4,5-二溴-1H-吡咯-2-羧肼 | 50371-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4,5-二溴-1H-吡咯-2-羧肼
• 英文名称: 4,5-dibromo-1H-pyrrole-2-carbohydrazide
• 英文别名: 4,5-dibromopyrrole-2-carbohydrazide；4,5-dibromo-pyrrole-2-carboxylic acid hydrazide
• CAS: 50371-65-8
• 化学式: C₅H₅Br₂N₃O
• 分子量: 282.922
• InChiKey: XCTQDTHKSVMBDB-UHFFFAOYSA-N

物化性质

• 熔点：
  209-211°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4,5-二溴-1H-吡咯-2-羧肼 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 2-(4,5-dibromo-1H-pyrrol-2-yl)-5-ethylsulfanyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and evaluation of novel 1,3,4-oxadiazole derivatives of marine bromopyrrole alkaloids as antimicrobial agent

  摘要：

  In an attempt to identify new potential lead as antimicrobial agent, twenty hybrids of marine bromopyrrole alkaloids with 1,3,4-oxadiazole were designed based on molecular hybridization technique and synthesized. Synthesized molecules were evaluated for their antibacterial, antifungal and antitubercular activities. Hybrids 5d, 5i, 5j and 5k exhibited equivalent antibacterial activity (MIC of 1.56 mu g/mL) compared with standard drug ciprofloxacin against Staphylococcus aureus and Escherichia coli. Equal antifungal activity (MIC of 1.56 mu g/mL) was shown by of hybrids 5j, 5k and 7d compared with standard Amphotericin-B. The inhibition of Mycobacterium tuberculosis at concentrations as low as 1.6 and 1.5 mu g/mL by compounds 5f and 7d respectively indicates that these compounds can act as leads for development of newer anti-TB compounds. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.061
• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 在 溴 、 一水合肼 作用下， 以 N-甲基乙酰胺 、 水 、 溶剂黄146 为溶剂， 生成 4,5-二溴-1H-吡咯-2-羧肼
  参考文献：
  名称：

  4,5-Dihalopyrrole-2-carboxamides

  摘要：

  4,5-二卤吡咯-2-羧酰胺衍生物，通过相应的4,5-二卤吡咯-2-羧酸酰氯或相应的4,5-二卤吡咯-2-基三卤甲基酮与适当胺反应制备，可用作抗菌和除草剂。

  公开号：

  US04046775A1

文献信息

• Herbicidal pyrrole-2-carboxamides
  申请人：Sterling Drug Inc.

  公开号：US03963480A1

  公开（公告）日：1976-06-15

  4,5-Dihalopyrrole-2-carboxamide derivatives, prepared by reaction of a corresponding 4,5-dihalopyrrole-2-carboxylic acid halide or a corresponding 4,5-dihalopyrrol-2-yl trihalomethyl ketone with an appropriate amine, have antibacterial and herbicidal activities.

  4,5-二卤吡咯-2-羧酰胺衍生物，通过相应的4,5-二卤吡咯-2-羧酸酰氯或相应的4,5-二卤吡咯-2-基三卤甲基酮与适当的胺反应制备，具有抗菌和除草活性。
• Synthesis of Novel Hybrids Inspired from Bromopyrrole Alkaloids Inhibiting MMP-2 and -12 as Antineoplastic Agents
  作者：Rajesh A. Rane、Shital S. Naphade、Pavan Kumar Bangalore、Mahesh B. Palkar、Harun M. Patel、Mahamadhanif S. Shaikh、Wesam S. Alwan、Rajshekhar Karpoormath

  DOI：10.1111/cbdd.12481

  日期：2015.8

  Synthesis of novel set of forty semicarbazide/thiosemicarbazide hybrids inspired from marine bromopyrrole alkaloids is reported. Biological screening of these hybrids against a panel of five human cancer cell lines identified a number of hits endowed with interesting cytotoxicity profile. Compounds 5c and 5e (IC50 = 0.03 μm), 5t (IC50 = 0.03 μm), 4s (IC50 = 0.07 μm), and 5n (IC50 = 0.01 μm) displayed maximum cytotoxicity toward hormone‐dependent breast cancer cells MCF7, hepatic cancer cells WRL68, colon cancer cells CaCO2 and mouth and oral cancer cells KB403, respectively. The most active hits were further investigated for their potential to inhibit MMP‐2 and MMP‐12. Compound 5e showed maximum activity (IC50 = 1.8 μm) toward MMP‐2. Further, we preformed anti‐invasive assay on the most active compounds, where CaCO2 tumor cell migration was significantly decreased (77.9%) by hybrid 5e. The non‐toxicity toward human VERO cells (IC50 = 83.1 to 231.8 μm) indicated the selectivity of most active hits (5c, 5e, 5t and 5n) toward cancer cells.
• 4,5-Dihalopyrrole-2-carboxamides
  申请人：Sterling Drug Inc.

  公开号：US04046775A1

  公开（公告）日：1977-09-06

  4,5-Dihalopyrrole-2-carboxamide derivatives, prepared by reaction of a corresponding 4,5-dihalopyrrole-2-carboxylic acid halide or a corresponding 4,5-dihalopyrrol-2-yl trihalomethyl ketone with an appropriate amine, useful as antibacterial and herbicidal agents.

  4,5-二卤吡咯-2-羧酰胺衍生物，通过相应的4,5-二卤吡咯-2-羧酸酰氯或相应的4,5-二卤吡咯-2-基三卤甲基酮与适当胺反应制备，可用作抗菌和除草剂。
• Synthesis and evaluation of novel 1,3,4-oxadiazole derivatives of marine bromopyrrole alkaloids as antimicrobial agent
  作者：Rajesh A. Rane、Shweta D. Gutte、Niteshkumar U. Sahu

  DOI：10.1016/j.bmcl.2012.08.061

  日期：2012.10

  In an attempt to identify new potential lead as antimicrobial agent, twenty hybrids of marine bromopyrrole alkaloids with 1,3,4-oxadiazole were designed based on molecular hybridization technique and synthesized. Synthesized molecules were evaluated for their antibacterial, antifungal and antitubercular activities. Hybrids 5d, 5i, 5j and 5k exhibited equivalent antibacterial activity (MIC of 1.56 mu g/mL) compared with standard drug ciprofloxacin against Staphylococcus aureus and Escherichia coli. Equal antifungal activity (MIC of 1.56 mu g/mL) was shown by of hybrids 5j, 5k and 7d compared with standard Amphotericin-B. The inhibition of Mycobacterium tuberculosis at concentrations as low as 1.6 and 1.5 mu g/mL by compounds 5f and 7d respectively indicates that these compounds can act as leads for development of newer anti-TB compounds. (c) 2012 Elsevier Ltd. All rights reserved.