2,4,5-三溴-1-甲氧基甲基-1H-咪唑 | 22927-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2,4,5-三溴-1-甲氧基甲基-1H-咪唑
• 英文名称: 2,4,5-tribromo-1-methoxymethylimidazole
• 英文别名: 2,4,5-Tribromo-1-(methoxymethyl)-1H-imidazole；2,4,5-tribromo-1-(methoxymethyl)imidazole
• CAS: 22927-61-3
• 化学式: C₅H₅Br₃N₂O
• 分子量: 348.819
• InChiKey: YFXDMMDCUGCCGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  2,4,5-三溴-1-甲氧基甲基-1H-咪唑 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以86%的产率得到2,4,5-三溴咪唑
  参考文献：
  名称：

  Iddon, Brian; Khan, Nazir; Lim, Bee Lan, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1437 - 1444

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,5-三溴咪唑 、 氯甲基甲基醚 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到2,4,5-三溴-1-甲氧基甲基-1H-咪唑
  参考文献：
  名称：

  噻吩并[2,3- d ]咪唑的简便合成方法

  摘要：

  由咪唑经2,4,5-三生物基咪唑制备4-溴咪唑-5-甲醛的1-保护和1,2-二保护衍生物，并与2-巯基乙酸乙酯反应，得到标题化合物。

  DOI：

  10.1039/c39850001428

文献信息

• [EN] ANTI-INFECTIVE COMPOUNDS<br/>[FR] COMPOSÉS ANTI-INFECTIEUX
  申请人：PASTEUR INSTITUT KOREA

  公开号：WO2015193506A1

  公开（公告）日：2015-12-23

  The present invention relates to small molecule compounds having the general formula (I): wherein A is a moiety selected from the group consisting of formulae (A) to (K) and their use in the treatment of bacterial infections, in particular Tuberculosis.

  本发明涉及具有通式（I）的小分子化合物，其中A是从式（A）到（K）组成的基团之一，并且其在治疗细菌感染，特别是结核病中的用途。
• Total Synthesis of Nortopsentins A-D, Marine Alkaloids.
  作者：Ikuo KAWASAKI、Masayuki YAMASHITA、Shunsaku OHTA

  DOI：10.1248/cpb.44.1831

  日期：——

  Nortopsentins A-D, antifungal 1, 4-bisindolylimidazole marine alkaloids isolated from a sponge, were synthesized through palladium-catalyzed cross-coupling of 3-indolylboronic and 6-bromo-3-indolylboronic acids with halogenoimidazoles as the key reaction.

  以卤代咪唑为关键反应，通过钯催化 3-吲哚硼酸和 6-溴-3-吲哚硼酸的交叉偶联合成了从海绵中分离出的抗真菌 1，4-双吲哚基咪唑海洋生物碱 Nortopsentins A-D。
• Successive diarylation at the carbon positions (2/4 and 2/5) of 1H-imidazole and its application to the total synthesis of nortopsentin D
  作者：Ikuo Kaswasaki、Masayuki Yamashita、Shunsaku Ohta

  DOI：10.1039/c39940002085

  日期：——

  Nortopsentin D, an antifungal 2,4-diinodolylimidazole, is synthesized by use of a successive and regioselective diarylation, in which N-protected 2,4,5-tri- and 4,5-di-bromoimidazole derivatives are treated with N-silylated 3-indolylboric acid in the presence of a palladium(o) catalyst.

  Nortopsentin D 是一种抗真菌的 2,4-二吲哚基咪唑，它是通过连续和区域选择性二芳基化反应合成的。在这种反应中，N 保护的 2,4,5- 三溴咪唑和 4,5- 二溴咪唑衍生物与 N-硅烷化的 3-吲哚硼酸在钯（邻）催化剂存在下进行处理。
• POTENTIATORS OF BETA-LACTAM ANTIBIOTICS
  申请人：UNIVERSITY OF NOTRE DAME DU LAC

  公开号：US20180044316A1

  公开（公告）日：2018-02-15

  We disclose herein that the BlaR1 protein of methicillin-resistant Staphylococcus aureus (MRSA), an antibiotic sensor/signal transducer, is phosphorylated on exposure to β-lactam antibiotics. This event is critical for the onset of the biochemical events that unleash induction of antibiotic resistance. The BlaR1 phosphorylation and the antibiotic-resistance phenotype are abrogated in the presence of inhibitors described herein that restore susceptibility of the organism to β-lactam antibiotics. The invention thus provides compounds and methods for abrogating antibiotic resistance to β-lactam antibiotics and for treating infections causes by antibiotics prone to developing resistance.

  我们在此披露，甲氧西林耐药金黄色葡萄球菌（MRSA）的BlaR1蛋白质是一种抗生素感受器/信号转导器，当暴露于β-内酰胺类抗生素时，该蛋白质被磷酸化。这一事件对于引发生物化学事件并释放抗生素耐药性的发生至关重要。BlaR1的磷酸化和抗生素耐药表型在存在本文所述的抑制剂时被废除，这些抑制剂恢复了该生物对β-内酰胺类抗生素的敏感性。因此，本发明提供了用于废除β-内酰胺类抗生素的抗生素耐药性和治疗由易于产生耐药性的抗生素引起的感染的化合物和方法。
• Potent BRAF kinase inhibitors based on 2,4,5-trisubstituted imidazole with naphthyl and benzothiophene 4-substituents
  作者：Dan Niculescu-Duvaz、Ion Niculescu-Duvaz、Bart M.J.M. Suijkerbuijk、Delphine Ménard、Alfonso Zambon、Lawrence Davies、Jean-Francois Pons、Steven Whittaker、Richard Marais、Caroline J. Springer

  DOI：10.1016/j.bmc.2012.12.035

  日期：2013.3

  The RAS-RAF-MEK-ERK pathway is hyperactivated in 30% of human cancers. BRAF is a serine-threonine kinase, belonging to this pathway that is mutated with high frequency in human melanoma and other cancers thus BRAF is an important therapeutic target in melanoma. We have designed inhibitors of BRAF based on 2,4,5-trisubstituted imidazoles with naphthyl and benzothiophene-4-substituents. Two compounds were discovered to be potent BRAF inhibitors: 1-(6-2-[4-(2-dimethylamino-ethoxy) phenyl]-5-(pyridin-4-yl)-1H-imidazol-4-yl} benzo[b]thiophen-3-yl)-2,2,2-trifluoroethanol (1i) with BRAF IC50 = 190 nM and with cellular GI(50) = 2100 nM, and 6-2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-naphthalen-1-ol (1q) with IC50 = 9 nM and GI(50) = 220 nM. (C) 2013 Elsevier Ltd. All rights reserved.