2-((3,4,5-trimethoxyphenyl)amino)nicotinic acid | 115891-03-7

• 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-((3,4,5-trimethoxyphenyl)amino)nicotinic acid
• 英文别名: 2-(3,4,5-trimethoxyphenylamino) nicotinic acid；2-(3,4,5-trimethoxyphenylamino)nicotinic acid；2-(3,4,5-Trimethoxy-phenylamino)-nicotinic acid；2-(3,4,5-trimethoxyanilino)pyridine-3-carboxylic acid
• CAS: 115891-03-7
• 化学式: C₁₅H₁₆N₂O₅
• 分子量: 304.302
• InChiKey: WZVSBGCAFFQRAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((3,4,5-trimethoxyphenyl)amino)nicotinic acid 在 1-羟基苯并三唑 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.17h， 生成 3-(6-nitrobenzo[d]thiazol-2-yl)-1-(3,4,5-trimethoxyphenyl)-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one
  参考文献：
  名称：

  Synthesis and anticancer potential of benzothiazole linked phenylpyridopyrimidinones and their diones as mitochondrial apoptotic inducers

  摘要：

  A series of benzothiazole linked phenylpyridopyrimidinones (8a-g) and their diones (9a-g) have been designed, synthesized and evaluated for their anticancer activity. Among the series one of the conjugate 8b showed significant cytotoxicity against human cervical cancer cell line ME-180 with IC50 value of 4.01 mu M. This compound was tested on the cell cycle perturbations and DNA damage. Flow cytometry analysis revealed that the compound 8b showed drastic cell cycle perturbations due to concentration dependent increase in the sub-G0 phase in ME-180 cell line. DNA fragmentation and Hoechst staining reveals that this compound induced cell death by apoptosis. Further caspase-3 and loss of mitochondrial membrane potential suggested that the compound induces cell death by apoptosis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.057
• 作为产物：
  描述：

  2-氯烟酸乙酯 在 sodium hydroxide 作用下， 以 乙醇 、 乙二醇 为溶剂， 反应 8.0h， 生成 2-((3,4,5-trimethoxyphenyl)amino)nicotinic acid
  参考文献：
  名称：

  通过雌激素信号传导调节MCF-7细胞增殖的2-苯胺基烟酰-吡唑并[1,5- a ]嘧啶共轭物的合成及其机理

  摘要：

  合成了一系列的壬基烟酰胺基连接的吡唑并[1,5- a ]嘧啶共轭物（6a – x），并评估了它们的抗增殖活性。这些缀合物中的一些在MCF-7细胞系中显示出有希望的细胞毒性作用，并且在这些6a和6c中，除了G2 / M细胞周期停滞外，还显示出显着的作用。有趣的是，它们对调节乳腺癌细胞增殖的cyclin D1，Bcl-2和survivin蛋白显示出深远的影响。此外，研究了ERα蛋白的表达，以了解这些偶联物在雌激素阳性乳腺癌细胞（如MCF-7和化合物6a和6c）中对雌激素活性的调节作用。 减少了他们的活动。

  DOI：

  10.1016/j.bmcl.2016.02.072

文献信息

• 2-ANILINO NICOTINYL LINKED 2-AMINO BENZOTHIAZOLE CONJUGATES AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Kamal Ahmed

  公开号：US20130324734A1

  公开（公告）日：2013-12-05

  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 R 1 ═H or CI; R 2 ═H, OCH 3 or F; R 3 ═H, OCH 3 , F or CI; R 4 ═H, OCH 3 or F and X═OCH 3 , F or N0 2 .

  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。
• 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。
• Antiallergy agents. 1. Substituted 1,8-naphthyridin-2(1H)-ones as inhibitors of SRS-A release
  作者：Margaret H. Sherlock、James J. Kaminski、Wing C. Tom、Joe F. Lee、Shing Chun Wong、William Kreutner、Robert W. Bryant、Andrew T. McPhail

  DOI：10.1021/jm00119a010

  日期：1988.11

  A novel class of antiallergy agents, the substituted 1,8-naphthyridin-2(1H)-ones, is described. The present compounds are orally active, potent inhibitors of allergic and nonallergic bronchospasm in animal models. Structure-activity studies of the lead compound in this series, 1-phenyl-3-n-butyl-4-hydroxynaphthyridin-2(1H)-one (11), identified three compounds of interest, 1-phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one (12), 1-(3'-chlorophenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H )-one (87), and 1-(3'-methoxyphenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1 H)-one (89). The mechanism of antiallergy activity may involve inhibition of the release of the sulfidopeptide leukotrienes. 1-Phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one, Sch 33303 (12), was selected for preclinical development as an antiallergy agent.
• [EN] 2-ANILINO NICOTINYL LINKED 2-AMINO BENZOTHIAZOLE CONJUGATES AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] CONJUGÉS DE 2-AMINO BENZOTHIAZOLE À LIAISON 2-ANILINO NICOTINYL ET PROCÉDÉ DE PRÉPARATION CORRESPONDANT
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2012111016A8

  公开（公告）日：2013-08-01
• Synthesis of 2-anilinopyridine dimers as microtubule targeting and apoptosis inducing agents
  作者：Ahmed Kamal、S.M. Ali Hussaini、V. Lakshma Nayak、M. Shaheer Malik、M. Lakshmi Sucharitha、Thokhir Basha Shaik、Md. Ashraf、Chandrakant Bagul

  DOI：10.1016/j.bmc.2014.11.001

  日期：2014.12

  A series of 2-anilinopyridine dimers have been synthesized and evaluated for their anticancer potential. Most of the compounds have showed significant growth inhibition of the cell lines tested and compound 4d was most effective amongst the series displaying a GI(50) of 0.99 mu M specifically against the prostate cancer cell line (DU145). Studies to understand the mechanism of action of 4d indicates that it disrupts microtubule dynamics by inhibiting tubulin polymerization thereby arresting the cell cycle in G2/M phase. Competitive colchicine binding assay suggests that 4d binds into colchicine binding site of the tubulin. Further from some detailed biological studies like mitochondrial membrane potential, caspase-3 assay, DNA fragmentation analysis and Annexin V-FITC assay it is evident that 4d induces apoptosis. Molecular modeling studies provide an insight into the binding modes of 4d with colchicine binding site of tubulin and the data obtained correlates with the antiproliferative activity. (C) 2014 Elsevier Ltd. All rights reserved.