3-氰基-2-羟基-6-(2-噻吩)-吡啶 | 56304-76-8

• 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: 3-氰基-2-羟基-6-(2-噻吩)-吡啶
• 英文名称: 1,2-dihydro-2-oxo-6-(2-thienyl)pyridine-3-carbonitrile
• 英文别名: 2-oxo-6-(thiophen-2-yl)-1,2-dihydropyridine-3-carbonitrile；6-(2-Thienyl)-1,2-dihydro-2-oxonicotinonitrile；2-oxo-6-thiophen-2-yl-1H-pyridine-3-carbonitrile
• CAS: 56304-76-8
• 化学式: C₁₀H₆N₂OS
• mdl: MFCD00981119
• 分子量: 202.236
• InChiKey: JTXFPILITXFNSM-UHFFFAOYSA-N

物化性质

• 熔点：
  300-302 °C(Solv: acetic acid (64-19-7))
• 沸点：
  458.2±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  亚磷酸二异丙酯 、 3-氰基-2-羟基-6-(2-噻吩)-吡啶 在 四氯化碳 、 三乙胺 作用下， 以 乙腈 为溶剂， 以85%的产率得到3-cyano-6-(thien-2-yl)pyridin-2-yl diisopropyl phosphate
  参考文献：
  名称：

  3-氰基吡啶-2-基磷酸盐的除草活性与磷酸酶有关吗？

  摘要：

  根据基于机制的灭活剂的思想设计的 3-氰基吡啶-2-基磷酸酯的除草活性可能与磷酸酶有关。

  DOI：

  10.1080/10426500802514442
• 作为产物：
  描述：

  2-cyano-5-(dimethylamino)-5-(thiophen-2-yl)penta-2,4-dienamide 在 水 、 sodium acetate 作用下， 反应 0.5h， 以95%的产率得到3-氰基-2-羟基-6-(2-噻吩)-吡啶
  参考文献：
  名称：

  Enaminones 作为杂环合成中的构件：重新研究 Enaminones 与丙二腈的产品结构。6-Substituted-3-Oxo-2,3-Dihydropyridazine-4-Carboxylic Acids 的新途径

  摘要：

  对烯胺酮与丙二腈在乙醇哌啶中反应产物的结构进行了修订。通过 2-cyano-5-(二甲氨基)-5-arylpenta-2,4-dienamides 8a-c 与亚硝酸或与重氮苯氯化物反应获得 2,3-二氢哒嗪-4-羧酸 4a-c 的新途径是报道。化合物8a-c在EtOH/HCl和AcOH中回流时转化为1,2-二氢吡啶-3-羧酸和1,2-二氢吡啶-3-甲腈衍生物。

  DOI：

  10.3390/molecules14010068

文献信息

• About the reaction of β-dimethylamino-α,β-enones with active methylene nitriles
  作者：Fathy M. Abdelrazek、Akram N. Elsayed

  DOI：10.1002/jhet.181

  日期：2009.9

  The reaction of 3-dimethylamino-1-arylpropenone derivatives with active methylene nitriles was reinvestigated and a plausible mechanism to account for the results is suggested. X-ray crystallographic study supported the suggested mechanism. Based on these findings, the reaction of 3-acetylamino-4-dimethylaminobut-3-en-2-one with malononitrile was also reinvestigated and the correct structures verified

  对3-二甲基氨基-1-芳基丙烯酮衍生物与活性亚甲基腈的反应进行了重新研究，并提出了一种可能的机制来解释这一结果。X射线晶体学研究支持所提出的机理。根据这些发现，3-乙酰氨基-4-二甲基氨基丁-3-en-2-one与还对丙二腈进行了重新研究，并验证了正确的结构。J.杂环化​​学，（2009）。
• Al-Omran, Fatima; Al-Awadhi, Nouria; Khalik, Mervat Mohammed Abdel, Journal of Chemical Research, Miniprint, 1997, # 3, p. 601 - 615
  作者：Al-Omran, Fatima、Al-Awadhi, Nouria、Khalik, Mervat Mohammed Abdel、Kaul, Kamini、EL-Khair, Adel Abu、Elnagdi, Mohammed Hilmy

  DOI：——

  日期：——
• Discovery and structure–activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors
  作者：Ning-Yu Wang、Wei-Qiong Zuo、Ying Xu、Chao Gao、Xiu-Xiu Zeng、Li-Dan Zhang、Xin-Yu You、Cui-Ting Peng、Yang Shen、Sheng-Yong Yang、Yu-Quan Wei、Luo-Ting Yu

  DOI：10.1016/j.bmcl.2014.01.075

  日期：2014.3

  Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[ 2,3-b] pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 mu M, SI > 30.3, 12b, EC50 = 3.5 mu M, SI > 28.6, 10l, EC50 = 3.9 mu M, SI > 25.6, 12o, EC50 = 4.5 mu M, SI > 22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.
• US3948903A
  申请人：——

  公开号：US3948903A

  公开（公告）日：1976-04-06
• [EN] PYRAZOLOPYRIDINE DERIVATIVES<br/>[FR] DERIVES DE PYRAZOLOPYRIDINE
  申请人：GLAXO GROUP LTD

  公开号：WO2003068773A1

  公开（公告）日：2003-08-21

  Certain compounds of formula (I), or a salt thereof, or a solvate thereof, wherein R1, R2, R3 and R4 are as defined in the specification, a procees for the preparation of such compounds, a pharmaceutical composition comprising such compounds and the use of such compounds in medicine. For the treatment of conditions associated with a need for inhibition of GSK-3 such as diabetes, conditions associated with diabetes, chronic neurodegenerative conditions including dementias such as Alzheimer's disease, Parkinson's disease, progressive supranuclear palsy, subacute sclerosing panencephalitic parkinsonism, postencephalitic parkinsonism, pugilistic encephalitis, guam parkinsonism-dementia complex, Picks's disease, corticobasal degeneration, frontotemporal dementia, Huntingdon's disease, AIDS associated dementia, amyotrophic lateral sclerosis, multiple sclerosis and neurotraumatic diseases such as acute stroke, mood disorders such as schizophrenia and bipolar disorders, promotion of functional recovery post stroke, cerebral bleeding (for example, due to solidary cerebral amyloid angiopathy), hair loss, obesity, atherosclerotic cardiovascular disease, hypertension, polycystic ovary syndrome, syndrome X, ischaemia, traumatic brain injury, cancer, leukopenia, Down's syndrome, Lewy body disease, inflammation, and immunodeficiency.