[(4S,6S,7R,8S)-7-methoxy-12-methyl-11-[2-[(3-nitropyridin-2-yl)disulfanyl]ethylamino]-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate | 95056-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [(4S,6S,7R,8S)-7-methoxy-12-methyl-11-[2-[(3-nitropyridin-2-yl)disulfanyl]ethylamino]-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
• CAS: 95056-43-2
• 化学式: C₂₂H₂₄N₆O₇S₂
• 分子量: 548.601
• InChiKey: BRWCVMSXGZIPDN-FBSHEPSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  242
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  、 [(4S,6S,7R,8S)-7-methoxy-12-methyl-11-[2-[(3-nitropyridin-2-yl)disulfanyl]ethylamino]-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以88%的产率得到(2S)-2-[[4-[(2-amino-4-oxo-8H-pteridin-6-yl)methylamino]benzoyl]amino]-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-3-[3-[2-[[(4S,6S,7R,8S)-8-(carbamoyloxymethyl)-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-11-yl]amino]ethyldisulfanyl]propanoylamino]-1-[[(1R)-1-carboxy-2-[2-[[[(1R,9R,10S,11R,12R,19R)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carbonyl]amino]carbamoyloxy]ethyldisulfanyl]ethyl]amino]-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
  参考文献：
  名称：

  An Assembly Concept for the Consecutive Introduction of Unsymmetrical Disulfide Bonds:  Synthesis of a Releasable Multidrug Conjugate of Folic Acid

  摘要：

  We describe the development of methodology which allows for the introduction of a second disulfide bond into a molecular framework with a pre-existing disulfide linker system. Compounds which contain an S-9-fluorenylmethyl-protected thiol and an additional disulfide linkage are deprotected in situ and trapped with an activated thiophile. This methodology allowed for the synthesis of the first molecule possessing two different biologically active agents covalently attached to a folate receptor targeting ligand unit via two disulfide-based release systems.

  DOI：

  10.1021/jo070411z
• 作为产物：
  描述：

  3-硝基-2-吡啶硫酰氯 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 [(4S,6S,7R,8S)-7-methoxy-12-methyl-11-[2-[(3-nitropyridin-2-yl)disulfanyl]ethylamino]-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
  参考文献：
  名称：

  An Assembly Concept for the Consecutive Introduction of Unsymmetrical Disulfide Bonds:  Synthesis of a Releasable Multidrug Conjugate of Folic Acid

  摘要：

  We describe the development of methodology which allows for the introduction of a second disulfide bond into a molecular framework with a pre-existing disulfide linker system. Compounds which contain an S-9-fluorenylmethyl-protected thiol and an additional disulfide linkage are deprotected in situ and trapped with an activated thiophile. This methodology allowed for the synthesis of the first molecule possessing two different biologically active agents covalently attached to a folate receptor targeting ligand unit via two disulfide-based release systems.

  DOI：

  10.1021/jo070411z