3,5-dimethylbenzofuran-2-carbonyl chloride | 16817-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3,5-dimethylbenzofuran-2-carbonyl chloride
• 英文别名: 3,5-dimethylbenzofuran-2-acylchloride；3,5-Dimethyl-benzofuran-2-carbonyl chloride；3,5-dimethyl-1-benzofuran-2-carbonyl chloride
• CAS: 16817-33-7
• 化学式: C₁₁H₉ClO₂
• 分子量: 208.644
• InChiKey: RUWQVSWMIOZFIL-UHFFFAOYSA-N

物化性质

• 沸点：
  305.2±37.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3,5-dimethylbenzofuran-2-carbonyl chloride 在 palladium on activated charcoal 碳酸氢铵 作用下， 生成 5-(3,5-dimethyl-benzofuran-2-yl)-imidazolidine-2,4-dione
  参考文献：
  名称：

  Sila,B., Roczniki Chemii, 1967, vol. 41, # 1, p. 157 - 162

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲苯并呋喃-2-羧酸乙酯 在 氢氧化钾 、 五氯化磷 作用下， 生成 3,5-dimethylbenzofuran-2-carbonyl chloride
  参考文献：
  名称：

  Sila,B., Roczniki Chemii, 1967, vol. 41, # 1, p. 157 - 162

  摘要：

  DOI：

文献信息

• 5-MEMBERED HETEROCYCLE FUSED WITH [3,4-D]PYRIDAZINONE, AND MANUFACTURING METHOD, PHARMACEUTICAL COMPOSITION, AND APPLICATION THEREOF
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP3470415A1

  公开（公告）日：2019-04-17

  The present invention provides a compound comprising a 5-membered heterocycle fused with a pyridazinone, wherein the compound is used as an FGFR kinase inhibitor, and a manufacturing method and application thereof. The invention specifically provides a compound as represented by formula (I). Various radicals are as defined in the specification. The compound provided by the invention effectively inhibits an activity of an FGFR kinase, and can be used to manufacture a pharmaceutical product for treating a disease related to the activity of the FGFR kinase.

  本发明提供了一种化合物，该化合物包括与吡啶并嗪酮融合的5-成员杂环，其中该化合物用作FGFR激酶抑制剂，以及其制备方法和应用。该发明具体提供了一种由式（I）表示的化合物。各种基团如规范中所定义。本发明提供的化合物有效抑制FGFR激酶的活性，并可用于制造用于治疗与FGFR激酶活性相关的疾病的药物产品。
• Palladium-Catalyzed Enantioselective Intramolecular Dearomative Heck Reaction
  作者：Xiang Li、Bo Zhou、Run-Ze Yang、Fu-Ming Yang、Ren-Xiao Liang、Ren-Rong Liu、Yi-Xia Jia

  DOI：10.1021/jacs.8b09186

  日期：2018.10.24

  Enantioselective intramolecular dearomative Heck reactions have been developed by Pd-catalyzed cross-coupling of aryl halides or aryl triflates with the internal C═C bond of indoles, benzofurans, pyrroles, and furans. A variety of structurally unique spiroheterocycles and benzofused heterocycles having N/O-substituted quaternary carbon stereocenters, and exocyclic olefin moieties were afforded in moderate

  对映选择性分子内脱芳基 Heck 反应是通过 Pd 催化的芳基卤化物或芳基三氟甲磺酸酯与吲哚、苯并呋喃、吡咯和呋喃的内部 C=C 键的交叉偶联开发的。各种结构独特的螺杂环和具有 N/O 取代的季碳立体中心和环外烯烃部分的苯并杂环以中等至优异的产率提供，具有良好至优异的对映选择性，显示了本协议的广泛范围。合成了一系列新的基于 BINOL 和 H8-BINOL 的亚磷酰胺配体，并证明在 C2 系底物形成螺杂环的反应中是有效的手性配体。(S)-SEGPHOS 被证明是用于传递苯并稠合二氢吲哚和吡咯啉的反应的良好配体。
• [EN] 5-MEMBERED HETEROCYCLE FUSED WITH [3,4-D]PYRIDAZINONE, AND MANUFACTURING METHOD, PHARMACEUTICAL COMPOSITION, AND APPLICATION THEREOF<br/>[FR] HÉTÉROCYCLE À 5 ÉLÉMENTS FUSIONNÉ AVEC [3,4-D]PYRIDAZINONE, SON PROCÉDÉ DE FABRICATION, COMPOSITION PHARMACEUTIQUE ET SON APPLICATION<br/>[ZH] 五元杂环并[3,4-d]哒嗪酮类化合物、其制备方法、药物组合物及其应用
  申请人：SHANGHAI INST MATERIA MEDICA CAS

  公开号：WO2017202343A1

  公开（公告）日：2017-11-30

  本发明提供了一种作为FGFR激酶抑制剂的五元杂环并哒嗪酮类化合物及其制备和应用，具体地，本发明提供了一种如下式（I）所示的化合物；其中，各基团的定义如说明书中所述。本发明的化合物具有很好的FGFR激酶抑制活性，可以用于制备一系列治疗FGFR激酶活性相关的疾病的药物。
• Antineoplastic activity of novel thiazole derivatives
  作者：N. S. Finiuk、V. P. Hreniuh、Yu. V. Ostapiuk、V. S. Matiychuk、D. A. Frolov、M. D. Obushak、R. S. Stoika、A. M. Babsky

  DOI：10.7124/bc.00094b

  日期：2017.4.30
• Proapoptotic effects of novel thiazole derivative on human glioma cells
  作者：Nataliya Finiuk、Olha Klyuchivska、Iryna Ivasechko、Volodymyr Hreniukh、Yuriy Ostapiuk、Yaryna Shalai、Rostyslav Panchuk、Vasyl Matiychuk、Mykola Obushak、Rostyslav Stoika、Andriy Babsky

  DOI：10.1097/cad.0000000000000686

  日期：2019.1

  The aim of the present study was to investigate the antiproliferative and proapoptotic actions of N-(5-benzyl-1,3-thiazol-2-yl)-3,5-dimethyl-1-benzofuran-2-carboxamide derivative (compound 5) in glioma cells in comparison with the actions of temozolomide (TMZ) and doxorubicin (Dox), used as positive controls. The antiproliferative activity of the compound 5, TMZ, and Dox on human glioblastoma U251 and human glioblastoma multiform T98G cells was measured using the MTT test. Western blot analysis, fluorescent microscopy, agarose gel retardation assay, flow cytometric analysis, and the DNA comet assay under alkaline conditions were carried out to study the effect of compound 5 on U251 cells. This compound showed similar to 20 times higher cytotoxicity toward U251 and T98G cells compared with the effects of TMZ and approximately two times higher activity than that of the Dox. Compound 5 induced apoptosis in U251 cells by PARP1 and caspase 3 cleavage mechanisms, also inducing an increase in the level of Bax and Bim proapoptotic proteins and a decrease in the level of phosho-ERK1/ 2 kinase. The cytotoxicity of compound 5 was associated with an increase in the production of the hydrogen peroxide and the formation of DNA single-strand breaks. This compound 5 did not intercalate into a DNA molecule. Thus, the novel thiazole derivative (compound 5) proved to be a potential antiglioma drug that showed much higher cytotoxic action on human glioma cells compared with the effects of TMZ and Dox. Its cytotoxicity is associated with apoptosis induction, production of the reactive oxygen species, and formation of DNA single-strand breaks without significant DNA intercalation. Copyright (c) 2018 Wolters Kluwer Health, Inc. All rights reserved.