ethyl 4-(3,5-dimethylphenylsulfanyl)-2-methyl-6-oxo-1,6-dihydropyridin-3-ylcarboxylate | 1185189-75-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 4-(3,5-dimethylphenylsulfanyl)-2-methyl-6-oxo-1,6-dihydropyridin-3-ylcarboxylate
• 英文别名: Ethyl 4-[(3,5-dimethylphenyl)-thio]-1,6-dihydro-2-methyl-6-oxo-3-pyridinecarboxylate；ethyl 4-(3,5-dimethylphenyl)sulfanyl-2-methyl-6-oxo-1H-pyridine-3-carboxylate
• CAS: 1185189-75-6
• 化学式: C₁₇H₁₉NO₃S
• 分子量: 317.409
• InChiKey: OWPZHZZONFCUGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(3,5-dimethylphenylsulfanyl)-2-methyl-6-oxo-1,6-dihydropyridin-3-ylcarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到5-hydroxymethyl-6-methyl-4-(3,5-dimethylphenylsulfanyl)pyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of C-5 Methyl Substituted 4-Arylthio and 4-Aryloxy-3-Iodopyridin-2(1H)-one Type Anti-HIV Agents

  摘要：

  A series of C-5 methyl substituted 4-arylthio- and 4-aryloxy-3-iodopyridin-2(1H)-ones hits been synthesized its new pyridinone analogues for their evaluation as anti-HIV inhibitors. The optimization at the 5-position wits developed through an efficient use of the key intermediates 5-ethoxycarbonyl- and 5-cyano-pyridin-2(1H)-ones (14 and 15). Biological studies revealed that several compounds show potent HIV-1 reverse transcriptase inhibitory properties, for example, compounds 93 and 99 are active at 0.6-50 nM against wild type HIV-1 and a panel of major simple/double HIV mutant strains.

  DOI：

  10.1021/jm900802y
• 作为产物：
  描述：

  ethyl 4-chloro-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate 、 3,5-二甲基苯硫酚 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以80%的产率得到ethyl 4-(3,5-dimethylphenylsulfanyl)-2-methyl-6-oxo-1,6-dihydropyridin-3-ylcarboxylate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of C-5 Methyl Substituted 4-Arylthio and 4-Aryloxy-3-Iodopyridin-2(1H)-one Type Anti-HIV Agents

  摘要：

  A series of C-5 methyl substituted 4-arylthio- and 4-aryloxy-3-iodopyridin-2(1H)-ones hits been synthesized its new pyridinone analogues for their evaluation as anti-HIV inhibitors. The optimization at the 5-position wits developed through an efficient use of the key intermediates 5-ethoxycarbonyl- and 5-cyano-pyridin-2(1H)-ones (14 and 15). Biological studies revealed that several compounds show potent HIV-1 reverse transcriptase inhibitory properties, for example, compounds 93 and 99 are active at 0.6-50 nM against wild type HIV-1 and a panel of major simple/double HIV mutant strains.

  DOI：

  10.1021/jm900802y

文献信息

• Pyridinone and pyridinethione derivatives having hiv inhibiting properties
  申请人：——

  公开号：US20040229847A1

  公开（公告）日：2004-11-18

  The present invention is concerned among others with compounds of formula (I), the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and stereochemically isomeric forms thereof, wherein Q is halo, C 1-6 alkyl or C 2-6 alkenyl; X is (a-2) with q and r being O and Z being O, S or SO; R 1 is aryl; R 2 is selected from formyl; C 1-6 alkyloxycarbonylalkyl; Het 2 ; Het 2 C 1-6 alkyl, C 1-6 alkylthio; C 1-6 alkyl optionally substituted with one or two substituents each independently selected from hydroxy, and halo; R 3 is selected from formyl; C 1-6 alkyl optionally substituted with one or two C 1-6 alkyloxy; R 1 is hydrogen, with HTV inhibiting properties. 1

  本发明涉及式(I)的化合物，其N-氧化物，药学上可接受的加成盐，季铵盐和立体化学异构体形式，其中Q是卤素，C1-6烷基或C2-6烯基; X为(a-2)，其中q和r为O，Z为O，S或SO; R1为芳基; R2选自甲酰基; C1-6烷氧羰基烷基; Het2; Het2C1-6烷基，C1-6烷基硫醚; C1-6烷基，可选用一个或两个取代基，独立地选自羟基和卤素; R3选自甲酰基; C1-6烷基，可选用一个或两个C1-6烷氧基; R1为氢，具有HTV抑制性能。
• Pyridinone and pyridinethione derivatives having HIV inhibiting properties
  申请人：Centre National de la Recherche Schentifique

  公开号：US07115608B2

  公开（公告）日：2006-10-03

  The present invention is concerned among others with compounds of formula (1), the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and stereochemically isomeric forms thereof, wherein Q is halo, C1-6 alkyl or C2-6 alkenyl; X is (a-2) with q and r being O and Z being O, S or SO; R1 is aryl; R2 is selected from formyl; C1-6alkyloxycarbonylalkyl; Het2; Het2C1-6alkyl, C1-6alkylthio; C1-6alkyl optionally substituted with one or two substituents each independently selected from hydroxy, and halo; R3 is selected from formyl; C1-6alkyl optionally substituted with one or two C1-6alkyloxy; R4 is hydrogen, with HTV inhibiting properties

  本发明涉及公式（1）的化合物，其N-氧化物，药学上可接受的加合盐，季铵盐和立体化学异构体形式，其中Q是卤素，C1-6烷基或C2-6烯基; X是（a-2），其中q和r为O，Z为O，S或SO; R1是芳基; R2选择自甲酰基; C1-6烷氧羰基烷基; Het2; Het2C1-6烷基，C1-6烷基硫代基; C1-6烷基，可选地被一个或两个取代基取代，每个取代基独立选择自羟基和卤素; R3选择自甲酰基; C1-6烷基，可选地被一个或两个C1-6烷氧基取代; R4为氢，具有HTV抑制性能。
• PYRIDINONE AND PYRIDINETHIONE DERIVATIVES HAVING HIV INHIBITING PROPERTIES
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：EP1318995B1

  公开（公告）日：2006-03-08
• US7115608B2
  申请人：——

  公开号：US7115608B2

  公开（公告）日：2006-10-03