1-[2-[6-[5-(2-Carboxypyrrol-1-yl)tetrazol-2-yl]hexyl]tetrazol-5-yl]pyrrole-2-carboxylic acid | 1370349-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-[2-[6-[5-(2-Carboxypyrrol-1-yl)tetrazol-2-yl]hexyl]tetrazol-5-yl]pyrrole-2-carboxylic acid
• CAS: 1370349-74-8
• 化学式: C₁₈H₂₀N₁₀O₄
• 分子量: 440.421
• InChiKey: CEJWQXSJEXHEFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  809.9±75.0 °C(predicted)
• 密度：
  1.63±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-[2-[6-[5-(2-Carboxypyrrol-1-yl)tetrazol-2-yl]hexyl]tetrazol-5-yl]pyrrole-2-carboxylic acid 、 甲胺 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以177 mg的产率得到N-methyl-1-[2-[6-[5-[2-(methylcarbamoyl)pyrrol-1-yl]tetrazol-2-yl]hexyl]tetrazol-5-yl]pyrrole-2-carboxamide
  参考文献：
  名称：

  Bis-pyrrolyl-tetrazolyl derivatives as hybrid polar compounds: A case of lipophilic functional bioisosterism with bis-acetamides

  摘要：

  Based on previous studies on bis-acetamides that act as hybrid polar compounds to induce leukemia cell differentiation, an attempt was made to bioisosterically replace the amide moiety with the lipophilic non-classical bioisostere tetrazole. A pyrrole group was also included in the molecule in order to retain the hydrogen bond donor capability. Thus, by linking the two polar ring systems with a highly lipophilic methylene chain compounds 2-4 were synthesized and assessed for their anti-proliferative activity in combination with their ability to induce murine erythroleukemia (MEL) cell differentiation. Furthermore, an initial investigation of the structure activity relation points for the active compound 3 was undertaken by synthesizing compound 5 (a p-xylene analog) and compound 8 (a methylamidopyrrolyl analog). All compounds caused a dose-dependent inhibition of MEL cell growth but to a different extent. Compound 3 (1,6-bis[5-(1H-pyrrol-1-yl)-2H-tetrazol-2-yl]hexane) promoted erythroid differentiation in a fifty-fold lower concentration than hexamethylenebisacetamide (HMBA). Though induction of differentiation was to a lesser extent than HMBA, it caused accumulation of 80% Hb-producing cells as compared to that produced by HMBA, leading to differentiation-depended cell growth inhibition equal to that of HMBA after 96 h in culture. Compound 3 represents a potent inducer of hemoglobin gene activation in leukemic cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.041
• 作为产物：
  描述：

  1-[1-[2-[6-[5-(2-Acetylpyrrol-1-yl)tetrazol-2-yl]hexyl]tetrazol-5-yl]pyrrol-2-yl]ethanone 在 溴 、 sodium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 1-[2-[6-[5-(2-Carboxypyrrol-1-yl)tetrazol-2-yl]hexyl]tetrazol-5-yl]pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Bis-pyrrolyl-tetrazolyl derivatives as hybrid polar compounds: A case of lipophilic functional bioisosterism with bis-acetamides

  摘要：

  Based on previous studies on bis-acetamides that act as hybrid polar compounds to induce leukemia cell differentiation, an attempt was made to bioisosterically replace the amide moiety with the lipophilic non-classical bioisostere tetrazole. A pyrrole group was also included in the molecule in order to retain the hydrogen bond donor capability. Thus, by linking the two polar ring systems with a highly lipophilic methylene chain compounds 2-4 were synthesized and assessed for their anti-proliferative activity in combination with their ability to induce murine erythroleukemia (MEL) cell differentiation. Furthermore, an initial investigation of the structure activity relation points for the active compound 3 was undertaken by synthesizing compound 5 (a p-xylene analog) and compound 8 (a methylamidopyrrolyl analog). All compounds caused a dose-dependent inhibition of MEL cell growth but to a different extent. Compound 3 (1,6-bis[5-(1H-pyrrol-1-yl)-2H-tetrazol-2-yl]hexane) promoted erythroid differentiation in a fifty-fold lower concentration than hexamethylenebisacetamide (HMBA). Though induction of differentiation was to a lesser extent than HMBA, it caused accumulation of 80% Hb-producing cells as compared to that produced by HMBA, leading to differentiation-depended cell growth inhibition equal to that of HMBA after 96 h in culture. Compound 3 represents a potent inducer of hemoglobin gene activation in leukemic cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.041