7-氯-2-甲基-1H-吲哚 | 623177-14-0

• 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
• 中文名称: 7-氯-2-甲基-1H-吲哚
• 英文名称: 7-chloro-2-methyl-1H-indole
• CAS: 623177-14-0
• 化学式: C₉H₈ClN
• mdl: MFCD09701268
• 分子量: 165.622
• InChiKey: YIJQQOHTYWFLQH-UHFFFAOYSA-N

物化性质

• 沸点：
  302.7±22.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-氯-2-甲基-1H-吲哚 在 sodium hydroxide 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-[[2-[7-chloro-1-(diphenylmethyl)-2-methyl-1H-indol-3-yl]-ethyl]sulfonyl]benzoic acid
  参考文献：
  名称：

  Inhibition of Cytosolic Phospholipase A₂α: Hit to Lead Optimization

  摘要：

  Compound I was previously reported to be a potent inhibitor of cPLA,(x in both artificial monomeric substrate and cell-based assays. However, I was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC(50) of 1 increased dramatically with cell number or lipid/detergent concentration. In an attempt to insert an electrophilic ketone between the indole and benzoic acid moieties, we discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-gamma-linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA a inhibition. The IC(50)s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Compounds 25, 39, and 94 emerged as potent, selective inhibitors of cPLA(2)alpha and represent well-validated starting points for further optimization.

  DOI：

  10.1021/jm0507882
• 作为产物：
  描述：

  acetone-(2-chloro-phenylhydrazone) 在 zinc(II) chloride 作用下， 生成 7-氯-2-甲基-1H-吲哚
  参考文献：
  名称：

  Inhibition of Cytosolic Phospholipase A₂α: Hit to Lead Optimization

  摘要：

  Compound I was previously reported to be a potent inhibitor of cPLA,(x in both artificial monomeric substrate and cell-based assays. However, I was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC(50) of 1 increased dramatically with cell number or lipid/detergent concentration. In an attempt to insert an electrophilic ketone between the indole and benzoic acid moieties, we discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-gamma-linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA a inhibition. The IC(50)s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Compounds 25, 39, and 94 emerged as potent, selective inhibitors of cPLA(2)alpha and represent well-validated starting points for further optimization.

  DOI：

  10.1021/jm0507882

文献信息

• CHEMICAL SUBSTANCES WHICH INHIBIT THE ENZYMATIC ACTIVITY OF HUMAN KALLIKREIN-RELATED PEPTIDASE 6 (KLK6)
  申请人：Deutsches Krebsforschungszentrum

  公开号：EP3305781A1

  公开（公告）日：2018-04-11

  The invention relates to compounds which are suitable for the treatment of a disease associated with kallikrein-like peptidase 6 overexpression and to pharmaceutical compositions containing such compounds. The invention further relates to a kit of parts comprising such compounds or pharmaceutical compositions.

  这项发明涉及适用于治疗与kallikrein样肽酶6过度表达相关疾病的化合物，以及含有这些化合物的药物组合物。该发明还涉及包括这些化合物或药物组合物的配套工具包。
• INHIBITORS OF CAMKK2 AND USES OF SAME
  申请人：New York University

  公开号：US20200369656A1

  公开（公告）日：2020-11-26

  The present disclosure provides compounds suitable for inhibiting CaMKK2. Also provided are compositions and methods of treating diseases associated with CaMKK2.

  本公开提供适用于抑制CaMKK2的化合物。还提供了与CaMKK2相关疾病的治疗方法和组合物。
• [EN] SELECTIVE D3 DOPAMINE RECEPTOR AGONISTS AND METHODS OF THEIR USE<br/>[FR] AGONISTES SÉLECTIFS DU RÉCEPTEUR DE LA DOPAMINE D3 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：US HEALTH

  公开号：WO2017181004A1

  公开（公告）日：2017-10-19

  The disclosure of a compound of Formula (I) or a pharmaceutically acceptable salt thereof (I) The variables W, R1, R2, R3, and R4 are defined in the disclosure. The disclosure provides a compound or salt of Formula (I) together with a pharmaceutically acceptable carrier. The disclosure also provides methods of treating a patient for Parkinson's disease and related syndromes, dyskinesia, especially dyskinesias secondary to treating Parkinson's disease with L-DOPA, neurodegenerative disorders such as Alzheimer's disease and dementia, Huntington's disease, restless legs syndrome, bipolar disorder and depression, schizophrenia, cognitive dysfunction, or substance use disorders, the methods comprising administering a compound of Formula I or salt thereof to the patient. The disclosure provides combination methods of treatment in which the compound of Formula (I) is administered to the patient together with one or more additional active agents.

  公式(I)的化合物或其药用可接受的盐的披露。变量W、R1、R2、R3和R4在披露中有定义。该披露提供了公式(I)的化合物或盐，以及药用可接受的载体。该披露还提供了治疗帕金森病和相关综合征、特别是因治疗帕金森病使用L-DOPA而引起的运动障碍、神经退行性疾病如阿尔茨海默病和痴呆症、亨廷顿病、不安腿综合征、躁郁症和抑郁症、精神分裂症、认知功能障碍或物质使用障碍的方法，包括向患者施用公式I的化合物或其盐。该披露提供了联合治疗方法，其中将公式(I)的化合物与一个或多个额外活性剂一起施用给患者。
• Synthesis of Indoles by Palladium-Catalyzed Reductive Cyclization of β-Nitrostyrenes with Carbon Monoxide as the Reductant
  作者：Francesco Ferretti、Mohamed A. EL-Atawy、Stefania Muto、Mohamed Hagar、Emma Gallo、Fabio Ragaini

  DOI：10.1002/ejoc.201500933

  日期：2015.9

  An efficient catalytic cyclization of β-nitrostyrenes to indoles was developed. The reaction was applied to the synthesis of 3-arylindoles and 2-alkylindoles. Given that in the latter case the starting β-nitrostyrenes can be easily obtained by a Henry reaction, the present method allows indoles to be obtained in a two-step sequence starting from cheap reactants.

  开发了一种有效的 β-硝基苯乙烯催化环化成吲哚。该反应用于合成3-芳基吲哚和2-烷基吲哚。鉴于在后一种情况下起始 β-硝基苯乙烯可以很容易地通过亨利反应获得，本方法允许从廉价的反应物开始以两步顺序获得吲哚。
• Efficient direct 2,2,2-trifluoroethylation of indoles via C–H functionalization
  作者：Gergely L. Tolnai、Anna Székely、Zita Makó、Tamás Gáti、János Daru、Tamás Bihari、András Stirling、Zoltán Novák

  DOI：10.1039/c5cc00519a

  日期：——

  Metal free direct trifluoroethylation of unprotected indoles at position 3 via C–H functionalization is presented: straightforward synthesis and DFT studies.

  无金属直接在未保护的吲哚位置3上进行三氟乙基化，通过C-H官能化呈现：直接合成和密度泛函理论研究。