2-chloro-1-(6-nitroindolin-1-yl)ethan-1-one | 87866-12-4

• 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: 2-chloro-1-(6-nitroindolin-1-yl)ethan-1-one
• 英文别名: 2-chloro-1-(6-nitroindolin-1-yl)ethanone；PCM-0102777；2-chloro-1-(6-nitro-2,3-dihydro-1H-indol-1-yl)ethan-1-one；2-chloro-1-(6-nitro-2,3-dihydroindol-1-yl)ethanone
• CAS: 87866-12-4
• 化学式: C₁₀H₉ClN₂O₃
• mdl: MFCD11043509
• 分子量: 240.646
• InChiKey: HZENLBQVZSRAMH-UHFFFAOYSA-N

物化性质

• 沸点：
  480.0±45.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(6-nitroindolin-1-yl)ethan-1-one 在 硼烷四氢呋喃络合物 、 potassium carbonate 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 54.58h， 生成 tert-butyl 2-hydroxyethyl(2-(6-(thiophene-2-carboximidamido)indolin-1-yl)ethyl)carbamate
  参考文献：
  名称：

  Discovery of cis-N-(1-(4-(Methylamino)cyclohexyl)indolin-6-yl)thiophene-2-carboximidamide: A 1,6-Disubstituted Indoline Derivative as a Highly Selective Inhibitor of Human Neuronal Nitric Oxide Synthase (nNOS) without Any Cardiovascular Liabilities

  摘要：

  A series of 1,6-disubstituted indoline derivatives were synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS) designed to mitigate the cardiovascular liabilities associated with previously reported tetrahydroquinoline-based selective neuronal NOS inhibitors due to higher lipophilicity (J. Med. Chem. 2011, 54, 5562-5575). This new series produced similar potency and selectivity among the NOS isoforms and was devoid of any cardiovascular liabilities associated with QT prolongation due to hERG activity or endothelial NOS mediated vasoconstriction effect. The SAR studies led to the identification of cis-45, which was shown to reverse thermal hyperalgesia in vivo in the spinal nerve ligation model of neuropathic pain with excellent safety profile (off-target activities at 80 CNS related receptors/ion channels/transporters). The results presented in this report make cis-45 as an ideal tool for evaluating the potential role of selective nNOS inhibitors in CNS related disorders where excess NO produced by nNOS is thought to play a crucial role.

  DOI：

  10.1021/jm201564u
• 作为产物：
  描述：

  6-硝基吲哚 在 硼烷-三甲胺络合物 、 TEA 作用下， 以 氯仿 为溶剂， 反应 18.0h， 生成 2-chloro-1-(6-nitroindolin-1-yl)ethan-1-one
  参考文献：
  名称：

  吲哚啉和哌嗪类衍生物作为新型的混合D（2）/ D（4）受体拮抗剂。第1部分：识别和结构活动关系。

  摘要：

  通过系统结构-活性关系最优化铅化合物2-[-4-（4-氯苄基）-哌嗪-1-基] -1-（2,3-二氢-吲哚-1-基）-乙酮1 （SAR）研究产生了两种有效的化合物2-[-4-（4-氯-苄基）-哌嗪-1-基] -1-（2-甲基-2,3-二氢-吲哚-1-基）-乙酮2n和2-[-4-（4-氯苄基）-哌嗪-1-基] -1-（2-甲基-2,3-二氢-吲哚-1-基）-乙酮7b。还报道了它们的相关合成。

  DOI：

  10.1016/s0960-894x(02)00655-8

文献信息

• Substituted alkylamine derivatives and methods of use
  申请人：Amgen Inc.

  公开号：US20030225106A1

  公开（公告）日：2003-12-04

  Selected amines are effective for prophylaxis and treatment of diseases, such as angiogenesis mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  选定的胺对预防治疗疾病有效，如血管生成介导的疾病。本发明包括新的化合物、类似物、前药和药用可接受的盐，药物组合物和预防治疗疾病和其他疾病或状况的方法，包括癌症等。本发明还涉及制造这类化合物的过程以及在此类过程中有用的中间体。
• [EN] 5HT1F RECEPTOR AGONISTS AND MITOCHONDRIAL BIOGENESIS<br/>[FR] AGONISTES DU RÉCEPTEUR 5 HT1F ET BIOGENÈSE MITOCHONDRIALE
  申请人：MUSC FOUND FOR RES DEV

  公开号：WO2018085491A1

  公开（公告）日：2018-05-11

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, promote mitochondrial biogenesis and are useful for the treatment of, for example, acute kidney injury and chronic kidney disease.

  提供的化合物公式(I)如下所示，以及其药学上可接受的盐，其中取代基如规范中所述。这些化合物和含有它们的药物组合物促进线粒体生成，可用于治疗急性肾损伤和慢性肾病等疾病。
• 5HT1F receptor agonists and mitochondrial biogenesis
  申请人：MUSC FOUNDATION FOR RESEARCH DEVELOPMENT

  公开号：US11014892B2

  公开（公告）日：2021-05-25

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, promote mitochondrial biogenesis and are useful for the treatment of, for example, acute kidney injury and chronic kidney disease.

  本文提供了式(I)：的化合物及其药学上可接受的盐类，其中取代基与说明书中公开的相同。这些化合物以及含有它们的药物组合物能促进线粒体的生物生成，可用于治疗急性肾损伤和慢性肾病等。
• MORI, KOGORO;OI, XIDEHO;SASO, YASUO
  作者：MORI, KOGORO、OI, XIDEHO、SASO, YASUO

  DOI：——

  日期：——
• 5HT1F RECEPTOR AGONISTS AND MITOCHONDRIAL BIOGENESIS
  申请人：MUSC FOUNDATION FOR RESEARCH DEVELOPMENT

  公开号：US20200055827A1

  公开（公告）日：2020-02-20

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, promote mitochondrial biogenesis and are useful for the treatment of, for example, acute kidney injury and chronic kidney disease.