against A431, A549, and PC3. Compound 1b relatively displayed a higher cytotoxic activity than the others. The antitumor effect of 1b were evaluated in established nude mice PANC-1 xenograft model. The results suggest that compound 1b could potentially inhibit tumor growth.