4,5-dibromo-1H-pyrrole-2-carboxylic acid [3-(2-amino-1H-imidazol-4-yl)-propyl]-amide hydrochloride | 202391-65-9

• 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: 4,5-dibromo-1H-pyrrole-2-carboxylic acid [3-(2-amino-1H-imidazol-4-yl)-propyl]-amide hydrochloride
• 英文别名: N-[3-(2-amino-1H-imidazol-5-yl)propyl]-4,5-dibromo-1H-pyrrole-2-carboxamide;hydrochloride
• CAS: 202391-65-9
• 化学式: C₁₁H₁₃Br₂N₅O*ClH
• 分子量: 427.526
• InChiKey: SOARCAQQMQCLJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  20
• 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：
  5
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dibromo-1H-pyrrole-2-carboxylic acid [3-(2-amino-1H-imidazol-4-yl)-propyl]-amide hydrochloride 在 溴 作用下， 以 溶剂黄146 、 二甲基亚砜 为溶剂， 生成 rac-(3aR,9aS)-2-amino-4'-bromo-3,3a,8,9-tetrahydro-5H,7H-spiro[imidazo[4,5-g]pyrrolizine-4,2'-pyrrole]-5,5'(1'H)-dione
  参考文献：
  名称：

  Biomimetic synthesis of dibromophakellin

  摘要：

  DOI：

  10.1021/ja00370a072
• 作为产物：
  描述：

  tert-butyl 2-amino-4-[3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]propyl]imidazole-1-carboxylate 在 三氟乙酸 、 盐酸 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 12.0h， 以98%的产率得到4,5-dibromo-1H-pyrrole-2-carboxylic acid [3-(2-amino-1H-imidazol-4-yl)-propyl]-amide hydrochloride
  参考文献：
  名称：

  Antibiofilm Activity of a Diverse Oroidin Library Generated through Reductive Acylation

  摘要：

  A diverse 20-compound library of analogues based on the marine alkaloid oroidin were synthesized via a reductive acylation strategy. The final target was then assayed for inhibition and dispersion activity against common proteo-bacteria known to form biofilms. This methodology represents a significant improvement over the generality of known methods to acylate substrates containing 2-aminoimidazoles and has the potential to have broad application to the synthesis of more advanced oroidin family members and their corresponding analogues.

  DOI：

  10.1021/jo802260t

文献信息

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

  公开号：US20110150819A1

  公开（公告）日：2011-06-23

  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.

  本文提供了一种咪唑衍生物化合物的披露，其可以预防、去除和/或抑制生物膜的形成，包括这些化合物的组合物、含有这些化合物的装置以及使用它们的方法。
• Improved Conversion of Dihydrooroidin to Oroidin and Ugibohlin
  作者：Rareş-Petru Moldovan、Thomas Lindel

  DOI：10.1515/znb-2009-11-1247

  日期：2009.12.1

  Dihydrooroidin was converted to the marine natural product oroidin in 75% overall yield by chlorination of the 2-aminoimidazole unit in DMF, followed by dehydrochlorination. The natural product ugibohlin was synthesized for the first time by ring opening of dibromoisophakellin, which was obtained in a quantitative manner by heating the free base of dibromophakellin in neutral aqueous solution

  二氢海绵素在DMF中通过2-氨基咪唑单元的氯化和脱氢氯化反应，以75%的总产率转化为海洋天然产物海绵素。通过环开放反应合成了天然产物乌吉伯林，首次通过在中性水溶液中加热二溴异帕克林的游离碱，定量得到了二溴异帕克林。
• 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.
• US7906544B2
  申请人：——

  公开号：US7906544B2

  公开（公告）日：2011-03-15
• Antibiofilm Activity of a Diverse Oroidin Library Generated through Reductive Acylation
  作者：T. Eric Ballard、Justin J. Richards、Arianexys Aquino、Catherine S. Reed、Christian Melander

  DOI：10.1021/jo802260t

  日期：2009.2.20

  A diverse 20-compound library of analogues based on the marine alkaloid oroidin were synthesized via a reductive acylation strategy. The final target was then assayed for inhibition and dispersion activity against common proteo-bacteria known to form biofilms. This methodology represents a significant improvement over the generality of known methods to acylate substrates containing 2-aminoimidazoles and has the potential to have broad application to the synthesis of more advanced oroidin family members and their corresponding analogues.