2-[2-[[[5-(1,1-Dioxothiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carbonyl]amino]methyl]phenyl]acetic acid | 606138-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-[2-[[[5-(1,1-Dioxothiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carbonyl]amino]methyl]phenyl]acetic acid
• CAS: 606138-93-6
• 化学式: C₂₂H₂₂N₄O₆S
• 分子量: 470.506
• InChiKey: QTDOGVNCDWWWTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[2-[[[5-(1,1-Dioxothiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carbonyl]amino]methyl]phenyl]acetic acid 、 二甲胺 在 TEA 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[[2-[2-(dimethylamino)-2-oxo-ethyl]phenyl]methyl]-5-(1,1-dioxothiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carboxamide
  参考文献：
  名称：

  A potent and orally active HIV-1 integrase inhibitor

  摘要：

  A 1,6-naphthyridine inhibitor of HIV-1 integrase has been discovered with excellent inhibitory activity in cells, good pharmacokinetics, and an excellent ability to inhibit virus with mutant enzyme. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.080
• 作为产物：
  描述：

  Tert-butyl 2-[2-[[[5-(1,1-dioxothiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carbonyl]amino]methyl]phenyl]acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以71%的产率得到2-[2-[[[5-(1,1-Dioxothiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carbonyl]amino]methyl]phenyl]acetic acid
  参考文献：
  名称：

  A potent and orally active HIV-1 integrase inhibitor

  摘要：

  A 1,6-naphthyridine inhibitor of HIV-1 integrase has been discovered with excellent inhibitory activity in cells, good pharmacokinetics, and an excellent ability to inhibit virus with mutant enzyme. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.080

文献信息

• [EN] N-(SUBSTITUTED BENZYL)-8-HYDROXY-1,6-NAPHTHYRIDINE-7- CARBOXAMIDES USEFUL AS HIV INTEGRASE INHIBITORS<br/>[FR] N-(BENZYL SUBSTITUE)-8-HYDROXY-1,6-NAPHTYRIDINE-7-CARBOXAMIDES UTILES COMME INHIBITEURS DE L'INTEGRASE DU VIH
  申请人：MERCK & CO INC

  公开号：WO2003077857A2

  公开（公告）日：2003-09-25

  N-(Substituted benzyl)-8-hydroxy- 1,6-naphthyridine-7-carboxamides are inhibitors of HIV integrase and inhibitors of HIV replication. In one embodiment, the naphthyridine carboxamides are of Formula (II): (II),wherein R1', R2' and R3' are defined herein. The compounds are useful in the prevention and treatment of infection by HIV and in the prevention, delay in the onset, and treatment of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of preventing, treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are described.
• A potent and orally active HIV-1 integrase inhibitor
  作者：Melissa S. Egbertson、H. Marie Moritz、Jeffrey Y. Melamed、Wei Han、Debra S. Perlow、Michelle S. Kuo、Mark Embrey、Joseph P. Vacca、Matthew M. Zrada、Amanda R. Cortes、Audrey Wallace、Yvonne Leonard、Daria J. Hazuda、Michael D. Miller、Peter J. Felock、Kara A. Stillmock、Marc V. Witmer、William Schleif、Lori J. Gabryelski、Gregory Moyer、Joan D. Ellis、Lixia Jin、Wei Xu、Matthew P. Braun、Kellem Kassahun、Nancy N. Tsou、Steven D. Young

  DOI：10.1016/j.bmcl.2006.11.080

  日期：2007.3

  A 1,6-naphthyridine inhibitor of HIV-1 integrase has been discovered with excellent inhibitory activity in cells, good pharmacokinetics, and an excellent ability to inhibit virus with mutant enzyme. (c) 2006 Elsevier Ltd. All rights reserved.