ethyl (7-bromo-indol-3-yl)glyoxylate | 908135-76-2

• 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
• 英文名称: ethyl (7-bromo-indol-3-yl)glyoxylate
• 英文别名: ethyl 2-(7-bromo-1H-indol-3-yl)-2-oxoacetate；ethyl (7-bromo-1H-indol-3-yl)glyoxylate；ethyl (7-bromo-1H-indole-3-yl)(oxo)acetate；ethyl (7-bromo-1H-indol-3-yl)(oxo)acetate；ethyl 7-bromo-3-indolylglyoxylate
• CAS: 908135-76-2
• 化学式: C₁₂H₁₀BrNO₃
• 分子量: 296.12
• InChiKey: HXVJJMOQDPQAOU-UHFFFAOYSA-N

物化性质

• 沸点：
  441.0±25.0 °C(Predicted)
• 密度：
  1.591±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (7-bromo-indol-3-yl)glyoxylate 在 咪唑 、 lithium aluminium tetrahydride 、 氨 、 碘 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 2-(3"-(7"-bromo-indolyl)ethyloxy)adenosine
  参考文献：
  名称：

  Structure−Activity Relationships of 2,N⁶,5‘-Substituted Adenosine Derivatives with Potent Activity at the A_2B Adenosine Receptor

  摘要：

  2, N-6, and 5'-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A(2B)AR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N-6-ethyl or N-6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-( 3-( indolyl)ethyloxy) adenosine series. Indole 5 ''- or 6 ''-halo substitution was favored at the A(2B)AR, but a 5'-N-ethylcarboxyamide did not further enhance potency. 2-(3 ''-(6 ''-Bromoindolyl)ethyloxy)adenosine 28 displayed an A(2B)AR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5'-N-ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A(2B) and A(2A)ARs and a low efficacy partial agonist at A(1) and A(3)ARs. Thus, we have identified and optimized 2-(2-arylethyl) oxo moieties in AR agonists that enhance A(2B)AR potency and selectivity.

  DOI：

  10.1021/jm061278q
• 作为产物：
  描述：

  7-溴吲哚 以 乙醚 为溶剂， 反应 10.0h， 生成 ethyl (7-bromo-indol-3-yl)glyoxylate
  参考文献：
  名称：

  Structure−Activity Relationships of 2,N⁶,5‘-Substituted Adenosine Derivatives with Potent Activity at the A_2B Adenosine Receptor

  摘要：

  2, N-6, and 5'-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A(2B)AR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N-6-ethyl or N-6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-( 3-( indolyl)ethyloxy) adenosine series. Indole 5 ''- or 6 ''-halo substitution was favored at the A(2B)AR, but a 5'-N-ethylcarboxyamide did not further enhance potency. 2-(3 ''-(6 ''-Bromoindolyl)ethyloxy)adenosine 28 displayed an A(2B)AR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5'-N-ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A(2B) and A(2A)ARs and a low efficacy partial agonist at A(1) and A(3)ARs. Thus, we have identified and optimized 2-(2-arylethyl) oxo moieties in AR agonists that enhance A(2B)AR potency and selectivity.

  DOI：

  10.1021/jm061278q

文献信息

• Investigation of solid state architectures in tetrazolyl tryptophol stabilized by crucial aromatic interactions and hydrogen bonding: Experimental and theoretical analysis
  作者：Aliya Ibrar、Sumera Zaib、Tuncer Hökelek、Jim Simpson、Christopher John McAdam、Islam H. El Azab、Gaber A.M. Mersal、Mohamed M. Ibrahim、Antonio Frontera、Imtiaz Khan

  DOI：10.1016/j.molstruc.2022.133079

  日期：2022.8

  achieved through a multistep synthetic approach. The structure of the target tetrazole-indole hybrid was established using FTIR, 1H- and 13C NMR, HRMS, and X-ray diffraction data. Investigation of solid state architectures in tetrazolyl tryptophol revealed that an intramolecular N5-H5N…N4 hydrogen bond links the 5-membered ring of the indole to the tetrazole ring. O1-H1O…N3 and N1-H1N…O1 hydrogen bonds

  本研究报告了通过多步合成方法合成一种新的富氮杂化化合物，即四唑基色氨酸6 。使用 FTIR、 1 H- 和13建立了目标四唑-吲哚杂化物的结构C NMR、HRMS 和 X 射线衍射数据。对四唑基色氨酸中固态结构的研究表明，分子内 N5-H5N…N4 氢键将吲哚的 5 元环与四唑环相连。O1-H1O…N3 和 N1-H1N…O1 氢键和 π…π 接触也成为形成四唑-吲哚杂化物超分子拓扑结构的关键因素。涉及吲哚环系统和四唑环的芳环的许多质心到质心接触以正面面对面的方式连接相邻分子。Hirshfeld 表面分析进一步揭示了 π…π 和 H 键接触的普遍意义。还通过晶体空隙分析和分子间相互作用能计算了晶体堆积的机械稳定性。最后，
• Synthesis, structure–affinity relationships, and molecular modeling studies of novel pyrazolo[3,4-c]quinoline derivatives as adenosine receptor antagonists
  作者：Ombretta Lenzi、Vittoria Colotta、Daniela Catarzi、Flavia Varano、Lucia Squarcialupi、Guido Filacchioni、Katia Varani、Fabrizio Vincenzi、Pier Andrea Borea、Diego Dal Ben、Catia Lambertucci、Gloria Cristalli

  DOI：10.1016/j.bmc.2011.05.001

  日期：2011.6

  This paper reports the study of new 2-phenyl- and 2-methylpyrazolo[3,4-c]quinolin-4-ones (series A) and 4-amines (series B), designed as adenosine receptor (AR) antagonists. The synthesized compounds bear at the 6-position various groups, with different lipophilicity and steric hindrance, that were thought to increase human A(1) and A(2A) AR affinities and selectivities, with respect to those of the parent 6-unsubstituted compounds. In series A, this modification was not tolerated since it reduced AR affinity, while in series B it shifted the binding towards the hA(1) subtype. To rationalize the observed structure-affinity relationships, molecular docking studies at A(2A)AR-based homology models of the A(1) and A(3) ARs and at the A(2A)AR crystal structure were carried out. (C) 2011 Elsevier Ltd. All rights reserved.
• WO2006/90817
  申请人：——

  公开号：——

  公开（公告）日：——
• Indole compounds for treating respiratory disorders
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1852420B1

  公开（公告）日：2012-10-17
• [EN] A2 ADENOSINE RECEPTOR AGONISTS<br/>[FR] AGONISTES DES RÉCEPTEURS D'ADÉNOSINE A2
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2009006089A2

  公开（公告）日：2009-01-08

  Disclosed are AZB adenosine receptor (AR) agonists of formula (I), in which R1, R2, R3, R4, Z, and n are defined herein. The invention also provides compositions comprising at least one compound of formula I and methods of use thereof, for example, in the treatment of septic shock, cystic fibrosis, restenosis, erectile dysfunction, inflammation, myocardial ischemia, and reperfusion injury.