5-cyanoindole-3-carboxylic acid | 174500-89-1

• 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: 5-cyanoindole-3-carboxylic acid
• 英文别名: 5-cyano-1H-indole-3-carboxylic acid
• CAS: 174500-89-1
• 化学式: C₁₀H₆N₂O₂
• 分子量: 186.17
• InChiKey: PQKDHLJDXYCJRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  509.0±30.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-cyanoindole-3-carboxylic acid 在 吡啶 、 4-二甲氨基吡啶 、 硫化氢 、 ammonium acetate 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 碘甲烷 作用下， 生成 8-{[5-(tert-Butoxycarbonylamino-imino-methyl)-1H-indole-3-carbonyl]-amino}-octanoic acid methyl ester
  参考文献：
  名称：

  Platelet glycoprotein IIb–IIIa receptor (GPIIb–IIIa) antagonists derived from amidinoindoles

  摘要：

  A series of substituted amidinoindoles have been prepared as mimics of the RGD sequence and were studied as antagonists of the platelet glycoprotein IIb-IIIa receptor (GPIIb-IIIa). The agents were potent and selective antagonists of GPIIb-IIIa. Compared to their acyclic counterparts, the amidinoindole series bound with 10- to 20-fold greater affinity, indicating the advantages of added conformational restriction and/or hydrophobicity in the basic region of RGD mimics.

  DOI：

  10.1016/0960-894x(95)00563-9
• 作为产物：
  描述：

  5-氰基吲哚-3-甲醛 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 作用下， 以 水 、 二甲基亚砜 为溶剂， 以75 %的产率得到5-cyanoindole-3-carboxylic acid
  参考文献：
  名称：

  鉴定 5-[5-氰基-1-(吡啶-2-基甲基)-1H-吲哚-3-甲酰氨基]噻唑-4-羧酸作为尿酸转运蛋白 1 和黄嘌呤氧化酶的有前途的双重抑制剂

  摘要：

  曲尼司特与别嘌呤醇联合作为尿酸转运蛋白1（URAT1）抑制剂用于治疗高尿酸血症，但其与URAT1抑制活性的构效关系鲜有研究。在本文中，在曲尼司特和优先支架吲哚的基础上，使用支架跳跃策略设计和合成了类似物。然后，使用 HEK293-URAT1 过表达细胞的 C-尿酸摄取测定来评估 URAT1 活性。与曲尼司特（10 μM 时抑制率为 44.9%）相比，大多数化合物对 URAT1 表现出明显的抑制作用，10 μM 时抑制率为 40.0% 至 81.0%。令人惊讶的是，随着在吲哚环5位引入氰基，化合物和 - 发挥了黄嘌呤氧化酶（XO）抑制活性。特别是，化合物对 URAT1（10 μM 时为 48.0%）和 XO（IC = 1.01 μM）具有效力。分子模拟分析表明该化合物的基本结构与URAT1、XO具有亲和力。此外，在测试期间，口服剂量为 10 mg/kg 的化合物在氧酸钾诱导的高尿酸血症大鼠模

  DOI：

  10.1016/j.ejmech.2023.115532

文献信息

• Decarboxylation of indole-3-carboxylic acids under metal-free conditions
  作者：Xia Chen、Xiao-Yu Zhou

  DOI：10.1080/00397911.2019.1703137

  日期：2020.3.18

  Abstract Two reaction systems have been developed for the decarboxylation of indole-3-carboxylic acids. The decarboxylation can be achieved smoothly under K2CO3-catalyzed or acetonitrile-promoted basic conditions. It provided an efficient and simple method for the transformation of indole-3-carboxylic acids and the corresponding indoles were isolated with good to excellent yields. From the experimental

  摘要 已经开发了两种反应体系用于吲哚-3-羧酸的脱羧反应。在 K2CO3 催化或乙腈促进的碱性条件下，脱羧反应可以顺利完成。它为吲哚-3-羧酸的转化提供了一种有效且简单的方法，并且相应的吲哚以良好到极好的收率被分离出来。从实验事实出发，我们提出了可能的反应机理。图形概要
• Access to 2-Arylindoles via Decarboxylative C−C Coupling in Aqueous Medium and to Heteroaryl Carboxylates under Base-Free Conditions using Diaryliodonium Salts
  作者：Velladurai Arun、Meenakshi Pilania、Dalip Kumar

  DOI：10.1002/asia.201601290

  日期：2016.12.6

  accessible heteroaromatic carboxylic acids and diaryliodonium salts were successfully employed to construct valuable 2‐arylindoles and heteroaryl carboxylates in a regioselective fashion. C2‐arylated indoles were produced using a Pd‐catalyzed decarboxylative strategy in water without any base, oxidant, or ligand. Heteroaryl carboxylates were prepared under metal and base‐free conditions. This protocol was

  容易获得的杂芳族羧酸和二芳基碘鎓盐已成功用于以区域选择性的方式构建有价值的2-芳基吲哚和杂芳基羧酸盐。C2芳基吲哚是在水中没有任何碱，氧化剂或配体的情况下使用Pd催化的脱羧策略生产的。杂芳基羧酸盐是在无金属和无碱条件下制备的。该方案已成功用于合成细胞周期蛋白依赖性激酶（CDK）抑制剂Paullone。
• [EN] COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH STING ACTIVITY<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR TRAITER DES ÉTATS PATHOLOGIQUES ASSOCIÉS À UNE ACTIVITÉ DE STING
  申请人：IFM DUE INC

  公开号：WO2022015977A1

  公开（公告）日：2022-01-20

  This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt, and/or hydrate, and/or cocrystal, and/or drug combination of the compound) that inhibit (e.g., antagonize) Stimulator of Interferon Genes (STING). Said chemical entities are useful, e.g., for treating a condition, disease or disorder in which increased (e.g., excessive) STING activation (e.g., STING signaling) contributes to the pathology and/or symptoms and/or progression of the condition, disease or disorder (e.g., cancer) in a subject (e.g., a human). This disclosure also features compositions containing the same as well as methods of using and making the same.

  本公开涉及化学实体（例如，化合物或药物可接受的盐，水合物，共晶体或化合物的药物组合），其抑制（例如，对抗）干扰素基因刺激剂（STING）。这些化学实体是有用的，例如，用于治疗在该主题（例如，人类）中增加（例如，过度）STING激活（例如，STING信号传导）对病理学和/或症状和/或病情进展有贡献的状况，疾病或障碍（例如，癌症）。本公开还涉及包含相同的组合物以及使用和制造相同的方法。
• 5-HT3 RECEPTOR ANTAGONISTS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20160185801A1

  公开（公告）日：2016-06-30

  The present invention provides compounds of the formula: that are 5HT3 receptor antagonists and are therefore useful for the treatment of diseases treatable by inhibition of 5HT3 receptor such as emesis, pain, drug addiction, neurodegenerative and psychiatric disorders, and GI disorders. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

  本发明提供的化合物具有以下公式： 这些化合物是5HT3受体拮抗剂，因此可用于治疗可通过抑制5HT3受体治疗的疾病，例如呕吐、疼痛、药物成瘾、神经退行性和精神障碍以及胃肠道疾病。还提供了包含这些化合物的制药组合物和制备这些化合物的方法。
• Use of Conformationally Restricted Benzamidines as Arginine Surrogates in the Design of Platelet GPIIb-IIIa Receptor Antagonists
  作者：Daniel J. Sall、Ann E. Arfsten、Jolie A. Bastian、Michael L. Denney、Cathy S. Harms、Jefferson R. McCowan、John M. Morin,、Jack W. Rose、Robert M. Scarborough、Mark S. Smyth、Suzane L. Um、Barbara G. Utterback、Robert T. Vasileff、James H. Wikel、Virginia L. Wyss、Joseph A. Jakubowski

  DOI：10.1021/jm970020k

  日期：1997.8.1

  The use of 5,6-bicyclic amidines as arginine surrogates in the design of a novel class of potent platelet glycoprotein IIb-IIIa receptor (GPIIb-IIIa) antagonists is described. The additional conformational restriction offered by the bicyclic nucleus results in 20-400-fold increases in potency compared to the freely flexible, acyclic benzamidine counterpart. The design, synthesis, structure-activity relationships (SAR), and in vitro activity of this novel class of GPIIb-IIIa antagonists are presented.