2,4-dichloro-N-(2-nitrophenyl)aniline | 86514-69-4

• 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: 2,4-dichloro-N-(2-nitrophenyl)aniline
• CAS: 86514-69-4
• 化学式: C₁₂H₈Cl₂N₂O₂
• 分子量: 283.114
• InChiKey: FWFNOOPNXWJMGM-UHFFFAOYSA-N

物化性质

• 熔点：
  142-144 °C
• 沸点：
  379.8±42.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-N-(2-nitrophenyl)aniline 在 ammonium hydroxide 、 sodium dithionite 、 三甲基铝 、 sodium 2,2,2-trifluoroacetate 、 红铝 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 90.67h， 生成 Cyclopropylmethyl-[9-(2,4-dichloro-phenyl)-2-trifluoromethyl-9H-benzo[d]imidazo[1,2-a]imidazol-3-ylmethyl]-propyl-amine
  参考文献：
  名称：

  Synthesis and structure–activity relationship of imidazo[1,2-a]benzimidazoles as corticotropin-releasing factor 1 receptor antagonists

  摘要：

  8-Aryl-1,3a,8-triaza-cyclopenta[a]indenes represent a novel series of high binding affinity corticotropin-releasing factor 1 receptor antagonists. Here, we report their synthesis, SAR, and pharmacokinetic properties of compound 8e (K-i = 23 nM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.028
• 作为产物：
  描述：

  2,4-二氯苯胺 、 硝基氯苯 在 potassium carbonate 作用下， 反应 2.0h， 生成 2,4-dichloro-N-(2-nitrophenyl)aniline
  参考文献：
  名称：

  新型fenfuram-diarylamine杂种的设计，合成和抗真菌活性。

  摘要：

  设计并合成了十种新型的呋喃喃-二芳基胺杂化物。并已在体外评估了它们对四种植物病原真菌的抗真菌活性，并且大多数化合物均显示出对茄状枯萎病菌和菌核盘菌具有显着的抗真菌活性。化合物5e表现出最强的对茄尼古丁菌的抗真菌活性，EC50值为0.037mg / L，远优于市售的杀菌剂博卡利杀灭剂（EC50 = 1.71mg / L）和杀菌剂芬氟拉姆（EC50 = 6.18mg / L）。 。此外，扫描电子显微镜图像显示，与阴性对照相比，处理过的培养基上的菌丝体异常生长，菌落脆弱，呈干状和重叠。分子对接研究表明，化合物5e对琥珀酸脱氢酶（SDH）的亲和力比芬呋喃高。此外，

  DOI：

  10.1016/j.bmcl.2016.11.026

文献信息

• Design, synthesis and biological evaluation of novel 4-phenoxypyridine based 3-oxo-3,4-dihydroquinoxaline-2-carboxamide derivatives as potential c-Met kinase inhibitors
  作者：Zhen Wang、Jiantao Shi、Xianglong Zhu、Wenwen Zhao、Yilin Gong、Xuechen Hao、Yunlei Hou、Yajing Liu、Shi Ding、Ju Liu、Ye Chen

  DOI：10.1016/j.bioorg.2020.104371

  日期：2020.12

  Blocking c-Met kinase activity by small-molecule inhibitors has been identified as a promising approach for the treatment of cancers. Herein, we described the design, synthesis, and biological evaluation of a series of 4-phenoxypyridine-based 3-oxo-3,4-dihydroquinoxaline derivatives as c-Met kinase inhibitors. Inhibitory activitives against c-Met kinase evaluation indicated that most of compounds showed

  通过小分子抑制剂阻断c-Met激酶活性已被认为是治疗癌症的有前途的方法。在这里，我们描述了一系列基于4-苯氧吡啶的3-氧代-3,4-二氢喹喔啉衍生物作为c-Met激酶抑制剂的设计，合成和生物学评估。对c-Met激酶的抑制活性评估表明，大多数化合物在体外均表现出出色的c-Met激酶活性，十种化合物（23a，23e，23f，23l，23r，23s，23v，23w，23x和23y）的IC 50值）小于10.00 nM。值得注意的是，它们中的三个（23v，23w和23y）显示出显着的效价，IC 50值分别为2.31 nM，1.91 nM和2.44 nM，因此它们比阳性对照药物foretinib（c-Met，IC 50  = 2.53 nM）。细胞毒性评估表明，最有希望的化合物23w对A549，H460和HT-29细胞系表现出显着的细胞毒性，IC 50值分别为1.57μM，0.94μM和0.65μM
• Synthesis and biological evaluation of novel pyrazole carboxamide with diarylamine-modified scaffold as potent antifungal agents
  作者：Xiao-Xiao Zhang、Hong Jin、Yuan-Jie Deng、Xu-Heng Gao、Yong Li、Yong-Tian Zhao、Ke Tao、Tai-Ping Hou

  DOI：10.1016/j.cclet.2017.04.021

  日期：2017.8

  Abstract Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed, synthesized and characterized in detail via 1H NMR, 13C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani, Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest

  摘要设计，合成并通过1H NMR，13C NMR，IR和ESI-HRMS详细表征了二十七种新型的带有二芳基胺修饰的支架的吡唑甲酰胺。初步的生物测定结果表明，某些目标化合物对茄状枯萎病菌，谷粒状枯萎病菌和菌核盘菌具有良好的抗真菌活性。其中，化合物9c-7表现出最高的对solani solani，R。grainis和S. sclerotiorum的抗真菌活性，IC50值分别为0.013、1.608和1.874μg/ mL。值得注意的是，化合物9c-7仍然在体内具有最高的对茄红假单胞菌的杀真菌活性，IC50值为22.21μg/ mL。分子对接模拟结果表明，化合物9c-7与受体蛋白琥珀酸脱氢酶的疏水口袋结合良好。
• Design, synthesis and biological evaluation of novel 4-phenoxyquinoline derivatives containing 3-oxo-3,4-dihydroquinoxaline moiety as c-Met kinase inhibitors
  作者：Ju Liu、Di Yang、Xiuxiu Yang、Minhua Nie、Guodong Wu、Zhunchao Wang、Wei Li、Yajing Liu、Ping Gong

  DOI：10.1016/j.bmc.2017.06.037

  日期：2017.8

  A series of novel 4-phenoxyquinoline derivatives containing 3-oxo-3,4-dihydroquinoxaline moiety were synthesized and evaluated for their c-Met kinase inhibitory activity and antiproliferative activity against five cancer cell lines (HT-29, H460, A549, MKN-45 and U87MG) in vitro. Most of the compounds exhibited moderate-to-significant cytotoxicity as compared with foretinib. The most promising compound

  合成了一系列包含3-oxo-3,4-dihydroquinoxaline部分的新颖的4-phenoxyquinoline衍生物，并评估了它们对5种癌细胞系（HT-29，H460，A549，MKN- 45和U87MG）体外。与福替尼相比，大多数化合物表现出中度至显着的细胞毒性。最有前途的化合物41（c-Met IC 50值为0.90 nM）对具有IC 50的HT-29，H460，A549，MKN-45和U87MG细胞系表现出显着的细胞毒性分别为0.06μM，0.05μM，0.18μM，0.023μM和0.66μM，因此其效力比福替尼大1.22至3.50倍。他们的初步结构-活性关系（SAR）研究表明，末端苯环上的吸电子基团有助于改善抗肿瘤活性。
• Imidazolyl derivatives as corticotropin releasing factor inhibitors
  申请人：——

  公开号：US20020183375A1

  公开（公告）日：2002-12-05

  The present invention relates to novel heterocyclic antagonists of Formula (I) and pharmaceutical compositions comprising said antagonists of the corticotropin releasing factor receptor (“CRF receptor”) 1 useful for the treatment of depression, anxiety, affective disorders, feeding disorders, post-traumatic stress disorder, headache, drug addiction, inflammatory disorders, drug or alcohol withdrawal symptoms and other conditions the treatment of which can be effected by the antagonism of the CRF-1 receptor.

  本发明涉及一种新型杂环拮抗剂，其化学式为(I)，以及包含所述拮抗剂的药物组合物，用于治疗抑郁症、焦虑症、情感障碍、进食障碍、创伤后应激障碍、头痛、药物成瘾、炎症性疾病、药物或酒精戒断症状以及其他可以通过拮抗CRF-1受体来治疗的病症。
• Tricyclic polyazaheterocycles for treating depression or anxiety
  申请人：Ciba-Geigy Corporation

  公开号：US04510141A1

  公开（公告）日：1985-04-09

  The invention relates to novel polycyclic polyazaheterocycles having psychopharmacological properties, especially antidepressive and anxiolytic activity, corresponding to the formula I ##STR1## in which R.sub.1 and R.sub.2 each represents, independently of the other, hydrogen, lower alkyl or hydroxy-lower alkyl, or together represent lower alkylene or ethyleneoxyethylene, ethyleneazaethylene or N-lower alkyl- or N-(2-hydroxy-lower alkyl)-ethyleneazaethylene, R.sub.3 represents hydrogen or a lower aliphatic hydrocarbon radical or a saturated lower cycloaliphatic hydrocarbon radical or unsubstituted or substituted phenyl, R.sub.4 and R.sub.5 represent hydrogen or lower alkyl, and Ar represents an unsubstituted or substituted benzo or pyrido radical, and to acid addition salts of compounds of the general formula I, especially the pharmaceutically acceptable acid addition salts of compounds of the general formula I, to pharmaceutical preparations containing these novel substances and to a method of treating conditions of depression or anxiety by administering them.

  该发明涉及具有心理药理学特性的新型多环多氮杂环化合物，特别是抗抑郁和抗焦虑活性，对应于式I ##STR1## 其中R.sub.1和R.sub.2分别独立地代表氢、较低烷基或羟基较低烷基，或者一起代表较低烷基或乙烯氧基乙烷、乙烯氮基乙烷或N-较低烷基或N-(2-羟基较低烷基)-乙烯氮基乙烷，R.sub.3代表氢或较低脂肪烃基或饱和较低环脂烃基或未取代或取代的苯基，R.sub.4和R.sub.5代表氢或较低烷基，Ar代表未取代或取代的苯并或吡啶基，以及一般式I化合物的酸加合物盐，特别是一般式I化合物的药用可接受的酸加合物盐，含有这些新型物质的制药制剂以及通过给予它们治疗抑郁或焦虑症状的方法。