3-chlorofuran-2-carboxylic acid | 66204-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-chlorofuran-2-carboxylic acid
• CAS: 66204-31-7
• 化学式: C₅H₃ClO₃
• mdl: MFCD12828428
• 分子量: 146.53
• InChiKey: ZVMWPHWOEUYUKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chlorofuran-2-carboxylic acid 在 甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以92%的产率得到3-氯呋喃
  参考文献：
  名称：

  一种杂环羧酸类化合物的脱羧方法

  摘要：

  本发明涉及一种杂环羧酸类化合物的脱羧方法，将杂环羧酸类化合物溶于非质子性极性溶剂N,N‑二甲基甲酰胺，在85℃～150℃，有机酸作为催化剂的条件下进行脱羧。本发明相较于现有技术中的脱羧方法，反应得到的脱羧产物收率更高，且不需要使用昂贵的金属催化剂；同时，相较DMSO，本发明中的溶剂(DMF)更加稳定，高温下不易分解，还可以回收套用，降低了成本。本发明操作过程简单，零污染，绿色环保，具有很好的应用前景。

  公开号：

  CN109694343B
• 作为产物：
  描述：

  3-氯呋喃 、 二氧化碳 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以51%的产率得到3-chlorofuran-2-carboxylic acid
  参考文献：
  名称：

  Discovery and Structure−Activity Relationship of 3-Aryl-5-aryl-1,2,4-oxadiazoles as a New Series of Apoptosis Inducers and Potential Anticancer Agents

  摘要：

  We have identified 5-(3-chlorothiophen-2-yl)-3-(4-trifluoromethylphenyl)-1,2,4-oxadiazole (1d) as a novel apoptosis inducer through our caspase- and cell-based high-throughput screening assay. Compound 1d has good activity against several breast and colorectal cancer cell lines but is inactive against several other cancer cell lines. In a flow cytometry assay, treatment of T47D cells with 1d resulted in arrest of cells in the G, phase, followed by induction of apoptosis. SAR studies of 1d showed that the 3-phenyl group can be replaced by a pyridyl group, and a substituted five-member ring in the 5-position is important for activity. 5-(3-Chlorothiophen-2-yl)-3-(5-chloropyridin-2-yl)-1,2,4-oxadiazole (41) has been found to have in vivo activity in a MX-1 tumor model. Using a photoaffinity agent, the molecular target has been identified as TIP47, an IGF II receptor binding protein. Therefore, our cell-based chemical genetics approach for the discovery of apoptosis inducers can identify potential anticancer agents as well as their molecular targets.

  DOI：

  10.1021/jm050292k

文献信息

• Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：——

  公开号：US20030045546A1

  公开（公告）日：2003-03-06

  The present invention is directed to substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs thereof, represented by the Formula I: 1 wherein Ar 1 , Ar 3 , A, B and D are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代的3-芳基-5-芳基-[1,2,4]-噁二唑及其类似物，由以下式I表示： 1 其中Ar1，Ar3，A，B和D在此处定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生未受控制的异常细胞生长和扩散的细胞死亡。
• Identification of Non-Nucleoside Inhibitors of the Respiratory Syncytial Virus Polymerase Complex
  作者：Alberto Jiménez-Somarribas、Shuli Mao、Jeong-Joong Yoon、Marco Weisshaar、Robert M. Cox、Jose R. Marengo、Deborah G. Mitchell、Zachary P. Morehouse、Dan Yan、Ivan Solis、Dennis C. Liotta、Michael G. Natchus、Richard K. Plemper

  DOI：10.1021/acs.jmedchem.6b01568

  日期：2017.3.23

  Respiratory syncytial virus (RSV) represents a threat to infants, the elderly, and the immunocompromised. RSV entry blockers are in clinical trials, but escape mutations challenge their potential. In search of RSV inhibitors, we have integrated a signature resistance mutation into a recombinant RSV virus and applied the strain to high-throughput screening. Counterscreening of candidates returned 14

  呼吸道合胞病毒（RSV）对婴儿，老年人和免疫力低下者构成威胁。RSV进入阻滞剂正在临床试验中，但是逃逸突变挑战了其潜力。为了寻找RSV抑制剂，我们已经将特征抗性突变整合到重组RSV病毒中，并将该菌株应用于高通量筛选。对候选物的反筛选返回了从纳摩尔到低微摩尔范围内有活性的14支经确认的命中。在微型基因组测定中，所有受阻的RSV聚合酶活性均被阻止。根据活性选择化合物1a（GRP-74915）进行开发（EC 50= 0.21μM，选择性指数（SI）40）和支架。重新合成证实了该化合物的效力，它抑制了感染细胞中病毒RNA的合成。但是，代谢测试显示在小鼠肝细胞组分存在下半衰期很短。代谢物跟踪和化学精制结合3D定量的结构-活性关系模型，产生了类似物（即8n：EC 50 = 0.06μM，SI 500），为开发候选药物建立了平台。
• MET kinase inhibitors
  申请人：Borzilleri M. Robert

  公开号：US20070078140A1

  公开（公告）日：2007-04-05

  The present invention is directed to compounds having the formula I or II: including salts thereof, and methods for using them for the treatment of cancer.

  本发明涉及具有以下化学式I或II的化合物：包括其盐，并且使用它们用于治疗癌症的方法。
• Tetrazolinone herbicides
  申请人：NIHON BAYER AGROCHEM K.K.

  公开号：EP0695748A1

  公开（公告）日：1996-02-07

  Novel tetrazolinone derivatives of the formula:    wherein    R¹ represents alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy or phenyl which may be substituted,    R² represents alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy or phenyl which may be substituted,    R¹ and R² may form, together with the nitrogen atom to which R¹ and R² are bonded, a 5- or 6-membered heterocyclic ring, and said heterocyclic ring, may be fused with carbocyclic ring and/or may be substituted by C₁₋₄ alkyl, and    R³ represents 5-membered heterocyclic ring comprising hetero atom optionally selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as well as carbon atom, and said 5-membered heterocyclic ring may be optionally substituted by substituent (s) selected from the group consisting of halogen, benzyl, phenyl, halogen-substituted phenyl, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, C₁₋₄ alkylthio, C₁₋₄ alkyl-sulfonyl and C₃₋₈ cycloalkyl, processes for their preparation and their use as herbicides.

  式中的新型四唑啉酮衍生物： 其中 R¹ 代表可能被取代的烷基、卤代烷基、环烷基、烯基、卤代烯基、炔基、烷氧基或苯基、 R² 代表可被取代的烷基、卤代烷基、环烷基、烯基、卤代烯基、炔基、烷氧基或苯基、 R¹ 和 R² 可与 R¹ 和 R² 键合的氮原子一起形成 5 或 6 元杂环，且所述杂环可与碳环融合和/或可被 C₁₋₄ 烷基取代，以及 R³ 代表 5 元杂环，包含可选自氮原子、氧原子、硫原子和碳原子组成的组中的杂原子，且所述 5 元杂环可被可选自卤素组成的组中的取代基取代、苄基、苯基、卤素取代的苯基、C₁₋₄ 烷基、C₁₋₄ 烷氧基、C₁₋₄ 卤代烷基、C₁₋₄ 卤代烷氧基、C₁₋₄ 烷硫基、C₁₋₄ 烷磺酰基和 C₃₋₈ 环烷基、 它们的制备工艺及其作为除草剂的用途。
• SUBSTITUTED 3-ARYL-5-ARYL- 1,2,4]-OXADIAZOLES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF
  申请人：Cytovia, Inc.

  公开号：EP1406632A2

  公开（公告）日：2004-04-14