(4-aminophenyl)-4'-pyridylacetylene | 162379-77-3

• 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: (4-aminophenyl)-4'-pyridylacetylene
• 英文别名: 4-(2-Pyridin-4-ylethynyl)aniline
• CAS: 162379-77-3
• 化学式: C₁₃H₁₀N₂
• 分子量: 194.236
• InChiKey: OWYICEQPPIRPEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  fac-{Re(2,2'-bipyridine)(CO)3(acetonitrile)}PF6 、 (4-aminophenyl)-4'-pyridylacetylene 以 四氢呋喃 为溶剂， 以50%的产率得到[fac-Re(CO)3(2,2'-bipyridine)(4-aminophenyl-4'-pyridylacetylene)][PF6]
  参考文献：
  名称：

  Rhenium carbonyls containing pyridyl ligands incorporating an alkyne entity

  摘要：

  Reactions of pyridyl ligands, 4,4'-dipyridylbutadiyne (DPB), 1,4-bis(4'-pyridylethynyl)benzene (BPEB), ferrocenyl-4-pyridylacetylene (FPA), 4-nitrophenyl-4'-pyridylacetylene (NPPA) and 4-aminophenyl-4'-pyridylacetylene (APPA), with Re(CO)(5)X (X = Cl,Br), cis-Re(CO)(4)(L)Cl (L = PPh(3), P(OMe)(3)), and [Re(CO)(3)(2,2'-bipy)(MeCN)][PF6], provides fac-Re(CO)(3)(eta(1)-DPB)(2)Cl (1), fac-Re(CO)(3)(PY)(2)Br (2, PY = FPA; 3, L = NPPA; 4, L = APPA), [fac-Re(CO)(3)(PPh(3))Cl](2)(mu-PY) (5, PY = BPEB; 6, PY = DPB), [fac-Re(CO)(3)(P(OMe)(3))Cl](2)(mu-DPB) (7), fac-Re(CO)(3)(PPh(3))(PY)Cl (8, PY = NPPA; 9, PY = FPA), [fac-Re(CO)(3)(2,2'-bipy)(PY)][PF6] (10, PY = NPPA; 11, PY = APPA; 12, PY = FPA), and [(fac-Re(CO)(3)(2,2'-bipy)}(2)(mu-PY)][PF6](2) (13, PY = DPB; 14, PY = BPEB). The energy of the metal to pyridyl pi* charge-transfer (MLCT) is investigated by electronic absorption spectra and cyclic voltammetry, X-ray structural analyses for 2 . CH2Cl2 and 12 . 2H(2)O were carried out. 2 . CH2Cl2:C12H28BrClN2O3P2Fe2Re; monoclinic; P2(1)/n, Z = 4; a = 15.188(2), b = 15.100(2), c = 16.254(1) Angstrom; beta = 102.22(1)degrees; R = 0.047; Rw = 0.040. 12 . 2H(2)O: C30H21F6N3O3PFeRe; monoclinic; P2(1)/n, Z = 4; a = 19.022(4), b = 9.339(2), c = 21.111(3) Angstrom; beta = 116.156(9)degrees; R = 0.043; Rw = 0.061.

  DOI：

  10.1016/0022-328x(96)06167-0
• 作为产物：
  描述：

  4-乙炔基苯胺 、 4-溴吡啶氢溴酸盐 在 copper(l) iodide 、 二(氰基苯)二氯化钯 、 二异丙胺 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 生成 (4-aminophenyl)-4'-pyridylacetylene
  参考文献：
  名称：

  Structure−Activity Relationships of Substituted 1-Pyridyl-2-phenyl-1,2-ethanediones: Potent, Selective Carboxylesterase Inhibitors

  摘要：

  Inhibition of intestinal carboxylesterases may allow modification of the pharmacokinetics/pharmacodynamic profile of existing drugs by altering half-life or toxicity. Since previously identified diarylethane-1,2-dione inhibitors are decidedly hydrophobic, a modified dione scaffold was designed and elaborated into a > 300 member library, which was subsequently screened to establish the SAR for esterase inhibition. This allowed the identification of single digit nanomolar hiCE inhibitors that showed improvement in selectivity and measured solubility.

  DOI：

  10.1021/jm101101q

文献信息

• Polynuclear metal complexes linked by conjugated pyridines
  作者：Jiann T. Lin、Ming-Fa Yang、Chiitang Tsai、Yuh S. Wen

  DOI：10.1016/s0022-328x(98)00701-3

  日期：1998.8

  ferrocenyl-4-pyridylacetylene (FPA) and 1,6-diferrocenyl-3-ene-1,5-hexadiyne (DFEHD) can be readily ligated to Cp2Mo2(CO)4 and ‘Co2(CO)6’, derived from Co2(CO)8. Both alkyne and pyridine entities in DPB or BPEB can be ligated to metal carbonyls, and (μ4-η1:1:2:2-DPB)[W(CO)5]2[Cp2Mo2(CO)4] (11), (μ4-η1:1:2:2-BPEB)[W(CO)5]2[Cp2Mo2(CO)4] (12), (μ6-η1:1:2:2:2:2-BPEB)[W(CO)5]2[Cp2Mo2(CO)4]2 (13), (μ6-η1:1:2:

  4,4'-二吡啶基丁二炔（DPB），1,4-双（4'-吡啶基乙炔基）苯（BPEB），（4-氨基苯基）-4'-吡啶基乙炔（APPA），二茂铁基-4-吡啶基乙炔（ FPA）和1,6-茂铁-3-烯-1,5-己二炔（DFEHD）可以很容易地连接到的Cp 2沫2（CO）4和'钴2（CO）6 '，从Co衍生2（CO ）8。在DPB或BPEB两者炔和吡啶实体可以连接到金属羰基化合物，和（μ 4 - η 1：1：2：2 -DPB）[W（CO）5 ] 2混合[Cp 2沫2（CO）4 ] （11），（μ 4 - η 1：1：2：2 -BPEB）[W（CO）5 ] 2混合[Cp 2沫2（CO）4 ]（12），（μ 6 - η 1：1：2： 2：2：2 -BPEB）[W（CO）5 ] 2混合[Cp 2沫2（CO）4 ] 2（13），（μ 6 - η 1：1：2：2：2：2 -BPEB） [W（CO）5 ] 2 [Co
• Lin, Jiann T.; Sun, Shih-Sheng; Wu, Jiann Jung, Inorganic Chemistry, 1995, vol. 34, # 9, p. 2323 - 2333
  作者：Lin, Jiann T.、Sun, Shih-Sheng、Wu, Jiann Jung、Lee, Liangshiu、Lin, Kuan-Jiuh、Huang, Yi Fong

  DOI：——

  日期：——
• [EN] BENZODIAZEPINE BRADYKININ ANTAGONISTS<br/>[FR] BENZODIAZEPINES ANTAGONISTES DE BRADYKININE
  申请人：MERCK & CO INC

  公开号：WO2002099388A2

  公开（公告）日：2002-12-12

  Compounds disclosed here or a pharmaceutically acceptable salt thereof, are bradykinin B1 antagonist compounds useful in the treatment or prevention of symptoms such as pain and inflammation associated with the bradykinin B1 pathway.
• Rhenium carbonyls containing pyridyl ligands incorporating an alkyne entity
  作者：Jiann T. Lin、Shih-Sheng Sun、Jiann Jung Wu、Yen-Chywan Liaw、Kuan-Jiuh Lin

  DOI：10.1016/0022-328x(96)06167-0

  日期：1996.6

  Reactions of pyridyl ligands, 4,4'-dipyridylbutadiyne (DPB), 1,4-bis(4'-pyridylethynyl)benzene (BPEB), ferrocenyl-4-pyridylacetylene (FPA), 4-nitrophenyl-4'-pyridylacetylene (NPPA) and 4-aminophenyl-4'-pyridylacetylene (APPA), with Re(CO)(5)X (X = Cl,Br), cis-Re(CO)(4)(L)Cl (L = PPh(3), P(OMe)(3)), and [Re(CO)(3)(2,2'-bipy)(MeCN)][PF6], provides fac-Re(CO)(3)(eta(1)-DPB)(2)Cl (1), fac-Re(CO)(3)(PY)(2)Br (2, PY = FPA; 3, L = NPPA; 4, L = APPA), [fac-Re(CO)(3)(PPh(3))Cl](2)(mu-PY) (5, PY = BPEB; 6, PY = DPB), [fac-Re(CO)(3)(P(OMe)(3))Cl](2)(mu-DPB) (7), fac-Re(CO)(3)(PPh(3))(PY)Cl (8, PY = NPPA; 9, PY = FPA), [fac-Re(CO)(3)(2,2'-bipy)(PY)][PF6] (10, PY = NPPA; 11, PY = APPA; 12, PY = FPA), and [(fac-Re(CO)(3)(2,2'-bipy)}(2)(mu-PY)][PF6](2) (13, PY = DPB; 14, PY = BPEB). The energy of the metal to pyridyl pi* charge-transfer (MLCT) is investigated by electronic absorption spectra and cyclic voltammetry, X-ray structural analyses for 2 . CH2Cl2 and 12 . 2H(2)O were carried out. 2 . CH2Cl2:C12H28BrClN2O3P2Fe2Re; monoclinic; P2(1)/n, Z = 4; a = 15.188(2), b = 15.100(2), c = 16.254(1) Angstrom; beta = 102.22(1)degrees; R = 0.047; Rw = 0.040. 12 . 2H(2)O: C30H21F6N3O3PFeRe; monoclinic; P2(1)/n, Z = 4; a = 19.022(4), b = 9.339(2), c = 21.111(3) Angstrom; beta = 116.156(9)degrees; R = 0.043; Rw = 0.061.
• Structure−Activity Relationships of Substituted 1-Pyridyl-2-phenyl-1,2-ethanediones: Potent, Selective Carboxylesterase Inhibitors
  作者：Brandon M. Young、Janice L. Hyatt、David C. Bouck、Taosheng Chen、Parimala Hanumesh、Jeanine Price、Vincent A. Boyd、Philip M. Potter、Thomas R. Webb

  DOI：10.1021/jm101101q

  日期：2010.12.23

  Inhibition of intestinal carboxylesterases may allow modification of the pharmacokinetics/pharmacodynamic profile of existing drugs by altering half-life or toxicity. Since previously identified diarylethane-1,2-dione inhibitors are decidedly hydrophobic, a modified dione scaffold was designed and elaborated into a > 300 member library, which was subsequently screened to establish the SAR for esterase inhibition. This allowed the identification of single digit nanomolar hiCE inhibitors that showed improvement in selectivity and measured solubility.