N-(2-diethylaminoethyl)-2-methoxy-4-nitrobenzamide | 476615-23-3

• 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: N-(2-diethylaminoethyl)-2-methoxy-4-nitrobenzamide
• 英文别名: N-(2-diethylamino-ethyl)-4-nitro-2-methoxybenzamide；2-methoxy-4-nitro-benzoic acid-(2-diethylamino-ethylamide)；2-Methoxy-4-nitro-benzoesaeure-(2-diaethylamino-aethylamid)；4-nitro-N-(2-diethylamino-ethyl)-2-methoxy-benzamide；N-(2-diethylamino-ethyl)-2-methoxy-4-amino-benzamide；N-[2-(diethylamino)ethyl]-2-methoxy-4-nitrobenzamide
• CAS: 476615-23-3
• 化学式: C₁₄H₂₁N₃O₄
• 分子量: 295.338
• InChiKey: WTFSSDYAZCHKSU-UHFFFAOYSA-N

物化性质

• 沸点：
  453.3±45.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-diethylaminoethyl)-2-methoxy-4-nitrobenzamide 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.0h， 以88.3%的产率得到4-氨基-N-[2-(二乙基氨基)乙基]-2-甲氧基苯甲酰胺
  参考文献：
  名称：

  Synthesis ofN-(2-diethylamino-ethyl)-4-(4-fluoro-benzamido)-2-methoxybenzamide (desiodo-MIP-1145) by coupling technique and its radioiodination: a potential melanoma imaging agent

  摘要：

  放射性碘化的MIP-1145，特异性地靶向黑色素，是黑色素瘤靶向治疗的理想候选者。合成了缺乏碘取代基的MIP-1145类似物（去碘MIP-1145）作为标记前驱体，合成过程简单，共分为三步。通过电亲核取代反应实现了对去碘MIP-1145的碘-125放射性碘化。对碘化反应进行了优化研究。通过电泳和高效液相色谱（HPLC）分离和纯化了标记化合物。获得的最大放射化学产率为76%，放射化学纯度超过99%。测得[125I]MIP-1145的log P值为4.5。

  DOI：

  10.1002/jlcr.3415
• 作为产物：
  描述：

  N,N-二乙基乙二胺 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 反应 2.0h， 以98%的产率得到N-(2-diethylaminoethyl)-2-methoxy-4-nitrobenzamide
  参考文献：
  名称：

  Radiohalogenated benzamide derivatives and their use in tumor diagnosis and tumor therapy

  摘要：

  这项发明涉及新的放射性卤代苯甲酰胺衍生物及其在肿瘤诊断和肿瘤治疗中的应用。根据本发明，放射性卤代苯甲酰胺衍生物表现出新颖和特别有利的特性，特别是在肿瘤浓集和延迟、肝脏浓集和血液积聚方面。与健康身体组织相比，本发明的化合物在肿瘤中实现的放射治疗剂量具有优势。

  公开号：

  US20050207972A1

文献信息

• [EN] NOVEL BENZAMIDE COMPOUNDS FOR USE IN MCH RECEPTOR RELATED DISORDERS<br/>[FR] NOUVEAUX COMPOSES DE BENZAMIDE DESTINES A ETRE UTILISES DANS DES TROUBLES ASSOCIES AU RECEPTEUR DE MCH
  申请人：7TM PHARMA AS

  公开号：WO2004048319A1

  公开（公告）日：2004-06-10

  Novel compounds of Formula I which modulate MCH activity are disclosed, in which A is a linker, Ar, is an aryl or heteroaryl group; R1 is hydrogen or a lower alkoxy group; Q together with the carbonyl forms an amide group, which is further substituted with an amine group; R5 is 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, -SO2AIk; R8 is hydrogen, halogen atoms, alkyl, alkenyl or alkynyl groups, cycloalkyl groups, alkylcycloalkyl groups, alkoxy groups, dialkylamino groups, -CONHAIk, -CONAIk2, - NHCO-Alk, -CO-Alk, -SCH3, partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups such as -CH2CF3, -CF2CF3, -CF3, -OCF3, -SCF3; X is H, F, Cl, Br, I, -SCH3, partially or fully fluorinated alkyl, alkoxy or thioalkoxy groups such as -CH2CF3, - CF2CF3, -CF3, -OCF3, -SCF3; OCH3 or lower alkyl or alkenyl group; and which are useful in the treatment or prevention of e.g. obesity, depression, diabetes, bulimia etc.

  公开了调节MCH活性的Formula I的新化合物，其中A是连接剂，Ar是芳基或杂环芳基；R1是氢或较低的烷氧基；Q与羰基一起形成酰胺基团，该基团进一步被氨基取代；R5是氢、卤素原子、烷氧基、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、腈基、烷基、烯基或炔基、-SCH3、部分或完全氟代烷基、烷氧基或硫代烷氧基基团，如-CH2CF3、-CF2CF3、-CF3、-OCF3、-SCF3；-SO2NH2、-SO2NHAlk、-SO2NAlk2、-SO2AIk；R8是氢、卤素原子、烷基、烯基或炔基、环烷基、烷基环烷基、烷氧基、二烷基氨基基团、-CONHAIk、-CONAIk2、-NHCO-Alk、-CO-Alk、-SCH3、部分或完全氟代烷基、烷氧基或硫代烷氧基基团，如-CH2CF3、-CF2CF3、-CF3、-OCF3、-SCF3；X是H、F、Cl、Br、I、-SCH3、部分或完全氟代烷基、烷氧基或硫代烷氧基基团，如-CH2CF3、-CF2CF3、-CF3、-OCF3、-SCF3；OCH3或较低的烷基或烯基基团；这些化合物在治疗或预防肥胖、抑郁症、糖尿病、暴食症等方面是有用的。
• [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。
• Pharmaceutical Composition Of A Radioiodinated Benzamide Derivative And Methods Of Making Same
  申请人：Chen Jianqing

  公开号：US20110206608A1

  公开（公告）日：2011-08-25

  Provided is a pharmaceutical composition comprising radioiodinated N-(2-(diethylamino)ethyl)-4-(4-fluorobenzamido)-5-iodo-2-methoxybenzamide of Formula I. The pharmaceutical composition provides a stable formulation for both storing and administering to patients having melanoma. Also provided is a novel method of iodinating the precursor compound.

  提供的是一种药物组合物，包括公式I的放射性碘化N-（2-（二乙氨基）乙基）-4-（4-氟苯甲酰胺）-5-碘-2-甲氧基苯甲酰胺。该药物组合物提供了一种稳定的配方，既可用于储存，也可用于治疗患有黑色素瘤的患者。此外，还提供了一种新的前体化合物碘化的方法。
• 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。
• Radiohalogenated Benzamide Derivatives And Their Use In Tumor Diagnosis And Tumor Therapy
  申请人：Friebe Matthias

  公开号：US20090012090A1

  公开（公告）日：2009-01-08

  This invention relates to new radiohalogenated benzamide derivatives and their use in tumor diagnosis and tumor therapy. The radiohalogenated benzamide derivatives according to the invention exhibit novel and especially advantageous properties, in particular with respect to tumor concentration and retardation, liver concentration and blood accumulation. The radiation-therapy doses to be achieved in the tumor, compared to healthy body tissue, are advantageous for the compounds according to the invention.

  这项发明涉及新的放射性卤代苯甲酰胺衍生物及其在肿瘤诊断和肿瘤治疗中的应用。根据本发明，放射性卤代苯甲酰胺衍生物表现出新颖和特别有利的性质，特别是在肿瘤浓度和延迟、肝脏浓度和血液积累方面。与健康体组织相比，本发明中化合物在肿瘤中所需的放射治疗剂量具有优势。