4-nitrophenyl N-nitroso-N-methylcarbamate | 75744-83-1

• 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: 4-nitrophenyl N-nitroso-N-methylcarbamate
• 英文别名: (4-nitrophenyl) N-methyl-N-nitrosocarbamate
• CAS: 75744-83-1
• 化学式: C₈H₇N₃O₅
• 分子量: 225.161
• InChiKey: UQHICQFZQPCVOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  119-122 °C(Solv: ethanol (64-17-5))
• 沸点：
  339.9±44.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  102.11
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(2-aminoethoxy)ethyl-9-hydroxy-6-methylellipticinium chloride 、 4-nitrophenyl N-nitroso-N-methylcarbamate 在 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 7.0h， 以40%的产率得到3-[2-[2-(9-Hydroxy-5,6,11-trimethylpyrido[4,3-b]carbazol-2-ium-2-yl)ethoxy]ethyl]-1-methyl-1-nitrosourea;chloride
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

  摘要：

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.032
• 作为产物：
  描述：

  对硝基苯基氯甲酸酯 在 sodium acetate 、 dinitrogen tetraoxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 4-nitrophenyl N-nitroso-N-methylcarbamate
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

  摘要：

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.032

文献信息

• Selective Modification of Streptozotocin at the C3 Position to Improve Its Bioactivity as Antibiotic and Reduce Its Cytotoxicity towards Insulin-Producing β Cells
  作者：Ji Zhang、Liubov Yakovlieva、Bart J. de Haan、Paul de Vos、Adriaan J. Minnaard、Martin D. Witte、Marthe T. C. Walvoort

  DOI：10.3390/antibiotics9040182

  日期：——

  resistance of bacteria to current antibiotics, novel compounds are urgently needed to treat bacterial infections. Streptozotocin (STZ) is a natural product that has broad-spectrum antibiotic activity, albeit with limited use because of its toxicity to pancreatic β cells. In an attempt to derivatize STZ through structural modification at the C3 position, we performed the synthesis of three novel STZ analogues

  随着细菌对当前抗生素的抗性增加，迫切需要新型化合物来治疗细菌感染。链脲佐菌素（STZ）是一种具有广谱抗生素活性的天然产物，尽管由于其对胰腺β细胞的毒性而用途有限。为了尝试通过C3位置的结构修饰衍生STZ，我们通过利用我们最近开发的区域选择性氧化方案进行了三种新颖的STZ类似物的合成。Keto-STZ（2）对细菌的生长具有最高的抑制作用（最小抑制浓度（MIC）和活力测定），但也是最具细胞毒性的化合物。用GlcNAc对细菌进行预敏化可以提高抗菌效果，但并不能完全杀死细菌。有趣的是
• Synthesis and cytotoxic activity of novel 11-methyl-6H-pyrido[4,3-b]carbazole derivatives linked to amine, N-methylurea, and N-methyl-N-nitrosourea moieties with various types of carbamoyl tethers at the C-5 atom
  作者：Asako Kato、Yusuke Nagatsuka、Tomokazu Hiratsuka、Satoko Kiuchi、Yoko Iwase、Yuri Okuno、Tetsuya Tsukamoto、Y.B. Kiran、Norio Sakai、Takeo Konakahara

  DOI：10.1016/j.tet.2016.05.068

  日期：2016.7

  high yields, and their cytotoxic activities were evaluated against Sarcoma-180, NIH3T3, HeLa S-3, and L1210 cell lines. These compounds exhibited potent cytotoxic activity (IC50=1.6–50 μM) and odd-even alternation effect. 9-Methoxy-2,11-dimethyl-5-((2-(3-methyl-3-nitrosoureido)ethyl)carbamoyl)-6H-pyrido[4,3-b]carbazol-2-ium chloride exhibited the most potent cytotoxic activity (IC50=0.15 μM) and cell

  三十五种新型吡啶并咔唑（5-（N-烷基）氨基甲酰基-11-甲基-6 H-吡啶并[4,3- b ]咔唑和5-（N-烷基）氨基甲酰基-2,11-二甲基-6通过烷基-，氧烷基-和亚氨基烷基氨基甲酰基连接基与胺，N-甲基脲和N-甲基-N-亚硝基脲部分共轭的H-吡啶并[4,3 - b ]咔唑-2-氯化物衍生物是通过一系列甲基11-甲基-6 H-吡啶并[4,3 - b ]咔唑-5-羧酸酯与聚亚甲基二胺（n = 2–5），对硝基苯基N的反应合成-甲基氨基甲酸酯和N-甲基-N-亚硝基氨基甲酸酯，并评估了它们对肉瘤180，NIH3T3，HeLa S-3和L1210细胞系的细胞毒活性。这些化合物表现出有效的细胞毒活性（IC 50 = 1.6–50μM）和奇偶交替效应。9-甲氧基-2,11-二甲基-5-（（2-（3-甲基-3-亚硝基脲基）乙基）氨基甲酰基）-6 H-吡啶基[4,3 - b ]咔唑-2-氯化铵显示最多强大的细胞毒活性（IC
• [EN] FUSED RING DIIMIDE DERIVATIVE, PREPARATION METHOD THEREFOR AND USE THEREOF<br/>[FR] DÉRIVÉ DE DIIMIDE CYCLIQUE CONDENSÉ, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 一种稠环二酰亚胺衍生物、其制备方法和应用
  申请人：GUANGZHOU XIN CHUANGYI BIOPHARMACEUTICAL CO LTD

  公开号：WO2022073445A1

  公开（公告）日：2022-04-14

  提供一种稠环二酰亚胺衍生物，具有式I所述的化学结构。还提供了其制备方法。稠环二酰亚胺衍生物具有优异的抗肿瘤活性，对多种癌细胞的抗增殖活性显著优于类似化合物。
• Martinez; Oiry; Imbach, European Journal of Medicinal Chemistry, 1980, vol. 15, # 3, p. 211 - 213
  作者：Martinez、Oiry、Imbach、Winternitz

  DOI：——

  日期：——
• A novel macroreticular-type fluorous polystyrene resin and its application to the synthesis of a 3-amino-β-carboline derivative with N-methyl-N-nitrosourea conjugation via fluorous solid-phase reaction: a comparative study of fluorous solid-, solid-, and liquid-phase reactions
  作者：Keiko Suzuki、Munenori Kumagai、Masamichi Utsunomiya、Norio Sakai、Takeo Konakahara

  DOI：10.1016/j.tet.2015.05.072

  日期：2015.7

  A novel fluorous polystyrene (FPS) MR-resin was applied to a fluorous solid-phase (FSP) reaction. The MR-FPS resin actually was developed previously and possessed excellent chemical resistance to acids and alkalis, and a fluorous-tagged compound was homogeneously and loosely immobilized on the resin. The synthesis of an antitumor drug, an N-methyl-N-nirosourea conjugated 3-amino-beta-carboline derivative, was accomplished with a high yield by using this new fluorous reaction system. Using only filtration, the fluorous 3-amino-beta-carboline derivatives immobilized on the MR-FPS resin were easily recovered from the reaction mixtures. As an extention of this approach, a diversity synthesis of 3-amino-9-benzyl-beta-carboline derivatives was applied to the FSP method giving high yields. Finally, the FSP synthesis was compared with the corresponding conventional solid- and liquid-phase methods of synthesis. The FSP reaction was superior in terms of the reactivity of the substrate and the ease of product separation. (C) 2015 Elsevier Ltd. All rights reserved.