3-(5-Chloro-pentyl)-pyridine | 150057-34-4

• 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: 3-(5-Chloro-pentyl)-pyridine
• 英文别名: 3-(5-Chloropentyl)pyridine
• CAS: 150057-34-4
• 化学式: C₁₀H₁₄ClN
• 分子量: 183.681
• InChiKey: WLTOSYPJJCXRTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(5-Chloro-pentyl)-pyridine 在 sodium hydroxide 、 ammonium cerium(IV) nitrate 、 sodium hydride 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 15.5h， 生成 (E)-3-(2-methoxy-3,6-dimethyl-1,4-benzoquinon-5-yl)-2-[5-(pyridin-3-yl)pentyl]-2-propenoic acid
  参考文献：
  名称：

  Structure−Activity Relationships of (E)-3-(1,4-Benzoquinonyl)-2-[(3-pyridyl)- alkyl]-2-propenoic Acid Derivatives That Inhibit Both 5-Lipoxygenase and Thromboxane A₂ Synthetase

  摘要：

  As part of our research for the development of novel antiinflammatory drug candidates, we have designed and synthesized a series of (E)-3-(1,4-benzoquinonyl)-2-[(3-pyridyl)alkyl]-2-propenoic acid derivatives as dual inhibitors of 5-lipoxygenase (5-LO) and thromboxane (TX) A(2) synthetase. In order to increase the absorption after oral administration, we introduced a carboxylic acid moiety into the 1,4-benzoquinone skeleton, which has 5-LO-inhibitory character. Introduction of a 3-pyridylalkyl group at the double bond of the 1,4-benzoquinonyl propenoic acid moiety afforded good to moderate inhibitory activities against the production of leukotriene (LT) Bq and TXA(2) while not significantly inhibiting that of prostaglandin E(2) by glycogen-induced peritoneal cells of rat (in vitro). The length of the methylene chain of the 3-pyridylalkyl group influenced the inhibition of LTB(4) and TXB(2) production. An increase of lipophilicity by introducing a more lipophilic alkoxy group did not markedly increase the inhibitory activity on LTB(4) production. The position of an alkoxy group on the 1,4-benzoquinone skeleton played an important role in TXA(2) synthetase inhibition. Compounds such as 20c (E6700) with an appropriate alkoxy group and proper length of methylene side chain, together with a polar substituent (carboxylic acid), showed good inhibition of both 5-LO and TXA(2) synthetase and possess a variety of pharmacologically beneficial effects.

  DOI：

  10.1021/jm950725r
• 作为产物：
  描述：

  5-(吡啶-3-基)戊酸乙酯 在 氯化亚砜 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 3-(5-Chloro-pentyl)-pyridine
  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

• Practical and Selective sp ³ C−H Bond Chlorination via Aminium Radicals
  作者：Alastair J. McMillan、Martyna Sieńkowska、Piero Di Lorenzo、Gemma K. Gransbury、Nicholas F. Chilton、Michela Salamone、Alessandro Ruffoni、Massimo Bietti、Daniele Leonori

  DOI：10.1002/anie.202100030

  日期：2021.3.22

  also the fine‐tuning of physicochemical and biological properties of drugs, agrochemicals and polymers. We report here a general and practical photochemical strategy enabling the site‐selective chlorination of sp3 C−H bonds. This process exploits the ability of protonated N‐chloroamines to serve as aminium radical precursors and also radical chlorinating agents. Upon photochemical initiation, an efficient

  将氯原子引入有机分子对于工业化学品的制造、先进合成中间体的精制以及药物、农用化学品和聚合物的物理化学和生物特性的微调至关重要。我们在这里报告了一种通用且实用的光化学策略，能够实现 sp 3 C−H 键的位点选择性氯化。该过程利用了质子化的N-氯胺作为铵自由基前体和自由基氯化剂的能力。在光化学引发后，建立了有效的自由基链传播，由于存在大量兼容的官能团，因此允许多种底物的官能化。通过适当选择铵基，能够协同最大化 H 原子转移过渡态中的极性和空间效应，为自由基 sp 3 C−H 氯化提供了已知的最高选择性。
• TANOUCHI, TADAO;KAWAMURA, MASANORI;OHYAMA, ISAO;KAJIWARA, IKUO;IGUCHI, YO+, J. MED. CHEM., 1981, 24, N 10, 1149-1155
  作者：TANOUCHI, TADAO、KAWAMURA, MASANORI、OHYAMA, ISAO、KAJIWARA, IKUO、IGUCHI, YO+

  DOI：——

  日期：——