3-(2-Nitrophenyl)propane-1,2-diol | 211935-16-9

• 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: 3-(2-Nitrophenyl)propane-1,2-diol
• CAS: 211935-16-9
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: AGOIBNLGYCTAGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-Nitrophenyl)propane-1,2-diol 在 palladium on activated charcoal 咪唑 、 2,6-二甲基吡啶 、 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.08h， 生成 (2S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-propan-2-yl-1,2,5,6-tetrahydro-4,1-benzoxazocin-3-one
  参考文献：
  名称：

  Synthesis, conformation and PKC isozyme surrogate binding of new lactone analogues of benzolactam-V8s

  摘要：

  To investigate the role of the amide hydrogen of benzolactam-V8s (1-3) on protein kinase C (PKC) isozyme binding, new lactone analogues of benzolactam-V8s with hydrophobic side chains at positions 8 and/or 9 (5-8) were synthesized. The PKC binding affinities of 8- and 9-decylbenzolactone-V8 (5,6) were much lower than those of 8- and 9-decylbenzolactam-V8 (2,3), respectively, indicating that the amide hydrogen of benzolactam-V8s plays a critical role in PKC binding. 8-Decylbenzolactam-V8 (2) showed lower binding affinities to all PKC isozymes compared with those of 9-decylbenzolactam-V8 (3). The binding affinities of 8-substituted benzolactones (5,7,8) were also lower than those of 9-decylbenzolactone-V8 (6), but their PKC isozyme selectivity was higher than those of 2, 3 and 6. 8-Decybenzolactone-V8 (5) exhibited the most significant eta-C1B selectivity among the four benzolactones (5-8) synthesized in this study. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00099-6
• 作为产物：
  描述：

  1-烯丙基-2-硝基苯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-(2-Nitrophenyl)propane-1,2-diol
  参考文献：
  名称：

  Réactivé d'iminophosphoranes polyfonctionnalisés

  摘要：

  DOI：

  10.1016/s0040-4039(00)97229-0

文献信息

• Synthesis and binding selectivity of 7- and 15-decylbenzolactone-V8 for the C1 domains of protein kinase C isozymes
  作者：Yu Nakagawa、Kazuhiro Irie、Nobuhiro Yamanaka、Hajime Ohigashi、Ken-ichiro Tsuda

  DOI：10.1016/s0960-894x(03)00637-1

  日期：2003.9

  lactone analogue of the artificial tumor promoter benzolactam-V8 (1). To investigate the effect of hydrophobic substituents at positions 7 and 15 of 4 on binding selectivity for protein kinase C (PKC) isozymes, 7- and 15-decylbenzolactone-V8 (7, 8) were synthesized and their binding affinities for synthetic PKC isozyme C1 peptides were examined. Compound 8 showed moderate selectivity for novel PKC isozymes

  苯甲内酯-V8（4）是人工肿瘤启动子苯并内酰胺-V8（1）的内酯类似物。为了研究4位7和15上的疏水取代基对蛋白激酶C（PKC）同工酶的结合选择性的影响，合成了7-和15-癸基苯甲内酯-V8（7，8）以及它们对合成PKC同工酶C1的结合亲和力检查肽。化合物8对类似于9-癸基苯甲内酯-V8（5）的新型PKC同工酶显示出中等选择性，而7则选择性较低。与8-癸基苯并内酯-V8不同，化合物7和8在新型PKC同工酶中没有显示出明显的选择性（6）。这些结果表明，在4的8位上引入疏水取代基最有效地开发了PKCε-和PKCeta-选择性粘合剂。
• The amide hydrogen of (−)-indolactam-V and benzolactam-V8’s plays a critical role in protein kinase c binding and tumor-promoting activities
  作者：Yu Nakagawa、Kazuhiro Irie、Yoshimasa Nakamura、Hajime Ohigashi

  DOI：10.1016/s0960-894x(01)00047-6

  日期：2001.3

  To investigate the role of the amide hydrogen of (-)-indolactam-V (1) and benzolactam-V8's on protein kinase C (PKC) binding and tumor promotion, 8-decylbenzolactone-V8 (6), a new lactone analogue of 8-decylbenzolactam-V8 (4), was synthesized from 2-nitrophenylpyruvic acid (7) in 11 steps. The PKC binding ability and tumor-promoting activities in vitro of 6 were much lower than those of 1 and 4, suggesting that the amide hydrogen of 1 and benzolactam-V8's plays a critical role in tumor promotion. However, it is noteworthy that 6 showed significant selectivity in the PKC isozyme surrogate binding. (C) 2001 Published by Elsevier Science Ltd.