2-bromo-4-amino-N-acetylaniline | 436090-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-4-amino-N-acetylaniline
• 英文别名: N-(4-amino-2-bromophenyl)acetamide；2'-bromo-4'-aminoacetanilide；acetic acid-(4-amino-2-bromo-anilide)；2-Brom-N¹-acetyl-p-phenyldiamin；N¹-Acetyl-2-brom-phenylendiamin-(1.4)；Essigsaeure-(4-amino-2-brom-anilid)；2-Brom-4-amino-acetanilid
• CAS: 436090-22-1
• 化学式: C₈H₉BrN₂O
• 分子量: 229.076
• InChiKey: JHBHGPWXILVPII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-4-amino-N-acetylaniline 在 tris(dibenzylideneacetone)dipalladium (0) 盐酸 、 copper(l) iodide 、 三乙胺 、 三苯基膦 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 36.5h， 生成 N-[4-(diethylaminodiazenyl)-2-(2-trimethylsilylethynyl)phenyl]acetamide
  参考文献：
  名称：

  Hydrogen Bond-Stabilized Helix Formation of a m-Phenylene Ethynylene Oligomer

  摘要：

  [GRAPHICS]Incorporation of a single hydrogen bonded beta-turn mimic in the backbone of a m-phenylene ethynylene oligomer is shown to affect the thermodynamic properties of the folding reaction. Oligomers 1 and 2 both undergo solvophobic helix formation, but hydrogen bonded oligomer 1 was found to form a more stable helix with a higher tolerance to solvent denaturation than isomeric, non-hydrogen bonded oligomer 2.

  DOI：

  10.1021/ol0270982
• 作为产物：
  描述：

  2-溴-4-硝基苯胺 在 硫酸 、 铁粉 、 溶剂黄146 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 2-bromo-4-amino-N-acetylaniline
  参考文献：
  名称：

  wt RET和V804M RET抑制剂的发现：从命中到领先。

  摘要：

  RET激酶的致癌激活已在多种肿瘤疾病中发现，如甲状腺髓样癌，多发性内分泌肿瘤，甲状腺乳头状癌和非小细胞肺癌。目前批准的RET抑制剂最初并未设计为RET抑制剂，而且它们对RET激酶的效能尚未优化。因此，需要能够抑制野生型RET（wt RET）及其突变体（例如V804M RET）的新型化合物。本文中，我们介绍了新型亚微摩尔wt RET / V804M RET抑制剂N-（2-氟-5-三氟甲基苯基）-N'-{4'-[（2''-苯甲酰胺基）吡啶的开发和初步评估从我们先前鉴定的4-苯胺基嘧啶命中化合物开始，具有4-苯胺基吡啶结构的-4”-基氨基]苯基}脲（69）。

  DOI：

  10.1002/cmdc.201700243

文献信息

• Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions
  作者：Jianzhong Liu、Kai Wu、Tao Shen、Yujie Liang、Miancheng Zou、Yuchao Zhu、Xinwei Li、Xinyao Li、Ning Jiao

  DOI：10.1002/chem.201605476

  日期：2017.1.12

  A novel and efficient Fe‐catalyzed direct C−H amination (NH2) of arenes is reported using a new redox‐active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox‐neutral conditions. This protocol has a broad substrate scope and could be used in the late‐stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved

  据报道，使用新型的氧化还原活性胺化试剂，新型有效的铁催化的芳烃直接CH-H胺化（NH 2）。该反应很简单，可以在空气，温和和氧化还原中性条件下进行。该方案具有广泛的底物范围，可用于生物活性化合物的后期修饰。机理研究表明，自由基途径可能参与了这种转化。
• [EN] DEOXYNOJIRIMYCIN DERIVATIVES AS GLUCOSIDASE INHIBITORS<br/>[FR] DÉRIVÉS DE DÉSOXYNOJIRIMYCINE EN TANT QU'INHIBITEURS DE GLUCOSIDASE
  申请人：EMERGENT PRODUCT DEV GAITHERSBURG INC

  公开号：WO2022011211A1

  公开（公告）日：2022-01-13

  The present application provides novel iminosugars and their use as glucosidase inhibitors. The present inventors have discovered that certain deoxynojirimycin derivatives may be effective in inhibiting glucosidases. In particular, such deoxynojirimycin derivatives may be useful for treating a disease or condition where inhibiting glucosidase may be important.

  本申请提供了新颖的亚胺糖以及它们作为葡萄糖苷酶抑制剂的用途。本发明人发现某些脱氧诺吉霉素衍生物可能有效地抑制葡萄糖苷酶。特别是，这些脱氧诺吉霉素衍生物可能对治疗需要抑制葡萄糖苷酶的疾病或病况有用。
• 1,2,4-Oxadiazole derivatives targeting EGFR and c-Met degradation in TKI resistant NSCLC
  作者：Eman M.E. Dokla、Chun-Sheng Fang、Khaled A.M. Abouzid、Ching S. Chen

  DOI：10.1016/j.ejmech.2019.111607

  日期：2019.11

  Development of small-molecule agents with the ability to facilitate oncoprotein degradation has emerged as a promising strategy for cancer therapy. Since EGFR and c-Met are both implicated in oncogenesis and tumor progression, we initiated a screening program by using an in-house library to identify agents capable of inducing the concomitant suppression of EGFR and c-Met expression, which led to the identification of compound 1, a 1,2,4-oxadiazole derivative. Based on the scaffold of 1, we developed a series of derivatives to assess their efficacies in facilitating the downregulation of EGFR and c-Met, among which compound 48 represented the optimal agent. 48 showed equipotent anti-proliferative activity against a panel of five NSCLC cell lines with different EGFR mutational status (IC50 = 0.2-0.6 mu M), while the same panel exhibited differential sensitivity to different EGFR kinase inhibitors tested. Cell cycle analysis indicated that the antiproliferative activity of 48 was associated with its ability to cause G2/M arrest and, to a lesser extent, apoptosis. Western blot and RT-PCR analyses revealed that 48 facilitated the downregulation of EGFR and c-Met at the protein level. In vivo data showed that oral administration of 48 was effective in suppressing gefitinib-resistant H1975 xenograft tumor growth in nude mice, and at a suboptimal dose, could sensitize H1975 tumors to gefitinib. Based on these findings, 48 represents a promising candidate for further development to target EGFR TKI-resistant NSCLC via dual inhibition of EGFR and c-Met oncoproteins. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Niyogy, Journal of the Indian Chemical Society, 1927, vol. 4, p. 401
  作者：Niyogy

  DOI：——

  日期：——
• Nicolet; Ray, Journal of the American Chemical Society, 1927, vol. 49, p. 1805
  作者：Nicolet、Ray

  DOI：——

  日期：——