2-(2,4-dichlorophenylamino)nicotinic acid | 343221-63-6

• 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-(2,4-dichlorophenylamino)nicotinic acid
• 英文别名: 2-(2,4-Dichlorophenylamino) nicotinic acid；2-(2,4-dichloroanilino)pyridine-3-carboxylic acid
• CAS: 343221-63-6
• 化学式: C₁₂H₈Cl₂N₂O₂
• mdl: MFCD03114544
• 分子量: 283.114
• InChiKey: SUPGBAYZQRCPAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 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-(2,4-dichlorophenylamino)nicotinic acid 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 56.0h， 生成 N-(2,4-dichlorophenyl)-3-(phenylsulfanylmethyl)pyridin-2-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：

  2,4-二氯苯胺 在 乙醇 、 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 7.0h， 生成 2-(2,4-dichlorophenylamino)nicotinic acid
  参考文献：
  名称：

  2-ANILINO NICOTINYL LINKED 2-AMINO BENZOTHIAZOLE CONJUGATES AND PROCESS FOR THE PREPARATION THEREOF

  摘要：

  本发明提供了一种通式A的化合物，作为潜在的抗人类癌细胞系和诱导凋亡剂。本发明还提供了一种用于制备通式（A）的2-苯胺基烟酰基连接的2-氨基苯并噻唑共轭物的方法，其中R1═H或CI；R2═H，OCH3或F；R3═H，OCH3，F或CI；R4═H，OCH3或F，X═OCH3，F或N02。

  公开号：

  US20130324734A1

文献信息

• 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 Heteroaryl Carboxylic Acid Derivatives as Anti-inflammatory-Analgesic Agents
  作者：Khaled Abouzid Mohamed Abouzid、Nadia Abdalla Khalil、Eman Mohamed Ahmed、Sawsan Abo-Bakr Zaitone

  DOI：10.1248/cpb.c12-00949

  日期：——

  A series of nicotinic acid derivatives structurally related to niflumic acid and certain pyridazine-containing compounds have been synthesized and characterized by analytical and spectral data. All compounds were screened for their potential analgesic and anti-inflammatory activities. The compounds which displayed analgesic and anti-inflammatory activities were tested for ulcerogenicity and screened for in vivo inhibition of certain inflammatory cytokines such as tumor necrosis factor-alpha (TNF-α), interleukin-6 (IL-6), and cyclooxygenase-2 (COX-2). Compounds 1c, 2a, 2b, and 5a have shown potent analgesic and anti-inflammatory activities.

  一系列与尼氟替酸和某些含吡唑的化合物在结构上相关的烟酸衍生物已经合成并通过分析和光谱数据进行了表征。所有化合物均被筛选以评估其潜在的镇痛和抗炎活性。显示出镇痛和抗炎活性的化合物经过了溃疡毒性测试，并对某些炎症细胞因子（如肿瘤坏死因子-alpha (TNF-α)、白介素-6 (IL-6) 和环氧合酶-2 (COX-2)）的体内抑制进行了筛选。化合物1c、2a、2b和5a表现出了强效的镇痛和抗炎活性。
• 2-anilino nicotinyl linked 2-amino benzothiazole conjugates and process for the preparation thereof
  申请人：Kamal Ahmed

  公开号：US09029553B2

  公开（公告）日：2015-05-12

  The present invention provides compounds of general formula A useful as potential anticancer agents against human cancer cell lines and apoptosis inducers. The present invention further provides a process for the preparation of 2-anilino nicotinyl linked 2-amino benzothiazole conjugates of general formula (A), wherein R1═H or Cl; R2═H, OCH3 or F; R3═H, OCH3, F or Cl; R4═H, OCH3 or F and X═OCH3, F or N02.

  本发明提供了一般式A的化合物，可用作潜在的抗癌剂，对人类癌细胞系和诱导凋亡剂具有作用。本发明还提供了制备一般式（A）的2-苯胺基烟酰基连接的2-氨基苯并噻唑共轭物的方法，其中R1 = H或Cl；R2 = H，OCH3或F；R3 = H，OCH3，F或Cl；R4 = H，OCH3或F，X = OCH3，F或N02。
• 2-Anilinonicotinyl linked 2-aminobenzothiazoles and [1,2,4]triazolo[1,5-b] [1,2,4]benzothiadiazine conjugates as potential mitochondrial apoptotic inducers
  作者：Ahmed Kamal、Y.V.V. Srikanth、M. Naseer Ahmed Khan、Md. Ashraf、M. Kashi Reddy、Farheen Sultana、Tandeep Kaur、Gousia Chashoo、Nitasha Suri、Irum Sehar、Zahoor A. Wani、Arpita Saxena、Parduman R. Sharma、Shashi Bhushan、Dilip M. Mondhe、Ajit K. Saxena

  DOI：10.1016/j.bmc.2011.09.060

  日期：2011.12

  A series of N-(2-anilino-pyridyl) linked 2-amino benzothiazoles (4a-n) and [1,2,4]triazolo [1,5-b]benzothiadiazine conjugates (5a-j) have been designed, synthesized and evaluated for their antiproliferative activity. Some of these compounds (4h-k, 4n, and 5e) have exhibited potent cytotoxicity specifically against human leukemia HL-60 cell lines with IC50 values in the range of 0.08-0.70 mu M. All these compounds were tested for their effects on the cell cycle perturbations and induction of apoptosis. Morphological evidences of apoptosis, including fragmentation of nuclei and inter nucleosomal DNA laddering formation were clearly observed after 24 h exposure to compound 4i. Flow cytometry analysis revealed that compound 4i showed drastic cell cycle perturbations due to concentration dependant increase in the sub-G0 region which comprises of both the apoptotic and debris fraction, thus implying the extent of cell death. These compounds trigger the mitochondrial apoptotic pathway that results in the loss of mitochondrial membrane potential through activation of multiple caspases followed by activation of caspase-3, and finally cleavage of PARP. Further the mechanism of cell death was analysed by fluorescent microscopic analysis and also by scanning electron microscopy. The cytotoxicity of 4i correlated with induction of apoptosis, caspases activation and DNA damage and thus indicating the apoptotic pathway of anticancer effect of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.