(3'-methylbiphenyl-2-yl)methanamine | 918811-88-8

• 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: (3'-methylbiphenyl-2-yl)methanamine
• 英文别名: 2-aminomethyl-3'-methylbiphenyl；[2-(3-Methylphenyl)phenyl]methanamine
• CAS: 918811-88-8
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: XHUHFMWMCLXWJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3'-methylbiphenyl-2-yl)methanamine 、 5-(4-(2-methoxyphenyl)piperazin-1-yl)pentanoic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.5h， 以90%的产率得到5-(4-(2-methoxyphenyl)piperazin-1-yl)-N-((3'-methylbiphenyl-2-yl)methyl)pentanamide
  参考文献：
  名称：

  Novel N-biphenyl-2-ylmethyl 2-methoxyphenylpiperazinylalkanamides as 5-HT7R antagonists for the treatment of depression

  摘要：

  5-HT7 receptor (5-HT7R) is a promising target for the treatment of depression and neuropathic pain. 5-HT7R antagonists exhibited antidepressant effects, while the agonists produced strong anti-hyperalgesic effects. In our efforts to discover selective 5-HT7R antagonists or agonists, N-biphenylylmethyl 2-methoxyphenylpiperazinylalkanamides 1 were designed, synthesized, and biologically evaluated against 5-HT7R. Among the synthesized compounds, N-2'-chlorobiphenylylmethyl 2-methoxyphenylpiperazinylpentanamide 1-8 showed the best binding affinity with a Ki value of 8.69nM and it was verified as a novel antagonist according to functional assays. The compound 1-8 was very selective over 5-HT1DR, 5-HT2AR, 5-HT3R, 5-HT5AR and 5-HT6R and moderately selective over 5-HT1AR, 5-HT1BR and 5-HT2CR. The novel 5-HT7R antagonist 1-8 exhibited an antidepressant effect at a dose of 25mg/kg in the forced swimming test in mice and showed a U-shaped dose-response curve which typically appears in 5-HT7R antagonists such as SB-269970 and lurasidone.

  DOI：

  10.1016/j.bmc.2014.07.026
• 作为产物：
  描述：

  2-碘氰基苯 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (3'-methylbiphenyl-2-yl)methanamine
  参考文献：
  名称：

  Novel N-biphenyl-2-ylmethyl 2-methoxyphenylpiperazinylalkanamides as 5-HT7R antagonists for the treatment of depression

  摘要：

  5-HT7 receptor (5-HT7R) is a promising target for the treatment of depression and neuropathic pain. 5-HT7R antagonists exhibited antidepressant effects, while the agonists produced strong anti-hyperalgesic effects. In our efforts to discover selective 5-HT7R antagonists or agonists, N-biphenylylmethyl 2-methoxyphenylpiperazinylalkanamides 1 were designed, synthesized, and biologically evaluated against 5-HT7R. Among the synthesized compounds, N-2'-chlorobiphenylylmethyl 2-methoxyphenylpiperazinylpentanamide 1-8 showed the best binding affinity with a Ki value of 8.69nM and it was verified as a novel antagonist according to functional assays. The compound 1-8 was very selective over 5-HT1DR, 5-HT2AR, 5-HT3R, 5-HT5AR and 5-HT6R and moderately selective over 5-HT1AR, 5-HT1BR and 5-HT2CR. The novel 5-HT7R antagonist 1-8 exhibited an antidepressant effect at a dose of 25mg/kg in the forced swimming test in mice and showed a U-shaped dose-response curve which typically appears in 5-HT7R antagonists such as SB-269970 and lurasidone.

  DOI：

  10.1016/j.bmc.2014.07.026

文献信息

• Phenylglycinamide and pyridylglycinamide derivatives useful as anticoagulants
  申请人：Zhang Xiaojun

  公开号：US20070003539A1

  公开（公告）日：2007-01-04

  The present invention provides novel phenylglycinamide derivatives of Formula (I) or (IV): or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein the variables W, W 1 , Y, Z, R 7 , R 8 , R 9 , and R 11 are as defined herein. These compounds are selective inhibitors of factor VIIa which can be used as medicaments.

  本发明提供了式(I)或(IV)的新型苯基甘氨酰衍生物：或其立体异构体、互变异构体、药学上可接受的盐、溶剂合物或前药，其中变量W、W1、Y、Z、R7、R8、R9和R11如本文所定义。这些化合物是选择性因子VIIa的抑制剂，可用作药物。
• METHOD FOR PRODUCING BIARYL COMPOUND
  申请人：Sato Koichi

  公开号：US20100087680A1

  公开（公告）日：2010-04-08

  A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

  一种制备双芳基化合物的方法，包括在零价镍催化剂、膦配体和碱的存在下，将芳香有机化合物与选自芳香基有机硼化合物和硼氧化物化合物组的至少一种化合物反应。
• PROCESS FOR PRODUCING BIARYL COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1914221A1

  公开（公告）日：2008-04-23

  A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

  一种生产双芳基化合物的方法，包括在零价镍催化剂、膦配体和碱存在下，使芳香族有机化合物与至少一种选自由芳香族有机硼化合物和硼氧化合物组成的组中的化合物反应。
• 10.1021/acs.orglett.4c01968
  作者：Dong, Sifan、Cai, Xinghao、Ma, Chen、Li, Haolong、Kang, Ying、Feng, Juan、Fan, Shiming、Liu, Shouxin

  DOI：10.1021/acs.orglett.4c01968

  日期：——

  We developed a new transient directing group, N-(2-benzoyl-4-chlorophenyl)-1,1,1-trifluoromethanesulfonamide, which can facilitate the γ-monoarylation of free amines containing symmetric γ-C–H bonds. A variety of amines containing symmetric and identical γ-C(sp3)–H and γ-C(sp2)–H reacted with a diverse range of aryl and heteroaryl iodides to provide γ-monoarylated products exclusively.

  我们开发了一种新的瞬时导向基团N- (2-苯甲酰基-4-氯苯基)-1,1,1-三氟甲磺酰胺，它可以促进含有对称γ-C-H键的游离胺的γ-单芳基化。含有对称且相同的 γ-C(sp 3 )-H 和 γ-C(sp 2 )-H 的各种胺与各种芳基和杂芳基碘化物反应，专门提供 γ-单芳基化产物。
• Pyrazolo[3,4-B] Pyridine Compounds and Their Use as Pde4 Inhibitors
  申请人：Cook Caroline Mary

  公开号：US20080275078A1

  公开（公告）日：2008-11-06

  The invention provides a compound of formula (I) or a salt thereof: wherein: R 1 is C 1-3 alkyl, C 1-3 fluoroalkyl, or —CH 2 CH 2 OH; R 2 is hydrogen, methyl or C 1 fluoroalkyl; R 3 is of sub-formula (aa) or (bb): wherein Y is NCONH 2 and n 1 is 0 or 1; R 4 is H; and R 5 is a group of the sub-formula (x), (y), (y1) or (z): These compounds are PDE4 inhibitors.