1-(5-氨基-2-溴苯基)乙酮 | 149914-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(5-氨基-2-溴苯基)乙酮
• 英文名称: 1-(5-amino-2-bromophenyl)ethanone
• 英文别名: 2’-bromo-5’-amino-acetophenone
• CAS: 149914-98-7
• 化学式: C₈H₈BrNO
• 分子量: 214.062
• InChiKey: PNZIHAVVVVPFDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  332.0±27.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 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：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922399090
• 危险性防范说明：
  P261,P280,P305+P351+P338,P304+P340
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  1-(5-氨基-2-溴苯基)乙酮 在 2,6-二甲基吡啶 、 copper(l) iodide 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 27.0h， 生成 pentafluorophenyl 5-(butyl sulfonamido)-3-methyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  A Preclinical Candidate Targeting Mycobacterium tuberculosis KasA

  摘要：

  Published Mycobacterium tuberculosis beta-ketoacyl-ACP synthase KasA inhibitors lack sufficient potency and/or pharmacokinetic properties. A structure-based approach was used to optimize existing KasA inhibitor DG167. This afforded indazole JSF-3285 with a 30-fold increase in mouse plasma exposure. Biochemical, genetic, and X-ray studies confirmed JSF-3285 targets KasA. JSF-3285 offers substantial activity in an acute mouse model of infection and in the corresponding chronic infection model, with efficacious reductions in colony-forming units at doses as low as 5 mg/kg once daily orally and improvement of the efficacy of front-line drugs isoniazid or rifampicin. JSF-3285 is a promising preclinical candidate for tuberculosis.

  DOI：

  10.1016/j.chembiol.2020.02.007
• 作为产物：
  描述：

  2'-溴苯乙酮 在 盐酸 、 硫酸 、 铁粉 、 potassium nitrate 作用下， 以 甲醇 、 水 为溶剂， 反应 17.0h， 生成 1-(5-氨基-2-溴苯基)乙酮
  参考文献：
  名称：

  偶发的一锅氰化/水解/酰胺形成：直接获得3-亚甲基异吲哚-1-酮。

  摘要：

  据报道，使用CuCN作为唯一试剂，可以在无水或无氧条件下直接将2'-卤代苯乙酮一次转化为3-亚甲基异吲哚-1-酮支架。这种偶然发现的具有宽泛底物范围的转化为这些重要的支架提供了截然不同的途径。该方法的范围也进一步扩展到了三种特殊支架的合成，这三种支架类似于各种生物活性药物。

  DOI：

  10.1002/chem.202003209

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：BORAGEN INC

  公开号：WO2021003501A1

  公开（公告）日：2021-01-07

  The present disclosure describes novel compounds, or their pharmaceutically acceptable salts, pharmaceutical compositions containing them, and their medical uses. Compounds of the disclosure have activity as dual modulators of Janus kinase (JAK), alone, or in combination with one or more of an additional mechanism, including a tyrosine kinase, such as TrkA or Syk, and PDE4, and are useful in the in the treatment or control of inflammation, auto-immune diseases, cancer, and other disorders and indications where modulation of JAK would be desirable. Also described herein are methods of treating inflammation, auto-immune diseases, cancer, and other conditions susceptible to inhibition of JAK and PDE4 by administering a compound herein described.

  本公开描述了新颖的化合物，或其药用可接受的盐，含有它们的药物组合物，以及它们的医疗用途。本公开的化合物具有作为Janus激酶（JAK）的双重调节剂的作用，单独使用，或与一个或多个附加机制（包括酪氨酸激酶，如TrkA或Syk，以及PDE4）结合使用，并且在治疗或控制炎症、自身免疫疾病、癌症以及其他调节JAK会可取的失调和其他适应症中是有用的。此外，还描述了通过施用本处所述的化合物来治疗炎症、自身免疫疾病、癌症以及其他易受JAK和PDE4抑制的状况的方法。
• The Synthesis of Chiral Benzothiazine and Thiazinoquinoline Derivatives
  作者：Long Wang、Daniel L. Priebbenow、Xiao Yun Chen、Fang-Fang Pan、Carsten Bolm

  DOI：10.1002/ejoc.201500250

  日期：2015.5

  3-aminoacetophenone and (S)-S-methyl-S-phenylsulfoximine. By using a short reaction sequence, the 8-amino-2,1-benzothiazine derivative was readily prepared, which served as a valuable intermediate for the synthesis of additional derivatives. Initial experiments show that employing such compounds in copper-catalyzed asymmetric Mukaiyama-type aldol reactions provided products with moderate enantioselectivity.

  介绍了一系列对映纯构象受限的苯并噻嗪和噻嗪喹啉衍生物的合成。主要原料是 3-氨基苯乙酮和 (S)-S-甲基-S-苯基亚砜亚胺。通过使用较短的反应序列，可以很容易地制备 8-氨基-2,1-苯并噻嗪衍生物，它是合成其他衍生物的有价值的中间体。初步实验表明，在铜催化的不对称 Mukaiyama 型羟醛反应中使用此类化合物可提供具有中等对映选择性的产物。
• Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process
  作者：Qian Cai、Zhengqiu Li、Jiajia Wei、Chengyong Ha、Duanqing Pei、Ke Ding

  DOI：10.1039/b918345k

  日期：——

  A straightforward synthesis of indole-2-carboxylic esters was developed through a ligand-free copper-catalysed condensation/coupling/deformylation cascade process from 2-halo aryl aldehydes or ketones with ethyl isocyanoacetate. The reactions proceeded well for most of the 2-iodo-, bromo-, and chloro-substrates under room temperature or mild conditions.

  通过无配体的铜催化的2-卤代芳基醛或酮与异氰基乙酸乙酯的合成，开发了吲哚-2-羧酸酯的直接合成方法。在室温或温和条件下，大多数2-碘，溴和氯底物的反应进展顺利。
• Electrophilic Bromination of meta-Substituted Anilines with N-Bromosuccin­imide: Regioselectivity and Solvent Effect
  作者：Daniela Fattori、Sandra Bartoli、Amalia Cipollone、Antonella Squarcia、Andrea Madami

  DOI：10.1055/s-0028-1088016

  日期：2009.4

  N-Bromosuccinimide-mediated electrophilic aromatic bromination of a series of anilines substituted with an electron-withdrawing group in the meta position was investigated. The regioselectivity of the reaction is markedly dependent on the polarity of the solvent and the bromination reaction can be tuned by appropriate selection of the reaction medium.

  研究了N-溴琥珀酰亚胺介导的电亲核芳香族溴化反应，目标是一些在中位位置带有电子吸引基团的苯胺系列。反应的区位选择性明显依赖于溶剂的极性，通过适当选择反应介质可以调节溴化反应。
• BORON CONTAINING PYRIMIDINE COMPOUNDS, COMPOSITIONS COMPRISING THEM, METHODS AND USES THEREOF
  申请人：BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

  公开号：WO2023244775A1

  公开（公告）日：2023-12-21

  The present disclosure describes boron containing pyrimidine compounds, or their pharmaceutically acceptable salts, pharmaceutical compositions containing them, and their medical uses. The compounds of the present disclosure have activity as Janus kinase (JAK) inhibitors and are useful in the in the treatment or control of inflammation, auto-immune diseases, cancer, and other disorders and indications where modulation of JAK would be desirable. Also described are methods of treating inflammation, auto-immune diseases, cancer, and other conditions that are susceptible to the inhibition of a Janus kinase by administering a compound herein described.

  本公开描述了含硼嘧啶化合物或其药学上可接受的盐、含有它们的药物组合物及其医疗用途。本公开的化合物具有 Janus 激酶 (JAK) 抑制剂的活性，可用于治疗或控制炎症、自身免疫性疾病、癌症以及其他希望调节 JAK 的疾病和适应症。还描述了通过施用本文所述化合物治疗炎症、自身免疫性疾病、癌症和其它易受Janus激酶抑制的疾病的方法。