5-((2-chloroquinolin-3-yl)methylene)thiazolidine-2,4-dione | 319454-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-((2-chloroquinolin-3-yl)methylene)thiazolidine-2,4-dione
• 英文别名: 2-Chloro-3-(2,4-dioxothiazolidin-5-ylidene-methyl)quinoline；5-[(2-chloroquinolin-3-yl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 319454-44-9
• 化学式: C₁₃H₇ClN₂O₂S
• 分子量: 290.73
• InChiKey: UIOFCEMFKABUAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-((2-chloroquinolin-3-yl)methylene)thiazolidine-2,4-dione 、 2-(4-哌啶)-1H-苯并咪唑 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到5-((2-(4-(1H-benzo[d]imidazol-2-yl)piperidino)-quinolin-3-yl)methylene)thiazolidine-2,4-dione
  参考文献：
  名称：

  Darsi, S. S. Praveen Kumar; Devi, B. Rama; Naidu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 1, p. 142 - 145

  摘要：

  DOI：
• 作为产物：
  描述：

  N-乙酰苯胺 在 三氯氧磷 作用下， 生成 5-((2-chloroquinolin-3-yl)methylene)thiazolidine-2,4-dione
  参考文献：
  名称：

  Ahsan, Mohamed Jawed; Kumar, Ajay; Kumar, Rajnish, Indian Journal of Heterocyclic Chemistry, 2021, vol. 31, # 3, p. 357 - 364

  摘要：

  DOI：

文献信息

• A facile regioselective 1,3-dipolar cycloaddition protocol for the synthesis of new class of quinolinyl dispiro heterocycles
  作者：Gopal Senthil Kumar、Rajendran Satheeshkumar、Werner Kaminsky、James Platts、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1016/j.tetlet.2014.08.036

  日期：2014.10

  The 1,3-dipolar cycloaddition reaction of azomethine ylides generated in situ from isatin and secondary amino acids with quinolinyl dipolarophiles in refluxing methanol afforded new class of quinolinyl dispiro heterocycles with multi hetero core units. The regio and stereochemistry of the product was unambiguously assigned by 1H, 13C, 2D NMR techniques and single crystal X-ray analysis. The structures

  在回流的甲醇中，由靛红和仲氨基酸与喹啉基双极性亲和剂就地生成的甲亚胺基亚基的1，3-偶极环加成反应提供了一类新的具有多个杂核单元的喹啉基双螺杂环。通过1 H，13 C，2D NMR技术和单晶X射线分析明确分配了产品的区域和立体化学。化合物的结构通过分子间氢键和分子内非共价相互作用的存在而得以稳定。
• L-Proline Catalyzed Synthesis of Novel 5-{[2-(2-phenylpiperazin-1-yl)quinolin] methylene}-2,4-dione Derivatives
  作者：S.S. Praveen Kumar Darsi、K. Shiva Kumar、B. Rama Devi、A. Naidu、P.K. Dubey

  DOI：10.2174/1570178611999140404113821

  日期：2014.6

  L-proline is found to be an efficient catalyst for the Knoevenagel condensation of 2-chloroquinoline-3- carboxaldehyde 1a-c with an active methylene compound i.e., 2,4-thazolidinedione 2 in IPA affording novel substituted olefins 3a-c. The latter products reacted with N-substituted-3-phenylpiperazine 4a-c in the presence of KF in DMF to afford the corresponding 5-[2-(2-phenylpiperazin-1-yl)quinolin]methylene}-2,4-dione derivatives 6a-i. Alternatively, 6ai were also synthesized from another reaction sequence 1 → 5 → 6. The structures of the synthesized compounds have been established on the basis of spectral and analytical data.

  研究发现，L-脯氨酸是一种高效催化剂，可用于 2-氯喹啉-3-甲醛 1a-c 与活性亚甲基化合物（即 2,4-噻唑烷二酮 2）在 IPA 中进行 Knoevenagel 缩合反应，生成新型取代烯烃 3a-c。后者与 N-取代-3-苯基哌嗪 4a-c 在 DMF 中的 KF 存在下反应，得到相应的 5-[2-（2-苯基哌嗪-1-基）喹啉]亚甲基}-2,4-二酮衍生物 6a-i。另外，6ai 也是由另一个反应序列 1 → 5 → 6 合成的。根据光谱和分析数据确定了合成化合物的结构。
• Telomerase inhibitors and methods of their use
  申请人：Geron Corporation

  公开号：US06518268B1

  公开（公告）日：2003-02-11

  Thiazolidinedione compounds, compositions, and methods of inhibiting telomerase activity in vitro and treatment of telomerase mediated conditions or diseases ex vivo and in vivo are provided. The methods, compounds and compositions of the invention may be employed alone, or in combination with other pharmacologically active agents in the treatment of conditions or diseases mediated by telomerase activity, such as in the treatment of cancer. Also disclosed are novel methods for assaying or screening for inhibitors of telomerase activity.

  本发明提供了噻唑烷二酮化合物、组合物以及抑制体外端粒酶活性和体内外端粒酶介导的疾病或病症的治疗方法。本发明的方法、化合物和组合物可以单独或与其他药理活性剂结合使用，用于治疗由端粒酶活性介导的疾病或病症，例如治疗癌症。此外，本发明还公开了用于测定或筛选抑制端粒酶活性的新方法。
• Dicationic Ionic Liquid Mediated Synthesis of 5-Arylidine-2,4-thiazolidinediones
  作者：Dhanaji V. Jawale、Umesh R. Pratap、Dinesh L. Lingampalle、Ramrao A. Mane

  DOI：10.1002/cjoc.201190192

  日期：2011.5

  AbstractAn efficient synthesis of 5‐arylidine‐2,4‐thiazolidinediones has been developed using dicationic ionic liquid as green medium and catalyst. This method performed well for the condensation of both aryl as well as heteryl aldehydes with 2,4‐thiazolidinedione and gave 5‐arylidine‐2,4‐thiazolidinediones with excellent yields.