ethyl 1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylate | 665020-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylate
• 英文别名: 1(2),4-dihydro-indeno[1,2-c]pyrazole-3-carboxylic acid ethyl ester；1(2),4-Dihydro-indeno[1,2-c]pyrazol-3-carbonsaeure-aethylester
• CAS: 665020-27-9
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: UAJZMISAJBEUGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.98
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylate 在 氢氧化钾 作用下， 生成 1,4-dihydro-1H-indeno[1,2-c]pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Ruhemann, Journal of the Chemical Society, 1912, vol. 101, p. 1737

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl β-(1-oxo-2,3-dihydro-1H-inden-2-yl)-α-oxoacetate 在 盐酸肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 ethyl 1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylate
  参考文献：
  名称：

  Design, synthesis, and antimicrobial evaluation of 1,4-dihydroindeno[1,2-c]pyrazole tethered carbohydrazide hybrids: exploring theirin silicoADMET, ergosterol inhibition and ROS inducing potential

  摘要：

  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。

  DOI：

  10.1039/c9md00155g

文献信息

• 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
• Leuchs; Kowalski, Chemische Berichte, 1925, vol. 58, p. 2293
  作者：Leuchs、Kowalski

  DOI：——

  日期：——
• Chromophore-modified bis-benzo[g]indole carboxamides: synthesis and antiproliferative activity of bis-benzo[g]indazole-3-carboxamides and related dimers
  作者：Gérard A Pinna、Maria A Pirisi、Jean-Mario Mussinu、Gabriele Murineddu、Giovanni Loriga、Amedeo Pau、Giuseppe E Grella

  DOI：10.1016/s0014-827x(03)00131-9

  日期：2003.9

  Tricyclic pyrazole dimers that comprise two kinds of CONH-(CH(2))(n)-N(CH(3))-(CH(2))(n)-NHCO bridges to which are linked potential DNA-intercalating groups such as 1H-benzo[g]indazole, 2H-benzo[g]indazole and 1,4-dihydroindeno[1,2-c]pyrazole were designed, synthesized and some of them evaluated in vitro by NCI (Bethesda, USA) against nine types of cancer cells. Compounds 2a, 2f-i and 2o-r demonstrated significant antiproliferative activity, all with GI(50) values in the low micromolar range. Preliminary analysis of the structure-activity relationship for dimers 2 indicated that: (i) in the ground terms (2a and 2k) antitumor activities were strongly related to the type of chromophore, (ii) in contrast, either 1H-benzo[g]indazole- or 1,4-dihydroindeno[1,2-c]pyrazole-dimers when bore a N(1)-aryl group (2g, 2h, 2i, 2o, 2p, 2q and 2r) generally showed a good level of antitumor potency and (iii) for the most representative compounds (pairs of compounds: 2g,2h; 2o,2p and 2q,2r) the length of the bridges did not significantly contribute to the variations in cytotoxicity. Two members of this series, 2f and 2q, were selected and tested in the hollow fiber cell assay to evaluate in a preliminary fashion their in vivo antitumor activity. Finally, viscosity measurement of 2f with poly(dA-dT)(2), confirmed that these promising compounds behaved as typical DNA-intercalating agents.