2,2,2-trichloro-1-(4,5-dibromo-1-methyl-1H-pyrrol-2-yl)ethanone | 120309-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-trichloro-1-(4,5-dibromo-1-methyl-1H-pyrrol-2-yl)ethanone
• 英文别名: 2,2,2-Trichloro-1-(4,5-dibromo-1-methyl-pyrrol-2-yl)-ethanone；2,2,2-trichloro-1-(4,5-dibromo-1-methylpyrrol-2-yl)ethanone
• CAS: 120309-50-4
• 化学式: C₇H₄Br₂Cl₃NO
• 分子量: 384.282
• InChiKey: QCIVVBFXHLJKNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2,2,2-trichloro-1-(4,5-dibromo-1-methyl-1H-pyrrol-2-yl)ethanone 在 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 4,5-dibromo-N-(2-(2-hydroxy-4-methoxyphenyl)-4-oxothiazolidin-3-yl)-1-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Synthesis and antibiofilm activity of marine natural product-based 4-thiazolidinones derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.09.073
• 作为产物：
  描述：

  N-甲基吡咯 在 溴 、 potassium carbonate 作用下， 以 乙醚 、 氯仿 为溶剂， 生成 2,2,2-trichloro-1-(4,5-dibromo-1-methyl-1H-pyrrol-2-yl)ethanone
  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

• INHIBITION OF BACTERIAL BIOFILMS WITH IMIDAZOLE DERIVATIVES
  申请人：Melander Christian

  公开号：US20080181923A1

  公开（公告）日：2008-07-31

  Disclosure is provided for imidazole derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

  提供了关于咪唑衍生物化合物的披露，这些化合物可以预防、去除和/或抑制生物膜的形成，包括这些化合物的组合物、包含这些化合物的设备，以及使用它们的方法。
• INHIBITION OF BIOFILMS IN PLANTS WITH IMIDAZOLE DERIVATIVES
  申请人：Melander Christian

  公开号：US20090143230A1

  公开（公告）日：2009-06-04

  Disclosure is provided for methods of preventing, removing or inhibiting microbial biofilm formation or microbial infection in a plant or plant part thereof, including applying thereto a treatment effective amount of an active compound as described herein, or an agriculturally acceptable salt thereof. Methods of enhancing a microbicide (e.g., including a copper, antibiotic, bacteriophage, etc.) and/or plant defense activator are also provided, including applying an active compound as described herein. Compositions comprising an active compound as described herein in an agriculturally acceptable carrier are also provided, and in some embodiments the compositions further include a microbicide (e.g., including copper, antibiotic, bacteriophage, etc.) and/or plant defense activator.

  本公开提供了一种防止、去除或抑制植物或其部分中微生物生物膜形成或微生物感染的方法，包括向其施加本文所述的活性化合物的有效量或其农业可接受的盐。还提供了增强微生物杀灭剂（例如，包括铜、抗生素、噬菌体等）和/或植物防御激活剂的方法，包括施加本文所述的活性化合物。还提供了包含本文所述的活性化合物在农业可接受载体中的组合物，并在某些实施例中，这些组合物进一步包括微生物杀灭剂（例如，包括铜、抗生素、噬菌体等）和/或植物防御激活剂。
• INHIBITION AND DISPERSION OF BACTERIAL BIOFILMS WITH IMIDAZOLE-TRIAZOLE DERIVATIVES
  申请人：Melander Christian

  公开号：US20090263438A1

  公开（公告）日：2009-10-22

  Disclosure is provided for imidazole-triazole derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

  披露了咪唑-三唑衍生物化合物，用于防止、移除和/或抑制生物膜的形成，包含这些化合物的组合物，包含这些化合物的设备，以及使用这些化合物的 methods。
• Synthesis of the Pyrrole-Imidazole Alkaloid Sventrin from the Marine Sponge Agelas sventres
  作者：Gregor Breckle、Kurt Polborn、Thomas Lindel

  DOI：10.1515/znb-2003-0516

  日期：2003.5.1

  The marine pyrrole-imidazole alkaloid sventrin (1) and the hitherto unknown dehydrooroidin (3) have been synthesized stereoselectively via alkyne intermediates. The pathways start from a 2-azido-4-alkynylimidazole which can be chemo- and stereoselectively reduced to the corresponding amino alkene using NaAlH₂(OCH₂CH₂OMe)₂ (Red-Al) or, alternatively, to the amino alkyne. Selective removal of simultaneously present Boc or trityl protecting groups was possible employing either p-TsOH or acetic resp. formic acid.

  已合成海洋吡咯咪唑生物碱sventrin（1）和迄今未知的脱氢顶咪唑（3），通过炔中间体进行立体选择性合成。这些途径始于2-叠氮-4-炔基咪唑，可以通过NaAlH₂(OCH₂CH₂OMe)₂（Red-Al）进行化学和立体选择性还原为相应的氨基烯，或者选择性地还原为氨基炔。利用p-TsOH或乙酸或甲酸可以选择性地去除同时存在的Boc或三苯甲基保护基。
• Extending Pummerer Reaction Chemistry: (±)-Dibromoagelaspongin Synthesis and Related Studies
  作者：Ken S. Feldman、Matthew D. Fodor

  DOI：10.1021/jo900283g

  日期：2009.5.1

  The sponge-derived alkaloid dibromoagelaspongin was prepared from a dihydrooroidin derivative by exploiting the Pummerer reaction twice in succession. Oxidative cyclization of the substrate’s pyrrole-2-carboxamide function into the imidazole moiety was achieved in a regiospecific manner to establish both C−N bonds to C(6) of the target.

  通过连续两次利用Pummerer反应，由二氢吗啡啉衍生物制备海绵衍生的生物碱二溴agelaspongin。底物的吡咯-2-羧酰胺功能氧化成咪唑部分的氧化环化以区域特异性方式实现，以建立与目标C（6）的两个C-N键。