ethyl 7-phenyl-1H-indole-2-carboxylate | 154422-25-0

• 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-phenyl-1H-indole-2-carboxylate
• 英文别名: ethyl 7-phenylindole-2-carboxylate；Ethyl 7-phenyl-2-indolecarboxylate
• CAS: 154422-25-0
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: YVRGQDXIRQGSEU-UHFFFAOYSA-N

物化性质

• 沸点：
  463.2±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 7-phenyl-1H-indole-2-carboxylate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (R)-7-phenyl-N-[1-(1-naphthyl)ethyl]-1H-indole-2-carboxamide
  参考文献：
  名称：

  Design and synthesis of calindol derivatives as potent and selective calcium sensing receptor agonists

  摘要：

  We report the first comprehensive structure-activity study of calindol (4, (R)-N-[(1H-indol-2-yl) methyl]1-(1-naphthyl) ethanamine), a positive allosteric modulator, or calcimimetic, of the calcium sensing receptor (CaSR). While replacement of the naphthyl moiety of calindol by other aromatic groups (phenyl, biphenyl) was largely detrimental to calcimimetic activity, incorporation of substituents on the 4, 5 or 7 position of the indole portion of calindol was found to provide either equipotent derivatives compared to calindol (e.g., 4-phenyl, 4-hydroxy, 5-hydroxycalindol 44, 52, 53) or, in the case of 7-nitrocalindol (51), a 6-fold more active calcimimetic displaying an EC50 of 20 nM. Unlike calindol, the more active CaSR calcimimetics were shown not to act as antagonists of the closely related GPRC6A receptor, suggesting a more selective profile for these new analogues. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.019
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer potassium carbonate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 1,4-二氧六环 、 正庚烷 、 水 为溶剂， 反应 17.5h， 生成 ethyl 7-phenyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  A highly selective Ir-catalyzed borylation of 2-substituted indoles: a new access to 2,7- and 2,4,7-substituted indoles

  摘要：

  The selective CH-functionalization of 2-substituted indoles is presented. Using bis(pinacolato)diboron (2) in the presence of iridium complexes, a novel catalytic mono-borylation is observed preferentially at the 7-position of the indole. This allows for an efficient synthesis of various 2,7-di- and 2,4,7-trisubstituted indoles, which are otherwise difficult to access. The scope and limitation of the method is demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.083

文献信息

• Indoles via Knoevenagel–Hemetsberger reaction sequence
  作者：William L. Heaner IV、Carol S. Gelbaum、Leslie Gelbaum、Pamela Pollet、Kent W. Richman、William DuBay、Jeffrey D. Butler、Gregory Wells、Charles L. Liotta

  DOI：10.1039/c3ra42296h

  日期：——

  sequential reaction of aromatic aldehydes with ethyl azidoacetate in the presence of sodium ethoxide to form the corresponding ethyl α-azido-β-arylacrylates (Knoevenagel process) followed by a solvent mediated thermolysis (Hemetsberger process). The isolated yields of the ethyl α-azido-β-arylacrylates were significantly increased when employing the sacrificial electrophile ethyl trifluoroacetate. 1H NMR and

  通过芳族醛与环戊烯的顺序反应合成了一系列取代的吲哚 叠氮基乙酸乙酯 在......的存在下 乙醇钠形成相应的乙基α-叠氮基-β-芳基丙烯酸乙酯（Knoevenagel法），然后进行溶剂介导的热分解（Hemetsberger法）。使用牺牲亲电试剂时，α-叠氮基-β-芳基丙烯酸乙酯的分离收率显着提高三氟乙酸乙酯。对α-叠氮基-β-芳基丙烯酸乙酯的1 H NMR和1 H- 13 C NMR耦合分析表明，该缩合反应具有立体特异性，只能检测到Z异构体。溶剂介导的间位取代的乙基α-叠氮基-β-芳基丙烯酸酯的热处理导致5位和7位取代的吲哚的形成，其中5位区域异构体比7位区域异构体略受青睐。（2 Z，2 Z '）-二乙基3,3'-（1,3-亚苯基）双（2-叠氮基丙烯酸酯）和（2 Z，2 Z '）-二乙基3,3'-（1的相似热处理，4-亚苯基）双（2-叠氮基丙烯酸酯）专门生产吡咯并吲哚，1,5-二氢吡咯并[2
• Fischer Indolization of Variously ortho-Substituted Phenylhydrazones. Fischer Indolization and Its Related Compounds. XXV.
  作者：Yasuoki MURAKAMI、Toshiko WATANABE、Yuusaku YOKOYAMA、Junko NAOMACHI、Haruo IWASE、Noriko WATANABE、Michiyo MORIHATA、Naomi OKUYAMA、Hiroyuki KAMAKURA、Tomoko TAKAHASHI、Hideko ATODA、Toshiaki TOJO、Kenji MORITA、Hisashi ISHII

  DOI：10.1248/cpb.41.1910

  日期：——

  Various kinds of ethyl pyruvate 2-(2-substituted phenyl)hydrazones (1) were subjected to Fischer indolization with acid catalysts. All the phenylhydrazones gave corresponding normal 7-substituted indoles (2). In addition, phenyl-hydrazones whose ortho-substituent is electron-donative or has a central atom with an unshared electron pair tended to give the 4- or 5-substituted indole (3), which was produced by migration of the ortho-substituent during cyclization, whereas those whose ortho-substituent is electron-attractive tended to give little or no such abnormal product. The kind of acid catalyst used had some effect on the yield ratio of products but not on the kind of products.

  各种丙酮酸乙酯 2-（2-取代苯基）酰肼（1）在酸催化剂作用下进行费歇尔吲哚化反应。所有的苯肼都得到了相应的 7-取代吲哚（2）。此外，如果苯肼的正位取代基是电子疏导型的，或者其中心原子上有一个未共享的电子对，则往往会产生 4 或 5 取代的吲哚（3），这是由正位取代基在环化过程中发生迁移而产生的；而如果苯肼的正位取代基是电子吸引型的，则往往很少或根本不会产生这种异常产物。所使用的酸催化剂对产物的产率有一定影响，但对产物的种类没有影响。
• Scaffold hopping derived novel benzoxazepinone RIPK1 inhibitors as anti-necroptosis agents
  作者：Jiaqin Tang、Yanran Wu、Wenli Zhao、Zhuo Qu、Jianqiang Yu、Zhizhong Wang、Ying Shi

  DOI：10.1016/j.bmc.2023.117385

  日期：2023.8

  protein kinase 1 (RIPK1)-mediated necroptosis is believed to have a significant role in contributing to inflammatory diseases. Inhibiting RIPK1 has shown promise in effectively alleviating the inflammation process. In our current study, we employed scaffold hopping to develop a series of novel benzoxazepinone derivatives. Among these derivatives, compound o1 displayed the most potent antinecroptosis

  受体相互作用蛋白激酶1 (RIPK1) 介导的坏死性凋亡被认为在导致炎症性疾病中发挥着重要作用。抑制 RIPK1 有望有效缓解炎症过程。在我们目前的研究中，我们采用支架跳跃技术开发了一系列新型苯并氧氮杂酮衍生物。在这些衍生物中，化合物 o1 在细胞测定中表现出最有效的抗坏死性凋亡活性（EC50  =  16.17  ±  1.878 nM），并且表现出与靶位点最强的结合亲和力。分子对接分析进一步阐明了o1的作用机制，揭示了其完全占据蛋白质口袋并与氨基酸形成氢键的能力 残留Asp156。我们的研究结果强调，o1 通过阻碍由 TNFα、Smac 模拟物和 z 触发的 RIPK1/受体相互作用蛋白激酶 3 (RIPK3)/混合谱系激酶结构域样 (MLK​​L) 通路的磷酸化来特异性抑制坏死性凋亡，而不是凋亡。 -VAD（TSZ）。此外，o1 对患有全身炎症反应综合征 (SIRS) 的小鼠的存活率显示出剂量依赖性的改善，超过了
• Murakami Yasuoki, Watanabe Toshiko, Yokoyama Yuusaku, Naomachi Junko, Iwa+, Chem. and Pharm. Bull, 41 (1993) N 11, S 1910-1919
  作者：Murakami Yasuoki, Watanabe Toshiko, Yokoyama Yuusaku, Naomachi Junko, Iwa+

  DOI：——

  日期：——
• Indoloylguanidine derivatives as inhibitors of sodium-hydrogen exchange
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0622356B1

  公开（公告）日：1998-07-01