2-(benzylthio)-6-(p-ethylanilino)-4-pyrimidone | 98421-08-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(benzylthio)-6-(p-ethylanilino)-4-pyrimidone
• 英文别名: 2-(Benzylthio)-6-(4-ethylanilino)-4-pyrimidinol；2-benzylsulfanyl-4-(4-ethylanilino)-1H-pyrimidin-6-one
• CAS: 98421-08-0
• 化学式: C₁₉H₁₉N₃OS
• 分子量: 337.445
• InChiKey: UWMYWYLHHZMIDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  78.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(benzylthio)-6-(p-ethylanilino)-4-pyrimidone 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 3-methyl-6-(p-ethylanilino)-2-thiouracil
  参考文献：
  名称：

  Synthesis of 6-anilino-2-thiouracils and their inhibition of human placenta iodothyronine deiodinase

  摘要：

  Several 6-anilino-2-thiouracils were synthesized and tested for their ability to inhibit the inner-ring iodothyronine deiodinase from human placenta. The p-ethyl and p-n-butyl analogues were strongly inhibitory to the enzyme and were much more effective than the standard deiodinase inhibitor, 6-propyl-2-thiouracil. The degree of inhibition caused by 6-(p-n-butylanilino)-2-thiouracil was, moreover, unaffected by high concentrations of reducing agent in the enzyme assay. Attempts to prepare 3-alkyl derivatives via S-debenzylation of 2-benzylthio intermediates led to rearrangement to, for example, 3-methyl-5-benzyl-6-amino-2-thiouracil. This compound also strongly inhibited the deiodinase reaction. Preliminary results suggest that these compounds are useful to study in vitro and in vivo metabolism of thyroid hormones and may be clinically useful to enhance the availability of active thyroid hormones to certain organs.

  DOI：

  10.1021/jm00149a026
• 作为产物：
  描述：

  4-乙基苯胺 在 氢氧化钾 、 p-Ethylaniline hydrochloride 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 2-(benzylthio)-6-(p-ethylanilino)-4-pyrimidone
  参考文献：
  名称：

  Synthesis of 6-anilino-2-thiouracils and their inhibition of human placenta iodothyronine deiodinase

  摘要：

  Several 6-anilino-2-thiouracils were synthesized and tested for their ability to inhibit the inner-ring iodothyronine deiodinase from human placenta. The p-ethyl and p-n-butyl analogues were strongly inhibitory to the enzyme and were much more effective than the standard deiodinase inhibitor, 6-propyl-2-thiouracil. The degree of inhibition caused by 6-(p-n-butylanilino)-2-thiouracil was, moreover, unaffected by high concentrations of reducing agent in the enzyme assay. Attempts to prepare 3-alkyl derivatives via S-debenzylation of 2-benzylthio intermediates led to rearrangement to, for example, 3-methyl-5-benzyl-6-amino-2-thiouracil. This compound also strongly inhibited the deiodinase reaction. Preliminary results suggest that these compounds are useful to study in vitro and in vivo metabolism of thyroid hormones and may be clinically useful to enhance the availability of active thyroid hormones to certain organs.

  DOI：

  10.1021/jm00149a026

文献信息

• NOGIMORI, T.;EMERSON, C. H.;BRAVERMAN, L. E.;WU, C. -F.;GAMBINO, J.;WRIGH+, J. MED. CHEM., 1985, 28, N 11, 1692-1694
  作者：NOGIMORI, T.、EMERSON, C. H.、BRAVERMAN, L. E.、WU, C. -F.、GAMBINO, J.、WRIGH+

  DOI：——

  日期：——
• Synthesis of 6-anilino-2-thiouracils and their inhibition of human placenta iodothyronine deiodinase
  作者：T. Nogimori、C. H. Emerson、L. E. Braverman、C. F. Wu、J. Gambino、G. E. Wright

  DOI：10.1021/jm00149a026

  日期：1985.11

  Several 6-anilino-2-thiouracils were synthesized and tested for their ability to inhibit the inner-ring iodothyronine deiodinase from human placenta. The p-ethyl and p-n-butyl analogues were strongly inhibitory to the enzyme and were much more effective than the standard deiodinase inhibitor, 6-propyl-2-thiouracil. The degree of inhibition caused by 6-(p-n-butylanilino)-2-thiouracil was, moreover, unaffected by high concentrations of reducing agent in the enzyme assay. Attempts to prepare 3-alkyl derivatives via S-debenzylation of 2-benzylthio intermediates led to rearrangement to, for example, 3-methyl-5-benzyl-6-amino-2-thiouracil. This compound also strongly inhibited the deiodinase reaction. Preliminary results suggest that these compounds are useful to study in vitro and in vivo metabolism of thyroid hormones and may be clinically useful to enhance the availability of active thyroid hormones to certain organs.