5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-羧酸乙酯 | 124730-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-羧酸乙酯
• 中文别名: 乙基2,3-二氢-1H-吡咯并[3,2,1-IJ]喹啉-6-羧酸
• 英文名称: 5,6-dihydro-4H-pyrrolo [3,2,1-ij]quinoline-1-carboxylic acid ethyl ester
• 英文别名: (5,6-dihydro-4H-pyrrolo-[3,2,1-ij]-quinolin-1-yl)-carboxylic acid ethyl ester；ethyl 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylate；ethyl 1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraene-3-carboxylate
• CAS: 124730-53-6
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: QWYWUGSDJVIVBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-羧酸乙酯 以85的产率得到5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-羧酸
  参考文献：
  名称：

  COMBINATIONAL COMPOSITIONS AND METHODS FOR TREATMENT OF CANCER

  摘要：

  本发明提供了一种治疗细胞增殖性疾病（如癌症）的方法，通过向需要治疗的受试者施用一种吡咯喹啉基吡咯-2,5-二酮化合物或吡咯喹啉基吡咯啶-2,5-二酮化合物的治疗有效剂量，结合一种第二个抗增殖剂的治疗有效剂量。

  公开号：

  US20100297075A1
• 作为产物：
  描述：

  1,2,3,4-四氢喹啉 在 magnesium chloride 作用下， 以 四氢呋喃 、 乙二醇甲醚 为溶剂， 反应 30.0h， 生成 5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-羧酸乙酯
  参考文献：
  名称：

  Development of high-affinity 5-HT3 receptor antagonists. Structure-affinity relationships of novel 1,7-annulated indole derivatives. 1

  摘要：

  On the basis of the structures of ondansetron and GR 65,630, its ring-opened C-linked methylimidazole analogue, novel 1,7-annelated indole derivatives were synthesized as potential 5-HT3 antagonists. Receptor binding studies show that all compounds display a high affinity for the 5-HT3 receptors. In both series annelation results in compounds being 7 and 4 times more potent than the references ondansetron and GR 65,630, respectively. Similar to ondansetron, the 1,7-annelated indoles show little stereoselectivity. The (-)-isomers are only slightly more potent than the (+)-isomers. The receptor binding profile of l-10-[(2-methyl-1H-imidazol-1-yl)methyl]-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-11-one hydrochloride (24b) (INN cilansetron) shows that the compound displays, besides a high affinity for 5-HT3 receptors (K(i) = 0. 19 nM), a weak affinity for sigma-receptors (K(i) = 340 nM), muscarine M1 receptors (K(i) = 910 nM), and 5-HT4 receptors (K(i_ = 960 nM) and no affinity (K(i) greater-than-or-equal-to 5000 nM) for all the other receptor types tested (n = 37). The new compounds fit the proposed necessary chemical template for binding: a heteroaromatic ring system, a coplanar carbonyl group, and a nitrogen center at well-defined distances. The enhanced potency of the annelated 1,7-indole derivatives indicates that the extra ring provides a favorable hydrophobic area for interaction with the 5-HT3 receptor site. In vivo cilansetron is more potent and induces less central side effects than ondansetron. At present cilansetron is in clinical trials.

  DOI：

  10.1021/jm00075a026

文献信息

• [EN] PURINE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DERIVES DE LA PURINE EN TANT QU'INHIBITEURS DE LA KINASE
  申请人：LILLY CO ELI

  公开号：WO2003076442A1

  公开（公告）日：2003-09-18

  The present invention provides kinase inhibitors of Formula I.

  本发明提供了化合物I的激酶抑制剂。
• Agents and methods for the treatment of proliferative diseases
  申请人：——

  公开号：US20030229026A1

  公开（公告）日：2003-12-11

  The present invention provides selective kinase inhibitors of formula (I). 1

  这项发明提供了式（I）的选择性激酶抑制剂。
• Substituted Heterocyclic Compounds
  申请人：Ali Syed M.

  公开号：US20110160237A1

  公开（公告）日：2011-06-30

  The present invention relates to substituted heterocyclic compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted heterocyclic compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

  本发明涉及替代杂环化合物及其合成方法。本发明还涉及含有替代杂环化合物的药物组合物以及通过向需要的受试者投与这些化合物和药物组合物来治疗细胞增殖性疾病，如癌症的方法。
• Ir-catalyzed chemoselective reduction of β-amido esters: A versatile approach to β-enamino esters
  作者：Zhi-Ping Yang、Guang-Sheng Lu、Jian-Liang Ye、Pei-Qiang Huang

  DOI：10.1016/j.tet.2018.12.024

  日期：2019.3

  The conversion of β-amido esters to β-enamino esters is an indispensable step for some synthetic approaches to alkaloids and related medicines. Known methods for such transformation are not only stepwise, but also proceed with low atom-efficiency. Herein, we report a direct and versatile approach that features the Ir-catalyzed chemoselective reduction of β-amido esters with 1,1,3,3-tetramethyldisiloxane

  对于某些生物碱和相关药物的合成方法，β-酰胺基酯向β-烯氨基酯的转化是必不可少的步骤。用于这种转化的已知方法不仅是逐步的，而且以低原子效率进行。本文中，我们报道了一种直接且通用的方法，其特征在于用1,1,3,3-四甲基二硅氧烷（TMDS）进行Ir催化的β-酰胺基酯的化学选择性还原。另外，在某些脂环族β-烯胺酯的13 C NMR光谱中观察到缺少某些信号。这揭示了文献中长期存在但被忽略的现象。
• METHOD FOR PRODUCING TRICYCLIC HETEROCYCLIC COMPOUND
  申请人：DAIICHI SANKYO COMPANY, LIMITED

  公开号：US20160137644A1

  公开（公告）日：2016-05-19

  It is an object of the present invention to provide a method for producing a high-purity tricyclic heterocyclic compound represented by formula (I), which is useful as a production intermediate for a pharmaceutical agent, wherein the method is an efficient production method with short steps and with a high yield, which does not use, as raw materials, expensive bromopyruvate and highly harmful copper chromite, and does not need silica gel column chromatography that generates, as by-products, large quantities of waste. The present invention relates to production of Compound (I) by the following method.

  本发明的目的是提供一种用作制药中间体的高纯度三环杂环化合物的生产方法，该方法是一种高效的生产方法，步骤简短，产率高，不使用昂贵的溴丙酮和高度有害的铜铬酸盐作为原料，并且不需要产生大量废物的硅胶柱层析色谱法。本发明涉及通过以下方法生产化合物（I）。