(4-氧代-6,7-二氢-环戊二烯并[4,5]噻吩并[2,3-d]嘧啶-3-基)乙酸乙酯 | 433702-79-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (4-氧代-6,7-二氢-环戊二烯并[4,5]噻吩并[2,3-d]嘧啶-3-基)乙酸乙酯
• 英文名称: ethyl 2-(4-oxo-4,5,6,7-tetrahydro-3H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-3-yl)acetate
• 英文别名: ethyl 2-(12-oxo-7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(8),2(6),9-trien-11-yl)acetate
• CAS: 433702-79-5
• 化学式: C₁₃H₁₄N₂O₃S
• 分子量: 278.332
• InChiKey: BSNPBSNWKULNJU-UHFFFAOYSA-N

物化性质

• 沸点：
  478.8±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-氧代-6,7-二氢-环戊二烯并[4,5]噻吩并[2,3-d]嘧啶-3-基)乙酸乙酯 在 肼 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 24.0h， 生成 N'-[(4-cyanophenyl)methylene]-(4-oxo-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazone
  参考文献：
  名称：

  Synthesis and anti-tumor activities of N′-benzylidene-2-(4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazone derivatives

  摘要：

  A compound with a cyclic thienopyrimidine moiety and an aceto-hydrazone moiety in its chemical structure was discovered in a cell-based screening to have noticeable cytotoxicity on several tumor cell lines. A total of 38 derivatives of this compound were synthesized at five steps with high yields. These compounds were tested in standard MTT assays, and several compounds exhibited improved cytotoxic activities. The most potent compounds have IC50 values of 10-20 mu M on A549, HeLa, and MBA-MD-231 tumor cells. Flow cytometry analysis of several active compounds and subsequent examination of caspase activation indicate that they induce caspase-dependent apoptosis in tumor cells. In addition, these compounds do not have obvious effect on a normal cell line HEK-293T, demonstrating the desired selectivity against tumor cells. Results from a fluorescence polarization-based in vitro binding assay indicate that this class of compounds does not significantly interrupt the interactions between Mcl-1 and Bid. Their cytotoxicity is achieved presumably through other mechanisms. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.061
• 作为产物：
  描述：

  2-氨基-5,6-二氢-4H-环戊并[b]噻吩-3-甲酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 49.5h， 生成 (4-氧代-6,7-二氢-环戊二烯并[4,5]噻吩并[2,3-d]嘧啶-3-基)乙酸乙酯
  参考文献：
  名称：

  Synthesis and anti-tumor activities of N′-benzylidene-2-(4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazone derivatives

  摘要：

  A compound with a cyclic thienopyrimidine moiety and an aceto-hydrazone moiety in its chemical structure was discovered in a cell-based screening to have noticeable cytotoxicity on several tumor cell lines. A total of 38 derivatives of this compound were synthesized at five steps with high yields. These compounds were tested in standard MTT assays, and several compounds exhibited improved cytotoxic activities. The most potent compounds have IC50 values of 10-20 mu M on A549, HeLa, and MBA-MD-231 tumor cells. Flow cytometry analysis of several active compounds and subsequent examination of caspase activation indicate that they induce caspase-dependent apoptosis in tumor cells. In addition, these compounds do not have obvious effect on a normal cell line HEK-293T, demonstrating the desired selectivity against tumor cells. Results from a fluorescence polarization-based in vitro binding assay indicate that this class of compounds does not significantly interrupt the interactions between Mcl-1 and Bid. Their cytotoxicity is achieved presumably through other mechanisms. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.061

文献信息

• [EN] COMPOUNDS FOR TREATING RESPIRATORY SYNCYTIAL VIRUS INFECTIONS<br/>[FR] COMPOSÉS POUR LE TRAITEMENT D'INFECTIONS PAR LE VIRUS RESPIRATOIRE SYNCYTIAL
  申请人：BIOTA PHARMACEUTICALS INC

  公开号：WO2016133888A1

  公开（公告）日：2016-08-25

  The present disclosure provides compounds useful in the treatment of viral infections, in particular respiratory syncytial viral (RSV) infections. In one aspect of the invention, there is provided compounds of the formula (I): These an additional compounds are provided which are advantageously used in methods of treating RSV wherein an effective amount of a compound or pharmaceutical compound thereof is administered to a patient in need thereof. Processes for preparing the compounds and intermediates used in their preparation are also provided.

  本公开提供了在治疗病毒感染，特别是呼吸道合胞病毒（RSV）感染方面有用的化合物。在发明的一个方面，提供了一种具有以下结构的化合物（I）：此外，还提供了其他有益的化合物，这些化合物在治疗RSV的方法中得到优越应用，其中将有效量的化合物或其药用化合物给予需要的患者。还提供了制备这些化合物和用于制备它们的中间体的方法。
• Synthesis and anti-tumor activities of N′-benzylidene-2-(4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetohydrazone derivatives
  作者：Jiangping Lou、Zhen Liu、Yan Li、Mi Zhou、Zhengxi Zhang、Shu Zheng、Renxiao Wang、Jian Li

  DOI：10.1016/j.bmcl.2011.09.061

  日期：2011.11

  A compound with a cyclic thienopyrimidine moiety and an aceto-hydrazone moiety in its chemical structure was discovered in a cell-based screening to have noticeable cytotoxicity on several tumor cell lines. A total of 38 derivatives of this compound were synthesized at five steps with high yields. These compounds were tested in standard MTT assays, and several compounds exhibited improved cytotoxic activities. The most potent compounds have IC50 values of 10-20 mu M on A549, HeLa, and MBA-MD-231 tumor cells. Flow cytometry analysis of several active compounds and subsequent examination of caspase activation indicate that they induce caspase-dependent apoptosis in tumor cells. In addition, these compounds do not have obvious effect on a normal cell line HEK-293T, demonstrating the desired selectivity against tumor cells. Results from a fluorescence polarization-based in vitro binding assay indicate that this class of compounds does not significantly interrupt the interactions between Mcl-1 and Bid. Their cytotoxicity is achieved presumably through other mechanisms. (C) 2011 Elsevier Ltd. All rights reserved.