N-methylmorpholinium 3-cyano-4-(2-furyl)-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate | 1391631-81-4

• 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: N-methylmorpholinium 3-cyano-4-(2-furyl)-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate
• CAS: 1391631-81-4
• 化学式: C₅H₁₁NO*C₁₀H₈N₂O₂S
• 分子量: 321.4
• InChiKey: SPPGNVQRJSSZEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.5
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(2-氯乙酰氨基)苯甲酸 、 N-methylmorpholinium 3-cyano-4-(2-furyl)-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以74 %的产率得到4-[({[3-Cyano-4-(furan-2-yl)-6-oxo-1,4,5,6-tetrahydropyridin-2-yl]sulfanyl}acetyl)amino]benzoic acid
  参考文献：
  名称：

  新型烟腈-呋喃分子杂化物的合成及其降血糖活性

  摘要：

  摘要 目的：合成一些新型烟腈-呋喃杂化物并评价其降血糖活性。方法：以糠醛、氰硫基乙酰胺和Meldrum酸（或乙酰乙酸烯丙酯）为起始试剂，基于Knoevenagel缩合迈克尔加成-杂环化串联反应进行三组分吡啶合成。在地塞米松诱导的糖尿病大鼠模型上研究降血糖作用。结果与讨论：所有四种新化合物（XX-XXIII）均通过光谱方法进行表征，并发现具有显着的降血糖活性。结论：制备了一些新的烟腈-呋喃杂化物并进行了体内降血糖活性测试。化合物( XX )显示出比参比药物二甲双胍更有效的降血糖作用，且没有明显的肝毒性。

  DOI：

  10.1134/s1068162024020183
• 作为产物：
  描述：

  N-甲基吗啉 以 乙醇 为溶剂， 反应 1.0h， 生成 N-methylmorpholinium 3-cyano-4-(2-furyl)-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate
  参考文献：
  名称：

  Reaction of ethyl 4-aryl-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates with N-methylmorpholinium 3-cyano-1,4-dihydro- and 3-cyano-1,4,5,6-tetrahydropyridine-2-thiolates

  摘要：

  Alkylation of N-methylmorpholinium 4-Ar-1-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates using ethyl 4-Ar-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (10 % KOH, DMF) gives mixtures of diastereomers of ethyl 4-Ar-6-[(4-Ar-1-3-cyano-1,4,5,6-tetrahydropyridin-2-ylthio)methyl]-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates in overall 30-58 % yield. Under these conditions the N-methylmorpholinium 4-Ar1-5-(N-Ar-2-carbamoyl)-3-cyano-6-methyl-1,4-dihydropyridine-2-thiolates undergo aromatization of the dihydropyridine ring to give ethyl 4-Ar-6-[4-Ar-1-5-(N-Ar-2-carbamoyl)-3-cyano-6-methylpyridin-2-ylthio)methyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (37-51 %). In the absence of KOH, only the substituted pyridine-2(1 H)-thione is formed as a product of oxidation of the dihydropyridine ring in the starting substrate. Some of the alkylation products obtained possess weak or moderate antibacterial activity towards the specific strains of Escherichia coli and Bacillus subtilis but are inactive towards Candida albicans and Staphylococcus aureus.

  DOI：

  10.1007/s10593-012-1016-0

文献信息

• New 4-(2-Furyl)-1,4-dihydronicotinonitriles and 1,4,5,6-Tetrahydronicotinonitriles: Synthesis, Structure, and Analgesic Activity
  作者：D. S. Krivokolysko、V. V. Dotsenko、E. Yu. Bibik、A. A. Samokish、Yu. S. Venidiktova、K. A. Frolov、S. G. Krivokolysko、V. K. Vasilin、A. A. Pankov、N. A. Aksenov、I. V. Aksenova

  DOI：10.1134/s1070363221090073

  日期：2021.9

  and partially saturated pyridine fragments was obtained based on the reaction of cyanothioacetamide with furfural and 1,3-dicarbonyl compounds. The resulting compounds were tested in vivo for analgesic activity (rats) in the orofacial trigeminal pain test. Some the tested compounds showed an antinociceptive effect, superior to that of the reference drug (metamizole sodium).

  摘要 基于氰硫代乙酰胺与糠醛和1,3-二羰基化合物的反应，获得了一系列含有2-呋喃基和部分饱和吡啶片段的新型杂化分子。在口面部三叉神经痛试验中测试所得化合物的体内镇痛活性(大鼠)。一些测试化合物显示出镇痛作用，优于参考药物（安乃近钠）。
• Synthesis of thiazolo[3,2-<i>a</i>]pyridines via an unusual Mannich-type cyclization
  作者：Victor V. Dotsenko、Ivan S. Bushmarinov、Alexander S. Goloveshkin、Elena A. Chigorina、Konstantin A. Frolov、Sergey G. Krivokolysko

  DOI：10.1080/10426507.2016.1224877

  日期：2017.1.2

  with 3-(1,3-benzodioxol-5-yl)-2-methylpropanal (ocean propanal) and p-toluidine afforded 7-aryl-2-(1,3-benzodioxol-5-ylmethyl)-2-methyl-3-[(4-methylphenyl)amino]-5-oxo-2,3,6,7-tetrahydro-5H-thiazolo[3,2-a]pyridine-8-carbonitriles in modest (25–46%) yields. The structure of the key compound was confirmed by X-ray crystal structure analysis. GRAPHICAL ABSTRACT

  摘要 N-甲基吗啉鎓 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates 与 3-(1,3-benzodioxol-5-yl)- 2-甲基丙醛（海洋丙醛）和对甲苯胺得到 7-芳基-2-（1,3-苯并二恶醇-5-基甲基）-2-甲基-3-[（4-甲基苯基）氨基]-5-氧代-2 ,3,6,7-四氢-5H-噻唑并[3,2-a]吡啶-8-腈的产率适中（25-46%）。通过X射线晶体结构分析确认了关键化合物的结构。图形概要
• Synthesis of derivatives of a novel heterocyclic system 7-thia-1,4,6,8-tetraazabenzo[de]anthracene
  作者：Victor V. Dotsenko、Elena A. Chigorina、Sergey G. Krivokolysko

  DOI：10.1007/s10593-017-2103-z

  日期：2017.5

  8,9,10,11-tetrahydro-7-thia-1,4,6,8-tetraazabenzo[de]anthracene, were obtained by interaction of 5Н-pyrido[2′,3′:2,3]thiopyrano[4,5-b]pyridines, formed by treating N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with malononitrile dimer, Ас2О or carboxylic acid chlorides.

  新型杂环体系的衍生物8,9,10,11-四氢-7-thia-1,4,6,8-四氮杂苯并[ de ]蒽，是通过5Н-吡啶基[2'，3'的相互作用而获得的：2,3]硫代吡喃并[4,5- b ]吡啶，是通过丙二腈二聚体处理N-甲基吗啉鎓4-芳基-3-氰基-6-氧代-1,4,5,6-四氢吡啶-2-硫醇盐而形成的， Ас 2 О或羧酸氯化物。
• Design and Synthesis of Pyrido[2,1-<i>b</i>][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction
  作者：Victor V. Dotsenko、Konstantin A. Frolov、Tatyana M. Pekhtereva、Olena S. Papaianina、Sergey Yu. Suykov、Sergey G. Krivokolysko

  DOI：10.1021/co5000807

  日期：2014.10.13

  This Research Article describes the synthesis of an over 700-member library of (8R/8S)-3-R-8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazin-9-carbonitriles by uncatalyzed Mannich-type reaction of N-methylmorpholinium (4R/4S)-4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridin-2-thiolates with a set of primary amines and excessive HCHO. The scope and limitations of the reaction were studied. Starting thiolates were obtained in yields of 53-82% by multicomponent reaction of aromatic aldehydes, cyanothioacetamide, 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid), and N-methylmorpholine, followed by heterocyclization of the resulting Michael adducts.
• Mannich reaction in the synthesis of N,S-containing heterocycles. 14*. Unexpected formation of thiazolo[3,2-a]pyridines in the aminoalkylation of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates by isobutyraldehyde and primary amines
  作者：V. V. Dotsenko、S. G. Krivokolysko

  DOI：10.1007/s10593-012-1042-y

  日期：2012.7

  Treatment of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with an excess of isobutyraldehyde and primary aromatic amines in refluxing ethanol gives the corresponding 7-aryl-3-arylamino-2,2-dimethyl-5-oxo-2,3,6,7-tetrahydro-5 H-thiazolo[3,2-a]pyridine-8-carbonitriles in 18-38 % yields.