(2,5-二氧代吡咯烷-1-基)N-甲基-N-亚硝基氨基甲酸酯 | 80354-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2,5-二氧代吡咯烷-1-基)N-甲基-N-亚硝基氨基甲酸酯
• 英文名称: N-methyl-N-nitrosocarbamic acid N'-hydroxysuccinimide ester
• 英文别名: N-methyl N-nitroso-carbamate de succinimidyle；succinimidyl N-nitroso-N-methylcarbamate；Carbamic acid, methylnitroso-2,5-dioxo-1-pyrrolidinyl ester；(2,5-dioxopyrrolidin-1-yl) N-methyl-N-nitrosocarbamate
• CAS: 80354-48-9
• 化学式: C₆H₇N₃O₅
• 分子量: 201.139
• InChiKey: HOLCTFBQQQICEX-UHFFFAOYSA-N

物化性质

• 沸点：
  286.1±23.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-氨基-TEMPO 、 (2,5-二氧代吡咯烷-1-基)N-甲基-N-亚硝基氨基甲酸酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以72%的产率得到1-methyl-3-(2'.2'.6'.6'-tetramethyl-piperidin-4'-yl-1'-oxyl)-1-nitrosourea
  参考文献：
  名称：

  Synthesis of nitroxide derivatives of alkylnitrosourea

  摘要：

  Nitroxide derivatives of alkylnitrosoureas were prepared by the reaction of amino nitroxide radicals with activated N-alkyl-N-nitrosocarbamates or by the selective reduction of oxoammonium derivatives of alkylnitrosoureas.

  DOI：

  10.1007/bf00698442
• 作为产物：
  描述：

  N-琥珀酰亚胺基 N-甲基氨基甲酸酯 在 吡啶 、 亚硝酰氯 作用下， 反应 0.5h， 以98%的产率得到(2,5-二氧代吡咯烷-1-基)N-甲基-N-亚硝基氨基甲酸酯
  参考文献：
  名称：

  Activated N-nitrosocarbamates for regioselective synthesis of N-nitrosoureas

  摘要：

  A practical and convenient method for synthesizing antitumor compounds, N-alkyl-N-nitrosoureas, regioselectively nitrosated on the nitrogen atom bearing the alkyl group is proposed. N-Alkyl-N-nitrosocarbamates are interesting intermediates in these syntheses and yield, by reaction with amino compounds, the regioselectively nitrosated N-alkyl-N-nitrosoureas. As an interesting example, N,N'-bis[(2-chloroethyl)nitrosocarbamoyl]cystamine, a new attractive oncostatic derivative, has been prepared. The cytotoxic activity of these various compounds were tested on L1210 leukemia.

  DOI：

  10.1021/jm00344a017

文献信息

• 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
• 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
  作者：Ryota Mori、Asako Kato、Kousuke Komenoi、Haruaki Kurasaki、Touru Iijima、Masashi Kawagoshi、Y.B. Kiran、Sho Takeda、Norio Sakai、Takeo Konakahara

  DOI：10.1016/j.ejmech.2014.05.032

  日期：2014.7

  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.
• OIRY, J.;MARTINEZ, J.;IMBACH, J. -L.;WINTERNITZ, F., EUR. J. MED. CHEM.-CHIM. THER., 1981, 16, N 6, 539-543
  作者：OIRY, J.、MARTINEZ, J.、IMBACH, J. -L.、WINTERNITZ, F.

  DOI：——

  日期：——
• KONAKAHARA, TAKEO;WURDEMAN, RICHARD L.;GOLD, BARRY, BIOCHEMISTRY, 27,(1988) N 23, C. 8606-8613
  作者：KONAKAHARA, TAKEO、WURDEMAN, RICHARD L.、GOLD, BARRY

  DOI：——

  日期：——
• Activated N-nitrosocarbamates for regioselective synthesis of N-nitrosoureas
  作者：Jean Martinez、Joel Oiry、Jean Louis Imbach、Francois Winternitz

  DOI：10.1021/jm00344a017

  日期：1982.2

  A practical and convenient method for synthesizing antitumor compounds, N-alkyl-N-nitrosoureas, regioselectively nitrosated on the nitrogen atom bearing the alkyl group is proposed. N-Alkyl-N-nitrosocarbamates are interesting intermediates in these syntheses and yield, by reaction with amino compounds, the regioselectively nitrosated N-alkyl-N-nitrosoureas. As an interesting example, N,N'-bis[(2-chloroethyl)nitrosocarbamoyl]cystamine, a new attractive oncostatic derivative, has been prepared. The cytotoxic activity of these various compounds were tested on L1210 leukemia.