2-(1-methyl-4,5-dibromo-1H-pyrrole-2-carbonyl)-N-(3,4,5-trimethoxyphenyl) hydrazine carbothioamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(1-methyl-4,5-dibromo-1H-pyrrole-2-carbonyl)-N-(3,4,5-trimethoxyphenyl) hydrazine carbothioamide
• 英文别名: 2-(1-Methyl-4,5-dibromo-1H-pyrrole-2-carbonyl)-N-(3,4,5-trimethoxyphenyl) hydrazine carbothioamide (5t)；1-[(4,5-dibromo-1-methylpyrrole-2-carbonyl)amino]-3-(3,4,5-trimethoxyphenyl)thiourea
• 化学式: C₁₆H₁₈Br₂N₄O₄S
• 分子量: 522.217
• InChiKey: VBUNYHIMTDBQTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,5-dibromo-1-methyl-1H-pyrrole-2-carbohydrazide 、 3,4,5-三甲氧基异硫氰酸苯酯 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到2-(1-methyl-4,5-dibromo-1H-pyrrole-2-carbonyl)-N-(3,4,5-trimethoxyphenyl) hydrazine carbothioamide
  参考文献：
  名称：

  Synthesis of Novel Hybrids Inspired from Bromopyrrole Alkaloids Inhibiting MMP-2 and -12 as Antineoplastic Agents

  摘要：

  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.

  DOI：

  10.1111/cbdd.12481

文献信息

• 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.