β-amino-β-(pyrid-4-yl)acrylonitrile | 55330-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: β-amino-β-(pyrid-4-yl)acrylonitrile
• 英文别名: 3-amino-3-pyridin-4-yl-acrylonitrile；3-Amino-3-(4-pyridyl)acrylonitrile；3-amino-3-pyridin-4-ylprop-2-enenitrile
• CAS: 55330-53-5
• 化学式: C₈H₇N₃
• 分子量: 145.164
• InChiKey: ZVNIUIBZGBTMOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  β-amino-β-(pyrid-4-yl)acrylonitrile 在 一水合肼 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 5-Pyridin-4-yl-3-(4-trifluoromethyl-phenylamino)-1H-pyrazole-4-carbonitrile
  参考文献：
  名称：

  Pyrazole Bioisosteres of Leflunomide as B-Cell Immunosuppressants for Xenotransplantation and Chronic Rejection:  Scope and Limitations

  摘要：

  T-cell immunosuppressant-based therapies efficiently control early graft rejection in allotransplantation settings. They fail, however, to prevent those rejection events which are mediated by transplant-induced antibody (Ab) responses such as those involved in xenograft and chronic allograft rejection. This is mainly due to their inability to block T-cell-independent Ab production against the transplanted organs. The bioactive metabolite 2(Z) of leflunomide (1) inhibits the formation of such Ab, but the drug has pharmacokinetic properties and a therapeutic window incompatible with transplantation indications. Pyrazole 3, a constrained analogue of 2(Z), was designed and shown to be conformationally and biologically similar to 2(Z). Further investigations with derivatives of 3 demonstrated that the pyrazoles had very tight structure-activity relationships, the only equipotent compound being 3o. However, in contrast to 2(Z), both 3 and 3o were inactive in vivo due to short half-life and drug concentrations lower than the in vitro obtained IC50 values, Compound 3o inhibits T-cell-independent Ab production by a different biochemical mechanism from that of 2(Z) and 3 and may therefore represent a valuable tool for the identification of new targets for B-cell inhibition.

  DOI：

  10.1021/jm981028c
• 作为产物：
  描述：

  4-氰基吡啶 、 乙腈 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 β-amino-β-(pyrid-4-yl)acrylonitrile
  参考文献：
  名称：

  钴配位聚合物受原位配体转化调控†

  摘要：

  一系列钴（II）配位聚合物{[Co（L 1）2（H 2 O）2 ]·4H 2 O·2DMF} n（1；HL 1 = 4-（3,5-（dicyano-2， 6-二吡啶基）二氢吡啶基）苯甲酸; DMF = N，N-二甲基甲酰胺），{[Co（L 1a）2（H 2 O）2 ]·2H 2 O} n（2，HL 1a = 4-（3， 5-氰基-三联吡啶）苯甲酸），和[CO 3（μ 3-OH）2（大号1A）2（TP）（H 2 O）2 ] Ñ（3，TPA =对苯二甲酸）的报告，其中，所述第一配体的构象大号1 -已被调节的原位氧化脱氢到大号1A -在不同的溶剂体系。单晶结构分析表明，化合物1只显示出一个4 4 - SQL从钴中心和父构造协调层结构大号1 -配体; 复合2是从Co构成2+阳离子通过双重连接大号1A -阴离子，其中产生原位通过氧化脱氢大号1 - ; 而化合物3设有一个棒状包装三维网络PCU型的拓扑结构，其中钴-氧链单元通过互连大号1A

  DOI：

  10.1039/c6ce00104a

文献信息

• Exceptional Thermal Stability in a Supramolecular Organic Framework: Porosity and Gas Storage
  作者：Wenbin Yang、Alex Greenaway、Xiang Lin、Ryotaro Matsuda、Alexander J. Blake、Claire Wilson、William Lewis、Peter Hubberstey、Susumu Kitagawa、Neil R. Champness、Martin Schröder

  DOI：10.1021/ja1042935

  日期：2010.10.20

  CO(2) > CH(4) > N(2). Overall, C(2)H(2)(270 K)/CH(4)(273 K) selectivity is 33.7 based on Henry's Law constant, while the C(2)H(2)(270 K)/CO(2)(273 K) ratio of uptake at 1 bar is 2.05. The less bulky analogue L(2) crystallizes in the triclinic space group P1 as two different solvates [L(2)]·2DMF·5C(6)H(6) (S2A) and [L(2)]·2DMF·4MeOH (S2B) as pale yellow tablets and blocks, respectively. Each L(2) molecule

  β-氨基-β-(吡啶-4-基)丙烯腈与芳香族二甲醛9,10-双(4-甲酰基苯基)蒽和对苯二醛反应得到二氢吡啶基产物9,10-双(4-((3,5 -二氰基-2,6-二吡啶基)二氢吡啶基)苯基)蒽(L(1))和1,4-双(4-(3,5-二氰基-2,6-二吡啶基)二氢吡啶基)苯(L(2) ）， 分别。在固态[L(1)]·2.5DMF·3MeOH (SOF-1)在单斜空间群P2(1)/c中结晶并通过强NH…N(py)形成3D稳定的超分子有机骨架氢键和 π-π 相互作用。该材料包含吡啶基修饰的通道，并在固态下显示出永久的孔隙率。从 125 K 的 N(2) 等温线和 195 K 的 CO(2) 等温线计算的去溶剂化框架 SOF-1a 的孔隙体积分别为 0.227 和 0.244 cm(3) g(-1)。SOF-1a 在 77 K 时的 N(2) 吸收能力非常低，在 1 bar 时吸收量为 0.63 mmol
• Pyrazole Bioisosteres of Leflunomide as B-Cell Immunosuppressants for Xenotransplantation and Chronic Rejection:  Scope and Limitations
  作者：Christos Papageorgiou、Rainer Albert、Philipp Floersheim、Michel Lemaire、Francis Bitch、Hans-Peter Weber、Elsebeth Andersen、Valerie Hungerford、Max H. Schreier

  DOI：10.1021/jm981028c

  日期：1998.8.1

  T-cell immunosuppressant-based therapies efficiently control early graft rejection in allotransplantation settings. They fail, however, to prevent those rejection events which are mediated by transplant-induced antibody (Ab) responses such as those involved in xenograft and chronic allograft rejection. This is mainly due to their inability to block T-cell-independent Ab production against the transplanted organs. The bioactive metabolite 2(Z) of leflunomide (1) inhibits the formation of such Ab, but the drug has pharmacokinetic properties and a therapeutic window incompatible with transplantation indications. Pyrazole 3, a constrained analogue of 2(Z), was designed and shown to be conformationally and biologically similar to 2(Z). Further investigations with derivatives of 3 demonstrated that the pyrazoles had very tight structure-activity relationships, the only equipotent compound being 3o. However, in contrast to 2(Z), both 3 and 3o were inactive in vivo due to short half-life and drug concentrations lower than the in vitro obtained IC50 values, Compound 3o inhibits T-cell-independent Ab production by a different biochemical mechanism from that of 2(Z) and 3 and may therefore represent a valuable tool for the identification of new targets for B-cell inhibition.
• Cobalt coordination polymers regulated by in situ ligand transformation
  作者：Tao Huang、Yu-Ling Wang、Qi Yin、Bahar Karadeniz、Hong-Fang Li、Jian Lü、Rong Cao

  DOI：10.1039/c6ce00104a

  日期：——

  polymers [Co(L1)2(H2O)2]·4H2O·2DMF}n (1; HL1 = 4-(3,5-(dicyano-2,6-dipyridyl)dihydropyridyl)benzoic acid; DMF = N,N-dimethylformamide), [Co(L1a)2(H2O)2]·2H2O}n (2, HL1a = 4-(3,5-dicyano-terpyridyl)benzoic acid), and [Co3(μ3-OH)2(L1a)2(TP)(H2O)2]n (3, TPA = terephthalic acid) are reported, in which the conformation of the primary ligand L1− has been regulated by in situ oxidative dehydrogenation into

  一系列钴（II）配位聚合物[Co（L 1）2（H 2 O）2 ]·4H 2 O·2DMF} n（1；HL 1 = 4-（3,5-（dicyano-2， 6-二吡啶基）二氢吡啶基）苯甲酸; DMF = N，N-二甲基甲酰胺），[Co（L 1a）2（H 2 O）2 ]·2H 2 O} n（2，HL 1a = 4-（3， 5-氰基-三联吡啶）苯甲酸），和[CO 3（μ 3-OH）2（大号1A）2（TP）（H 2 O）2 ] Ñ（3，TPA =对苯二甲酸）的报告，其中，所述第一配体的构象大号1 -已被调节的原位氧化脱氢到大号1A -在不同的溶剂体系。单晶结构分析表明，化合物1只显示出一个4 4 - SQL从钴中心和父构造协调层结构大号1 -配体; 复合2是从Co构成2+阳离子通过双重连接大号1A -阴离子，其中产生原位通过氧化脱氢大号1 - ; 而化合物3设有一个棒状包装三维网络PCU型的拓扑结构，其中钴-氧链单元通过互连大号1A