2-(2-chlorophenylamino)nicotinic acid | 57978-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2-chlorophenylamino)nicotinic acid
• 英文别名: 2-[(2-chlorophenyl)amino]pyridine-3-carboxylic acid；2-(2-Chloroanilino)pyridine-3-carboxylic acid
• CAS: 57978-40-2
• 化学式: C₁₂H₉ClN₂O₂
• mdl: MFCD03822710
• 分子量: 248.669
• InChiKey: MBYZLOUZGSCMAR-UHFFFAOYSA-N

物化性质

• 熔点：
  250 °C(Solv: benzene (71-43-2))
• 沸点：
  392.4±37.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-chlorophenylamino)nicotinic acid 在 lithium aluminium tetrahydride 、 三丁基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (2-Chloro-phenyl)-(3-phenylsulfanylmethyl-pyridin-2-yl)-amine
  参考文献：
  名称：

  Substituted 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-ones as potential antiinflammatory agents

  摘要：

  A series of analogues based on the 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one ring system have been synthesized and shown to possess oral antiinflammatory activity in both the reverse passive Arthus reaction (RPAR) pleural cavity assay in rats and in the adjuvant-induced arthritic rat model (AAR). Several members of this series additionally exhibit an inhibitory effect on the in vivo production of prostaglandin- and leukotriene-derived products or arachidonic acid metabolism although these compounds exhibit no significant inhibitory activity against the cyclooxygenase and 5-lipoxygenase enzymes in vitro. Structure-activity relationships in this series are discussed.

  DOI：

  10.1021/jm00172a004
• 作为产物：
  描述：

  2-((2-Chlorophenyl)amino)nicotinonitrile 以25%的产率得到
  参考文献：
  名称：

  BOTROS, S.;EL-BAIH, F., EGYPT. J. CHEM., 29,(1986) N 3, C. 275-281

  摘要：

  DOI：

文献信息

• PYRIDOPYRIMIDINONE INHIBITORS OF KINASES
  申请人：AbbVie Inc.

  公开号：US20130225589A1

  公开（公告）日：2013-08-29

  The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts, wherein R 1 , R 2 , R 3 , R 4 , and B are defined in the description. The present invention relates also to compositions containing said compounds which are useful for inhibiting kinases such as wee-1 and methods of treating diseases such as cancer.

  本发明涉及式(I)化合物或药理可接受的盐，其中R1、R2、R3、R4和B在描述中定义。本发明还涉及包含所述化合物的组合物，这些化合物可用于抑制诸如wee-1的激酶，以及治疗诸如癌症疾病的方法。
• Synthesis of 2-(arylamino)nicotinic acids in high-temperature water
  作者：Zhenghua Li、Shangyou Xiao、Ronghui Liang、Zhining Xia

  DOI：10.1007/s11164-012-0494-0

  日期：2012.9

  In hydrothermal reactions at 150–180 °C, 2-(arylamino)nicotinic acids were synthesized by amination of 2-chloronicotinic acid with aromatic amine derivatives, with potassium carbonate as base. The procedure is efficient, environmentally friendly, and practical, with moderate to excellent yields (up to 98%).

  在150–180°C的水热反应中，通过将2-氯烟酸与芳香胺衍生物（以碳酸钾为碱）胺化来合成2-（芳基氨基）烟酸。该过程高效，环保且实用，产率中等至极佳（高达98％）。
• Catalyst-Free Amination of 2-Chloronicotinic Acid in Water under Microwave Irradiation
  作者：Zheng-hua Li、Zhi-ning Xia、Gang Chen

  DOI：10.3184/174751911x13231642443092

  日期：2011.12

  A simple, efficient and environmental friendly method for the synthesis of 2-arylaminonicotinic acids derivatives by reacting 2-chloronicotinic acid with anilines with potassium carbonate as the base and water as the media under microwave irradiation is described. The synthesis of 2-arylaminonicotinic acids is important because they are nonsteroidal anti-inflammatory drugs.

  本研究介绍了一种简单、高效、环保的方法，即在微波辐照下，以碳酸钾为碱、水为介质，通过 2-氯烟酸与苯胺反应合成 2-芳基氨基烟酸衍生物。2- 芳基氨基烟酸是一种非甾体抗炎药，因此其合成非常重要。
• Synthesis and biological evaluation of new nicotinic acid derivatives as potential anti-inflammatory agents with enhanced gastric safety profile
  作者：Eman M. Ahmed、Nadia A. Khalil、Eman Ramadan、Toka Tharwat、Mohamed A. Ali、Zeinab Mahmoud

  DOI：10.1016/j.bioorg.2024.107136

  日期：2024.3

  evaluated for their anti-inflammatory activity. Ibuprofen, celecoxib and indomethacin were used as standard drugs. All the newly synthesized compounds were in vitro screened for their anti-inflammatory activity adopting 3-(4,5-dimethylthiazol-2-yl)2,5-diphenyltetrazolium bromide dye (MTT), as well as Griess assays. The results showed that all compounds exhibited significant anti-inflammatory activity without

  合成了两个源自烟酸支架的创新系列，并评估了它们的抗炎活性。使用布洛芬、塞来昔布和吲哚美辛作为标准药物。采用3-(4,5-二甲基噻唑-2-基)2,5-二苯基溴化四唑染料(MTT)以及Griess试验对所有新合成的化合物进行体外抗炎活性筛选。结果表明，与布洛芬相比，所有化合物均表现出显着的抗炎活性，且不影响巨噬细胞的活力。此外，化合物4d 、 4f 、 4g 、 4h和5b表现出最有效的亚硝酸盐抑制活性，因此具有优异的抗炎活性，MTT结果范围在值86.109±0.51至119.084±0.09之间。与作为参考化合物的布洛芬相比，对 LPS/INF γ 刺激的 RAW 264.7 巨噬细胞中最活跃的化合物进行 TNF-α、IL-6、iNOS 和 COX-2 水平的评估。与布洛芬相比，这五种化合物对这些炎症细胞因子的抑制效力相当。通过角叉菜胶诱导的大鼠关节炎，进一步体内评估了相同化合物的抗炎活性。
• TING, PAULINE C.;KAMINSKI, JAMES J.;SHERLOCK, MARGARET H.;TOM, WING C.;LE+, J. MED. CHEM., 33,(1990) N0, C. 2697-2706
  作者：TING, PAULINE C.、KAMINSKI, JAMES J.、SHERLOCK, MARGARET H.、TOM, WING C.、LE+

  DOI：——

  日期：——