ethyl 1-(2',4'-dichlorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate | 665020-24-6

• 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-(2',4'-dichlorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate
• 英文别名: ethyl 1-(2,4-dichlorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate
• CAS: 665020-24-6
• 化学式: C₂₀H₁₆Cl₂N₂O₂
• 分子量: 387.265
• InChiKey: ZLZSZFKPVIYYHV-UHFFFAOYSA-N

物化性质

• 熔点：
  158 °C
• 沸点：
  544.4±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-(2',4'-dichlorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以54%的产率得到ethyl 1-(2,4-dichlorophenyl)-1H-benzo[g]indazole-3-carboxylate
  参考文献：
  名称：

  Chromophore-modified bis-benzo[g]indole carboxamides: synthesis and antiproliferative activity of bis-benzo[g]indazole-3-carboxamides and related dimers

  摘要：

  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.

  DOI：

  10.1016/s0014-827x(03)00131-9
• 作为产物：
  描述：

  2-氧代-2-(1-氧代-1,2,3,4-四氢萘-2-基)乙酸乙酯 、 2,4-二氯苯肼盐酸盐 以 乙醇 为溶剂， 反应 3.0h， 以96%的产率得到ethyl 1-(2',4'-dichlorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate
  参考文献：
  名称：

  Tricyclic pyrazoles. Part 2: Synthesis and biological evaluation of novel 4,5-dihydro-1H-benzo[g]indazole-based ligands for cannabinoid receptors

  摘要：

  A series of 4,5-dihydro-1H-benzo[g]indazole-3-carboxamides (2a-k) as analogues of the previously reported CB2 ligands 6-chloro- and 6-methyl-1-(2',4'-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) was synthesized and their affinity and selectivity towards CB1 and CB2 receptors were evaluated. Several of the new compounds (2a,b,c,d and i) exhibited CB1 affinity in the nanomolar range with moderate or negligible affinity towards CB2 receptors. Compounds 2a and c increased intestinal propulsion in mouse. Their pro-kinetic effects were reversed by the reference CB agonist CP-55,940. Consequently, in vivo CB1 antagonistic activity was highlighted for these compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.032