2-甲氧基亚甲基-4-环戊烯-1,3-二酮 | 1043483-40-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 中文名称: 2-甲氧基亚甲基-4-环戊烯-1,3-二酮
• 英文名称: 2-methoxymethylene-4-cyclopentene-1,3-dione
• 英文别名: 2-(Methoxymethylidene)cyclopent-4-ene-1,3-dione；2-(methoxymethylidene)cyclopent-4-ene-1,3-dione
• CAS: 1043483-40-4
• 化学式: C₇H₆O₃
• 分子量: 138.123
• InChiKey: ASDNIRZULDMWLI-UHFFFAOYSA-N

物化性质

• 沸点：
  281.0±39.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲氧基亚甲基-4-环戊烯-1,3-二酮 、 (2S)-3-methoxy-1-(2-nitroimidazol-1-yl)-prop-2-yl 4'-aminobenzoate 以 乙醇 为溶剂， 反应 5.0h， 以54.9%的产率得到TX-2044
  参考文献：
  名称：

  Design of antiangiogenic hypoxic cell radiosensitizers: 2-Nitroimidazoles containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety

  摘要：

  We designed chiral 2-nitroimidazole derivatives containing a 2-aminomethylene- 4-cyclopentene-1,3-dione moiety as antiangiogenic hypoxic cell radiosensitizers. Based on results of molecular orbital calculations, the 2-aminomethylene-4-cyclopentene1,3-dione moiety is expected to show high electrophilicity comparable to that of the 2-methylene-4-cyclopentene-1,3-dione moiety included in TX-1123 and tyrphostin AG17. We evaluated the antiangiogenic and radiosensitizing effects of the new compounds, along with other biological properties including their activities as hypoxic cytotoxicities and protein tyrosine kinase (PTK) inhibitory activities. Among the compounds tested, 5 (TX-2036) proved to be the strongest antiangiogenic hypoxic cell radiosensitizer. All the other chiral 2-nitroimidazole derivatives having 2-aminomethylene-4-cyclopentene-1,3-dione moiety tested were also antiangiogenic hypoxic cell radiosensitizers. The PTK inhibitory activity of 5 (TX-2036) showed this to be a promising and potent EGFR kinase inhibitor, having an IC50 value of lower than 2 mu M. This compound also was an Flt-1 kinase inhibitor having an IC50 value of lower than 20 mu M. Our results show that these chiral 2- nitroimidazole derivatives that contain the 2- aminomethylene-4- cyclopentene1,3-dione moiety as a potent antiangiogenic pharmacophoric descriptor are promising lead candidates for the development of antiangiogenic hypoxic cell radiosensitizers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.041
• 作为产物：
  描述：

  4-环戊烯-1,3-二酮 、 原甲酸三甲酯 在 乙酸酐 、 zinc(II) chloride 作用下， 反应 6.0h， 以52%的产率得到2-甲氧基亚甲基-4-环戊烯-1,3-二酮
  参考文献：
  名称：

  Design of antiangiogenic hypoxic cell radiosensitizers: 2-Nitroimidazoles containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety

  摘要：

  We designed chiral 2-nitroimidazole derivatives containing a 2-aminomethylene- 4-cyclopentene-1,3-dione moiety as antiangiogenic hypoxic cell radiosensitizers. Based on results of molecular orbital calculations, the 2-aminomethylene-4-cyclopentene1,3-dione moiety is expected to show high electrophilicity comparable to that of the 2-methylene-4-cyclopentene-1,3-dione moiety included in TX-1123 and tyrphostin AG17. We evaluated the antiangiogenic and radiosensitizing effects of the new compounds, along with other biological properties including their activities as hypoxic cytotoxicities and protein tyrosine kinase (PTK) inhibitory activities. Among the compounds tested, 5 (TX-2036) proved to be the strongest antiangiogenic hypoxic cell radiosensitizer. All the other chiral 2-nitroimidazole derivatives having 2-aminomethylene-4-cyclopentene-1,3-dione moiety tested were also antiangiogenic hypoxic cell radiosensitizers. The PTK inhibitory activity of 5 (TX-2036) showed this to be a promising and potent EGFR kinase inhibitor, having an IC50 value of lower than 2 mu M. This compound also was an Flt-1 kinase inhibitor having an IC50 value of lower than 20 mu M. Our results show that these chiral 2- nitroimidazole derivatives that contain the 2- aminomethylene-4- cyclopentene1,3-dione moiety as a potent antiangiogenic pharmacophoric descriptor are promising lead candidates for the development of antiangiogenic hypoxic cell radiosensitizers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.041

文献信息

• Design of antiangiogenic hypoxic cell radiosensitizers: 2-Nitroimidazoles containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety
  作者：Yoshihiro Uto、Hideko Nagasawa、Cheng-Zhe Jin、Shinichi Nakayama、Ayako Tanaka、Saori Kiyoi、Hitomi Nakashima、Mariko Shimamura、Seiichi Inayama、Tomoya Fujiwara、Yoshio Takeuchi、Yoshimasa Uehara、Kenneth L. Kirk、Eiji Nakata、Hitoshi Hori

  DOI：10.1016/j.bmc.2008.04.041

  日期：2008.6

  We designed chiral 2-nitroimidazole derivatives containing a 2-aminomethylene- 4-cyclopentene-1,3-dione moiety as antiangiogenic hypoxic cell radiosensitizers. Based on results of molecular orbital calculations, the 2-aminomethylene-4-cyclopentene1,3-dione moiety is expected to show high electrophilicity comparable to that of the 2-methylene-4-cyclopentene-1,3-dione moiety included in TX-1123 and tyrphostin AG17. We evaluated the antiangiogenic and radiosensitizing effects of the new compounds, along with other biological properties including their activities as hypoxic cytotoxicities and protein tyrosine kinase (PTK) inhibitory activities. Among the compounds tested, 5 (TX-2036) proved to be the strongest antiangiogenic hypoxic cell radiosensitizer. All the other chiral 2-nitroimidazole derivatives having 2-aminomethylene-4-cyclopentene-1,3-dione moiety tested were also antiangiogenic hypoxic cell radiosensitizers. The PTK inhibitory activity of 5 (TX-2036) showed this to be a promising and potent EGFR kinase inhibitor, having an IC50 value of lower than 2 mu M. This compound also was an Flt-1 kinase inhibitor having an IC50 value of lower than 20 mu M. Our results show that these chiral 2- nitroimidazole derivatives that contain the 2- aminomethylene-4- cyclopentene1,3-dione moiety as a potent antiangiogenic pharmacophoric descriptor are promising lead candidates for the development of antiangiogenic hypoxic cell radiosensitizers. (C) 2008 Elsevier Ltd. All rights reserved.