toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methylphenyl) ester hydrochloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methylphenyl) ester hydrochloride
• 英文别名: [5-Tert-butyl-2-methyl-4-(4-methylphenyl)sulfonylsulfanylphenyl]azanium;chloride；[5-tert-butyl-2-methyl-4-(4-methylphenyl)sulfonylsulfanylphenyl]azanium;chloride
• 化学式: C₁₈H₂₃NO₂S₂*ClH
• 分子量: 385.979
• InChiKey: IAEUBBJKPRBAOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  93.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one 、 toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methylphenyl) ester hydrochloride 在 potassium carbonate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 以62%的产率得到3-(4-amino-2-tert-butyl-5-methyl-phenylsulfanyl)-6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  [EN] INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME
  [FR] INHIBITEURS DE L'ARN POLYMERASE ARN-DEPENDANTE DU VIRUS DE L'HEPATITE C ET COMPOSITIONS ET TRAITEMENTS UTILISANT CETTE POLYMERASE

  摘要：

  化合物的化学式（I）是丙型肝炎病毒（HCV）RNA依赖性RNA聚合酶（RdRp）抑制剂，对感染丙型肝炎病毒的人进行治疗和预防性治疗具有用处。

  公开号：

  WO2003095441A1
• 作为产物：
  描述：

  4-叔丁基-1-甲基-2-硝基苯 在 镍 盐酸 、 potassium dihydrogenphosphate 、 氢气 、 溴 、 三乙胺 、 sodium bromide 、 1,4-二巯基-2,3-丁二醇 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醇 、 二氯甲烷 为溶剂， 60.0 ℃ 、358.54 kPa 条件下， 反应 88.17h， 生成 toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methylphenyl) ester hydrochloride
  参考文献：
  名称：

  5,6-Dihydropyran-2-ones Possessing Various Sulfonyl Functionalities:  Potent Nonpeptidic Inhibitors of HIV Protease

  摘要：

  On the basis of previous SAR findings and molecular modeling studies, a series of compounds were synthesized which possessed various sulfonyl moieties substituted at the 4-position of the C-3 phenyl ring substituent of the dihydropyran-2-one ring system. The sulfonyl substituents were added in an attempt to fill the additional S-3' pocket and thereby produce increasingly potent inhibitors of the target enzyme. Racemic and enantiomerically resolved varieties of selected compounds were synthesized. All analogues in the study displayed decent binding affinity to HIV protease, and several compounds were shown to possess very good antiviral efficacy and safety margins. X-ray crystallographic structures confirmed that the sulfonamide and sulfonate moieties were filling the S3' pocket of the enzyme. However, the additional substituent did not provide improved enzymatic inhibitory or antiviral activity as compared to the resolved unsubstituted aniline. The addition of the sulfonyl moiety substitution does not appear to provide favorable pharamacokinectic parameters. Selected inhibitors were tested for antiviral activity in clinical isolates and exhibited similar antiviral activity against all of the HIV-1 strains tested as they did against the wild-type HIV-1, In addition, the inhibitors exhibited good antiviral efficacies against HIV-1 strains that displayed resistance to the currently marketed protease inhibitors.

  DOI：

  10.1021/jm990281p

文献信息

• Methods of making dihydropyrone HIV protease inhibitors
  申请人：——

  公开号：US06380400B1

  公开（公告）日：2002-04-30

  The present invention relates to methods of making dihydropyrone HIV inhibitors.

  本发明涉及制备二氢吡喃类HIV抑制剂的方法。
• Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same
  申请人：Agouron Pharmaceuticals, Inc.

  公开号：US20040023958A1

  公开（公告）日：2004-02-05

  Compounds of formula I are hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors, and are useful in therapeutic and prophylactic treatment of persons infected with hepatitis C virus. 1

  式 I 的化合物是丙型肝炎病毒（HCV）RNA 依赖性 RNA 聚合酶（RdRp）抑制剂，可用于丙型肝炎病毒感染者的治疗和预防。 1
• US6380400B1
  申请人：——

  公开号：US6380400B1

  公开（公告）日：2002-04-30
• US7115658B2
  申请人：——

  公开号：US7115658B2

  公开（公告）日：2006-10-03
• [EN] METHODS OF MAKING DIHYDROPYRONE HIV PROTEASE INHIBITORS<br/>[FR] PROCEDES DE PREPARATION D'INHIBITEURS DIHYDROPYRONE DE PROTEASE DE VIH
  申请人：WARNER LAMBERT CO

  公开号：WO2000015625A2

  公开（公告）日：2000-03-23

  The present invention relates to methods of making dihydropyrone HIV protease inhibitors.