4,5-dibromo-1-methyl-1H-pyrrole-2-carbohydrazide | 1415036-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4,5-dibromo-1-methyl-1H-pyrrole-2-carbohydrazide
• 英文别名: 4,5-Dibromo-1-methylpyrrole-2-carbohydrazide
• CAS: 1415036-38-2
• 化学式: C₆H₇Br₂N₃O
• 分子量: 296.949
• InChiKey: SGFYHIXWLPPAFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 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：
  60
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

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

  Novel synthetic organic compounds inspired from antifeedant marine alkaloids as potent bacterial biofilm inhibitors

  摘要：

  In this paper, we have reported seventeen novel synthetic organic compounds derived from marine bromopyrrole alkaloids, exhibiting potential inhibition of biofilm produced by Gram-positive bacteria. Compound 5f with minimum biofilm inhibitory concentration (MBIC) of 0.39, 0.78 and 3.125 mu g/mL against MSSA, MRSA and SE respectively, emerged as promising anti-biofilm lead compounds. In addition, compounds 5b, 5c, 5d, 5e, 5f, 5h, 5i and 5j revealed equal potency as that of the standard drug Vancomycin (MBIC = 3.125 mu g/mL) against Streptococcus epidermidis. Notably, most of the synthesized compounds displayed better potency than Vancomycin indicating their potential as inhibitors of bacterial biofilm. The cell viability assay for the most active hybrid confirms its anti-virulence properties which need to be further researched. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.06.001
• 作为产物：
  描述：

  2,2,2-三氯-1-(1-甲基-1H-吡咯-2-基)-乙酮 在 溴 、 一水合肼 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 4,5-dibromo-1-methyl-1H-pyrrole-2-carbohydrazide
  参考文献：
  名称：

  海洋吡咯生物碱衍生物的设计，合成及抗葡萄球菌活性。

  摘要：

  设计，合成和评估了一组新的16种溴吡咯生物碱与芳酰的杂种，以评估其对耐甲氧西林金黄色葡萄球菌（MRSA; ATCC 43866），耐甲氧西林金黄色葡萄球菌（MSSA; ATCC 35556）的抗菌和抗生物膜活性（SE，表皮葡萄球菌ATCC 35984）。在测试的16个杂种中，相对于标准万古霉素，有14个对MSSA和MRSA具有相同或更高的抗生物膜活性。化合物4m的药效最高，对MSSA和MRSA的抗生物膜活性分别为0.39 µg / mL和0.78 µg / mL。因此，该化合物可以作为进一步开发新的抗葡萄球菌药物的潜在先导。

  DOI：

  10.3109/14756366.2013.793183

文献信息

• Synthesis and antibiofilm activity of marine natural product-based 4-thiazolidinones derivatives
  作者：Rajesh A. Rane、Niteshkumar U. Sahu、Chetan P. Shah

  DOI：10.1016/j.bmcl.2012.09.073

  日期：2012.12

  4-Thiazolidinones derivatives of marine bromopyrrole alkaloids were synthesized as potential antibiofilm compounds. Among the synthesized compounds, some showed promising antibiofilm activity. Biological data revealed that 1,3-thiazolidin-4-one derivatives are more potent antibiofilm agents compared to 1,3-thiazinan-4-ones. Antibiofilm activity of compound 4b, 4c (MIC = 0.78 mu g/ml) was 3-fold superior than standard vancomycin (MIC = 3.125 mu g/ml) while activity of compound 4d, 4f, 4g and 4h was 2-fold (MIC = 1.56 mu g/ml) against Staphylococcus aureus biofilm. Compound 4b-4h showed equal antibiofilm activity against Staphylococcus epidermidis compared to standard Vancomycin (MIC = 3.125 mu g/ml). (C) 2012 Elsevier Ltd. All rights reserved.
• 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.