6-ethyl-1H-indole-2-carboxylic acid | 383132-71-6

• 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
• 英文名称: 6-ethyl-1H-indole-2-carboxylic acid
• CAS: 383132-71-6
• 化学式: C₁₁H₁₁NO₂
• mdl: MFCD02664480
• 分子量: 189.214
• InChiKey: LZMHTROSSYBVAE-UHFFFAOYSA-N

物化性质

• 沸点：
  422.9±25.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-ethyl-1H-indole-2-carboxylic acid 在 水 、 copper diacetate 、 氯化铵 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[3-(2-Carbamoyl-6-ethylindol-1-yl)phenyl]propanoic acid
  参考文献：
  名称：

  Discovery of a Series of Indole-2 Carboxamides as Selective Secreted Phospholipase A₂ Type X (sPLA₂-X) Inhibitors

  摘要：

  In order to assess the potential of sPLA(2)-X as a therapeutic target for atherosclerosis, novel sPLA(2) inhibitors with improved type X selectivity are required. To achieve the objective of identifying such compounds, we embarked on a lead generation effort that resulted in the identification of a novel series of indole-2-carboxamides as selective sPLA2-X inhibitors with excellent potential for further optimization.

  DOI：

  10.1021/acsmedchemlett.7b00505
• 作为产物：
  描述：

  methyl 2-azido-3-(4-ethylphenyl)acrylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 对二甲苯 、 水 为溶剂， 反应 3.0h， 生成 6-ethyl-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Design of Potent Poxvirus Inhibitors of the Heterodimeric Processivity Factor Required for Viral Replication

  摘要：

  Smallpox constitutes a major bioterrorism threat, which underscores the need to develop antiviral drugs for rapid response in the event of an attack. Viral processivity factors are attractive drug targets in being both specific and essential for their cognate DNA polymerases to synthesize extended strands of DNA. An in silico model of the vacinnia virus processivity factor, comprised of the A20 and D4 heterocomplex, was constructed and used for lead optimization of an indole-based scaffold identified earlier from a high-throughput screening. On the basis of this model, a new class of potent antivirals against vaccinia virus was designed and synthesized, of which two (24a and 24b) exhibited superior improvement over the parent scaffold (IC50 = 42 and 46 vs 82000 nM, respectively). The ability of 24a to suppress vaccinia DNA synthesis is supported by the inhibition of late viral gene expression, as well as by the diminished incorporation of bromodeoxyuridine into viral replication factories.

  DOI：

  10.1021/jm301735k

文献信息

• [EN] PYRAZOLOSPIROKETONE ACETYL-C0A CARBOXYLASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PYRAZOLOSPIROCÉTONE ACÉTL-COA CARBOXYLASE
  申请人：PFIZER

  公开号：WO2009144554A1

  公开（公告）日：2009-12-03

  The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, and R3 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of acetyl-CoA carboxylase enzyme(s) in an animal.

  本发明提供了式(1)的化合物或所述化合物的药用可接受盐，其中R1、R2和R3如本文所述；其药物组合物；以及用于治疗通过抑制动物中的乙酰辅酶A羧化酶酶活性来调节的疾病、病症或障碍的使用方法。
• [EN] AZA-CYLIC INDOLE- 2 -CARBOXAMIDES AND METHODS OF USE THEREOF<br/>[FR] INDOLE-2-CARBOXAMIDES AZA-CYLIQUES ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：ABBOTT LAB

  公开号：WO2009158375A1

  公开（公告）日：2009-12-30

  The invention relates to aza-cyclic indole-2-carboxamide derivatives, compositions comprising such compounds, and methods of preventing or treating conditions and disorders using such compounds and compositions.

  本发明涉及氮杂环吲哚-2-羧酰胺衍生物、包含这些化合物的组合物以及使用这些化合物和组合物预防或治疗疾病和疾患的方法。
• NOVEL AZA-CYCLIC INDOLE-2-CARBOXAMIDES AND METHODS OF USE THEREOF
  申请人：Gopalakrishnan Murali

  公开号：US20100035862A1

  公开（公告）日：2010-02-11

  The invention relates to aza-cyclic-indole-2-carboxamide derivatives, compositions comprising such compounds, and methods of preventing or treating conditions and disorders using such compounds and compositions.

  本发明涉及氮杂环吲哚-2-羧酰胺衍生物，包括此类化合物的组合物以及使用此类化合物和组合物预防或治疗疾病和疾病的方法。
• Pyrazolospiroketone Acetyl-CoA Carboxylase Inhibitors
  申请人：Corbett Jeffrey W.

  公开号：US20110028390A1

  公开（公告）日：2011-02-03

  The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R 1 , R 2 , and R 3 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of acetyl-CoA carboxylase enzyme(s) in an animal.

  本发明提供公式（1）的化合物或其药学上可接受的盐，其中R1，R2和R3如本文所述；其药物组合物；以及将其用于治疗动物中受乙酰辅酶A羧化酶酶抑制调节的疾病，状况或障碍。
• Discovery of novel indole derivatives as potent and selective inhibitors of proMMP-9 activation
  作者：Rie Nishikawa-Shimono、Motoi Kuwabara、Sho Fujisaki、Daisuke Matsuda、Mayumi Endo、Masafumi Kamitani、Aya Futamura、Yusaku Nomura、Toru Yamaguchi-Sasaki、Tetsuya Yabuuchi、Chitose Yamaguchi、Nozomi Tanaka-Yamamoto、Shunya Satake、Kumi Abe-Sato、Kosuke Funayama、Mayumi Sakata、Shinji Takahashi、Koga Hirano、Takuya Fukunaga、Yoriko Uozumi、Sayaka Kato、Yunoshin Tamura、Tomoaki Nakamori、Masashi Mima、Chiemi Mishima-Tsumagari、Dai Nozawa、Yudai Imai、Taiji Asami

  DOI：10.1016/j.bmcl.2023.129541

  日期：2024.1

  synthesis, and in vitro studies of novel indole derivatives as inhibitors of proMMP-9 activation. High-throughput screening (HTS) of our internal compound library and subsequent merging of hit compounds 1 and 2 provided compound 4 as a bona-fide lead. X-ray structure-based design and subsequent lead optimization led to the discovery of compound 33, a highly potent and selective inhibitor of proMMP-9 activation

  基质金属蛋白酶-9 (MMP-9) 是一种分泌型锌依赖性内肽酶，可降解神经元的细胞外基质和基底膜，然后通过重塑细胞外基质来促进突触可塑性。抑制 MMP-9 活性具有治疗神经退行性疾病（例如脆性 X 综合征）的潜力。本文报道了新型吲哚衍生物作为 proMMP-9 激活抑制剂的分子设计、合成和体外研究。我们的内部化合物库的高通量筛选 (HTS) 以及随后对命中化合物1和2的合并提供了化合物4作为真正的先导化合物。基于 X 射线结构的设计和随后的先导化合物优化导致了化合物33的发现，它是一种高效、选择性的 proMMP-9 激活抑制剂。