o-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate | 68396-84-9

• 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: o-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate
• 英文别名: o-nitrophenyl N-(2-chloroethyl)N-nitrosocarbamate；(2-nitrophenyl) N-(2-chloroethyl)-N-nitrosocarbamate
• CAS: 68396-84-9
• 化学式: C₉H₈ClN₃O₅
• 分子量: 273.633
• InChiKey: BKMSOLUBIRSYFY-UHFFFAOYSA-N

物化性质

• 沸点：
  388.2±52.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  105
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2-氨基-3-苯基丙酸乙酯 、 o-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate 以 甲醇 为溶剂， 反应 2.5h， 以37%的产率得到L-Phenylalanine, N-[[(2-chloroethyl)nitrosoamino]carbonyl]-, ethyl ester
  参考文献：
  名称：

  N-[N'-(2-氯乙基)-N'-亚硝基氨基甲酰基]氨基酸的潜在抗肿瘤酰胺和酯的合成，II

  摘要：

  报道了 N-[N'-(2-氯乙基)-N'-亚硝基氨基甲酰基]氨基酸酰胺和酯作为潜在抗肿瘤物质的合成。N-[N'-(2-氯乙基)-N'-亚硝基氨基甲酰基]氨基酸（甘氨酸衍生物除外）是通过异氰酸2-氯乙基酯与氨基酸的钠盐在异质介质中反应制备的，然后在酸性条件下用亚硝酸钠亚硝化。使用 1,1-羰基二咪唑与胺或醇缩合生成酰胺或酯。

  DOI：

  10.1002/ardp.19843170602

文献信息

• Novel nitrosourea compounds, method for preparing same, and
  申请人：Gogo Kimura

  公开号：US04593090A1

  公开（公告）日：1986-06-03

  The invention provides pharmaceutically active agents of the structural formula ##STR1## wherein n is 1 or 2; X is Z if n is 1 and X is CH.sub.2 Y, CH.sub.2 OH or OH if n is 2; Y is OH if n is 1 and, if n is 2, one of the radicals Y is Z and all other radicals Y are OH; ##STR2## R.sub.11 is a C.sub.3 -C.sub.10 linear or branched alkyl; a C.sub.3 -C.sub.5 linear or branched alkenyl or alkynyl; a C.sub.2 -C.sub.4 linear or branched alkyl substituted by C.sub.1 -C.sub.4 alkoxy, methoxymethoxy, methoxyethoxy, or hydroxyethoxy radicals; C.sub.3-8 cycloalkyl; C.sub.1-3 alkyl substituted with C.sub.3-8 cycloalkyl groups; benzyl; benzyl having 1 to 3 substituents selected from the group consisting of C.sub.1-4 alkyl, C.sub.1-4 alkoxy and cyclopropyl; phenethyl; tetrahydrofurfuryl, furfuryl; morpholinoethyl, morpholinopropyl; piperidinoethyl; and R.sub.12 is a C.sub.1 -C.sub.10 linear or branched alkyl; C.sub.3 -C.sub.5 linear or branched alkenyl or alkynyl; C.sub.1-6 hydroxyalkyl; C.sub.2-4 linear or branched alkyl substituted by C.sub.1-4 alkoxy or C.sub.1-4 hydroxyalkoxy; C.sub.3-8 cycloalkyl; C.sub.1-3 alkyl substituted by a C.sub.3-8 cycloalkyl radical; benzyl, chlorobenzyl; benzyl having 1 to 3 substituents selected from the group consisting of C.sub.1-4 alkyl and C.sub.1-4 alkoxy; tetrahydrofurfuryl; furfuryl; morpholino; morpholinoethyl; morpholinopropyl; thiophen-2-yl-methyl; pyridylethyl; and piperidinoethyl.

  本发明提供具有结构式##STR1##的药理活性剂，其中n为1或2；当n为1时，X为Z，当n为2时，X为CH.sub.2 Y、CH.sub.2 OH或OH；当n为1时，Y为OH，当n为2时，其中一个Y基团为Z，其余所有Y基团均为OH；##STR2##R.sub.11为C.sub.3 -C.sub.10直链或支链烷基；C.sub.3 -C.sub.5直链或支链烯基或炔基；C.sub.2 -C.sub.4直链或支链烷基，被C.sub.1 -C.sub.4烷氧基、甲氧基甲氧基、甲氧基乙氧基或羟基乙氧基取代；C.sub.3-8环烷基；被C.sub.3-8环烷基取代的C.sub.1-3烷基；苄基；具有1至3个选自C.sub.1-4烷基、C.sub.1-4烷氧基和环丙基的取代基的苄基；苯乙基；四氢糠基，糠基；吗啉乙基，吗啉丙基；哌啶乙基；以及R.sub.12为C.sub.1 -C.sub.10直链或支链烷基；C.sub.3 -C.sub.5直链或支链烯基或炔基；C.sub.1-6羟基烷基；被C.sub.1-4烷氧基或C.sub.1-4羟基烷氧基取代的C.sub.2-4直链或支链烷基；C.sub.3-8环烷基；被C.sub.3-8环烷基取代的C.sub.1-3烷基；苄基，氯苄基；具有1至3个选自C.sub.1-4烷基和C.sub.1-4烷氧基的取代基的苄基；四氢糠基；糠基；吗啉；吗啉乙基；吗啉丙基；噻吩-2-基甲基；吡啶乙基；和哌啶乙基。
• Process for producing glucopyranose-nitrosourea compounds and novel
  申请人：Tokyo Tanabe Company, Limited

  公开号：US04156777A1

  公开（公告）日：1979-05-29

  Glucopyranose-nitrosourea compounds having lower alkyl group and/or 2-chloroethyl group as substituent(s), are produced at high yield by reacting amino-glucopyranose compounds having lower alkoxy group and/or amino group(s) (or an acid-added amino group) as substituent(s), with o-nitro- or o-cyano-phenyl N-substituted-N-nitrosocarbamate compounds having lower alkyl group or 2-chloroethyl group as substituent. 1-(Lower alkyl or 2-chloroethyl)-3-(D-glucopyranos-6-yl)-1-nitrosourea compounds included within the scope of the nitrosourea compounds are novel. The nitrosourea compounds produced by this invention all show antitumor activity, among which the novel compounds exhibit excellent physical and pharmacological properties.

  葡萄糖吡喃糖基-硝基脲化合物具有较低的烷基基团和/或2-氯乙基基团作为取代基，在高产率下通过将具有较低烷氧基和/或氨基（或加酸氨基）作为取代基的氨基葡萄糖吡喃糖化合物与具有较低烷基基团或2-氯乙基基团作为取代基的o-硝基或o-氰基苯基N-取代-N-亚硝基氨基甲酸酯化合物反应而产生。包含在硝基脲化合物范围内的1-(较低烷基或2-氯乙基)-3-(D-葡萄糖吡喃糖基-6-基)-1-硝基脲化合物是新颖的。本发明产生的硝基脲化合物均显示抗肿瘤活性，其中新颖化合物展现出优异的物理和药理特性。
• Novel nitrosourea compound, method for preparing same, and pharmaceutical composition containing same
  申请人：Kimura, Goro

  公开号：EP0067019A1

  公开（公告）日：1982-12-15

  The invention provides pharmaceutically active agents of the structural formula wherein n is 1 or2; X is Z if n is 1 and X is CH2Y, CH20H or OH if n is 2; Y is OH if n is 1 and if n is 2, one of the radicals Y is Z and all other radicals Y are OH; R11 is a C3-C10 linear or branched alkyl; a C3-C5 linear or branched alkenyl or alkynyl; a C2-C4 linear or branched alkyl substituted by C1-C4 alkoxy, methoxymethoxy, methoxyethoxy, or hydroxyethoxy radicals; C3-8 cycloalkyl; C1-3 alkyl substituted with C3-8 cycloalkyl groups; benzyl; benzyl having 1 to 3 substituents selected from the group consisting of C1-4 alkyl, C1-4 alkoxy and cyclopropyl; phenethyl; tetrahydrofurfuryl, furfuryl; morpholinoethyl, morpholinopropyl; piperidinoethyl; and R12 is a C1-C10 linear or branched alkyl; C3-C5 linear or branched alkenyl or alkynyl; C1-6 hydroxyalkyl; C2-4 linear or branched alkyl substituted by C1-4 alkoxy or C1-4 hydroxyalkoxy; C3-8 cycloalkyl; C1-3 alkyl substituted by a C3-8 cycloalkyl radical; benzyl, chlorobenzyl; benzyl having 1 to 3 substituents selected from the group consisting of C1-4 alkyl and C1-4 alkoxy; tetrahydrofurfuryl; furfuryl; morpholino; morpholinoethyl; morpholinopropyl; thiophen-2-yl-methyl; pyridylethyl; and piperidinoethyl.

  本发明提供了结构式如下的药物活性剂 其中 n 为 1 或 2； 如果 n 为 1，X 为 Z，如果 n 为 2，X 为 CH2Y、CH20H 或 OH； 如果 n 为 1，则 Y 为 OH；如果 n 为 2，则其中一个基 Y 为 Z，所有其他基 Y 为 OH； R11 是 C3-C10 直链或支链烷基； C3-C5 直链或支链烯基或炔基 被 C1-C4 烷氧基、甲氧基甲氧基、甲氧基乙氧基或羟基乙氧基取代的 C2-C4 直链或支链烷基； C3-8 环烷基； 被 C3-8 环烷基取代的 C1-3 烷基； 苄基； 具有 1 至 3 个取代基的苄基，这些取代基可从 C1-4 烷基、C1-4 烷氧基和环丙基组成的组中选出； 苯乙基 四氢糠基、糠基； 吗啉基乙基、吗啉基丙基； 哌啶基乙基；以及 R12 是 C1-C10 直链或支链烷基； C3-C5 直链或支链烯基或炔基； C1-6 羟基烷基 被 C1-4 烷氧基或 C1-4 羟基烷氧基取代的 C2-4 直链或支链烷基； C3-8 环烷基 被 C3-8 环烷基取代的 C1-3 烷基； 苄基、氯苄基； 具有 1 至 3 个取代基的苄基，取代基可从 C1-4 烷基和 C1-4 烷氧基组成的组中选出； 四氢糠基； 呋喃基 吗啉基 吗啉乙基 吗啉丙基 甲基噻吩-2-基 吡啶乙基；以及 哌啶基乙基。
• Novel N-nitroso compounds, compositions containing such compounds and processes for their preparation
  申请人：AB LEO

  公开号：EP0106123A1

  公开（公告）日：1984-04-25

  The invention concerns novel N-nitroso compounds having the general formula: wherein A is lower alkyl or halolower alkyl; B is hydrogen; lower alkenyl; lower alkynyl; 3-6 C cycloalkyl; -RSO2NR3R4, or lower alkyl optionally monosubstituted with lower alkoxy, or 3-6 C cycloalkyl; R is straight or branched 2-5 C alkylene, optionally monosubstituted with SO2NR3R4 or CONR3R4, said alkylene always containing at least two carbon atoms, separating the nitrogen atom of the urea from any SO2NR1R2 or SO2NR3R4; R' and R2 are the same or different and selected from hydrogen, 5-6 C cycloalkyl, lower alkoxy, phenyl, benzyl, and straight or branched 1-6 C alkyl, optionally monosubstituted with hydroxy, lower alkoxy, SO2NR3R4, or CONR3R4; R' and R2 may also together form a 4-5 C alkylene; and R3 and R4 are the same or different and selected from hydrogen or lower alkyl, or R3 and R4 together are a 4-5 C alkylene, together with pharmaceutical compositions thereof; processes for their manufacture, and methods of treatment. The compounds of formula (1) have antitumor activity.

  本发明涉及具有通式的新型 N-亚硝基化合物： 其中 A 是低级烷基或低级卤代烷基； B 是氢；低级烯基；低级炔基；3-6 C 环烷基；-RSO2NR3R4，或任选与低级烷氧基单取代的低级烷基，或 3-6 C 环烷基； R 是直链或支链 2-5 C 亚烷基，可选择用 SO2NR3R4 或 CONR3R4 单取代，所述亚烷基总是含有至少两个碳原子，将脲的氮原子与任何 SO2NR1R2 或 SO2NR3R4 分隔开来； R' 和 R2 相同或不同，选自氢、5-6 C 环烷基、低级烷氧基、苯基、苄基和直链或支链 1-6 C 烷基，可选择与羟基、低级烷氧基、SO2NR3R4 或 CONR3R4 单取代；R' 和 R2 也可共同形成 4-5 C 亚烷基；以及 R3 和 R4 相同或不同，且选自氢或低级烷基，或 R3 和 R4 共同构成 4-5 C 亚烷基，以及其药物组合物、制造工艺和处理方法。 式（1）化合物具有抗肿瘤活性。
• KIMURA, AKIRA
  作者：KIMURA, AKIRA

  DOI：——

  日期：——