ethyl 2-(4-(2-hydroxyethyl)piperazine-1-carboxamido)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl 2-(4-(2-hydroxyethyl)piperazine-1-carboxamido)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate
• 英文别名: ethyl 2-({[4-(2-hydroxyethyl)piperazin-1-yl]carbonyl}amino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate；ethyl 2-[[4-(2-hydroxyethyl)piperazine-1-carbonyl]amino]-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate
• 化学式: C₁₇H₂₅N₃O₄S
• 分子量: 367.469
• InChiKey: BBINVMJRNLNOCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 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 反应 8.0h， 生成 ethyl 2-(4-(2-hydroxyethyl)piperazine-1-carboxamido)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate
  参考文献：
  名称：

  Synthesis of urea analogues bearing N-alkyl-N'-(thiophen-2-yl) scaffold and evaluation of their innate immune response to toll-like receptors

  摘要：

  Previous high throughput virtual screening of 10 million-compound and following cell based validation led to the discovery of a novel, nonlipopeptide-like chemotype ZINC 6662436, as toll-like receptor 2 (TLR2) agonists. In this report, compounds belonging to four areas of structural modification of ZINC6662436 were evaluated for biological activity using human HEK-Blue TLR2 reporter cells, and human THP-1 monocytic cells, yield SMU-C13 as an optimized, direct and high potent (EC50 = 160 nM) agonist of human TLR2. Moreover, preliminary mechanism studies indicated that SMU-C13 through activates TLR1 and TLR2 then stimulates the NF-kappa B activation to trigger the downstream cytokines, such as TNF-alpha and secreted alkaline phosphatase (SEAP). (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.067

文献信息

• Synthesis of urea analogues bearing N-alkyl-N'-(thiophen-2-yl) scaffold and evaluation of their innate immune response to toll-like receptors
  作者：Zhipeng Chen、Xiaohong Cen、Junjie Yang、Zhiman Lin、Meihuan Liu、Kui Cheng

  DOI：10.1016/j.ejmech.2019.02.067

  日期：2019.5

  Previous high throughput virtual screening of 10 million-compound and following cell based validation led to the discovery of a novel, nonlipopeptide-like chemotype ZINC 6662436, as toll-like receptor 2 (TLR2) agonists. In this report, compounds belonging to four areas of structural modification of ZINC6662436 were evaluated for biological activity using human HEK-Blue TLR2 reporter cells, and human THP-1 monocytic cells, yield SMU-C13 as an optimized, direct and high potent (EC50 = 160 nM) agonist of human TLR2. Moreover, preliminary mechanism studies indicated that SMU-C13 through activates TLR1 and TLR2 then stimulates the NF-kappa B activation to trigger the downstream cytokines, such as TNF-alpha and secreted alkaline phosphatase (SEAP). (C) 2019 Elsevier Masson SAS. All rights reserved.