4’-fluoro-4-nitro-[1,1’-biphenyl]-3-amine | 694533-20-5

• 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: 4’-fluoro-4-nitro-[1,1’-biphenyl]-3-amine
• 英文别名: 4'-fluoro-4-nitro-[1,1'-biphenyl]-3-amine；[1,1'-Biphenyl]-3-amine, 4'-fluoro-4-nitro-；5-(4-fluorophenyl)-2-nitroaniline
• CAS: 694533-20-5
• 化学式: C₁₂H₉FN₂O₂
• 分子量: 232.214
• InChiKey: PVJGOQLUVGYRBD-UHFFFAOYSA-N

物化性质

• 沸点：
  412.6±35.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4’-fluoro-4-nitro-[1,1’-biphenyl]-3-amine 在 palladium on activated charcoal 、 甲酸铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Identification of novel HDAC inhibitors through cell based screening and their evaluation as potential anticancer agents

  摘要：

  A series of benzimidazole based HDAC inhibitors have been rationally designed, synthesized and screened. The SAR of this new chemotype is described. The lead compound, 11e, showed strong activity in several cellular assays and demonstrated in vivo efficacy in mouse xenograft pancreatic cancer models. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.001
• 作为产物：
  描述：

  5-溴-2-硝基苯胺 、 4-氟苯硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以93%的产率得到4’-fluoro-4-nitro-[1,1’-biphenyl]-3-amine
  参考文献：
  名称：

  [EN] HETEROBICYCLIC N-AMINOPHENYL-AMIDES AS INHIBITORS OF HISTONE DEACETYLASE
  [FR] N-AMINOPHÉNYL-AMIDES HÉTÉROCYCLIQUES EN TANT QU'INHIBITEURS DE L'HISTONE DÉSACÉTYLASE

  摘要：

  这项发明提供了抑制HDAC2的化合物。这些化合物（例如，符合式（I）的化合物或化合物100-175中的任何一种）可用于治疗、缓解或预防受试者中的某种疾病，如神经系统疾病、记忆或认知功能障碍或损伤、消退学习障碍、真菌疾病或感染、炎症性疾病、血液疾病或肿瘤性疾病，或用于改善记忆或治疗、缓解或预防记忆丧失或损伤。

  公开号：

  WO2017007755A1

文献信息

• [EN] HETEROBICYCLIC N-AMINOPHENYL-AMIDES AS INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] N-AMINOPHÉNYL-AMIDES HÉTÉROCYCLIQUES EN TANT QU'INHIBITEURS DE L'HISTONE DÉSACÉTYLASE
  申请人：RODIN THERAPEUTICS INC

  公开号：WO2017007755A1

  公开（公告）日：2017-01-12

  This invention provides compounds that are inhibitors of HDAC2. The compounds (e.g., compounds according to Formula (I) or any one of Compounds 100-175) accordingly are useful for treating, alleviating, or preventing a condition in a subject such as a neurological disorder, memory or cognitive function disorder or impairment, extinction learning disorder, fungal disease or infection, inflammatory disease, hematological disease, or neoplastic disease, or for improving memory or treating, alleviating, or preventing memory loss or impairment.

  这项发明提供了抑制HDAC2的化合物。这些化合物（例如，符合式（I）的化合物或化合物100-175中的任何一种）可用于治疗、缓解或预防受试者中的某种疾病，如神经系统疾病、记忆或认知功能障碍或损伤、消退学习障碍、真菌疾病或感染、炎症性疾病、血液疾病或肿瘤性疾病，或用于改善记忆或治疗、缓解或预防记忆丧失或损伤。
• Inhibitors of histone deacetylase
  申请人：The Broad Institute, Inc.

  公开号：US09365498B2

  公开（公告）日：2016-06-14

  The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, or prodrug thereof, wherein U, J, V, X, R2a, R2b, R2c, R5 and t are as described herein. The present invention relates generally to inhibitors of histone deacetylase and to methods of making and using them. These compounds are useful for promoting cognitive function and enhancing learning and memory formation. In addition, these compounds are useful for treating, alleviating, and/or preventing various conditions, including for example, neurological disorders, memory and cognitive function disorders/impairments, extinction learning disorders, fungal diseases and infections, inflammatory diseases, hematological diseases, and neoplastic diseases in humans and animals.

  本发明涉及以下式(I)的化合物： 或其药学上可接受的盐、水合物、溶剂合物或前药，其中U、J、V、X、R2a、R2b、R2c、R5和t如本文所述。本发明一般涉及组织脱乙酰酶抑制剂及其制备和使用方法。这些化合物对促进认知功能、增强学习和记忆形成有用。此外，这些化合物对治疗、缓解和/或预防各种疾病条件有用，例如神经系统疾病、记忆和认知功能障碍/损伤、消退学习障碍、真菌疾病和感染、炎症性疾病、血液病和人类及动物的肿瘤性疾病。
• Investigating Structural Requirements for the Antiproliferative Activity of Biphenyl Nicotinamides
  作者：Maria Majellaro、Angela Stefanachi、Piero Tardia、Chiara Vicenti、Angelina Boccarelli、Alessandra Pannunzio、Federica Campanella、Mauro Coluccia、Nunzio Denora、Francesco Leonetti、Modesto de Candia、Cosimo Damiano Altomare、Saverio Cellamare

  DOI：10.1002/cmdc.201700365

  日期：2017.8.22

  with the aim of identifying new anticancer agents. One of these compounds, which showed antiproliferative activity against resistant MCF-7 cell line, was selected as the hit structure. Replacement of the trimethoxybenzoyl moiety with a nicotinoyl group, in order to overcome solubility issues, led to a new series of N-biphenyl nicotinoyl anilides, among which a nitro derivative, N-(3',5'-difluoro-3-nitro-[1

  筛选了许多以前作为渗透性糖蛋白（P-gp）调节剂研究过的三甲氧基苯甲酸酐，目的是鉴定新的抗癌药。选择对抗MCF-7细胞系具有抗增殖活性的这些化合物之一作为命中结构。为了克服溶解性问题，用烟酰基取代三甲氧基苯甲酰基部分导致了一系列新的N-联苯基烟酰基苯甲酰苯胺，其中包括硝基衍生物N-（3'，5'-二氟-3-硝基- [1,1'-联苯] -4-基）烟酰胺（3）在纳摩尔范围内显示出对MCF-7和MDA-MB-231细胞的抗增殖活性。寻找硝基的生物等排体导致腈类似物N-（3-氰基-4'-氟-[1,1'-联苯] -4-基）烟酰胺（36），表明对MCF-7和MDA-MB-231细胞的活性大大增强。化合物36诱导了G2期和M期MCF-7细胞群体的剂量依赖性积累，并减少了S期细胞。相对于长春花碱（一种众所周知的有效抗有丝分裂剂），化合物36在低剂量（20-40 nm）下也能诱导G1期阻滞，但不抑制体外微管蛋白的聚合。
• Inhibitors of Histone Deacetylase
  申请人：The Broad Institute, Inc.

  公开号：US20140080800A1

  公开（公告）日：2014-03-20

  The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, or prodrug thereof, wherein U, J, V, X, R 2a , R 2b , R 2c , R 5 and t are as described herein. The present invention relates generally to inhibitors of histone deacetylase and to methods of making and using them. These compounds are useful for promoting cognitive function and enhancing learning and memory formation. In addition, these compounds are useful for treating, alleviating, and/or preventing various conditions, including for example, neurological disorders, memory and cognitive function disorders/impairments, extinction learning disorders, fungal diseases and infections, inflammatory diseases, hematological diseases, and neoplastic diseases in humans and animals.

  本发明涉及式（I）的化合物：或其药学上可接受的盐、水合物、溶剂合物或前药，其中U、J、V、X、R2a、R2b、R2c、R5和t如本文所述。本发明通常涉及组织脱乙酰化酶抑制剂及其制备和使用方法。这些化合物有助于促进认知功能和增强学习和记忆形成。此外，这些化合物对于治疗、缓解和/或预防各种疾病有用，包括但不限于神经系统疾病、记忆和认知功能障碍、消退学习障碍、真菌病和感染、炎症性疾病、血液病和动物的肿瘤疾病。
• INHIBITORS OF HISTONE DEACETYLASE
  申请人：The Broad Institute, Inc.

  公开号：US20160251351A1

  公开（公告）日：2016-09-01

  The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, or prodrug thereof, wherein U, J, V, X, R 1a , R 2b , R 2c , R 5 and t are as described herein. The present invention relates generally to inhibitors of histone deacetylase and to methods of making and using them. These compounds are useful for promoting cognitive function and enhancing learning and memory formation. In addition, these compounds are useful for treating, alleviating, and/or preventing various conditions, including for example, neurological disorders, memory and cognitive function disorders/impairments, extinction learning disorders, fungal diseases and infections, inflammatory diseases, hematological diseases, and neoplastic diseases in humans and animals.

  本发明涉及化合物式(I)或其药学上可接受的盐、水合物、溶剂合物或前药，其中U、J、V、X、R1a、R2b、R2c、R5和t如本文所述。本发明通常涉及组织脱乙酰化酶抑制剂及其制备和使用方法。这些化合物有助于促进认知功能，增强学习和记忆形成。此外，这些化合物在治疗、缓解和/或预防各种疾病方面也很有用，包括例如神经系统疾病、记忆和认知功能障碍、消退学习障碍、真菌疾病和感染、炎症性疾病、血液疾病和动物的肿瘤性疾病。