(2-chloroethyl)nitrosocarbamic acid 2,4,5-trichlorophenyl ester | 80354-51-4

• 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: (2-chloroethyl)nitrosocarbamic acid 2,4,5-trichlorophenyl ester
• 英文别名: N-(chloro-2 ethyl)N-nitrosocarbamate de trichloro-2,4,5 phenyle；2,4,5-trichlorophenyl N-(2-trichloroethyl)-N-nitrosocarbamate；2,43,5-trichlorophenyl N-(2-chloroethyl)-N-nitrosocarbamate；2,4,5-trichlorophenyl N-(2-chloroethyl)-N-nitrosocarbamate；2,4,5-trichlorophenyl-N-(2-chloroethyl)-N-nitrosocarbamate；2,4,5-trichlorophenyl-N(2-chloroethyl)-N-nitrosocarbamate；2,4,5-Trichlorophenyl (2-chloroethyl)nitrosocarbamate；(2,4,5-trichlorophenyl) N-(2-chloroethyl)-N-nitrosocarbamate
• CAS: 80354-51-4
• 化学式: C₉H₆Cl₄N₂O₃
• 分子量: 331.97
• InChiKey: WJSDAFAYDXCQLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-chloroethyl)nitrosocarbamic acid 2,4,5-trichlorophenyl ester 、 环己胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以80%的产率得到洛莫司汀
  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
• 作为产物：
  描述：

  2,4,5-三氯苯酚 在 吡啶 、 亚硝酰氯 作用下， 反应 25.0h， 生成 (2-chloroethyl)nitrosocarbamic acid 2,4,5-trichlorophenyl ester
  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

• Syntheses and evaluation as antifolates of MTX analogs derived from 2,.omega.-diaminoalkanoic acids
  作者：J. R. Piper、G. S. McCaleb、J. A. Montgomery、F. A. Schmid、F. M. Sirotnak

  DOI：10.1021/jm00146a008

  日期：1985.8

  (MTX) analogues 27a-c bearing 2, omega-diaminoalkanoic acids (ornithine and its two lower homologues) in place of glutamic acid were synthesized by routes proceeding through N2-[4-(methylamino)benzoyl]-N omega-[(1,1-dimethylethoxy)carbonyl]-2, omega-diaminoalkanoic acid ethyl esters and N2-[4-(methylamino)benzoyl]-N5-[(1,1-dimethylethoxy)carbonyl]-2, 5-diaminopentanoic acid followed by alkylation with

  通过N2- [4-（甲基氨基）苯甲酰基]-N-ω-[[（+] []]合成带有2的ω-二氨基链烷酸（鸟氨酸及其两个较低的同系物）的甲氨蝶呤（MTX）类似物27a-c 1,1-二甲基乙氧基）羰基] -2，ω-二氨基链烷酸乙酯和N2- [4-（甲基氨基）苯甲酰基] -N5-[（1,1-二甲基乙氧基）羰基] -2，5-二氨基戊酸用6-（溴甲基）-2，4-吡啶二胺氢溴酸盐进行烷基化。27型类似物或适当前体的末端氨基上的反应导致其他MTX衍生物的侧链终止于脲基，甲基脲基，N-甲基-N-亚硝基脲基，N-（2-氯乙基）-N-亚硝基脲基和4-氯苯甲酰胺基。还制备了通过将异氰酸根合乙酸乙酯和2-异氰酸根合戊二酸二乙酯加入27a，b的乙基酯中而形成的不对称的二取代脲基。在这些脲基加合物（分别为32a，b和33a，b）中，只有33a成功水解为相应的纯酸，在这种情况下为三羧酸34（MTX代谢物MTX-γ-Glu的假
• Pharmaceutical formulations for parenteral use
  申请人：University of Florida

  公开号：US04983586A1

  公开（公告）日：1991-01-08

  Aqueous parenteral solutions of drugs which are insoluble or only sparingly soluble in water and/or which are unstable in water, combined with hydroxypropyl-.beta.-cyclodextrin, provide a means for alleviating problems associated with drug precipitation at the injection site and/or in the lungs or other organs following parenteral administration.

  将不溶或在水中仅微溶或在水中不稳定的药物与羟丙基-β-环糊精结合，提供了一种缓解与药物在注射部位沉淀以及/或在注射后在肺部或其他器官中沉淀相关问题的方法。
• Redox systems for brain-targeted drug delivery
  申请人：University of Florida

  公开号：US05017566A1

  公开（公告）日：1991-05-21

  Inclusion complexes of hydroxypropyl, hydroxyethyl, glucosyl, maltosyl and maltotriosyl derivatives of .beta.- and .gamma.-cyclodextrin with the reduced, biooxidizable, blood-brain barrier penetrating, lipoidal forms of dihydropyridine.revreaction.pyridinium salt redox systems for brain-targeted drug delivery provide a means for stabilizing the redox systems, particularly against oxidation. The redox inclusion complexes also provide a means for decreasing initial drug concentrations in the lungs after administration of the systems, leading to decreased toxicity. In selected instances, complexation results in substantially improved water solubility of the redox systems as well.

  羟丙基、羟乙基、葡萄糖基、麦芽糖基和麦芽三糖基衍生物与β-和γ-环糊精的包含复合物，与还原的、可生物氧化的、能穿透血脑屏障的、脂质形式的二氢吡啶.反应.pyridinium盐氧化还原系统形成脑靶向药物输送的一种手段，用于稳定氧化还原系统，特别是对抗氧化作用。氧化还原包含复合物还提供了一种减少系统给药后肺部初始药物浓度的手段，从而降低毒性。在某些情况下，复合作用显著提高了氧化还原系统的水溶性。
• Nitrosoureido nucleosides as potential inhibitors of nucleotide biosynthesis
  作者：Robert D. Elliott、H. Jeanette Thomas、Sue C. Shaddix、Doris J. Adamson、R. Wallace Brockman、James M. Riordan、John A. Montgomery

  DOI：10.1021/jm00396a039

  日期：1988.1

  Several nitrosoureido nucleosides (3a, 3b, 5a, 7a, 7c, and 10a) designed as inhibitors of enzymes that metabolize pyrimidine nucleotides have been prepared and their chemical and biological properties studied. The methylnitrosoureas 3a and 3b were not significantly cytotoxic to H.Ep.-2 and L1210 cells in vitro but showed moderate activity in the P388 mouse leukemia screen (79% ILS for 3a and 56% ILS

  已制备了几种设计为代谢嘧啶核苷酸的酶抑制剂的亚硝基脲核苷（3a，3b，5a，7a，7c和10a），并对其化学和生物学特性进行了研究。甲基亚硝基脲3a和3b在体外对H.Ep.-2和L1210细胞无明显细胞毒性，但在P388小鼠白血病筛查中显示中等活性（3a为79％ILS，3b为56％ILS）。（氯乙基）亚硝基脲7a和7c抑制L1210细胞增殖，对H.Ep.-2细胞具有细胞毒性，并在体内对P388表现出良好的活性（135％ILS具有一个30天存活率的7a和191％ILS具有两个7天的30天幸存者）。L1210细胞过夜暴露于7a和7c导致细胞肿大并伴有细胞溶解。扩大细胞中的高分子合成，尤其是RNA和蛋白质合成，相对于未处理的对照细胞，其显着增加。确定每种亚硝基脲在pH 7缓冲液中的半衰期，并将其与生物学活性进行比较。
• Synthesis and antitumor evaluation of some nitrosourea and nitrogen mustard amino acid derivatives
  作者：Marc Rodriguez、Jean Louis Imbach、Jean Martinez

  DOI：10.1021/jm00375a025

  日期：1984.9

  series of (2-chloroethyl)nitrosourea and nitrogen mustard amino acid derivatives have been synthesized for antitumor evaluation. Reaction of an appropriate N-protected amino acid with 2-chloroethylamine followed by removal of the N-protecting group and condensation with an active (2-chloroethyl)nitrosocarbamate yielded N-[(2-chloroethyl)nitrosocarbamoyl]amino acid (2-chloroethyl)amides. Antitumor evaluation

  已经合成了一系列的（2-氯乙基）亚硝基脲和氮芥子酸氨基酸衍生物用于抗肿瘤评估。适当的N-保护的氨基酸与2-氯乙胺反应，然后除去N-保护基，并与活性（2-氯乙基）亚硝基氨基甲酸酯缩合，得到N-[（（2-氯乙基）亚硝基氨基甲酰基]氨基酸（2-氯乙基）。 ）酰胺。在小鼠体内针对白血病L1210进行了抗肿瘤评估。这些衍生物表现出非常有趣的活性，特别是肌氨酸和γ-氨基丁酸衍生物。