4-氯-5-氟-1H-吲哚-2,3-二酮 | 84378-94-9

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟靛红系列
• 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: 4-氯-5-氟-1H-吲哚-2,3-二酮
• 英文名称: 4-chloro-5-fluoro-isatin
• 英文别名: 4-chloro-5-fluoro-1H-indole-2,3-dione
• CAS: 84378-94-9
• 化学式: C₈H₃ClFNO₂
• mdl: MFCD03618550
• 分子量: 199.569
• InChiKey: SWUGYKGLXFMLEN-UHFFFAOYSA-N

物化性质

• 密度：
  1.613±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温下应存放在干燥密封的容器中。

反应信息

• 作为反应物：
  描述：

  4-氯-5-氟-1H-吲哚-2,3-二酮 在 钾硼氢 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 4,4'-dichloro-5,5'-difluoroindirubin
  参考文献：
  名称：

  一种仿生合成靛玉红及其衍生物的方法

  摘要：

  一种仿生合成靛玉红的方法，包括以下步骤：在吲哚醌中加入有机溶剂和还原剂反应，反应温度：-10.0～150.0℃，反应时间：0.5～72.0h，搅拌回流或无溶剂研磨后萃取得到靛玉红，所述的还原剂与吲哚醌的比为（物质的量）(50:1)？～(？0.001:1),吲哚醌与有机溶剂比为1:（3～6）？(物质的量（mol）：体积(L))；合成靛玉红衍生物的方法与合成靛玉红的方法相同。本发明合成路线简捷，原料廉价易得，反应条件温和，产率高，操作简单。

  公开号：

  CN103980182B
• 作为产物：
  描述：

  N-(3-Chloro-4-fluorophenyl)-2-(hydroxyimino)acetamide 在 硫酸 作用下， 生成 4-氯-5-氟-1H-吲哚-2,3-二酮
  参考文献：
  名称：

  Design and development of Isatin-triazole hydrazones as potential inhibitors of microtubule affinity-regulating kinase 4 for the therapeutic management of cell proliferation and metastasis

  摘要：

  Microtubule affinity-regulating kinase 4 (MARK4) is a potential drug target as the same is found to be over expressed in several types of cancers. In search of effective MARK4 inhibitors, we have synthesized and characterized Isatin-triazole hydrazones (9a-i) and evaluated their inhibitory potential. Of all the compounds, 9g showed better binding affinity and enzyme inhibition potential in sub micromolar range. Human serum albumin (HSA) binding assay suggested an easy transportation of 9g in blood stream due to its binding affinity. In vitro anticancer studies performed on MCF-7, MDA-MB-435s and HepG2 cells using 9g showed inhibition of cell proliferation and cell migration. Further, 9g induces apoptosis in these cancerous cells, with IC50 values of 6.22, 9.94 and 8.14 mu M, respectively. Putatively, 9g seems to cause oxidative stress resulting in apoptosis. Functional assay of 9g with a panel of 26 kinases showed MARK4 specific profile. In conclusion, 9g seems to possess an effective inhibitory potential towards MARK4 adding an additional repertoire to anticancer therapeutics. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.12.026

文献信息

• [EN] TRPV4 ANTAGONISTS<br/>[FR] ANTAGONISTES DE TRPV4
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011119701A1

  公开（公告）日：2011-09-29

  The present invention relates to quinoline analogs, pharmaceutical compositions containing them and their use as TRPV4 antagonists.

  本发明涉及喹啉类似物、含有它们的药物组合物以及它们作为TRPV4拮抗剂的用途。
• Synthesis of aminoquinolone derivatives
  作者：Raghavan Krishnan、S. A. Lang、Marshall M. Siegel

  DOI：10.1002/jhet.5570230640

  日期：1986.11

  The synthesis of 3-amino-7-chloro-1-ethyl-6-fluoro-4(1H)quinolinone derivatives is described. These were investigated for their antibacterial activity.

  描述了3-氨基-7-氯-1-乙基-6-氟-4（1 H）喹啉酮衍生物的合成。研究了它们的抗菌活性。
• Utilizing Solubility Differences to Achieve Regiocontrol in the Synthesis of Substituted Quinoline-4-carboxylic Acids
  作者：Peter Lindsay-Scott、Helen Barlow

  DOI：10.1055/s-0035-1561395

  日期：——

  A practical method for the regiocontrolled synthesis of substituted quinoline-4-carboxylic acids is described. Solubility differences between the product quinoline regioisomers enable their facile separation, thus avoiding any challenging chromatographic purifications and allowing access to highly substituted quinoline compounds in three steps from commercially available anilines.

  描述了一种用于区域控制合成取代喹啉-4-羧酸的实用方法。产品喹啉区域异构体之间的溶解度差异使其易于分离，从而避免了任何具有挑战性的色谱纯化，并允许通过三个步骤从市售苯胺中获得高度取代的喹啉化合物。
• Imidazobenzodiazepines
  申请人：Hoffmann-La Roche Inc.

  公开号：US04489003A1

  公开（公告）日：1984-12-18

  There are described novel pharmaceutically active substances which have a pronounced affinity to the central benzodiazepine receptors and which have only a low toxicity. These active substances, namely imidazobenzodiazepines of the formula ##STR1## wherein A is lower alkylene, n is zero or 1, R.sup.1 is lower alkynyl, lower alkenyl, aryl, (C.sub.3-8)-cycloalkyl optionally substituted by lower alkyl or (C.sub.5-8)-cycloalkenyl optionally substituted by lower alkyl, or a 5- or 6-membered saturated or unsaturated heterocycle which contains an oxygen or sulphur atom as a ring member and which is optionally substituted by lower alkyl, R.sup.4 and R.sup.5 each are hydrogen, halogen, trifluoromethyl, cyano, nitro, amino or lower alkyl and either R.sup.2 is hydrogen and R.sup.3 is lower alkyl or R.sup.2 and R.sup.3 together are dimethylene, trimethylene or propenylene, the compounds of formula I in which R.sup.2 and R.sup.3 together are dimethylene, trimethylene or propenylene having the (S) or (R,S) configuration with reference to the carbon atom denoted by .gamma., and their pharmaceutically acceptable acid addition salts, can be used as medicaments in the form of pharmaceutical preparations, especially in the control of convulsions and anxiety states and/or in the partial or complete antagonization of some or all activities which 1,4-benzodiazepines having tranquillizing activity or other substances display via the central benzodiazepine receptors.

  描述了一种新型具有显著亲和力的药用活性物质，它们对中枢苯二氮卓类受体具有高亲和力，且毒性低。这些活性物质，即具有以下结构的咪唑苯二氮卓类化合物：其中A为较低的烷基，n为零或1，R1为较低的炔基、较低的烯基、芳基、(C3-8)-环烷基（可选择地被较低的烷基取代）或(C5-8)-环烯烷基（可选择地被较低的烷基取代），或者是含有氧或硫原子作为环成员的5-或6-成员饱和或不饱和杂环，且可选择地被较低的烷基取代，R4和R5各自为氢、卤素、三氟甲基、氰基、硝基、氨基或较低的烷基，而R2为氢且R3为较低的烷基，或者R2和R3一起为二甲亚乙烷、三甲亚乙烷或丙烯亚乙烷，其中R2和R3一起为二甲亚乙烷、三甲亚乙烷或丙烯亚乙烷的具有对应于由γ表示的碳原子的(S)或(R,S)构型的I式化合物，以及它们的药学上可接受的酸盐加合物，可作为药物用于制备药物制剂，特别用于控制癫痫和焦虑状态，或者部分或完全拮抗一些或全部1,4-苯二氮卓类具有镇静作用或其他物质通过中枢苯二氮卓类受体表现出的活性。
• Synthesis of substituted tryptanthrin via aryl halides and amines as antitumor and anti-MRSA agents
  作者：Xudong Zheng、Baolong Hou、Rui Wang、Yinyin Wang、Cuiling Wang、Huan Chen、Li Liu、Jilin Wang、Xiumei Ma、Jianli Liu

  DOI：10.1016/j.tet.2019.05.030

  日期：2019.11

  tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione), and its analogues are found to exhibit potent antitumor and anti-MRSA activities. An efficient and convenient method has been developed for the synthesis of tryptanthrin D-ring derivatives through the reaction of substituted tryptanthrins and secondary amines in moderate to good yields. Some of the new compounds exhibited antitumor activities against the human

  发现天然生物碱类胰蛋白酶（吲哚[2,1-b]喹唑啉-6,12-二酮）及其类似物表现出有效的抗肿瘤和抗-MRSA活性。已经开发了一种有效且方便的方法，该方法通过使取代的色胺酮与仲胺反应以中等至良好的产率合成色胺酮D-环衍生物。一些新化合物对人肿瘤细胞系A549，HCT116和MDA-MB-231表现出抗肿瘤活性，低微摩尔水平的平均IC 50值。此外，某些化合物显示出优异的抗MRSA活性，并且比万古霉素更有效，Mu50，RN4220和Newman菌株的MIC值为0.31–1.25μg/ mL。