4-[5-(三氟甲基)-1,3-苯并噻唑-2-基]苯胺 | 920520-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 4-[5-(三氟甲基)-1,3-苯并噻唑-2-基]苯胺
• 英文名称: 2-(4-aminophenyl)-5-(trifluoromethyl)benzothiazole
• 英文别名: 4-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]aniline；4-(5-trifluoromethyl-benzothiazol-2-yl)-phenylamine
• CAS: 920520-33-8
• 化学式: C₁₄H₉F₃N₂S
• 分子量: 294.3
• InChiKey: LMPNKXKRMDWQSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[5-(三氟甲基)-1,3-苯并噻唑-2-基]苯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 2-[4-(β-alanylamino)phenyl]-5-trifluoromethylbenzothiazole bis(trifluoroacetic acid)
  参考文献：
  名称：

  Synthesis of 2-arylbenzothiazole derivatives and their application in bacterial detection

  摘要：

  A series of 2-arylbenzothiazole derivatives have been prepared as fluorogenic enzyme substrates in order to detect aminopeptidase, esterase, phosphatase and beta-galactosidase activity in clinically important Gram-negative and Gram-positive bacteria. Substrates were incorporated into an agar-based culture medium and this allowed growth of intensely fluorescent bacterial colonies based on hydrolysis by specific enzymes. Substrate 20 targeted L-alanine aminopeptidase activity and was hydrolysed exclusively by a range of Gram-negative bacteria and inhibited the growth of a range of Gram-positive bacteria. Substrate 19a targeted beta-alanyl aminopeptidase activity and generated fluorescent colonies of selected Gram-negative species including Pseudomonas aeruginosa. Substrate 21b targeted C8-esterase activity and resulted in strongly fluorescent colonies of selected species known to harbour such enzyme activity (e. g., Salmonella and Pseudomonas). Most Gram-negative species produced colonies with an intense blue fluorescence due to hydrolysis of phosphatase substrates 24a-c and substrate 24c was also hydrolysed by strains of Staphylococcus aureus. Compounds 26b and 26c targeted beta-galactosidase activity and generated strongly fluorescent colonies with coliform bacteria that produced this enzyme (e. g., Escherichia coli). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.013
• 作为产物：
  描述：

  2-氨基-4-(三氟甲基)苯硫酚盐酸盐 在 tin(II) chloride dihdyrate 、 四氯苯醌 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-[5-(三氟甲基)-1,3-苯并噻唑-2-基]苯胺
  参考文献：
  名称：

  Synthesis of 2-arylbenzothiazole derivatives and their application in bacterial detection

  摘要：

  A series of 2-arylbenzothiazole derivatives have been prepared as fluorogenic enzyme substrates in order to detect aminopeptidase, esterase, phosphatase and beta-galactosidase activity in clinically important Gram-negative and Gram-positive bacteria. Substrates were incorporated into an agar-based culture medium and this allowed growth of intensely fluorescent bacterial colonies based on hydrolysis by specific enzymes. Substrate 20 targeted L-alanine aminopeptidase activity and was hydrolysed exclusively by a range of Gram-negative bacteria and inhibited the growth of a range of Gram-positive bacteria. Substrate 19a targeted beta-alanyl aminopeptidase activity and generated fluorescent colonies of selected Gram-negative species including Pseudomonas aeruginosa. Substrate 21b targeted C8-esterase activity and resulted in strongly fluorescent colonies of selected species known to harbour such enzyme activity (e. g., Salmonella and Pseudomonas). Most Gram-negative species produced colonies with an intense blue fluorescence due to hydrolysis of phosphatase substrates 24a-c and substrate 24c was also hydrolysed by strains of Staphylococcus aureus. Compounds 26b and 26c targeted beta-galactosidase activity and generated strongly fluorescent colonies with coliform bacteria that produced this enzyme (e. g., Escherichia coli). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.013

文献信息

• 2-arylbenzothiazole analogues and uses thereof
  申请人：Ehlert Jan

  公开号：US20070021446A1

  公开（公告）日：2007-01-25

  The present invention relates to compounds of the general formula (I) and salts, prodrugs, and stereoisomers thereof, wherein Y independently represents S, O, NR 2 , SO, SO 2 ; A independently represents a fife- or six-membered aromatic carbocycle or heterocycle and wherein R 1 to R 20 in formula (I) represent independently of each other a variety of different substituents comprising alkyl, aryl, aralkyl, alkylaryl, heteroaryl groups and monofunctional moieties.

  本发明涉及一般式(I)的化合物及其盐、前药和立体异构体，其中Y独立表示S、O、NR2、SO、SO2；A独立表示五元或六元芳香碳环或杂环，式(I)中的R1至R20独立地表示各种不同取代基，包括烷基、芳基、芳基烷基、烷基芳基、杂芳基团和单官能团。
• 2-Arylbenzothiazole analogues and uses thereof in the treatment of cancer
  申请人：4SC AG

  公开号：EP1746096A1

  公开（公告）日：2007-01-24

  The present invention relates to anticancer compounds of the general formula (I) and salts and physiologically functional derivatives thereof, wherein Y independently represents S, O, NR2, SO, SO2; A independently represents a five- or six-membered aromatic carbocycle or heterocycle and wherein R1 in formula (I) represents one of the heteroaryl groups defined in the claims.

  本发明涉及一般式（I）的抗癌化合物及其盐和生理功能衍生物，其中Y独立表示S、O、NR2、SO、SO2；A独立表示五元或六元芳香碳环或杂环，式（I）中的R1表示权利要求中定义的杂芳基中的一个。
• Novel Heterocyclic NF-kB Inhibitors
  申请人：LEBAN Johann

  公开号：US20100004258A1

  公开（公告）日：2010-01-07

  The present invention relates to compounds of the general formula (III): or pharmaceutically acceptable salts thereof with an acid or a base, or pharmaceutically acceptable prodrugs or a stereoisomer thereof.

  本发明涉及一般式（III）的化合物：或其与酸或碱的药学上可接受的盐，或药学上可接受的前药或其立体异构体。
• Novel heterocyclic NF-kB inhibitors
  申请人：Leban Johann

  公开号：US20060247253A1

  公开（公告）日：2006-11-02

  The present invention relates to compounds of the general formula (III) or pharmaceutically acceptable salts thereof with an acid or a base, or pharmaceutically acceptable prodrugs or a stereoisomer thereof, wherein R 3 is H, —C(O)NR a R b , halogen, alkyl, haloalkyl, aryl, heteroaryl, OH, SH, NR 4′ OR 5′ , NH 2 , amine, alkylamine, alkoxy, cycloalkyl, heterocycloalkyl, hydroxyalkyl, or haloalkyloxy; R 4 is H, halogen, alkyl, —C(NR 7 )NR 7 R 8 , —(CH 2 ) p aryl, —(CH 2 ) p NR 7 R 8 , —C(O)NR 7 R 8 , —N═CR 7 R 8 , —NR 7 C(O)R 8 , cycloalkyl, heterocycloalkyl, haloalkyl, hydroxyalkyl, hyodroxyalkylamino, alkylamino, heteroaryl, or aryl; R 5 is halogen, alkyl, —C(NR 7 )NR 7 R 8 , —(CH 2 ) p aryl, —(CH 2 ) p NR 7 R 8 , —C(O)NR 7 R 8 , —N═CR 7 R 8 , —NR 7 C(O)R 8 , cycloalkyl, heterocycloalkyl, haloalkyl, hydroxyalkyl, hydroxyalkylamino, alkylamino, heteroaryl, or aryl.

  本发明涉及通式（III）的化合物或其药学上可接受的酸盐或碱盐，或其药学上可接受的前药或其立体异构体，其中R3为H，—C（O）NRaRb，卤素，烷基，卤代烷基，芳基，杂环芳基，OH，SH，NR4'OR5'，NH2，胺，烷基胺，烷氧基，环烷基，杂环环烷基，羟基烷基或卤代烷氧基；R4为H，卤素，烷基，—C（NR7）NR7R8，—（CH2）p 芳基，—（CH2）p NR7R8，—C（O）NR7R8，—N═CR7R8，—NR7C（O）R8，环烷基，杂环环烷基，卤代烷基，羟基烷基，羟基烷基氨基，烷基氨基，杂环芳基或芳基；R5为卤素，烷基，—C（NR7）NR7R8，—（CH2）p 芳基，—（CH2）p NR7R8，—C（O）NR7R8，—N═CR7R8，—NR7C（O）R8，环烷基，杂环环烷基，卤代烷基，羟基烷基，羟基烷基氨基，烷基氨基，杂环芳基或芳基。
• NOVEL HETEROCYCLIC NF-kB INHIBITORS
  申请人：Leban Johann

  公开号：US20100048574A1

  公开（公告）日：2010-02-25

  The present invention relates to compounds of the general formula (II): or pharmaceutically acceptable salts thereof with an acid or a base, or pharmaceutically acceptable prodrugs or a stereoisomer thereof.

  本发明涉及通式(II)的化合物或其与酸或碱的药物可接受盐，或药物可接受的前药，或其立体异构体。