(2R,11aS)-2-{[tert-butyl(diphenyl)silyl]oxy}-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-(10H,11aH)-dione | 894786-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (2R,11aS)-2-{[tert-butyl(diphenyl)silyl]oxy}-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-(10H,11aH)-dione
• 英文别名: (6aS,8R)-8-[tert-butyl(diphenyl)silyl]oxy-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-6,11-dione
• CAS: 894786-85-7
• 化学式: C₂₈H₃₀N₂O₃Si
• 分子量: 470.643
• InChiKey: WZTZQSGZHFBBDX-NLFFAJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,11aS)-2-{[tert-butyl(diphenyl)silyl]oxy}-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-(10H,11aH)-dione 、 溴乙酸叔丁酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到[(2R,11aS)-2-{[tert-butyl(diphenyl)silyl]oxy}-5,11-dioxo-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-yl]-acetic acid tert-butyl ester
  参考文献：
  名称：

  Design, Synthesis, and In Vitro Activity of Peptidomimetic Inhibitors of Myeloid Differentiation Factor 88

  摘要：

  We describe the design and synthesis of a peptidomimetic library derived from the heptapeptide Ac-RDVLPGT-NH(2), belonging to the Toll/IL-1 receptor (TIR) domain of the adaptor protein MyD88 and effective in inhibiting its homodimerization. The ability of the peptidomimetics to inhibit protein-protein interaction was assessed by yeast 2-hybrid assay and further validated in a mammalian cell system by evaluating the inhibition of NF-kappa B activation, a transcription factor downstream of MyD88 signaling pathway that allows production of essential effector molecules for immune and inflammatory responses.

  DOI：

  10.1021/jm070723u
• 作为产物：
  描述：

  (2R,11aS)-2-hydroxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以83%的产率得到(2R,11aS)-2-{[tert-butyl(diphenyl)silyl]oxy}-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-(10H,11aH)-dione
  参考文献：
  名称：

  Design, Synthesis, and In Vitro Activity of Peptidomimetic Inhibitors of Myeloid Differentiation Factor 88

  摘要：

  We describe the design and synthesis of a peptidomimetic library derived from the heptapeptide Ac-RDVLPGT-NH(2), belonging to the Toll/IL-1 receptor (TIR) domain of the adaptor protein MyD88 and effective in inhibiting its homodimerization. The ability of the peptidomimetics to inhibit protein-protein interaction was assessed by yeast 2-hybrid assay and further validated in a mammalian cell system by evaluating the inhibition of NF-kappa B activation, a transcription factor downstream of MyD88 signaling pathway that allows production of essential effector molecules for immune and inflammatory responses.

  DOI：

  10.1021/jm070723u

文献信息

• Design, Synthesis, and In Vitro Activity of Peptidomimetic Inhibitors of Myeloid Differentiation Factor 88
  作者：Nicola Fantò、Grazia Gallo、Andrea Ciacci、Mauro Semproni、Davide Vignola、Marco Quaglia、Valentina Bombardi、Domenico Mastroianni、M. Pia Zibella、Giancarlo Basile、Marica Sassano、Vito Ruggiero、Rita De Santis、Paolo Carminati

  DOI：10.1021/jm070723u

  日期：2008.3.13

  We describe the design and synthesis of a peptidomimetic library derived from the heptapeptide Ac-RDVLPGT-NH(2), belonging to the Toll/IL-1 receptor (TIR) domain of the adaptor protein MyD88 and effective in inhibiting its homodimerization. The ability of the peptidomimetics to inhibit protein-protein interaction was assessed by yeast 2-hybrid assay and further validated in a mammalian cell system by evaluating the inhibition of NF-kappa B activation, a transcription factor downstream of MyD88 signaling pathway that allows production of essential effector molecules for immune and inflammatory responses.