4-{[4-(trifluoromethyl)phenyl]amino}benzoic acid | 617245-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{[4-(trifluoromethyl)phenyl]amino}benzoic acid
• 英文别名: 4-[4-(trifluoromethyl)anilino]benzoic acid
• CAS: 617245-73-5
• 化学式: C₁₄H₁₀F₃NO₂
• 分子量: 281.234
• InChiKey: XWOQDRPMULQZIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-{[4-(trifluoromethyl)phenyl]amino}benzoic acid 在 盐酸 、 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 、 水 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Evaluation of NovelN-(piperidine-4-yl)benzamide Derivatives as Potential Cell Cycle Inhibitors in HepG2 Cells

  摘要：

  In this study, a series of novel N‐(piperidine‐4‐yl)benzamide derivatives was designed, synthesized, and evaluated for antitumor activity. Some compounds were found to have potent antitumor activity. In particular, compound 47 showed the most potent biological activity against HepG2 cells, with an IC50 value of 0.25 μm. Western blot analysis demonstrated that compound 47 inhibited the expression of cyclin B1 and p‐Rb and enhanced the expression of p21, p53, Rb, and phospho‐adenosine monophosphate‐activated protein kinase (p‐AMPK). Further, cell cycle arrest was observed by flow cytometry (FCM). In summary, compound 47 was screened to have potential activity for the treatment of hepatocarcinoma via the induction of cell cycle arrest by a p53/p21‐dependent pathway.

  DOI：

  10.1111/cbdd.12484
• 作为产物：
  描述：

  ethyl 4-{[4-(trifluoromethyl)phenyl]amino}benzoate 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-{[4-(trifluoromethyl)phenyl]amino}benzoic acid
  参考文献：
  名称：

  Evaluation of NovelN-(piperidine-4-yl)benzamide Derivatives as Potential Cell Cycle Inhibitors in HepG2 Cells

  摘要：

  In this study, a series of novel N‐(piperidine‐4‐yl)benzamide derivatives was designed, synthesized, and evaluated for antitumor activity. Some compounds were found to have potent antitumor activity. In particular, compound 47 showed the most potent biological activity against HepG2 cells, with an IC50 value of 0.25 μm. Western blot analysis demonstrated that compound 47 inhibited the expression of cyclin B1 and p‐Rb and enhanced the expression of p21, p53, Rb, and phospho‐adenosine monophosphate‐activated protein kinase (p‐AMPK). Further, cell cycle arrest was observed by flow cytometry (FCM). In summary, compound 47 was screened to have potential activity for the treatment of hepatocarcinoma via the induction of cell cycle arrest by a p53/p21‐dependent pathway.

  DOI：

  10.1111/cbdd.12484

文献信息

• [EN] NITROSO DERIVATIVES OF DIPHENYLAMINE<br/>[FR] DERIVES NITROSO DE DIPHENYLAMINE
  申请人：MERCK PATENT GMBH

  公开号：WO2005051896A1

  公开（公告）日：2005-06-09

  The invention relates to a compound of the formula (I) in which: - R1 represents, independently of each other, a halogen atom; an aliphatic hydrocarbon-based group optionally substituted and/or optionally interrupted by one or more oxygen or sulfur atoms; a nitro group; a cyano group; an amino group; a mono- or dialkylamino group; an alkylcarbonyl group; a carboxyl group; an alkylcarbonylamino group; an alkylsulfonyl group; - R2 represents, independently of each other, a cyano group; a hydroxyl group, an alkylcarbonyl group; a carboxyl group; an alkoxycarbonyl group; an unsubstituted amide group; or a linear or branched alkyl group substituted by a cyano, hydroxyl, carboxyl, alkoxycarbonyl or unsubstituted amide group; - i and j independently being 1 to 5, with the exclusion of the compound for which i and j = 1 and R1 = carboxyl and R2 = alkoxycarbonyl or R1 = CF3 and R2 = carboxyl, and also the pharmaceutically acceptable derivatives, salts, solvates and stereoisomers thereof, including mixtures thereof in all proportions.

  该发明涉及以下式(I)的化合物：- R1分别表示卤素原子；一种基于脂肪烃的基团，该基团可以选择性地被一个或多个氧或硫原子取代和/或中断；硝基团；氰基团；氨基团；一种单烷基或二烷基氨基团；一种烷基羰基团；羧基团；一种烷基羰基氨基团；一种烷基磺酰基团；- R2分别表示氰基团；羟基团；烷基羰基团；羧基团；烷氧羰基团；未取代酰胺基团；或由氰基、羟基、羧基、烷氧羰基或未取代酰胺基团取代的线性或支链烷基团；- i和j独立地为1到5，不包括当i和j = 1且R1 = 羧基和R2 = 烷氧羰基或R1 = CF3和R2 = 羧基时的化合物，以及其药学上可接受的衍生物、盐、溶剂合物和立体异构体，包括所有比例的混合物。
• [EN] NOVEL METHOXYBENZAMIDE COMPOUNDS FOR USE IN MCH RECEPTOR RELATED DISORDERS<br/>[FR] NOUVEAUX COMPOSES DE METHOXYBENZAMIDE DESTINES A ETRE UTILISES DANS LE TRAITEMENT DES TROUBLES LIES AU RECEPTEUR DE MCH
  申请人：7TM PHARMA AS

  公开号：WO2003087045A1

  公开（公告）日：2003-10-23

  Novel compounds of Formula (I) which modulate MCH activity are disclosed, in which A is a linker; Ar1 is an aryl or heteroaryl group; R1 is a lower alkoxy group; R2 is an R1 group or hydrogen, an OH or an NH2 group, Q together with the carbonyl forms an amide group, which is further substituted with an amine group; R5 is selected from hydrogen, halogen atoms, alkoxy groups, hydroxy, alkylamino groups, dialkylamino groups, hydroxylalkyl groups, carboxamido groups, acylamido groups, acyl groups, -CHO, nitrile, alkyl, alkenyl or alkynyl groups, -SCH3, partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups such as -CH2CF3, -CF2CF3, -CF3, -OCF3, -SCF3; -SO2NH2, -SO2NHAlk, -SO2NAlk2, -SO2Alk; X is H, F, Cl, Br, I, -SCH3, -CF3, -OCF3, -SCF3, OCH3, or lower alkyl or alkenyl group; R8 is halogen atoms, alkyl, alkenyl or alkynyl groups, cycloalkyl groups, aryl groups, heteroaryl groups, heterocyclyl groups, alkylcycloalkyl groups, alkylaryl groups, alkylheterocyclyl groups, alkylheteroaryl groups, arylalkoxy groups, aryloxy groups, alkoxy groups, dialkylamino groups, -CONHAlk, -CONHAr, -CONAlk2, -NHCO-Alk, -NHCO-Ar, -CO-Alk, -CO-Ar, -SCH3, partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups; or R8 is R6-Ar2-B-, in which B is a single bond or a connecting moiety; Ar2 is an Ar1 group; R6 is an R5 group; and which are useful in the treatment or prevention of e.g. obesity, depression, diabetes, bulimia etc.

  化合物的新颖化合物的公式（I），其调节MCH活性，其中A是连接剂；Ar1是芳基或杂芳基；R1是较低的烷氧基团；R2是R1基团或氢，OH或NH2基团，Q与羰基一起形成酰胺基团，该基团进一步被氨基团取代；R5从氢，卤素原子，烷氧基团，羟基，烷基氨基团，二烷基氨基团，羟基烷基基团，羧酰胺基团，酰胺基团，酰基，-CHO，腈，烷基，烯基或炔基团，-SCH3，部分或完全氟化的烷基，烷氧基或硫代烷氧基团，如-CH2CF3，-CF2CF3，-CF3，-OCF3，-SCF3；-SO2NH2，-SO2NHAlk，-SO2NAlk2，-SO2Alk；X是H，F，Cl，Br，I，-SCH3，-CF3，-OCF3，-SCF3，OCH3，或较低的烷基或烯基基团；R8是卤素原子，烷基，烯基或炔基团，环烷基团，芳基，杂芳基，杂环烷基团，烷基环烷基团，烷基芳基团，烷基杂环烷基团，烷基杂芳基团，芳基烷氧基团，芳氧基团，烷氧基团，二烷基氨基团，-CONHAlk，-CONHAr，-CONAlk2，-NHCO-Alk，-NHCO-Ar，-CO-Alk，-CO-Ar，-SCH3，部分或完全氟化的烷基，烷氧基或硫代烷氧基团；或R8是R6-Ar2-B-，其中B是单键或连接基；Ar2是Ar1基团；R6是R5基团；在治疗或预防肥胖，抑郁症，糖尿病，暴食症等方面是有用的。
• Novel methoxybenzamibe compounds for use in mch receptor related disorders
  申请人：Hogberg Thomas

  公开号：US20060235035A1

  公开（公告）日：2006-10-19

  Novel compounds of Formula (I) which modulate MCH activity are disclosed, in which A is a linker; Ar 1 is an aryl or heteroaryl group; R1 is a lower alkoxy group; R2 is an R1 group or hydrogen, an OH or an NH 2 group, Q together with the carbonyl forms an amide group, which is further substituted with an amine group; R5 is selected from hydrogen, halogen atoms, alkoxy groups, hydroxy, alkylamino groups, dialkylamino groups, hydroxylalkyl groups, carboxamido groups, acylamido groups, acyl groups, —CHO, nitrile, alkyl, alkenyl or alkynyl groups, —SCH 3 , partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups such as —CH 2 CF 3 , —CF 2 CF 3 , —CF 3 , —OCF 3 , —SCF 3 ; —SO 2 NH 2 , —SO 2 NHAlk, —SO 2 NAlk 2 , —SO 2 Alk; X is H, F, Cl, Br, I, —SCH 3 , —CF 3 , —OCF 3 , —SCF 3 , OCH 3 , or lower alkyl or alkenyl group; R8 is halogen atoms, alkyl, alkenyl or alkynyl groups, cycloalkyl groups, aryl groups, heteroaryl groups, heterocyclyl groups, alkylcycloalkyl groups, alkylaryl groups, alkylheterocyclyl groups, alkylheteroaryl groups, arylalkoxy groups, aryloxy groups, alkoxy groups, dialkylamino groups, —CONHAlk, —CONHAr, —CONAlk 2 , —NHCO-Alk, —NHCO—Ar, —CO-Alk, —CO—Ar, —SCH 3 , partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups; or R8 is R6-Ar 2 —B—, in which B is a single bond or a connecting moiety; Ar 2 is an Ar 1 group; R6 is an R5 group; and which are useful in the treatment or prevention of e.g. obesity, depression, diabetes, bulimia etc.

  本发明揭示了式（I）的新化合物，其调节MCH活性，其中A是连接剂；Ar1是芳基或杂环芳基基团；R1是较低的烷氧基团；R2是R1基团或氢、OH或NH2基团，Q与羰基一起形成酰胺基团，该酰胺基团进一步被取代为胺基团；R5选自氢、卤原子、烷氧基团、羟基、烷基氨基基团、二烷基氨基基团、羟基烷基基团、羧酰胺基团、酰胺基团、酰基、—CHO、腈、烷基、烯基或炔基基团、—SCH3、部分或完全氟化的烷基、烷氧基或硫代烷氧基团，如—CH2CF3、—CF2CF3、—CF3、—OCF3、—SCF3；—SO2NH2、—SO2NHAlk、—SO2NAlk2、—SO2Alk；X是H、F、Cl、Br、I、—SCH3、—CF3、—OCF3、—SCF3、OCH3或较低的烷基或烯基基团；R8是卤原子、烷基、烯基或炔基基团、环烷基基团、芳基基团、杂环芳基基团、烷基环烷基基团、烷基芳基基团、烷基杂环芳基基团、芳基烷氧基团、芳氧基团、烷氧基团、二烷基氨基基团、—CONHAlk、—CONHAr、—CONAlk2、—NHCO-Alk、—NHCO—Ar、—CO-Alk、—CO—Ar、—SCH3、部分或完全氟化的烷基、烷氧基或硫代烷氧基；或R8是R6-Ar2—B—，其中B是单键或连接基；Ar2是Ar1基团；R6是R5基团；并且这些化合物在治疗或预防肥胖症、抑郁症、糖尿病、贪食症等方面是有用的。
• Nitroso derivatives of diphenylamine
  申请人：Lardy Claude

  公开号：US20070123586A1

  公开（公告）日：2007-05-31

  The invention relates to a compound of the formula I in which: R 1 represents, independently of each other, a halogen atom; an aliphatic hydrocarbon-based group optionally substituted and/or optionally interrupted by one or more oxygen or sulfur atoms; a nitro group; a cyano group; an amino group; a mono- or dialkylamino group; an alkylcarbonyl group; a carboxyl group; an alkylcarbonylamino group; an alkylsulfonyl group; R 2 represents, independently of each other, a cyano group; a hydroxyl group, an alkylcarbonyl group; a carboxyl group; an alkoxycarbonyl group; an unsubstituted amide group; or a linear or branched alkyl group substituted by a cyano, hydroxyl, carboxyl, alkoxycarbonyl or unsubstituted amide group; i and j independently being 1 to 5, with the exclusion of the compound for which i and j=1 and R 1 =carboxyl and R 2 =alkoxycarbonyl or R 1 =CF 3 and R 2 =carboxyl, and also the pharmaceutically acceptable derivatives, salts, solvates and stereoisomers thereof, including mixtures thereof in all proportions.

  本发明涉及一种具有公式I的化合物，其中：R1分别表示卤素原子；一种基于脂肪族的羟基烃基团，可选地被一个或多个氧或硫原子取代和/或中断；硝基基团；氰基团；氨基团；一种单烷基或二烷基氨基团；烷基羰基基团；羧基团；烷基羰基氨基基团；烷基磺酰基基团；R2分别表示氰基团；羟基团；烷基羰基基团；羧基团；烷氧羰基基团；未取代酰胺基团；或线性或支链烷基团，被氰基，羟基，羧基，烷氧羰基或未取代酰胺基团取代；i和j分别独立地为1到5，除了i和j=1且R1=羧基和R2=烷氧羰基或R1=CF3和R2=羧基的化合物之外，还包括其药学上可接受的衍生物，盐，溶剂和立体异构体，包括所有比例的混合物。
• Diphenylamine derivatives
  申请人：Lardy Claude

  公开号：US20070129433A1

  公开（公告）日：2007-06-07

  The invention relates to compounds of the formula (I) in which: i and j=1; R 1 is in position 3 or 4 on the phenyl ring and represents a cyano group, an alkoxy group substituted by halogen, a thioalkyl group, an alkylcarbonyl group or an alkylsulfonyl group; and R 2 represents a carboxyl group, an aikoxycarbonyl group, an alkylcarbonyl group, an unsubstituted amide group or a linear or branched alkyl group substituted by a cyano, hydroxyl, cabboxyl, aikoxycarbonyl or unsubstituted amide group; and also the pharmaceutically acceptable derivatives, salts, solvates and stereoisomers thereof, including mixtures thereof in all proportions.

  本发明涉及式(I)的化合物，其中：i和j=1；R1位于苯环上的3或4位置，并表示氰基，被卤素取代的烷氧基，硫代烷基，烷基羰基基团或烷基磺酰基团；R2表示羧基，烷氧羰基基团，烷基羰基基团，未取代酰胺基团或被氰基，羟基，羧基，烷氧羰基或未取代酰胺基团取代的线性或支链烷基；以及其药学上可接受的衍生物，盐，溶剂合物和立体异构体，包括所有比例的混合物。