2-(4-(bromomethyl)phenyl)acetamide | 847486-99-1

• 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: 2-(4-(bromomethyl)phenyl)acetamide
• 英文别名: 2-[4-(Bromomethyl)phenyl]acetamide
• CAS: 847486-99-1
• 化学式: C₉H₁₀BrNO
• 分子量: 228.088
• InChiKey: NULKBLUDAUUXPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-(bromomethyl)phenyl)acetamide 在 吡啶 、 盐酸 、 三乙基硼氢化锂 、 potassium carbonate 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.75h， 生成 N-4-(2-aminoethyl)benzyl-1,4-dideoxy-1,4-imino-L-lyxitol
  参考文献：
  名称：

  具有高碱性官能团的N-苄基取代的1,4-亚氨基-1-lyxitols作为高尔基α-甘露糖苷酶IIb的选择性抑制剂的合成

  摘要：

  在高尔基体中抑制复杂的N-聚糖的生物合成是抑制肿瘤组织生长的另一种方法。八Ñ -苄基取代的1,4-亚氨基升制备具有碱性官能团（胺，脒，胍），羟基和氟基团-lyxitols，优化它们的合成及它们抑制几种α-甘露糖苷从GH的能力进行测试家族38（GMIIb，LManII和JBMan）作为人类高尔基体和溶酶体α-甘露糖苷II的模型。发现所有化合物都是GMIIb的选择性抑制剂。带有胍基的最有效结构在微摩尔水平上抑制GMIIb（K i = 19±2 µM），而未观察到LManII和JBMan的显着抑制（> 2 mM）。根据分子对接和p K a计算，与本研究和先前研究中发表的其他N-苄基取代衍生物相比，该结构可能与目标酶的天冬氨酸二聚体形成两个盐桥，从而提高了其抑制能力。

  DOI：

  10.1016/j.bioorg.2018.10.066
• 作为产物：
  描述：

  4-(溴甲基)苯乙酸 在 氯化亚砜 、 氨 作用下， 以84%的产率得到2-(4-(bromomethyl)phenyl)acetamide
  参考文献：
  名称：

  具有高碱性官能团的N-苄基取代的1,4-亚氨基-1-lyxitols作为高尔基α-甘露糖苷酶IIb的选择性抑制剂的合成

  摘要：

  在高尔基体中抑制复杂的N-聚糖的生物合成是抑制肿瘤组织生长的另一种方法。八Ñ -苄基取代的1,4-亚氨基升制备具有碱性官能团（胺，脒，胍），羟基和氟基团-lyxitols，优化它们的合成及它们抑制几种α-甘露糖苷从GH的能力进行测试家族38（GMIIb，LManII和JBMan）作为人类高尔基体和溶酶体α-甘露糖苷II的模型。发现所有化合物都是GMIIb的选择性抑制剂。带有胍基的最有效结构在微摩尔水平上抑制GMIIb（K i = 19±2 µM），而未观察到LManII和JBMan的显着抑制（> 2 mM）。根据分子对接和p K a计算，与本研究和先前研究中发表的其他N-苄基取代衍生物相比，该结构可能与目标酶的天冬氨酸二聚体形成两个盐桥，从而提高了其抑制能力。

  DOI：

  10.1016/j.bioorg.2018.10.066

文献信息

• New carboxamide compounds having melanin concentrating hormone antagonistic activity, pharmaceutical preparations comprising these compounds and process for their manufacture
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20040242572A1

  公开（公告）日：2004-12-02

  The present invention relates to carboxamide compounds of general formula I 1 wherein the groups and residues A, B, W, X, Y, Z, R 1 , R 2 , R 3 and k have the meanings given in claim 1. Moreover the invention relates to process for preparing the above mentioned carboxamides as well as pharmaceutical compositions containing at least one carboxamide according to the invention. In view of their MCH-receptor antagonistic activity the pharmaceutical compositions according to the invention are suitable for the treatment of metabolic disorders and/or eating disorders, particularly obesity, bulimia, anorexia, hyperphagia and diabetes.

  本发明涉及具有通式I的羧酰胺化合物 1 其中，A、B、W、X、Y、Z、R 1 、R 2 、R 3 和k的含义如权利要求1中所述。此外，本发明还涉及制备上述羧酰胺的方法以及含有至少一种根据本发明的羧酰胺的药物组合物。由于它们对MCH受体的拮抗活性，根据本发明的药物组合物适合用于治疗代谢紊乱和/或饮食紊乱，特别是肥胖症、厌食症、暴食症、糖尿病。
• [EN] AMINOETHYLAROMATIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR<br/>[FR] COMPOSES AMINOETHYLAROMATIQUES PERMETTANT DE TRAITER DES TROUBLES REPONDANT A UNE MODULATION DU RECEPTEUR D3 DE LA DOPAMINE
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2006040179A1

  公开（公告）日：2006-04-20

  The present invention relates to aromatic compounds of the formula (I) wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical Ra and wherein Ar may also carry 1 or 2 radicals Rb; X is N or CH; E is CR6R7 or NR3; R1 is C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated Cl-C4­-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3-C4­-alkenyl, formyl or C1-C3-alkylcarbonyl; R1a is H, C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1-­C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3­-C4-alkenyl, or R1a and R2 together are (CH2)n with n being 2, 3 or 4, or R1a and R2a together are (CH2)n with n being 2, 3 or 4; R2 and R2a are independently of each other H, C1-C4-alkyl or fluorinated C1-C4-alkyl or R2a and R2 together are (CH2)m with m being 1, 2, 3, 4 or 5; R3 is H or C1-C4-alkyl; R6, R7 independently of each other are selected from H, fluorine, C1-C4-alkyl and fluorinated C1-C4-alkyl or together form a moiety (CH2)p with p being 2, 3, 4 or 5; and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula (I) or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

  本发明涉及公式（I）的芳香族化合物，其中Ar为苯基或芳香族5-或6-成员C-键合杂环基，其中Ar可能携带1个基团Ra，Ar也可能携带1个或2个基团Rb；X为N或CH；E为CR6R7或NR3；R1为C1-C4-烷基，C3-C4-环烷基，C3-C4-环烷基甲基，C3-C4-烯基，氟代的Cl-C4-烷基，氟代的C3-C4-环烷基，氟代的C3-C4-环烷基甲基，氟代的C3-C4-烯基，甲酰基或C1-C3-烷基羰基；R1a为H，C1-C4-烷基，C3-C4-环烷基，C3-C4-环烷基甲基，C3-C4-烯基，氟代的C1-C4-烷基，氟代的C3-C4-环烷基，氟代的C3-C4-环烷基甲基，氟代的C3-C4-烯基，或R1a和R2一起为（CH2）n，其中n为2、3或4，或R1a和R2a一起为（CH2）n，其中n为2、3或4；R2和R2a彼此独立为H，C1-C4-烷基或氟代的C1-C4-烷基，或R2a和R2一起为（CH2）m，其中m为1、2、3、4或5；R3为H或C1-C4-烷基；R6、R7彼此独立地选自H、氟、C1-C4-烷基和氟代的C1-C4-烷基，或一起形成一个(CH2)p的基团，其中p为2、3、4或5；以及其生理耐受的酸盐。该发明还涉及使用公式（I）的化合物或其药学上可接受的盐来制备用于治疗可用多巴胺D3受体配体治疗的医疗疾病的药物组合物。
• Aminoethylaromatic Compounds Suitable For Treating Disorders That Respond To Modulation Of The Dopamine D3 Receptor
  申请人：Drescher Karla

  公开号：US20080096934A1

  公开（公告）日：2008-04-24

  The present invention relates to aromatic compounds of the formula I wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical R a and wherein Ar may also carry 1 or 2 radicals R b ; X is N or CH; E is CR 6 R 7 or NR 3 ; R 1 is C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkyl, C 3 -C 4 -cycloalkylmethyl, C 3 -C 4 -alkenyl, fluorinated C 1 -C 4 -alkyl, fluorinated C 3 -C 4 -cycloalkyl, fluorinated C 3 -C 4 -cycloalkylmethyl, fluorinated C 3 -C 4 -alkenyl, formyl or C 1 -C 3 -alkylcarbonyl; R 1a is H, C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkyl, C 3 -C 4 -cycloalkylmethyl, C 3 -C 4 -alkenyl, fluorinated C 1 -C 4 -alkyl, fluorinated C 3 -C 4 -cycloalkyl, fluorinated C 3 -C 4 -cycloalkylmethyl, fluorinated C 3 -C 4 -alkenyl, or R 1a and R 2 together are (CH 2 ) n with n being 2, 3 or 4, or R 1a and R 2a together are (CH 2 ) n with n being 2, 3 or 4; R 2 and R 2a are are independently of each other H, C 1 -C 4 -alkyl or fluorinated C 1 -C 4 -alkyl or R 2a and R 2 together are (CH 2 ) m with m being 1, 2, 3, 4 or 5; R 3 is H or C 1 -C 4 -alkyl; R 6 , R 7 independently of each other are selected from H, fluorine, C 1 -C 4 -alkyl and fluorinated C 1 -C 4 -alkyl or together form a moiety (CH 2 ) p with p being 2, 3, 4 or 5; and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula I or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

  本发明涉及式I的芳香族化合物，其中Ar是苯基或芳香族5-或6-成员C-连接的杂环基，其中Ar可以携带1个基团Ra，且Ar还可以携带1或2个基团Rb；X是N或CH；E是CR6R7或NR3；R1是C1-C4烷基、C3-C4环烷基、C3-C4环烷基甲基、C3-C4烯基、氟代C1-C4烷基、氟代C3-C4环烷基、氟代C3-C4环烷基甲基、氟代C3-C4烯基、甲酰基或C1-C3烷基羰基；R1a是H、C1-C4烷基、C3-C4环烷基、C3-C4环烷基甲基、C3-C4烯基、氟代C1-C4烷基、氟代C3-C4环烷基、氟代C3-C4环烷基甲基、氟代C3-C4烯基，或R1a和R2一起是(CH2)n，其中n为2、3或4，或R1a和R2a一起是(CH2)n，其中n为2、3或4；R2和R2a彼此独立地是H、C1-C4烷基或氟代C1-C4烷基，或者R2a和R2一起是(CH2)m，其中m为1、2、3、4或5；R3是H或C1-C4烷基；R6、R7彼此独立地选择自H、氟、C1-C4烷基和氟代C1-C4烷基，或者一起形成(CH2)p的基团，其中p为2、3、4或5；以及其生理耐受性酸盐。本发明还涉及使用式I的化合物或其药学上可接受的盐制备用于治疗易受多巴胺D3受体配体治疗的医疗疾病的制药组合物。
• AMINOETHYLAROMATIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR
  申请人：Drescher Karla

  公开号：US20120220635A1

  公开（公告）日：2012-08-30

  The present invention relates to aromatic compounds of the formula (I) and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula (I) or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D 3 receptor ligand.

  本发明涉及公式（I）的芳香族化合物及其生理耐受的酸加成盐。本发明还涉及使用公式（I）的化合物或其药学上可接受的盐来制备用于治疗易于用多巴胺D3受体配体治疗的医疗障碍的制药组合物。
• Aminoethylaromatic compounds suitable for treating disorders that respond to modulation of the dopamine D3 receptor
  申请人：Abbott GmbH & Co. KG

  公开号：US08232426B2

  公开（公告）日：2012-07-31

  The present invention relates to aromatic compounds of the formula I wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical Ra and wherein Ar may also carry 1 or 2 radicals Rb; X is N or CH; E is CR6R7 or NR3; R1 is C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1-C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3-C4-alkenyl, formyl or C1-C3-alkylcarbonyl; R1a is H, C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1-C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3-C4-alkenyl, or R1a and R2 together are (CH2)n with n being 2, 3 or 4, or R1a and R2a together are (CH2)n with n being 2, 3 or 4; R2 and R2a are are independently of each other H, C1-C4-alkyl or fluorinated C1-C4-alkyl or R2a and R2 together are (CH2)m with m being 1, 2, 3, 4 or 5; R3 is H or C1-C4-alkyl; R6, R7 independently of each other are selected from H, fluorine, C1-C4-alkyl and fluorinated C1-C4-alkyl or together form a moiety (CH2)p with p being 2, 3, 4 or 5; and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula I or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

  本发明涉及式I的芳香族化合物，其中Ar是苯基或芳香族5或6元环C-键杂芳基基团，其中Ar可以携带1个基团Ra，Ar还可以携带1个或2个基团Rb；X是N或CH；E是CR6R7或NR3；R1是C1-C4烷基，C3-C4环烷基，C3-C4环烷基甲基，C3-C4烯基，氟代C1-C4烷基，氟代C3-C4环烷基，氟代C3-C4环烷基甲基，氟代C3-C4烯基，甲酰基或C1-C3烷基羰基；R1a是H，C1-C4烷基，C3-C4环烷基，C3-C4环烷基甲基，C3-C4烯基，氟代C1-C4烷基，氟代C3-C4环烷基，氟代C3-C4环烷基甲基，氟代C3-C4烯基，或R1a和R2一起是(CH2)n，其中n为2、3或4，或R1a和R2a一起是(CH2)n，其中n为2、3或4；R2和R2a独立地是H，C1-C4烷基或氟代C1-C4烷基，或R2a和R2一起是(CH2)m，其中m为1、2、3、4或5；R3是H或C1-C4烷基；R6、R7独立地选择自H、氟、C1-C4烷基和氟代C1-C4烷基，或一起形成(CH2)p的基团，其中p为2、3、4或5；以及其生理上耐受的酸盐。本发明还涉及使用式I的化合物或其药学上可接受的盐制备用于治疗易于使用多巴胺D3受体配体治疗的医疗障碍的制药组合物。