ethyl 1-phenyl-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate | 60656-27-1

• 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-phenyl-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate
• 英文别名: ethyl 1-phenyl-4,5-dihydrobenzo[g]indazole-3-carboxylate
• CAS: 60656-27-1
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: CMSVXLLEIXXRHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-phenyl-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate 在 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.0h， 生成 N3-{2-[{2-[(1-phenyl-1H-benzo[g]indazole-3-yl-carbonyl)amino]ethyl}(methyl)amino]ethyl}-1-phenyl-1H-benzo[g]indazole-3-carboxamide
  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：

  ethyl (phenylhydrazono)chloroacetate 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 ethyl 1-phenyl-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate
  参考文献：
  名称：

  [3 + 2]腈亚胺与酰胺的环加成反应：一种功能化的吡唑啉和吡唑的方法

  摘要：

  已经建立了一种有效的[3 + 2]与酰胺共生的腈亚胺环加成反应。在非常温和的条件下，以中等至良好的收率（高达96％）获得了多种官能化的吡唑啉衍生物（53个实例）。该协议具有广泛的底物范围，良好的官能团耐受性和操作简便性。通过一锅法将产品实际转化为有用的吡唑，并且该协议的可扩展性突出了此合成方法的实用性。

  DOI：

  10.1021/acs.joc.0c02244

文献信息

• ‘One-pot’ synthesis of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates via lithium tert-butoxide-mediated sterically hindered Claisen condensation and Knorr reaction
  作者：Jian-An Jiang、Wei-Bin Huang、Jiao-Jiao Zhai、Hong-Wei Liu、Qi Cai、Liu-Xin Xu、Wei Wang、Ya-Fei Ji

  DOI：10.1016/j.tet.2012.11.012

  日期：2013.1

  A concise ‘one-pot’ synthesis of a variety of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates has been developed in moderate to good yields with excellent regioselectivity. Less cost lithium tert-butoxide has been identified as a base for sterically hindered Claisen condensation to efficiently generate the labile 3-substituted 4-aryl-2,4-diketoesters. Furthermore, extensive studies lead to a ‘one-pot’

  已经开发了一种简单的“一锅法”合成的各种4-取代的1,5-二芳基-1 H-吡唑-3-羧酸酯，具有中等到良好的产率，具有出色的区域选择性。成本较低的叔丁醇锂已被确定为空间受阻克莱森（Claisen）缩合反应的碱，可有效生成不稳定的3-取代的4-芳基-2,4-二酮酸酯。此外，广泛的研究通过克莱森缩合反应和克诺尔反应相结合而合成“有价值的4-取代的1,5-二芳基-1 H-吡唑-3-羧酸酯”的“一锅法”工艺。
• v. Auwers; Enbergs, Journal fur praktische Chemie (Leipzig 1954), 1932, vol. <2> 134, p. 97,102, 103
  作者：v. Auwers、Enbergs

  DOI：——

  日期：——
• HAMILTON R. W., J. HETEROCYCL. CHEM. <JHTC-AD>, 1976, 13, NO 3, 545-553
  作者：HAMILTON R. W.

  DOI：——

  日期：——
• US5420141A
  申请人：——

  公开号：US5420141A

  公开（公告）日：1995-05-30
• US5607958A
  申请人：——

  公开号：US5607958A

  公开（公告）日：1997-03-04