5-乙炔氰基吡啶 | 1211584-19-8

• 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-乙炔氰基吡啶
• 中文别名: 5-乙炔基吡啶-2-甲腈
• 英文名称: 5-ethynylpicolinonitrile
• 英文别名: 5-Ethynylpyridine-2-carbonitrile；5-ethynylpyridine-2-carbonitrile
• CAS: 1211584-19-8
• 化学式: C₈H₄N₂
• 分子量: 128.133
• InChiKey: KCFUVIOOBLULNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 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：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-乙炔氰基吡啶 在 盐酸羟胺 、 potassium tert-butylate 、 三丁基氧化锡 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Antiprotozoal activity of dicationic 3,5-diphenylisoxazoles, their prodrugs and aza-analogues

  摘要：

  Fifty novel prodrugs and aza-analogues of 3,5-bis(4-amidinophenyl)isoxazole and its derivatives were prepared. Eighteen of the 24 aza-analogues exhibited IC50 values below 25 nM against Trypanosoma brucei rhodesiense or Plasmodium falciparum. Six compounds had antitrypanosomal IC50 values below 10 nM. Twelve analogues showed similar antiplasmodial activities, including three with sub-nanomolar potencies. Forty-four diamidines (including 16 aza-analogues) and the 26 prodrugs were evaluated for efficacy in mice infected with T. b. rhodesiense STIB900. Six diamidines cured 4/4 mice at daily 5 mg/kg intraperitoneal doses for 4 days, giving results far superior to pentamidine and furamidine. One prodrug attained 3/4 cures at daily 25 mg/kg oral doses for 4 days. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.10.050
• 作为产物：
  描述：

  5-溴-2-氰基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 、 三乙胺 作用下， 以 甲苯 、 mineral oil 为溶剂， 反应 3.0h， 生成 5-乙炔氰基吡啶
  参考文献：
  名称：

  Antiprotozoal activity of dicationic 3,5-diphenylisoxazoles, their prodrugs and aza-analogues

  摘要：

  Fifty novel prodrugs and aza-analogues of 3,5-bis(4-amidinophenyl)isoxazole and its derivatives were prepared. Eighteen of the 24 aza-analogues exhibited IC50 values below 25 nM against Trypanosoma brucei rhodesiense or Plasmodium falciparum. Six compounds had antitrypanosomal IC50 values below 10 nM. Twelve analogues showed similar antiplasmodial activities, including three with sub-nanomolar potencies. Forty-four diamidines (including 16 aza-analogues) and the 26 prodrugs were evaluated for efficacy in mice infected with T. b. rhodesiense STIB900. Six diamidines cured 4/4 mice at daily 5 mg/kg intraperitoneal doses for 4 days, giving results far superior to pentamidine and furamidine. One prodrug attained 3/4 cures at daily 25 mg/kg oral doses for 4 days. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.10.050

文献信息

• Remarkable acceleration of a DNA/RNA inter-strand functionality transfer reaction to modify a cytosine residue: the proximity effect via complexation with a metal cation
  作者：Daichi Jitsuzaki、Kazumitsu Onizuka、Atsushi Nishimoto、Ikuya Oshiro、Yosuke Taniguchi、Shigeki Sasaki

  DOI：10.1093/nar/gku538

  日期：2014.7.29

  Modified nucleosides in natural RNA molecules are essential for their functions. Non-natural nucleoside analogues have been introduced into RNA to manipulate its structure and function. We have recently developed a new strategy for the in situ modification of RNA based on the functionality transfer reaction between an oligodeoxynucleotide probe and an RNA substrate. 2′-Deoxy-6-thioguanosine (6-thio-dG) was used as the platform to anchor the transfer group. In this study, a pyridinyl vinyl ketone moiety was newly designed as the transfer group with the expectation that a metal cation would form a chelate complex with the pyridinyl-2-keto group. It was demonstrated that the (E)-pyridinyl vinyl keto group was efficiently and specifically transferred to the 4-amino group of the opposing cytosine in RNA in the presence of NiCl2 with more than 200-fold accelerated rate compared with the previous system with the use of the diketo transfer group. Detailed mechanistic studies suggested that NiCl2 forms a bridging complex between the pyridinyl keto moiety and the N7 of the purine residue neighboring the cytosine residue of the RNA substrate to bring the groups in close proximity.

  天然RNA分子中的修饰核苷酸对其功能至关重要。非天然核苷酸类似物已被引入RNA，以操控其结构和功能。我们最近开发了一种基于寡脱氧核苷探针与RNA底物之间功能转移反应的新策略，以实现RNA的原位修饰。2′-脱氧-6-硫鸟苷（6-thio-dG）被用作锚定转移基团的平台。在本研究中，我们新设计了一种吡啶乙烯酮结构作为转移基团，期望金属阳离子能够与吡啶-2-羰基基团形成螯合物。实验表明，在NiCl2存在下，（E）-吡啶乙烯酮基团有效且特异性地转移至RNA中相对的胞嘧啶的4-氨基基团，速度比使用二酮转移基团的先前系统加快了200倍以上。详细的机理研究表明，NiCl2在吡啶羰基部分与RNA底物中靠近胞嘧啶的嘌呤残基N7之间形成了桥接复杂，以使这些基团接近。
• Visible-light-induced synthesis of a variety of trifluoromethylated alkenes from potassium vinyltrifluoroborates by photoredox catalysis
  作者：Yusuke Yasu、Takashi Koike、Munetaka Akita

  DOI：10.1039/c3cc39235j

  日期：——

  of trifluoromethylated alkenes by the radical-mediated trifluoromethylation of vinyltrifluoroborates has been developed. Togni's reagent serves as a CF(3) radical precursor in the presence of the photoredox catalyst [Ru(bpy)(3)](PF(6))(2) under visible light irradiation. This new photocatalytic protocol can be applicable to a wide variety of vinylborates containing electronically diverse substituents

  已经开发了通过自由基介导的三氟硼酸乙烯基酯的三氟甲基化来容易地合成三氟甲基化的烯烃。Togni的试剂在可见光照射下，在光氧化还原催化剂[Ru（bpy）（3）]（PF（6））（2）的存在下充当CF（3）自由基前体。这种新的光催化方案可适用于多种含有电子多样性取代基和杂芳族化合物的乙烯基硼酸酯。
• PYRROLOPYRIDAZINONE COMPOUND AS PDE4 INHIBITOR
  申请人：Ube Industries, Ltd.

  公开号：EP1982986B1

  公开（公告）日：2012-03-07
• Synthesis, DNA binding, fluorescence measurements and antiparasitic activity of DAPI related diamidines
  作者：Abdelbasset A. Farahat、Arvind Kumar、Martial Say、Alaa El-Din M. Barghash、Fatma E. Goda、Hassan M. Eisa、Tanja Wenzler、Reto Brun、Yang Liu、Leah Mickelson、W. David Wilson、David W. Boykin

  DOI：10.1016/j.bmc.2009.12.011

  日期：2010.1

  A novel series of extended DAPI analogues were prepared by insertion of either a carbon-carbon triple bond (16a-d) or a phenyl group (21a, b and 24) at position-2. The new amidines were evaluated in vitro against both Trypanosoma brucei rhodesiense (T. b. r.) and Plasmodium falciparum (P. f.). Five compounds (16a, 16b, 16d, 21a, 21b) exhibited IC50 values against T. b. r. of 9 nM or less which is two to nine folds more effective than DAPI. The same five compounds exhibited IC50 values against P. f. of 5.9 nM or less which is comparable to that of DAPI. The fluorescence properties of these new molecules were recorded, however; they do not offer any advantage over those of DAPI. (C) 2009 Elsevier Ltd. All rights reserved.
• WO2023/11574
  申请人：——

  公开号：——

  公开（公告）日：——