ethyl 5-(4-cyanophenyl)-2-furancarboxylate | 299203-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 5-(4-cyanophenyl)-2-furancarboxylate
• 英文别名: Ethyl 5-(4-cyanophenyl)furan-2-carboxylate
• CAS: 299203-59-1
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: MJEIEKUEKCZSLX-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C
• 沸点：
  416.0±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-cyanophenyl)-2-furancarboxylate 在 盐酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 36.0h， 生成 5-[4-[(N-isopropyl)amidino]phenyl]-2-furancarboxylic acid
  参考文献：
  名称：

  Aromatic Extended Bisamidines: Synthesis, Inhibition of Topoisomerases, and Anticancer Cytotoxicity in Vitro

  摘要：

  A series of four aromatic extended bisamidines (12-15) differing in the nature of their terminal basic side chains were synthesized and evaluated for cytotoxic activity in MCF-7 cultured breast cancer cells. The concentrations of 12, 13, 14, and 15 needed to inhibit [H-3]thymidine incorporation Into DNA by 50% (IC50) were found to be 53 muM, 85 muM, 77 muM, and 97 muM, respectively. To test whether cytotoxic properties were related to DNA-binding and topoisomerase action, the bisamidines 12-15 were evaluated in a cell-free system. Data from the ethidium displacement assay showed that bisamidines 12-15 have significant affinity for DNA and show moderate specificity for AT base pairs. In the topoisomerase II assay, the relaxation of DNA was inhibited with all four drugs and the extent of inhibition was directly proportional to the drug concentration. This suggests that DNA binding may be implicated in the cytotoxicity of these bisamidines, possibly by inhibiting interactions between topoisomerase II and their DNA targets.

  DOI：

  10.1002/1521-4184(200107)334:7<235::aid-ardp235>3.0.co;2-#
• 作为产物：
  描述：

  糠酸（呋喃甲酸） 在 盐酸 、 N,N'-羰基二咪唑 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 21.0h， 生成 ethyl 5-(4-cyanophenyl)-2-furancarboxylate
  参考文献：
  名称：

  Aromatic Extended Bisamidines: Synthesis, Inhibition of Topoisomerases, and Anticancer Cytotoxicity in Vitro

  摘要：

  A series of four aromatic extended bisamidines (12-15) differing in the nature of their terminal basic side chains were synthesized and evaluated for cytotoxic activity in MCF-7 cultured breast cancer cells. The concentrations of 12, 13, 14, and 15 needed to inhibit [H-3]thymidine incorporation Into DNA by 50% (IC50) were found to be 53 muM, 85 muM, 77 muM, and 97 muM, respectively. To test whether cytotoxic properties were related to DNA-binding and topoisomerase action, the bisamidines 12-15 were evaluated in a cell-free system. Data from the ethidium displacement assay showed that bisamidines 12-15 have significant affinity for DNA and show moderate specificity for AT base pairs. In the topoisomerase II assay, the relaxation of DNA was inhibited with all four drugs and the extent of inhibition was directly proportional to the drug concentration. This suggests that DNA binding may be implicated in the cytotoxicity of these bisamidines, possibly by inhibiting interactions between topoisomerase II and their DNA targets.

  DOI：

  10.1002/1521-4184(200107)334:7<235::aid-ardp235>3.0.co;2-#

文献信息

• NOVEL COMPOUND AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  申请人：AUTOPHAGYSCIENCES INC.

  公开号：US20210078987A1

  公开（公告）日：2021-03-18

  The present disclosure relates to a novel compound and a pharmaceutical composition comprising the same. The compound according to the present disclosure has effects for activating autophagy, and thus can be valuably used for preventing or treating diseases associated with autophagy regulation.

  本公开涉及一种新化合物和包含该化合物的药物组合物。根据本公开的化合物具有激活自噬的效果，因此可以用于预防或治疗与自噬调节相关的疾病。
• Synthesis and biological evaluation of new cyclic amidine analogs of chlorambucil
  作者：Anna Bielawska、Krzysztof Bielawski、Anna Muszyńska

  DOI：10.1016/j.farmac.2003.12.002

  日期：2004.2

  compounds were more active than chlorambucil. The degree to which these compounds inhibited cell growth breast cancer cells was directly correlated to DNA-binding affinity. These studies indicate that cyclic amidine analogs of chlorambucil are a potent catalytic inhibitor of topoisomerase II but not topoisomerase I. The highest degree of DNA binding and cytotoxicity in both MDA-MB-231 and MCF-7 breast

  合成了苯丁酸氮芥的许多新型环状am类似物，并检查了它们在乳腺癌细胞培养物中的细胞毒性以及对拓扑异构酶I和II的抑制作用。使用3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物测定并抑制[（3）H]-胸苷掺入DNA的MDA-MB-中这些化合物的细胞毒性评估231和MCF-7乳腺癌细胞证明这些化合物比苯丁酸氮芥更具活性。这些化合物抑制乳腺癌细胞生长的程度与DNA结合亲和力直接相关。这些研究表明，苯丁酸氮芥的环状am类似物是拓扑异构酶II的有效催化抑制剂，但不是拓扑异构酶I的有效催化抑制剂。
• Efficient Synthesis of Functionalized Organozinc Compounds by the Direct Insertion of Zinc into Organic Iodides and Bromides
  作者：Arkady Krasovskiy、Vladimir Malakhov、Andrei Gavryushin、Paul Knochel

  DOI：10.1002/anie.200601450

  日期：2006.9.11
• [EN] PROCESS FOR MAKING ORGANOBORON COMPOUNDS, PRODUCTS OBTAINABLE THEREBY, AND THEIR USE<br/>[FR] PROCÉDÉ DE FABRICATION DE COMPOSÉS ORGANO-BORÉS, PRODUITS OBTENUS ET LEUR UTILISATION
  申请人：HAAG BENJAMIN

  公开号：WO2012085170A3

  公开（公告）日：2012-10-26
• Facile synthesis of tetracyclic azepine and oxazocine derivatives and their potential as MAPKAP-K2 (MK2) inhibitors
  作者：Ashwin U. Rao、Dong Xiao、Xianhai Huang、Wei Zhou、James Fossetta、Dan Lundell、Fang Tian、Prashant Trivedi、Robert Aslanian、Anandan Palani

  DOI：10.1016/j.bmcl.2011.11.113

  日期：2012.1

  Facile synthesis of two new series of tetracyclic azepine and oxazocine analogs is described. These analogs were evaluated for their potential as MAPKAP-K2 (MK2) inhibitors and several were found to be potent at inhibiting MK2 with a non-ATP competitive binding mode. Published by Elsevier Ltd.