4,5-dibromo-1-methyl-1H-pyrrol-2-carbaldehyde | 33694-80-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-dibromo-1-methyl-1H-pyrrol-2-carbaldehyde
• 英文别名: 1-methyl-2-formyl-4,5-dibromopyrrole；4,5-dibromo-1-methyl-pyrrole-2-carbaldehyde；4,5-Dibrom-2-formyl-1-methyl-pyrrol；4,5-dibromo-1-methyl-1H-pyrrole-2-carbaldehyde；4,5-dibromo-1-methylpyrrole-2-carbaldehyde
• CAS: 33694-80-3
• 化学式: C₆H₅Br₂NO
• 分子量: 266.92
• InChiKey: IVRVZOTUFSXMCV-UHFFFAOYSA-N

物化性质

• 沸点：
  316.7±37.0 °C(Predicted)
• 密度：
  2.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,5-dibromo-1-methyl-1H-pyrrol-2-carbaldehyde 在 二甲基亚砜 、 2-碘酰基苯甲酸 作用下， 以 乙醇 为溶剂， 生成 tert-butyl [4-(4,5-dibromo-1-methyl-1H-pyrrol-2-yl)-1H-imidazo[4,5-c]pyridin-2-yl]carbamate
  参考文献：
  名称：

  Ageladine A类似物的合成及其基质金属蛋白酶-12抑制活性。

  摘要：

  通过使用我们之前探索过的天然阿格拉定A的总合成路线，可以完成37种阿格拉定A类似物的合成。从使用新型类似物进行的基质金属蛋白酶12（MMP-12）抑制活性分析中，可以明显看出吡咯环2位上的卤素原子对于抑制活性是必不可少的，并且引入了溴原子吡咯环的4-位上的杂合对于产生有效的活性非常有效。另外，吡咯环与咪唑环的交换在增加活性方面极其有效，并且发现由此获得的类似物29显示出比天然阿格拉德汀A强约4倍的有效活性。

  DOI：

  10.1248/cpb.59.579
• 作为产物：
  描述：

  N-甲基-2-吡咯甲醛 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 生成 4,5-dibromo-1-methyl-1H-pyrrol-2-carbaldehyde
  参考文献：
  名称：

  Synthesis and evaluation of novel marine bromopyrrole alkaloid-based hybrids as anticancer agents

  摘要：

  A series of twenty three novel hybrids of marine bromopyrrole alkaloids with chalcone, isoxazole and flavone structural features were synthesized and evaluated for in vitro anticancer activity by MTT assay against five human cancer cell lines. Among the synthesized chalcones, hybrids 4a and 4h (IC50 range: 0.18 mu M-12.00 mu M) showed anticancer activity against all the tested cancer cell lines. Promising cytotoxic activities were exhibited by flavones derivatives, 5a and 5b (0.41 mu M-1.28 mu M) against cell lines PA1 and KB403. Isoxazole hybrids, 6b-6e selectively inhibited oral and mouth cancer cell line KB403, among which 6c (IC50 = 2.45 mu M) was found to be most active. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.029

文献信息

• An Improved Method for the Preparation of 1-Methyl-2-formyl-5-bromopyrrole
  作者：Roderick Hai-Ying He、Xi-Kui Jiang

  DOI：10.1039/a803388i

  日期：——

  1-Methyl-2-formyl-5-bromopyrrole 1 was prepared in 48% total yield by initial bromination of the intermediate 1-methyl-2-(5,5-dimethyl-1,3-dioxan-2-yl)pyrrole 5 with N-bromosuccinimide to give the intermediate 1-methyl-2-(5,5-dimethyl-1,3-dioxan-2-yl)-5-bromopyrrole 6, which was finally hydrolyzed to the product 1.

  通过中间体 1-甲基-2-(5,5-二甲基-1,3-二恶烷-2-基)吡咯 5 的初始溴化，以 48% 的总收率制备 1-甲基-2-甲酰基-5-溴吡咯 1与N-溴代琥珀酰亚胺反应得到中间体1-甲基-2-(5,5-二甲基-1,3-二恶烷-2-基)-5-溴吡咯6，最终水解为产物1。
• Synthesis and matrix metalloproteinase (MMP)-12 inhibitory activity of ageladine A and its analogs
  作者：Naoki Ando、Shiro Terashima

  DOI：10.1016/j.bmcl.2007.06.005

  日期：2007.8

  Ageladine A (1) and its analogs 2-10 were expeditiously synthesized by featuring the biosynthetic route proposed for I (for 1-10) and by employing 2-(N-t-butoxycarbonylamino)imidazol-4-carbaldehyde as the starting material (for 1-8). From MMP-12 inhibitory activity assay, it appeared evident that the two bromine atoms and the three NH groups (1-NH, 14-NH, and 15-NH2) were indispensable for 1 to exhibit excellent activity. (c) 2007 Elsevier Ltd. All rights reserved.
• Kaye, Perry T.; Macrae, Robert; Meakins, G. Denis, Journal of the Chemical Society. Perkin transactions II, 1980, p. 1631 - 1635
  作者：Kaye, Perry T.、Macrae, Robert、Meakins, G. Denis、Patterson, Colin H.

  DOI：——

  日期：——
• Synthesis and evaluation of novel marine bromopyrrole alkaloid-based hybrids as anticancer agents
  作者：Rajesh A. Rane、Niteshkumar U. Sahu、Shweta D. Gutte、Anand A. Mahajan、Chetan P. Shah、Pavankumar Bangalore

  DOI：10.1016/j.ejmech.2013.03.029

  日期：2013.5

  A series of twenty three novel hybrids of marine bromopyrrole alkaloids with chalcone, isoxazole and flavone structural features were synthesized and evaluated for in vitro anticancer activity by MTT assay against five human cancer cell lines. Among the synthesized chalcones, hybrids 4a and 4h (IC50 range: 0.18 mu M-12.00 mu M) showed anticancer activity against all the tested cancer cell lines. Promising cytotoxic activities were exhibited by flavones derivatives, 5a and 5b (0.41 mu M-1.28 mu M) against cell lines PA1 and KB403. Isoxazole hybrids, 6b-6e selectively inhibited oral and mouth cancer cell line KB403, among which 6c (IC50 = 2.45 mu M) was found to be most active. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis and Matrix Metalloproteinase-12 Inhibitory Activity of Ageladine A Analogs
  作者：Naoki Ando、Shiro Terashima

  DOI：10.1248/cpb.59.579

  日期：——

  Synthesis of the 37 ageladine A analogs was accomplished by employing the total synthetic route of natural ageladine A previously explored by us. From the matrix metalloproteinase-12 (MMP-12) inhibitory activity assay carried out using the novel analogs, it appeared evident that the halogen atom at the 2-position of pyrrole ring was essential for the inhibitory activity and that the introduction of

  通过使用我们之前探索过的天然阿格拉定A的总合成路线，可以完成37种阿格拉定A类似物的合成。从使用新型类似物进行的基质金属蛋白酶12（MMP-12）抑制活性分析中，可以明显看出吡咯环2位上的卤素原子对于抑制活性是必不可少的，并且引入了溴原子吡咯环的4-位上的杂合对于产生有效的活性非常有效。另外，吡咯环与咪唑环的交换在增加活性方面极其有效，并且发现由此获得的类似物29显示出比天然阿格拉德汀A强约4倍的有效活性。