2,2-dimethyl-2H-thiochromene-4-carbonitrile | 1270009-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 2,2-dimethyl-2H-thiochromene-4-carbonitrile
• CAS: 1270009-55-6
• 化学式: C₁₂H₁₁NS
• 分子量: 201.292
• InChiKey: KCPMMHZKCANIJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-2H-thiochromene-4-carbonitrile 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 硫酸 、 水 、 硝酸 、 乙酸酐 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 (2,2,4-trimethyl-6-nitrothiochroman-4-yl)methyl acetate
  参考文献：
  名称：

  Synthesis of N-[3,4-Dihydro-4-(acetoxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N′-(4-nitrophenyl)thiourea and N-[3,4-dihydro-4-(hydroxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N′-(4-nitrophenyl)thiourea, a Major Metabolite of N-(3,4-Dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-YL)-N′-(4-nitrophenyl)thiourea

  摘要：

  The compound N-(3,4-dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-N'-(4-nitrophenyl)thiourea [NSC 726189] has exhibited strong anticancer activity in several assays and cell lines and is under consideration for clinical trials for the possible treatment of kidney cancer. Since the heterocycle has not shown any significant toxicity in animal studies, it is conceivable that a metabolite could be the active agent. In a previous study, major metabolites were tentatively identified via analyses of materials extracted from rat and human liver microsomes, as well as extracts from rat urine, by the use of HPLC-UV and MS/MS. However, no metabolite has been obtained in pure form. This article outlines a de novo synthesis of a primary metabolite, namely N-[3,4-dihydro-4-(hydroxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N'-(4-nitrophenyl)thiourea. A prodrug of the metabolite was also prepared, namely N-[3,4-dihydro-4-(acetoxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N'-(4-nitrophenyl)thio-urea. GRAPHICAL ABSTRACT[image omitted].

  DOI：

  10.1080/10426507.2010.534521
• 作为产物：
  描述：

  2,2-二甲基-2,3-二氢-1-苯并噻喃-4-酮 在 吡啶 、 zinc(II) iodide 、 三氯氧磷 作用下， 以 苯 为溶剂， 反应 28.0h， 生成 2,2-dimethyl-2H-thiochromene-4-carbonitrile
  参考文献：
  名称：

  Synthesis of N-[3,4-Dihydro-4-(acetoxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N′-(4-nitrophenyl)thiourea and N-[3,4-dihydro-4-(hydroxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N′-(4-nitrophenyl)thiourea, a Major Metabolite of N-(3,4-Dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-YL)-N′-(4-nitrophenyl)thiourea

  摘要：

  The compound N-(3,4-dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-N'-(4-nitrophenyl)thiourea [NSC 726189] has exhibited strong anticancer activity in several assays and cell lines and is under consideration for clinical trials for the possible treatment of kidney cancer. Since the heterocycle has not shown any significant toxicity in animal studies, it is conceivable that a metabolite could be the active agent. In a previous study, major metabolites were tentatively identified via analyses of materials extracted from rat and human liver microsomes, as well as extracts from rat urine, by the use of HPLC-UV and MS/MS. However, no metabolite has been obtained in pure form. This article outlines a de novo synthesis of a primary metabolite, namely N-[3,4-dihydro-4-(hydroxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N'-(4-nitrophenyl)thiourea. A prodrug of the metabolite was also prepared, namely N-[3,4-dihydro-4-(acetoxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N'-(4-nitrophenyl)thio-urea. GRAPHICAL ABSTRACT[image omitted].

  DOI：

  10.1080/10426507.2010.534521