ethyl 5-hydroxy-5-<4,5-bis(4-methoxyphenyl)thiazole-2-yl>-2-oxo-3-pyrrolin-1-ylacetate

• 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
• 英文名称: ethyl 5-hydroxy-5-<4,5-bis(4-methoxyphenyl)thiazole-2-yl>-2-oxo-3-pyrrolin-1-ylacetate
• 英文别名: Ethyl 2-[2-[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]-2-hydroxy-5-oxopyrrol-1-yl]acetate
• 化学式: C₂₅H₂₄N₂O₆S
• 分子量: 480.541
• InChiKey: WMLBXUWKVXICIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-[4,5-二(4-甲氧基苯基)-2-噻唑基]-1H-吡咯-1-乙酸乙酯 在 水 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 ethyl 5-hydroxy-5-<4,5-bis(4-methoxyphenyl)thiazole-2-yl>-2-oxo-3-pyrrolin-1-ylacetate
  参考文献：
  名称：

  Photo-Stability of the New Antiplatelet Agent, KBT-3022 (Ethyl 2-(4,5-Bis(4-methoxyphenyl)thiazole-2-yl)pyrrol-1-ylacetate) in Aqueous Solutions Containing Acetonitrile.

  摘要：

  在高压汞灯的照射下，研究了 2-[4，5-双(4-甲氧基苯基)噻唑-2-基]吡咯-1-基乙酸乙酯（KBT-3022）在含有乙腈的水溶液中的光稳定性。其主要光降解产物被认为是 5-羟基-5-[4, 5-双（4-甲氧基苯基）噻唑-2-基]-2-氧代-3-吡咯啉-1-基乙酸乙酯。研究还发现，KBT-3022 在酸性和碱性水溶液中都会受热发生酯水解，但在室温（25°C）下 pH 值为 3-9 的范围内，水解作用可忽略不计。此外，它在高压汞灯下的光稳定性与在荧光灯下的光稳定性相当。因此，如果可以通过光动测定法确定光子的累积数量，则可以通过暴露于所有其他光源（包括漫射日光）来模拟 KBT-3022 在含乙腈的水溶液中的光稳定性。

  DOI：

  10.1248/cpb.40.3048

文献信息

• Photo-Stability of the New Antiplatelet Agent, KBT-3022 (Ethyl 2-(4,5-Bis(4-methoxyphenyl)thiazole-2-yl)pyrrol-1-ylacetate) in Aqueous Solutions Containing Acetonitrile.
  作者：Masahiro HANAMORI、Tsunemasa MIZUNO、Koichi AKIMOTO、Hiroshi NAKAGAWA

  DOI：10.1248/cpb.40.3048

  日期：——

  The photo-stability of ethyl 2-[4, 5-bis(4-methoxyphenyl)thiazole-2-yl]pyrrol-1-ylacetate, KBT-3022 in aqueous solutions containing acetonitrile was investigated under the light of a high pressure mercury lamp. Its main photo-degradation product was assumed to be ethyl 5-hydroxy-5-[4, 5-bis(4-methoxyphenyl)thiazole-2-yl]-2-oxo-3-pyrrolin-1-ylacetate. KBT-3022 was also found to undergo ester hydrolysis by heat in both acidic and basic aqueous solutions, but its hydrolysis was confirmed to be negligible in the range of pH 3-9 at room temperature (25°C). Further, its photo-stability with exposure to the high pressure mercury lamp was comparable to that with exposure to a fluorescent lamp. Therefore, it is considered feasible to simulate the photo-stability of KBT-3022 in aqueous solutions containing acetonitrile by exposure to all other light sources including diffuse daylight, if the cumulative number of photons of the light can be determined by actinometry.

  在高压汞灯的照射下，研究了 2-[4，5-双(4-甲氧基苯基)噻唑-2-基]吡咯-1-基乙酸乙酯（KBT-3022）在含有乙腈的水溶液中的光稳定性。其主要光降解产物被认为是 5-羟基-5-[4, 5-双（4-甲氧基苯基）噻唑-2-基]-2-氧代-3-吡咯啉-1-基乙酸乙酯。研究还发现，KBT-3022 在酸性和碱性水溶液中都会受热发生酯水解，但在室温（25°C）下 pH 值为 3-9 的范围内，水解作用可忽略不计。此外，它在高压汞灯下的光稳定性与在荧光灯下的光稳定性相当。因此，如果可以通过光动测定法确定光子的累积数量，则可以通过暴露于所有其他光源（包括漫射日光）来模拟 KBT-3022 在含乙腈的水溶液中的光稳定性。
• Wavelength Dependency and Mechanism of the Photo-Degradation of Ethyl 2-[4,5-Bis(4-methoxyphenyl)thiazole-2-yl]pyrrol-1-ylacetate (KBT-3022) in Solution.
  作者：Tsunemasa MIZUNO、Masahiro HANAMORI、Koichi AKIMOTO、Hiroshi NAKAGAWA、Katsumasa ARAKAWA

  DOI：10.1248/cpb.42.160

  日期：——

  The wavelength dependency and the mechanism of photo-oxidation of ethyl 2-[4, 5-bis(4-methoxyphenyl)thiazole-2-yl]pyrrol-1-ylacetate (KBT-3022) in solution were investigated. The wavelength contributing to the photo-degradation of KBT-3022 in a mixture of acetonitrile-H2O (1 : 1) was found to be the near ultraviolet region, between 400 and 270 nm.The photo-oxidation of KBT-3022 was enhanced by the presence of rose bengal, which generates singlet oxygen as a photosensitizer, and by the presence of D2O in which the lifetime of singlet oxygen is about 10 times longer than in H2O. On the other hand, photo-oxidation was inhibited by the presence of sodium azide, or 1, 4-diazabicyclo[2.2.2]octane, both of which are known to be singlet oxygen quenchers. These results suggest that KBT-3022 acts by itself as a photosensitizer in its own photo-oxidation. Thus, the photo-degradation of N-methylpyrrole was enhanced by the presence of KBT-3022. It is concluded from these results that KBT-3022 reacts with singlet oxygen to form KBT-3022 endo-peroxide intermediate, and then undergoes hydrolysis to afford 5-hydroxylactam (D2).

  研究了溶液中 2-[4，5-双（4-甲氧基苯基）噻唑-2-基]吡咯-1-基乙酸乙酯（KBT-3022）的波长依赖性和光氧化机理。发现 KBT-3022 在乙腈-H2O（1:1）混合物中发生光降解的波长是近紫外区，介于 400 纳米和 270 纳米之间。玫瑰红能产生单线态氧作为光敏剂，而 D2O 的存在则增强了 KBT-3022 的光氧化作用，因为 D2O 中单线态氧的寿命比 H2O 中长约 10 倍。另一方面，叠氮化钠或 1，4-二氮杂双环[2.2.2]辛烷的存在会抑制光氧化反应，这两种物质都是众所周知的单线态氧淬灭剂。这些结果表明，KBT-3022 在自身的光氧化过程中充当了光敏剂的角色。因此，KBT-3022 的存在增强了 N-甲基吡咯的光降解。从这些结果可以得出结论，KBT-3022 与单线态氧反应形成 KBT-3022 内过氧化物中间体，然后发生水解生成 5-羟基内酰胺（D2）。