5-(1H-pyrrol-1-yl)-2H-tetrazole | 1225021-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(1H-pyrrol-1-yl)-2H-tetrazole
• 英文别名: 5-pyrrol-1-yl-2H-tetrazole
• CAS: 1225021-31-7
• 化学式: C₅H₅N₅
• mdl: MFCD25956768
• 分子量: 135.128
• InChiKey: GFAVHNNCWRSTLY-UHFFFAOYSA-N

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：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(1H-pyrrol-1-yl)-2H-tetrazole 在 aluminum (III) chloride 、 溴 、 苄基三丁基氯化铵 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 1,2-二氯乙烷 、 mineral oil 为溶剂， 反应 26.25h， 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
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 5-氨基四氮唑 在 4-氯吡啶盐酸盐 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以63%的产率得到5-(1H-pyrrol-1-yl)-2H-tetrazole
  参考文献：
  名称：

  设计和合成基于吡咯的新型化学型及其作为选择性醛糖还原酶抑制剂的评估。羧酸部分与四唑之间存在生物等排的情况

  摘要：

  合成吡咯基-丙酸和丁酸衍生物1和2是为了研究与以前报道的吡咯基-乙酸化合物I（被发现是有效的醛糖还原酶抑制剂）相比，亚甲基链变化的影响。吡咯基四唑衍生物3 - 5制备成羧酸部分的非经典生物电子等排。另外，合成在两个芳环之间没有烷基链的吡咯基-四唑异构体6和7。制备的1 – 7的体外醛糖还原酶抑制活性估计化合物并与初始化合物（I）比较。总体而言，数据表明，所提出的化学型6和7是开发选择性醛糖还原酶抑制剂的有前途的先导化合物，旨在治疗糖尿病的长期并发症。

  DOI：

  10.1016/j.bmc.2010.02.010

文献信息

• Bis-pyrrolyl-tetrazolyl derivatives as hybrid polar compounds: A case of lipophilic functional bioisosterism with bis-acetamides
  作者：Maria Chatzopoulou、Ioannis D. Bonovolias、Ioannis Nicolaou、Vassilis J. Demopoulos、Ioannis S. Vizirianakis、Asterios S. Tsiftsoglou

  DOI：10.1016/j.ejmech.2012.01.041

  日期：2012.4

  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.
• Design and synthesis of novel series of pyrrole based chemotypes and their evaluation as selective aldose reductase inhibitors. A case of bioisosterism between a carboxylic acid moiety and that of a tetrazole
  作者：Kyriaki Pegklidou、Catherine Koukoulitsa、Ioannis Nicolaou、Vassilis J. Demopoulos

  DOI：10.1016/j.bmc.2010.02.010

  日期：2010.3

  study the effect of the variation of the methylene chain in comparison to the previously reported pyrrolyl-acetic acid compound I, which was found as potent aldose reductase inhibitor, while the pyrrolyl-tetrazole derivatives 3–5 were prepared as a non-classical bioisosteres of a carboxylic acid moiety. Also, pyrrolyl-tetrazole isomers 6 and 7 without an alkyl chain between the two aromatic rings were synthesized

  合成吡咯基-丙酸和丁酸衍生物1和2是为了研究与以前报道的吡咯基-乙酸化合物I（被发现是有效的醛糖还原酶抑制剂）相比，亚甲基链变化的影响。吡咯基四唑衍生物3 - 5制备成羧酸部分的非经典生物电子等排。另外，合成在两个芳环之间没有烷基链的吡咯基-四唑异构体6和7。制备的1 – 7的体外醛糖还原酶抑制活性估计化合物并与初始化合物（I）比较。总体而言，数据表明，所提出的化学型6和7是开发选择性醛糖还原酶抑制剂的有前途的先导化合物，旨在治疗糖尿病的长期并发症。