N-（2-溴乙基）-2,2,2-三氟乙酰胺 | 75915-38-7

• 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
• 中文名称: N-（2-溴乙基）-2,2,2-三氟乙酰胺
• 英文名称: (2,2,2-trifluorocacetylamino)ethylbromide
• 英文别名: N-(2-bromoethyl)trifluoroacetamide；N-(2-bromoethyl)-2,2,2-trifluoroacetamide；1-bromo-2-(N-trifluoroacetylamino)ethane
• CAS: 75915-38-7
• 化学式: C₄H₅BrF₃NO
• 分子量: 219.989
• InChiKey: GKMSIJALDVKGQV-UHFFFAOYSA-N

物化性质

• 熔点：
  57-59°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-（2-溴乙基）-2,2,2-三氟乙酰胺 生成 2-(trifluoromethyl)-2-oxazoline
  参考文献：
  名称：

  ISIKAVA, NOBUO;SEHKIYA, AKIRA

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2-羟基乙基)三氟乙酰胺 在 四溴化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 49.0h， 以70%的产率得到N-（2-溴乙基）-2,2,2-三氟乙酰胺
  参考文献：
  名称：

  (E)-Alkene and Ethylene Isosteres Substantially Alter the Hydrogen-Bonding Network in Class II MHC A^q/Glycopeptide Complexes and Affect T-Cell Recognition

  摘要：

  The structural basis for antigen presentation by class II major histocompatibility complex (MHC) proteins to CD4(+) T-cells is important for understanding and possibly treating autoimmune diseases. In the work described in this paper, (E)-alkene and ethylene amide-bond isosteres were used to investigate the effect of removing hydrogen-bonding possibilities from the CII259-270 glycopeptide, which is bound by the arthritis-associated murine A(q) class II MHC protein. The isostere-modified glycopeptides showed varying and unexpectedly large losses of A(q) binding that could be linked to the dynamics of the system. Molecular dynamics (MD) simulations revealed that the backbone of CII259-270 and the A(q) protein are able to form up to 11 hydrogen bonds, but fewer than this number are present at any one time. Most of the strong hydrogen-bond interactions were formed by the N-terminal part of the glycopeptide, i.e., in the region where the isosteric replacements were made. The structural dynamics also revealed that hydrogen bonds were strongly coupled to each other; the loss of one hydrogen-bond interaction had a profound effect on the entire hydrogen-bonding network. The A(q) binding data revealed that an ethylene isostere glycopeptide unexpectedly bound more strongly to A(q) than the corresponding (E)-alkene, which is in contrast to the trend observed for the other isosteres. Analysis of the MD trajectories revealed that the complex conformation of this ethylene isostere was structurally different and had an altered molecular interaction pattern compared to the other A(q)/glycopeptide complexes. The introduced amide-bond isosteres also affected the interactions of the glycopeptide/A(q) complexes with T-cell receptors. The dynamic variation of the patterns and strengths of the hydrogen-bond interactions in the class II MHC system is of critical importance for the class II MHC/peptide/TCR signaling system.

  DOI：

  10.1021/ja2038722

文献信息

• Benzoazine mono-N-oxides and benzoazine 1,4 dioxides and compositions therefrom for the therapeutic use in cancer treatments
  申请人：Auckland Uniservices Limited

  公开号：EP1468688A2

  公开（公告）日：2004-10-20

  The present invention relates to a synergetistic composition comprising one or more benzoazine-mono-N-oxides, and one or more benzoazine 1,4 dioxides for use in cancer therapy. The invention also provides a range of novel 1,2,4 benzoazine-mono-N-oxides and related analogues. These can be used as potentiators of the cytotoxicity of existing anticancer drugs and therapies for cancer treatment.

  本发明涉及一种协同组合物，包括一种或多种苯并噁唑-单-N-氧化物，以及一种或多种苯并噁唑1,4-二氧化物，用于癌症治疗。 该发明还提供了一系列新颖的1,2,4苯并噁唑-单-N-氧化物及相关类似物。这些可以用作增强现有抗癌药物的细胞毒性和癌症治疗的治疗剂。
• [EN] DNA-TARGETED BENZOTRIAZINE 1,4-DIOXIDES AND THEIR USE IN CANCER THERAPY<br/>[FR] 1,4-DIOXIDES DE BENZOTRIAZINE CIBLEES SUR ADN ET LEUR UTILISATION DANS LE TRAITEMENT DU CANCER
  申请人：AUCKLAND UNISERVICES LTD

  公开号：WO2004026846A1

  公开（公告）日：2004-04-01

  The present invention relates to DNA-targeted 1,2,4-benzotriazine- 1,4-dioxides and related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.

  本发明涉及以DNA为靶标的1,2,4-苯并三氮唑-1,4-二氧化物及相关类似物，其制备方法，以及它们作为针对缺氧选择性药物和放射增敏剂在癌症治疗中的应用，无论是单独使用还是与放射线和/或其他抗癌药物结合使用。
• Nickel-catalyzed reductive coupling of unactivated alkyl bromides and aliphatic aldehydes
  作者：Cole L. Cruz、John Montgomery

  DOI：10.1039/d1sc03712a

  日期：——

  A mild, convenient coupling of aliphatic aldehydes and unactivated alkyl bromides has been developed. The catalytic system features the use of a common Ni(II) precatalyst and a readily available bioxazoline ligand and affords silyl-protected secondary alcohols. The reaction is operationally simple, utilizing Mn as a stoichiometric reductant, and tolerates a wide range of functional groups. The use

  已开发出一种温和、方便的脂肪醛和未活化烷基溴的偶联方法。该催化系统使用常见的 Ni( II ) 预催化剂和易于获得的生物恶唑啉配体，并提供甲硅烷基保护的仲醇。该反应操作简单，使用 Mn 作为化学计量还原剂，并且可以耐受多种官能团。使用 1,5-己二烯作为添加剂是一个重要的反应参数，可显着提高产量。最初的机械实验支持一种以 α-甲硅烷氧基镍物种为特征的机制，该物种通过还原性交叉偶联途径对烷基溴进行正式氧化加成。
• Combination of Antimicrobial and Endotoxin-Neutralizing Activities of Novel Oleoylamines
  作者：Mateja Zorko、Andreja Majerle、David Šarlah、Mateja Manček Keber、Barbara Mohar、Roman Jerala

  DOI：10.1128/aac.49.6.2307-2313.2005

  日期：2005.6

  A combination of antimicrobial and endotoxin-neutralizing activities is desired in order to prevent progression from infection to sepsis due to the release of lipopolysaccharide from dying gram-negative bacteria. Lipopolyamines have emerged as a new type of endotoxin-neutralizing compound, but their antimicrobial activity has not been investigated. We synthesized a series of 10 oleoylamines differing in the polyamino head group, particularly in the number and separation between nitrogen atoms and the position of the oleoyl moiety. Compounds showed activity against both gram-negative and gram-positive bacteria in the micromolar range. Compounds were able to provide penetration of ethidium bromide into bacteria, indicating effects on the bacterial membrane. Oleoylamines neutralized endotoxin inLimulusamoebocyte lysate assays and by neutralization of tumor necrosis factor alpha release in human blood. Comparison of biological activities of compounds identified structural properties responsible for antimicrobial activity, and quantitative structure-property relationship analysis provided a quantitative model for prediction of activity of oleoylamines.

  摘要：为了防止由于濒死的革兰氏阴性细菌释放脂多糖而导致感染发展为败血症，我们需要将抗菌活性和中和内毒素活性结合起来。脂多胺是一种新型的内毒素中和化合物，但其抗菌活性尚未得到研究。我们合成了一系列 10 种油酰基胺，它们在多氨基头基，特别是氮原子的数量和间隔以及油酰基的位置上各不相同。这些化合物在微摩尔范围内对革兰氏阴性菌和革兰氏阳性菌都具有活性。化合物能够使溴化乙锭渗透到细菌中，这表明它们对细菌膜产生了作用。油酰基胺能中和利木赞阿米巴细胞裂解物试验中的内毒素，并能中和人体血液中肿瘤坏死因子α的释放。对化合物的生物活性进行比较，确定了导致抗菌活性的结构特性，定量结构-特性关系分析为预测油酰基胺的活性提供了一个定量模型。
• Dirhodium-Catalyzed Transannulation of<i>N</i>-Sulfonyl-1,2,3-triazoles to 2,3-Dehydropiperazines
  作者：Michael J. Nutt、Jack W. Annear、Kieran D. Jones、Gavin R. Flematti、Stephen A. Moggach、Scott G. Stewart

  DOI：10.1021/acs.joc.3c01259

  日期：2023.8.18

  dirhodium(II)-catalyzed synthesis of a range of C2-substituted 2,3-dehydropiperazines using 1-mesyl-1,2,3-triazoles and β-haloalkylcarbamates is reported. The reaction is proposed to proceed through an α-imino rhodium carbene 1,3-insertion into N–H followed by a base-mediated cyclization. C-Substituted dehydropiperazines can also be conducted directly from terminal alkynes in a three-step, one-pot operation, forming

  据报道，使用 1-甲磺酰基-1,2,3-三唑和 β-卤代烷基氨基甲酸酯，二铑 (II) 催化合成了一系列 C2 取代的 2,3-脱氢哌嗪。该反应通过 α-亚氨基铑卡宾 1,3-插入 N-H 进行，然后进行碱介导的环化。C-取代的脱氢哌嗪也可以直接从末端炔烃以三步一锅操作进行，原位形成三唑。该方法也已得到扩展，可提供几种 2,5-二取代的 2,3-脱氢哌嗪以及更大的 4,5,6,7-四氢-1 H -1,4-二氮杂卓衍生物。