2-(3-benzyl-5-bromo-benzyl)-isothiazolidine 1,1-dioxide | 500732-66-1

• 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: 2-(3-benzyl-5-bromo-benzyl)-isothiazolidine 1,1-dioxide
• 英文别名: 1-(1,1-dioxo-isothiazolidin-2-ylmethyl)-3-benzyl-5-bromo-benzene；2-[(3-Benzyl-5-bromophenyl)methyl]-1,2-thiazolidine 1,1-dioxide
• CAS: 500732-66-1
• 化学式: C₁₇H₁₈BrNO₂S
• 分子量: 380.305
• InChiKey: CIAIJIRXYXUEOY-UHFFFAOYSA-N

物化性质

• 沸点：
  516.2±52.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-benzyl-5-bromo-benzyl)-isothiazolidine 1,1-dioxide 在 thallium(I) acetate 盐酸 、 palladium diacetate 、 三氯化铝 、 1,3-双(二苯基膦)丙烷 、 溴 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-{[3-benzyl-5-(1,1-dioxo-isothiazolidin-2-ylmethyl)]-phenyl}-2-bromo-ethanone
  参考文献：
  名称：

  Design and Synthesis of 8-Hydroxy-[1,6]Naphthyridines as Novel Inhibitors of HIV-1 Integrase in Vitro and in Infected Cells

  摘要：

  Naphthyridine 7 inhibits the strand transfer of the integration process catalyzed by integrase with an IC50 of 10 nM and inhibits 95% of the spread of HIV-1 infection in cell culture at 0.39 muM. It does not exhibit cytotoxicity in cell culture at less than or equal to 12.5 muM and shows a good pharmacokinetic profile when dosed orally to rats. The antiviral activity of 7 and its effect on integration were confirmed using viruses with specific integrase mutations.

  DOI：

  10.1021/jm025553u
• 作为产物：
  描述：

  3,5-dibromo-benzhydrol 在 三乙基硅烷 、 sodium tetrahydroborate 、 正丁基锂 、 四溴化碳 、 三氟化硼乙醚 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 36.67h， 生成 2-(3-benzyl-5-bromo-benzyl)-isothiazolidine 1,1-dioxide
  参考文献：
  名称：

  Design and Synthesis of 8-Hydroxy-[1,6]Naphthyridines as Novel Inhibitors of HIV-1 Integrase in Vitro and in Infected Cells

  摘要：

  Naphthyridine 7 inhibits the strand transfer of the integration process catalyzed by integrase with an IC50 of 10 nM and inhibits 95% of the spread of HIV-1 infection in cell culture at 0.39 muM. It does not exhibit cytotoxicity in cell culture at less than or equal to 12.5 muM and shows a good pharmacokinetic profile when dosed orally to rats. The antiviral activity of 7 and its effect on integration were confirmed using viruses with specific integrase mutations.

  DOI：

  10.1021/jm025553u

文献信息

• Aza-and polyaza-naphthalenly ketones useful as hiv integrase inhibitors
  申请人：Zhuang Linghang

  公开号：US20050010048A1

  公开（公告）日：2005-01-13

  Certain aza- and polyaza-naphthalenyl ketones including certain quinolinyl and naphthyridinyl ketones are described as inhibitors of HIV integrase and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HIV and the treatment or the delay in the onset of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.

  某些氮杂萘基酮和多氮杂萘基酮，包括某些喹啉基和萘啉基酮，被描述为HIV整合酶的抑制剂和HIV复制的抑制剂。这些化合物在预防或治疗HIV感染以及治疗或延缓艾滋病发作方面是有用的，可以作为化合物或药学上可接受的盐，或作为药物组合物中的成分，可选地与其他抗病毒药物、免疫调节剂、抗生素或疫苗结合使用。还描述了治疗或延缓艾滋病发作的方法以及预防或治疗HIV感染的方法。
• Design and Synthesis of 8-Hydroxy-[1,6]Naphthyridines as Novel Inhibitors of HIV-1 Integrase in Vitro and in Infected Cells
  作者：Linghang Zhuang、John S. Wai、Mark W. Embrey、Thorsten E. Fisher、Melissa S. Egbertson、Linda S. Payne、James P. Guare,、Joseph P. Vacca、Daria J. Hazuda、Peter J. Felock、Abigail L. Wolfe、Kara A. Stillmock、Marc V. Witmer、Gregory Moyer、William A. Schleif、Lori J. Gabryelski、Yvonne M. Leonard、Joseph J. Lynch,、Stuart R. Michelson、Steven D. Young

  DOI：10.1021/jm025553u

  日期：2003.2.1

  Naphthyridine 7 inhibits the strand transfer of the integration process catalyzed by integrase with an IC50 of 10 nM and inhibits 95% of the spread of HIV-1 infection in cell culture at 0.39 muM. It does not exhibit cytotoxicity in cell culture at less than or equal to 12.5 muM and shows a good pharmacokinetic profile when dosed orally to rats. The antiviral activity of 7 and its effect on integration were confirmed using viruses with specific integrase mutations.