5-(吡啶-3-基)-戊醛 | 78775-02-7

• 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
• 中文名称: 5-(吡啶-3-基)-戊醛
• 英文名称: 5-(pyridin-3-yl)-pentanal
• 英文别名: 3-Pyridinepentanal；5-pyridin-3-ylpentanal
• CAS: 78775-02-7
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: JAGXXKKLZUOARG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(吡啶-3-基)-戊醛 在 palladium on activated charcoal 氯化亚砜 、 氢气 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 6.17h， 生成 8-Pyridin-3-yl-octanenitrile
  参考文献：
  名称：

  Highly selective inhibitors of thromboxane synthetase. 2. Pyridine derivatives

  摘要：

  The enzyme thromboxane (TX) synthetase is inhibited by pyridine. The beta-substituted pyridine derivatives showed higher inhibitory potency than the gamma-substituted ones having the same side chain. Among the beta-substituted derivatives containing the omega-carboxyalkyl group, the compounds with 6-8 carbon atoms in the side chain were especially effective. The derivatives holding the phenylene group in the side chain exhibited much higher inhibitory activity than those of the alkylene type. Among them, (E)-3-[4-(3-pyridylmethyl)phenyl]-2-methylacrylic acid hydrochloride (5a) had the highest potency (IC50 = 3 x 10(-9) M). The beta-substituted pyridine derivatives and 1-substituted imidazole derivatives which had the same side chain showed almost the same potency. The beta-substituted pyridine derivatives do not inhibit arachidonic acid cyclooxygenase or prostaglandin I2 synthetase, two other enzymes of the arachidonic cascade.

  DOI：

  10.1021/jm00142a006
• 作为产物：
  描述：

  5-(吡啶-3-基)戊酸乙酯 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以35%的产率得到5-(吡啶-3-基)-戊醛
  参考文献：
  名称：

  Highly selective inhibitors of thromboxane synthetase. 2. Pyridine derivatives

  摘要：

  The enzyme thromboxane (TX) synthetase is inhibited by pyridine. The beta-substituted pyridine derivatives showed higher inhibitory potency than the gamma-substituted ones having the same side chain. Among the beta-substituted derivatives containing the omega-carboxyalkyl group, the compounds with 6-8 carbon atoms in the side chain were especially effective. The derivatives holding the phenylene group in the side chain exhibited much higher inhibitory activity than those of the alkylene type. Among them, (E)-3-[4-(3-pyridylmethyl)phenyl]-2-methylacrylic acid hydrochloride (5a) had the highest potency (IC50 = 3 x 10(-9) M). The beta-substituted pyridine derivatives and 1-substituted imidazole derivatives which had the same side chain showed almost the same potency. The beta-substituted pyridine derivatives do not inhibit arachidonic acid cyclooxygenase or prostaglandin I2 synthetase, two other enzymes of the arachidonic cascade.

  DOI：

  10.1021/jm00142a006

文献信息

• <p>Synthesis and antitumor activity of novel pyridinium fullerene derivatives</p>
  作者：Takumi Yasuno、Tomoyuki Ohe、Hitomi Ikeda、Kyoko Takahashi、Shigeo Nakamura、Tadahiko Mashino

  DOI：10.2147/ijn.s212045

  日期：——

  cis-14 (15 mg/kg) significantly exhibited antitumor activity in mouse xenograft model of human lung cancer. CONCLUSION We synthesized a novel set of mono-adduct fullerene derivatives functionalized with pyridinium groups and found that most of them show potent antiproliferative activities against cancer cell lines and some of them show significant antitumor activities in vivo. We propose that these fullerene

  目的我们之前曾报道过一些阳离子富勒烯衍生物具有抗癌活性，预计它们将成为一种潜在的抗癌药物的先导化合物。然而，它们是双加合物和多种区域异构体的混合物，由于富勒烯笼上取代基位置的可变性，它们不容易分离。为了克服这个问题，我们评估了一组单加合物衍生物的抗增殖活性并检查了它们的构效关系。此外，还检查了所选衍生物的体内抗肿瘤活性。方法本研究新设计合成了19种吡啶鎓富勒烯衍生物。使用包括耐药细胞在内的几种癌细胞系评估了它们的抗增殖活性。此外，在人肺癌的小鼠异种移植模型中研究了几种衍生物的体内抗肿瘤活性。结果 衍生物抑制癌细胞系的增殖，包括顺铂耐药细胞和多柔比星耐药细胞。还显示化合物 10 (10 μM)、13 (10 μM) 和 cis-14 (10 μM) 诱导细胞内氧化应激。此外，化合物 13 (20 mg/kg) 和 cis-14 (15 mg/kg) 在人肺癌小鼠异种移植模型中表现出显着的抗肿瘤活性。结论
• Spirocyclic PAF antagonists
  申请人：British Bio-Technology Limited

  公开号：US05300524A1

  公开（公告）日：1994-04-05

  Compounds of general formula I; ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, and R.sup.7 are variables. These compounds are antagonists of platelet activating factor (PAF) and as such are useful in the treatment or amelioration of various diseases or disorders mediated by PAF.

  通式I的化合物; ##STR1## 其中R.sup.1，R.sup.2，R.sup.3，R.sup.4，R.sup.5，R.sup.6和R.sup.7是变量。这些化合物是血小板活化因子（PAF）拮抗剂，因此可用于治疗或缓解由PAF介导的各种疾病或障碍。
• 1-Oxa-2,9-diphenyl-spiro[4.4]nonane derivatives as PAF antagonists
  申请人：BRITISH BIO-TECHNOLOGY LIMITED

  公开号：EP0502706A1

  公开（公告）日：1992-09-09

  Compounds of general formula I; wherein: each of R¹, R², and R³ independently represents hydrogen, -C₁-C₆ alkyl, -C₂-C₆ alkenyl, -C₁-C₆ alkyl, -SC₁-C₆ alkyl, halo, -CN, -NO₂, -SOC₁-C₆ alkyl, -SO₂C₁-C₆ alkyl, -SO₂NH₂, -COC₁-C₆ alkyl, -CHO, -COOC₁-C₆ alkyl, -CH₂OH, benzyl, benzoyl, -CF₃, -CONH₂, -NHCOC₁-C₆ alkyl; each of R⁴ and R⁵ independently represents hydrogen, -C₁-C₆ alkyl, -C₂-C₆ alkenyl, -OC₁-C₆ alkyl, -SC₁-C₆ alkyl, halo, -CN, -NO₂, -SOC₁-C₆ alkyl, -SO₂C₁-C₆ alkyl, -SO₂NH₂, -COOH, -COC₁-C₆ alkyl, -CHO, -COOC₁-C₆ alkyl, -CH₂OH, -OH, benzyl, benzoyl, -CF₃, -CONH₂, -NHCOC₁-C₆ alkyl or a -OC(=O)R⁸ group wherein R⁸ represents -C₁-C₆ alkyl, -C₂-C₆ alkenyl, -OC₁-C₆ alkyl, -SC₁-C₆ alkyl, -COC₁-C₆ alkyl, -COOC₁-C₆ alkyl, benzyl, benzoyl, -CF₃, -CN or a V group wherein V represents a) a group wherein t is an integer from 0 to 3 and each of R⁹, R¹⁰ and R¹¹ is independently hydrogen, -C₁-C₆ alkyl, -C₂-C₆ alkenyl, -OC₁-C₆ alkyl, -SC₁-C₆ alkyl, halo, -CN, -NO₂, -SOC₁-C₆ alkyl, -SO₂C₁-C₆ alkyl, -SO₂NH₂, -COOH, -COC₁-C₆ alkyl, -CHO, -COOC₁-C₆ alkyl, -CH₂OH, -OH, benzyl, benzoyl, -CF₃, -CONH₂, -NHCOC₁-C₆ alkyl; b) a group -(CH₂)s-Y wherein s is an integer from 0 to 5 and Y represents a 5- or 6-membered aromatic heterocyclic ring containing one or more sp2 nitrogen atoms in its ring, which heterocyclic ring may be optionally fused to a benzene ring or to a further 5- or 6-membered aromatic heterocyclic ring containing one or more nitrogen atoms, wherein at least one of the said heterocyclic rings may also contain an oxygen or sulphur atom, and wherein any of the rings may be optionally substituted with one or more substituents selected from -C₁-C₆ alkyl, -OC₁-C₆ alkyl, halo, -CF₃ and -CN; or R⁴ together with R⁵ forms a =O, =N-OH, =NHR⁸ or =CHR⁸ group, wherein R⁸ is as defined above; each of R⁶ and R⁷ independently represents hydrogen, -C₁-C₆ alkyl, -COC₁-C₆ alkyl, benzyl, a group V as defined above or a -COV group wherein V is as defined above; or R⁶ together with R⁷ form a =CR¹²R¹³ group wherein each of R¹² and R¹³ independently represent a hydrogen atom, a C₁-C₁₈ alkyl, a -C₂-C₆ alkenyl, pyrrole or a group V as defined above; and their pharmaceutically and veterinarily acceptable acid addition salts and hydrates are antagonists of platelet activating factor (PAF) and as such are useful in the treatment or amelioration of various diseases or conditions mediated by PAF.

  通式 I 的化合物； 其中 R¹、R² 和 R³ 各自独立地代表氢、-C₁-C₆ 烷基、-C₂-C₆ 烯基、-C₁-C₆ 烷基、-SC₁-C₆ 烷基、卤素、-CN、-NO₂、-SOC₁-C₆烷基、-SO₂C₁-C₆烷基、-SO₂NH₂、-COC₁-C₆烷基、-CHO、-COOC₁-C₆烷基、-CH₂OH、苄基、苯甲酰基、-CF₃、-CONH₂、-NHCOC₁-C₆烷基； R⁴ 和 R⁵ 中各自独立地代表氢、-C₁-C₆ 烷基、-C₂-C₆ 烯基、-OC₁-C₆ 烷基、-SC₁-C₆ 烷基、卤代、-CN、-NO₂，-SOC₁-C₆烷基，-SO₂C₁-C₆烷基，-SO₂NH₂，-COOH，-COC₁-C₆烷基，-CHO，-COOC₁-C₆烷基，-CH₂OH，-OH，苄基、苯甲酰基、-CF₃、-CONH₂、-NHCOC₁-C₆ 烷基或 -OC(=O)R⁸ 基团，其中 R⁸ 代表 -C₁-C₆ 烷基、-C₂-C₆ 烯基、-OC₁-C₆ 烷基、-SC₁-C₆烷基、-COC₁-C₆烷基、-COC₁-C₆烷基、苄基、苯甲酰基、-CF₃、-CN 或一个 V 基团，其中 V 代表 a) 一个基团 其中 t 是 0 至 3 的整数，且 R⁹、R¹⁰ 和 R¹¹ 中各自独立地是氢、-C₁-C₆ 烷基、-C₂-C₆ 烯基、-OC₁-C₆ 烷基、-SC₁-C₆ 烷基、卤代、-CN、-NO₂、-SOC₁-C₆ 烷基、-SO₂C₁-C₆ 烷基、-SO₂NH₂、-COOH、-COC₁-C₆ 烷基、-CHO、-COOC₁-C₆ 烷基、-CH₂OH、-OH、苄基、苯甲酰基、-CF₃、-CONH₂、-NHCOC₁-C₆ 烷基； b) 基团-(CH₂)s-Y，其中 s 为 0 至 5 的整数，Y 代表在其环中含有一个或多个 sp2 氮原子的 5 或 6 元芳香杂环，该杂环可选择与苯环或含有一个或多个氮原子的另一个 5 或 6 元芳香杂环融合、其中至少一个所述杂环还可包含一个氧原子或硫原子，并且其中任何一个环都可任选被一个或多个取代基取代，这些取代基可选自-C₁-C₆烷基、-OC₁-C₆烷基、卤素、-CF₃和-CN； 或 R⁴ 与 R⁵ 一起形成 =O、=N-OH、=NHR⁸ 或 =CHR⁸ 基团，其中 R⁸ 如上定义； R⁶ 和 R⁷ 各自独立地代表氢、-C₁-C₆ 烷基、-COC₁-C₆ 烷基、苄基、如上定义的基团 V 或其中 V 如上定义的-COV 基团； 或 R⁶ 与 R⁷ 共同形成一个 =CR¹²R¹³ 基团，其中 R¹² 和 R¹³ 各自独立地代表氢原子、C₁-C₁₈ 烷基、-C₂-C₆ 烯基、吡咯或如上定义的基团 V； 及其药学上和兽医学上可接受的酸加成盐和水合物是血小板活化因子（PAF）的拮抗剂，因此可用于治疗或改善由 PAF 介导的各种疾病或病症。
• Total synthesis of cytotoxic sponge alkaloids hachijodines F and G
  作者：William R.F. Goundry、Victor Lee、Jack E. Baldwin

  DOI：10.1016/s0040-4039(02)00379-9

  日期：2002.4

  The total synthesis of two cytotoxic sponge alkaloids haehijodines F (1) and G (2) via a common intermediate 3 is described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Heterocyclic Derivatives of 2-(3,5-Dimethylphenyl)tryptamine as GnRH Receptor Antagonists
  作者：Peter Lin、Mamta Parikh、Jane-Ling Lo、Yi Tien Yang、Kang Cheng、Roy G Smith、Michael H Fisher、Matthew J Wyvratt、Mark T Goulet

  DOI：10.1016/s0960-894x(01)00133-0

  日期：2001.4

  A series of heterocyclic 2-(3,5-dimethylphenyl)tryptamine derivatives was prepared and evaluated on a rat gonadotropin releasing hormone receptor assay. The carbon tether length and heterocyclic ring attached to the amino group of 2-(3,5-dimethylphenyl)tryptamine were varied. Several of these derivatives were potent GnRH antagonists with the most potent compound having an IC50 of 16nM. (C) 2001 Elsevier Science Ltd. All rights reserved.