5-tert-butyl-2-methyl-4-thiocyanatophenylamine | 207737-25-5

• 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: 5-tert-butyl-2-methyl-4-thiocyanatophenylamine
• 英文别名: 5-tert-Butyl-2-methyl-4-thiocyanato-phenylamine；(4-amino-2-tert-butyl-5-methylphenyl) thiocyanate
• CAS: 207737-25-5
• 化学式: C₁₂H₁₆N₂S
• 分子量: 220.338
• InChiKey: DQVDWTRKKXEEEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-tert-butyl-2-methyl-4-thiocyanatophenylamine 在 盐酸 、 sodium hydroxide 、 KH₂PO₄ buffer 、 DL-dithiothreitol 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-amino-2-tert-butyl-5-methyl-phenyl)sulfanyl-4-hydroxy-2-isopropyl-2-phenethyl-3H-pyran-6-one
  参考文献：
  名称：

  Nonpeptidic HIV protease inhibitors: 6-alkyl-5, 6-dihydropyran-2-ones possessing achiral 3-(4-amino/carboxamide-2-t-butyl, 5-methylphenyl thio) moiety: Antiviral activities and pharmacokinetic properties

  摘要：

  Dihydropyran-2-ones possessing amino and carboxamide functionalities on 3-SPh (2-tert-butyl, 5-methyl) ring were synthesized and evaluated for their antiviral activities. Both the enantiomers of inhibitor 15 were synthesized. The in vitro resistance profile, inhibitory activities against cytochrome P450 isozymes and pharmacokinetic properties of inhibitor 15S will be discussed.

  DOI：

  10.1016/s0960-894x(99)00237-1
• 作为产物：
  描述：

  4-叔丁基甲苯 在 palladium on activated charcoal 硫酸 、 氢气 、 溴 、 硝酸 、 sodium bromide 作用下， 生成 5-tert-butyl-2-methyl-4-thiocyanatophenylamine
  参考文献：
  名称：

  Nonpeptidic HIV protease inhibitors: 6-alkyl-5, 6-dihydropyran-2-ones possessing achiral 3-(4-amino/carboxamide-2-t-butyl, 5-methylphenyl thio) moiety: Antiviral activities and pharmacokinetic properties

  摘要：

  Dihydropyran-2-ones possessing amino and carboxamide functionalities on 3-SPh (2-tert-butyl, 5-methyl) ring were synthesized and evaluated for their antiviral activities. Both the enantiomers of inhibitor 15 were synthesized. The in vitro resistance profile, inhibitory activities against cytochrome P450 isozymes and pharmacokinetic properties of inhibitor 15S will be discussed.

  DOI：

  10.1016/s0960-894x(99)00237-1

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。
• Dihydropyrones with improved antiviral activity
  申请人：Warner-Lambert Company

  公开号：US06046355A1

  公开（公告）日：2000-04-04

  This invention pertains to improved antiviral activity of 6,6-disubstituted-5,6-dihydropyran-2-ones caused by judicious placement of certain polar substituents at the 3 and/or 6 positions. The same substituents which enhance the cellular activity also diminish cytotoxicity further enhancing the desirable properties of these agents as antivirals.

  本发明涉及通过在3和/或6位恰当地放置某些极性取代基，改善6,6-二取代-5,6-二氢吡喃-2-酮的抗病毒活性。这些增强细胞活性的相同取代基还降低了细胞毒性，进一步增强了这些化合物作为抗病毒药物的理想性能。
• 5,6-Dihydropyran-2-ones Possessing Various Sulfonyl Functionalities:  Potent Nonpeptidic Inhibitors of HIV Protease
  作者：Frederick E. Boyer、J. V. N. Vara Prasad、John M. Domagala、Edmund L. Ellsworth、Christopher Gajda、Susan E. Hagen、Larry J. Markoski、Bradley D. Tait、Elizabeth A. Lunney、Alexander Palovsky、Donna Ferguson、Neil Graham、Tod Holler、Donald Hupe、Carolyn Nouhan、Peter J. Tummino、A. Urumov、Eric Zeikus、Greg Zeikus、Stephen J. Gracheck、James M. Sanders、Steven VanderRoest、Joanne Brodfuehrer、Krishna Iyer、Michael Sinz、Sergei V. Gulnik、John W. Erickson

  DOI：10.1021/jm990281p

  日期：2000.3.1

  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.
• Thiocyanation of alkylanilines. A simple and efficient synthesis of thiosulfonates containing 2-aminobenzothiazole
  作者：J.V.N. Vara Prasad、A. Panapoulous、John R. Rubin

  DOI：10.1016/s0040-4039(00)00591-8

  日期：2000.5
• DIHYDROPYRONES WITH IMPROVED ANTIVIRAL ACTIVITY
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0935597A2

  公开（公告）日：1999-08-18