ethyl 4-(4-fluorobenzoyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate | 151982-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-(4-fluorobenzoyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 151982-60-4
• 化学式: C₁₆H₁₆FNO₃
• 分子量: 289.306
• InChiKey: WBGJSKAJMAUASF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-fluorobenzoyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate 在 三乙基硅烷 、 sodium hydroxide 作用下， 以 乙醇 、 三氟乙酸 为溶剂， 反应 18.0h， 生成 4-[(4-fluorophenyl)methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of acetic acid derivatives of pyrrolo[1,2-c]imidazole

  摘要：

  Various acetic acid derivatives of pyrrolo[1,2-c]imidazole were prepared and evaluated for aldose reductase inhibitory activity. Most of the compounds inhibited aldose reductase isolated from rat lens in vitro and decreased sorbitol formation in sciatic nerves of diabetic rats in vivo. Of the test compounds, 2-carboxymethyl-6-ethyl-5,7-dimethyl-3-oxo-1(2H)-thioxo-1H-pyrrolo[1,2-c] imidazole 124 was found to be the most orally active aldose reductase inhibitor, with an inhibitory potency similar to that of AD-5467.

  DOI：

  10.1016/0223-5234(93)90016-8
• 作为产物：
  描述：

  3,5-二甲基-1H-吡咯-2-甲酸乙酯 、 对氟苯甲酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到ethyl 4-(4-fluorobenzoyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of acetic acid derivatives of pyrrolo[1,2-c]imidazole

  摘要：

  Various acetic acid derivatives of pyrrolo[1,2-c]imidazole were prepared and evaluated for aldose reductase inhibitory activity. Most of the compounds inhibited aldose reductase isolated from rat lens in vitro and decreased sorbitol formation in sciatic nerves of diabetic rats in vivo. Of the test compounds, 2-carboxymethyl-6-ethyl-5,7-dimethyl-3-oxo-1(2H)-thioxo-1H-pyrrolo[1,2-c] imidazole 124 was found to be the most orally active aldose reductase inhibitor, with an inhibitory potency similar to that of AD-5467.

  DOI：

  10.1016/0223-5234(93)90016-8

文献信息

• PYRROLE COMPOUND
  申请人：Kabushiki Kaisha Yakult Honsha

  公开号：EP2808324A1

  公开（公告）日：2014-12-03

  Provided is a highly safe and effective compound represented by the following general formula (1) or a salt thereof which acts on tubulin and has an anticancer effect, wherein Ar represents an aryl group or a heteroaryl group; Z1, Z2, Z3, and Z4 each independently represent CH, a nitrogen atom, an oxygen atom, or a sulfur atom; R1 represents a hydrogen atom, a halogen atom, an alkyl group, or the like; R2 and R3 are the same or different and each represent a hydrogen atom, a halogen atom, a carboxyl group, or the like; n units of R4 are the same or different and each represent a hydrogen atom, an alkyl group, or the like; and n represents a number of 0 to 4.

  本发明提供了一种由以下通式（1）代表的高度安全有效的化合物或其盐，该化合物作用于微管蛋白并具有抗癌效果，其中 Ar 代表芳基或杂芳基；Z1、Z2、Z3 和 Z4 各自独立地代表 CH、氮原子、氧原子或硫原子；R1 代表氢原子、卤素原子、烷基或类似物；R2 和 R3 相同或不同，各自代表氢原子、卤素原子、羧基或类似物；R4 的 n 个单元相同或不同，各自代表氢原子、烷基或类似物；以及 n 代表 0 至 4 的数字。
• US20140343017A1
  申请人：——

  公开号：US20140343017A1

  公开（公告）日：2014-11-20
• [EN] PYRROLE COMPOUND<br/>[FR] COMPOSÉ PYRROLE
  申请人：YAKULT HONSHA KK

  公开号：WO2013111831A1

  公开（公告）日：2013-08-01

  　チューブリンに作用して抗癌作用を有し、かつ、安全性及び有効の高い、下記一般式（１）で表される化合物又はその塩を提供することを目的とする。 （式中、Ａｒは、アリール基又はヘテロアリール基を示し、Ｚ１、Ｚ２、Ｚ３及びＺ４はそれぞれ独立してＣＨ、窒素原子、酸素原子又は硫黄原子を示し、Ｒ１は、水素原子、ハロゲン原子、アルキル基等を示し、Ｒ２及びＲ３は、同一又は異なって、水素原子、ハロゲン原子、カルボキシル基等を意味し、ｎ個のＲ４は、同一又は異なって、水素原子、アルキル基等を示し、ｎは０～４の数を示す。）
• Synthesis and aldose reductase inhibitory activity of acetic acid derivatives of pyrrolo[1,2-c]imidazole
  作者：I Yamawaki、Y Matsushita、N Asaka、K Ohmori、N Nomura、K Ogawa

  DOI：10.1016/0223-5234(93)90016-8

  日期：1993.1

  Various acetic acid derivatives of pyrrolo[1,2-c]imidazole were prepared and evaluated for aldose reductase inhibitory activity. Most of the compounds inhibited aldose reductase isolated from rat lens in vitro and decreased sorbitol formation in sciatic nerves of diabetic rats in vivo. Of the test compounds, 2-carboxymethyl-6-ethyl-5,7-dimethyl-3-oxo-1(2H)-thioxo-1H-pyrrolo[1,2-c] imidazole 124 was found to be the most orally active aldose reductase inhibitor, with an inhibitory potency similar to that of AD-5467.