5-氯-7-(三氟甲基)吲哚啉-2,3-二酮 | 954586-11-9

• 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: 5-氯-7-(三氟甲基)吲哚啉-2,3-二酮
• 英文名称: 5-chloro-7-(trifluoromethyl)indoline-2,3-dione
• 英文别名: 5-Chloro-7-trifluoromethylindole-2,3-dione；5-chloro-7-(trifluoromethyl)-1H-indole-2,3-dione
• CAS: 954586-11-9
• 化学式: C₉H₃ClF₃NO₂
• mdl: MFCD09740044
• 分子量: 249.577
• InChiKey: WBEGSXWHZFUWGE-UHFFFAOYSA-N

物化性质

• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-氯-7-(三氟甲基)吲哚啉-2,3-二酮 在 sodium azide 、 硫酸 、 硫化氢 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-Amino-5-chloro-3-trifluoromethyl-thiobenzamide
  参考文献：
  名称：

  3-氨基-2,1-苯并异噻唑。某些氯和三氟甲基衍生物的合成

  摘要：

  3-氨基-2的7-氯-，4,7-二氯-，5-和7-三氟甲基，5-氯-6-三氟甲基-和5-氯-7-三氟甲基-衍生物的合成，描述了1-苯并异噻唑。包括许多苯并异噻唑衍生物的前体的制备细节，这些以前没有进行过描述。参考取代基效应，讨论了由标题化合物与选定的成色剂制备的某些偶氮染料的可见光谱。

  DOI：

  10.1002/jhet.5570170113
• 作为产物：
  描述：

  2-氨基-5-氯三氟甲苯 在 盐酸 、 硫酸 、 盐酸羟胺 、 sodium sulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 5-氯-7-(三氟甲基)吲哚啉-2,3-二酮
  参考文献：
  名称：

  Methods and Compositions for Selectin Inhibition

  摘要：

  本教学涉及到式I的新化合物： 其中组成变量如本文所定义。本教学的化合物可以作为被称为选择素的哺乳动物粘附蛋白的拮抗剂。提供了治疗或预防选择素介导的疾病的方法，包括以治疗有效剂量给予这些化合物。

  公开号：

  US20080255192A1

文献信息

• Discovery of 2-[1-(4-Chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic Acid (PSI-421), a P-Selectin Inhibitor with Improved Pharmacokinetic Properties and Oral Efficacy in Models of Vascular Injury
  作者：Adrian Huang、Alessandro Moretto、Kristin Janz、Michael Lowe、Patricia W. Bedard、Steve Tam、Li Di、Valerie Clerin、Natalia Sushkova、Boris Tchernychev、Desiree H. H. Tsao、James C. Keith、Gray D. Shaw、Robert G. Schaub、Qin Wang、Neelu Kaila

  DOI：10.1021/jm9013696

  日期：2010.8.26

  Previously, we reported the discovery of PSI-697 (1a), a C-2 benzyl substituted quinoline salicylic acid-based P-selectin inhibitor. It is active in a variety of animal models of cardiovascular disease. Compound 1a has also been shown to be well tolerated and safe in healthy volunteers at doses of up to 1200 mg in a phase 1 single ascending dose study. However, its oral bioavailability was low. Our goal was to identify a back up compound with equal potency, increased solubility, and increased exposure. We expanded our structure activity-studies in this series by branching at the alpha position of the C-2 benzyl side chain and through modification of substituents on the carboxylic A-ring of the quinoline. This resulted in discovery of PSI-421 with marked improvement in aqueous solubility and pharmacokinetic properties. This compound has shown oral efficacy in animal models of arterial and venous injury and was selected as a preclinical development compound for potential treatment of such diseases as atherosclerosis and deep vein thrombosis.
• Visible-Light-Promoted Radical C–H Trifluoromethylation of Free Anilines
  作者：Jin Xie、Xiangai Yuan、Ablimit Abdukader、Chengjian Zhu、Jing Ma

  DOI：10.1021/ol500469a

  日期：2014.3.21

  The trifluoromethyl-substituted anilines are biologically active compounds and useful building blocks. In this communication, we have developed the first visible-light-induced radical trifluoromethylation of free anilines with the commercially available and easily handled Togni reagent at room temperature. The resulting products were successfully transformed into a variety of valuable fluorine-containing molecules and heterocyclic compounds. This protocol provides an economical and powerful route to trifluoromethylated free anilines.
• Chlorination of isatins with trichloroisocyanuric acid
  作者：Bárbara V Silva、Pierre M Esteves、Angelo C Pinto

  DOI：10.1590/s0103-50532011000200010

  日期：——

  Isatin and its derivatives have been extensively reported in the literature as having range of potential pharmacological compounds. The Sandmeyer method is the most widely used for isatin synthesis and furnishes different substituted isatins, usually with high yields. Although efficient, the Sandmeyer route has certain limitations, such as the formation of a mixture of regiosiomers and low yields depending on the type and position of the substituent. Thus, overcome these limitations, it is preferable that some derivative isatins be obtained by alternative methods. This article has investigated the chlorination of isatin derivatives using trichloroisocyanuric acid [1,3,5-trichloro-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione or TCCA] at different reaction conditions.
• QUINOLINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM FOR SELECTIN INHIBITION
  申请人：Wyeth

  公开号：EP2134692A2

  公开（公告）日：2009-12-23
• [EN] METHODS AND COMPOSITIONS FOR SELECTIN INHIBITION<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR L'INHIBITION DE LA SÉLECTINE
  申请人：WYETH CORP

  公开号：WO2008121817A2

  公开（公告）日：2008-10-09

  [EN] The present teachings relate to novel compounds of formula I: wherein the constituent variables are as defined herein. Compounds of the present teachings can act as antagonists of the mammalian adhesion proteins known as selectins. Methods for treating or preventing selectin-mediated disorders are provided, which include administration of these compounds in a therapeutically effective amount.
  [FR] La présente invention concerne de nouveaux composés de la formule I: LA FORMULE CHIMIQUE DOIT ETRE INSEREE ICI TELLE QU'ELLE APPARAiT SUR LE RESUME DU FORMAT PAPIER, où les variables sont telles que définies ici. Les composés de la présente invention peuvent agir comme antagonistes des protéines mammaliennes d'adhésion connus comme sélectines. Des procédés de traitement ou de prévention de désordres à médiation par les sélectines sont décrits, lesquels comprennent l'administration de ces composés en une quantité thérapeutiquement efficace.