N-(3-(2-amino-1H-imidazol-4-yl)propyl)-4,5-dibromo-1H-pyrrole-2-carboxamide | 80822-63-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(3-(2-amino-1H-imidazol-4-yl)propyl)-4,5-dibromo-1H-pyrrole-2-carboxamide
• 英文别名: dihydrooroidin；dihydrooroidine；N-[3-(2-amino-1H-imidazol-5-yl)propyl]-4,5-dibromo-1H-pyrrole-2-carboxamide
• CAS: 80822-63-5
• 化学式: C₁₁H₁₃Br₂N₅O
• 分子量: 391.065
• InChiKey: LTBPDTOBRXMEAA-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C
• 密度：
  1.879±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  99.6
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-(2-amino-1H-imidazol-4-yl)propyl)-4,5-dibromo-1H-pyrrole-2-carboxamide 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 三氟乙酸 、 四氢呋喃 为溶剂， 反应 0.08h， 以90%的产率得到dibromophakellin
  参考文献：
  名称：

  二溴邻苯三酚他汀和二溴异邻苯二酚的合成

  摘要：

  描述了海洋海绵生物碱dibromophakellstatin（1）和dibromoisophakellin（2）的简短合成。1的合成以咪唑啉酮5的拟仿生氧化环化为中心。在存在K 2 CO 3的情况下，对二溴邻苯并菲林（9）进行热重排，得到二溴异邻苯并菲林（2）。

  DOI：

  10.1016/s0040-4039(02)00966-8
• 作为产物：
  描述：

  1-(3-(2-氨基-1H-咪唑-4-基)丙基)脲盐酸盐 在 sodium hydroxide 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 N-(3-(2-amino-1H-imidazol-4-yl)propyl)-4,5-dibromo-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Biomimetic synthesis of dibromophakellin

  摘要：

  DOI：

  10.1021/ja00370a072

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。
• Synthesis of Marine Sponge Alkaloids Oroidin, Clathrodin, and Dispacamides. Preparation and Transformation of 2-Amino-4,5-dialkoxy-4,5-dihydroimidazolines from 2-Aminoimidazoles
  作者：Anne Olofson、Kenichi Yakushijin、David A. Horne

  DOI：10.1021/jo9718298

  日期：1998.2.1

  The preparation and transformation of 2-amino-4,5-dialkoxy-4,5-dihydroimidazolines A from 2-aminoimidazoles (AIs) is described. The oxidation of 2-aminoimidazole 8 with NCS in methanol affords cyclic guanidine adduct 9 which, upon heating, affords vinylogous AI derivative 3 and 8-aminoimidazolinone (glycocyamidine) 13. Olefin 3 comprises the core structure found in the oroidin alkaloids. Furthermore, oxidation of 8 with B-2 and DMSO affords directly alpha,beta-unsaturated imidazolinone 14 which is the key structural unit comprising the dispacamides (2). A highly facile and practical synthesis of the C11N5 marine sponge alkaloids oroidin (la), clathrodin (1c), and dispacamides (2) is outlined.
• Clathrodin, hymenidin and oroidin, and their synthetic analogues as inhibitors of the voltage-gated potassium channels
  作者：Nace Zidar、Aleš Žula、Tihomir Tomašič、Marc Rogers、Robert W. Kirby、Jan Tytgat、Steve Peigneur、Danijel Kikelj、Janez Ilaš、Lucija Peterlin Mašič

  DOI：10.1016/j.ejmech.2017.08.015

  日期：2017.10

  We have prepared three alkaloids from the Agelas sponges, clathrodin, hymenidin and oroidin, and a series of their synthetic analogues, and evaluated their inhibitory effect against six isoforms of the KO subfamily of voltage-gated potassium channels, g(v)1.1-K(v)1.6, expressed in Chinese Hamster ovary (CHO) cells using automated patch clamp electrophysiology assay. The most potent inhibitor was the (E)-N-(3(2-amino-1H-imidazol-4-yl)ally1)-4,5-dichloro-1H-pyrrole-2-carboxamide (6g) with IC50 values between 1.4 and 6.1 mu M against K(v)1.3, K(v)1.4, K(v)1.5 and K(v)1.6 channels. All compounds tested displayed selectivity against K(v)1.1 and K(v)1.2 channels. For confirmation of their activity and selectivity, compounds were additionally evaluated in the second independent system against K(v)1.1-K(v)1.6 and K(v)10.1 channels expressed in Xenopus laevis oocytes under voltage clamp conditions where IC50 values against K(v)1.3K(v)1.6 channels for the most active analogues (e.g. 6g) were lower than 1 mu M. Because of the observed low sub-micromolar IC50 values and fairly low molecular weights, the prepared compounds represent good starting points for further optimisation towards more potent and selective voltage-gated potassium channel inhibitors. (C) 2017 Elsevier Masson SAS. All rights reserved.
• 2-Aminoimidazole-Functional Silicone Compositions And Methods Of Making The Same
  申请人：DOW CORNING CORPORATION

  公开号：US20160024257A1

  公开（公告）日：2016-01-28

  A method of making a 2-aminoimidazole-functional silicone elastomer includes forming a mixture by combining a silicone elastomer base material having vinyl functionality, a 2-aminoimidazole-functional monomer or a 2-aminoimidazole-functional oligomer, and a free-radical initiator. Optionally, one or more cross-linkers, pigments, vinyl polymer, non-functional silicone fluid, or any combination thereof may also be included in the mixture.
• Methods to Expand the Spectrum of Gram-Positive Antibiotics
  申请人：NORTH CAROLINA STATE UNIVERSITY

  公开号：US20210283107A1

  公开（公告）日：2021-09-16

  Provided herein is a method to treat a Gram-negative bacterial infection in a subject in need thereof, comprising administering a compound of Formula I: in combination with a Gram-positive antibiotic to said subject in a treatment-effective amount. Also provided is a method to control Gram-negative bacteria, comprising applying a compound of Formula I in combination with a Gram-positive antibiotic in a Gram-negative bactericidal-effective amount.