N-3-[6-(nitro-1,3-benzothiazol-2-yl)]-2-[(2,4-dichlorophenyl)amino]-3-pyridinecarboxamide | 1350515-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N-3-[6-(nitro-1,3-benzothiazol-2-yl)]-2-[(2,4-dichlorophenyl)amino]-3-pyridinecarboxamide
• 英文别名: N3-[6-nitro-1,3-benzothiazol-2-yl]-2-[(2,4-dichlorophenyl)amino]-3-pyridinecarboxamide；2-(2,4-dichloroanilino)-N-(6-nitro-1,3-benzothiazol-2-yl)pyridine-3-carboxamide
• CAS: 1350515-68-2
• 化学式: C₁₉H₁₁Cl₂N₅O₃S
• 分子量: 460.3
• InChiKey: AKEWTUBMOJPGTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4-二氯苯胺 在 乙醇 、 1-羟基苯并三唑 、 sodium hydroxide 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.17h， 生成 N-3-[6-(nitro-1,3-benzothiazol-2-yl)]-2-[(2,4-dichlorophenyl)amino]-3-pyridinecarboxamide
  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

• 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。
• [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
• US9029553B2
  申请人：——

  公开号：US9029553B2

  公开（公告）日：2015-05-12
• 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.