N₁-(2-chloroethyl)-N₁-nitrosocarbamoyl azide | 60784-40-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: N₁-(2-chloroethyl)-N₁-nitrosocarbamoyl azide
• 英文别名: N-(2-Chloroethyl)-N-nitrosocarbamoyl azide；N-nitroso-N-(2-chloroethyl)carbamoyl azide；2-chloroethylnitrosocarbamoyl azide；2-chloroethylnitrosocarbamoylazide；CNC-azide；N-(2-chloroethyl)-N-nitrosocarbamoylazide；1-(2-chloroethyl)-3-diazo-1-nitrosourea
• CAS: 60784-40-9
• 化学式: C₃H₄ClN₅O₂
• 分子量: 177.55
• InChiKey: VQVHVJMFEBRIPO-UHFFFAOYSA-N

物化性质

• 沸点：
  71.4°C (estimate)
• 密度：
  1.6700 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N₁-(2-chloroethyl)-N₁-nitrosocarbamoyl azide 以 四氯化碳 为溶剂， 生成 N-nitrosocarbamoyl azide
  参考文献：
  名称：

  Process for the preparation of unsymmetrically 1,3-disubstituted nitroso

  摘要：

  该发明涉及从相应的N-取代烷基-N-亚硝基氨基甲酰氨基甲酸酰胺制备不对称1,3-二取代亚硝基脲的方法，该方法是将N-取代烷基-N-亚硝基氨基甲酰氨基甲酸酰胺与胺、二胺、氨基醇、氨基酸或氨基酸衍生物发生反应。N-亚硝基氨基甲酰氨基甲酸酰胺是通过在低温下将相应的烷基氨基甲酰氨基甲酸酰胺与四氧化二氮反应而获得的。烷基氨基甲酰氨基甲酸酰胺是通过将相应的异氰酸酯与一种碱金属叠氮化合物反应而获得的。该发明还涉及由此获得的新型亚硝基脲，新型N-取代烷基-N-亚硝基氨基甲酰氨基甲酸酰胺，以及含有该新型亚硝基脲作为活性成分的新型治疗组合物。

  公开号：

  US04150146A1
• 作为产物：
  描述：

  2-Chloraethylcarbamoylazid 在 吡啶 、 亚硝酰氯 作用下， 以 溶剂黄146 为溶剂， 生成 N₁-(2-chloroethyl)-N₁-nitrosocarbamoyl azide
  参考文献：
  名称：

  具有抗肿瘤活性的甾体亚硝基脲的合成。

  摘要：

  合成了四个具有可能与雌激素受体特异性结合的结构的甾体亚硝基脲。观察到对DMBA诱导的可移植大鼠乳腺肿瘤13762的生长具有抑制作用。

  DOI：

  10.1021/jm00188a015

文献信息

• Synthesis and Characterization of Steroid-linked N-(2-Chloroethyl)nitrosoureas
  作者：Gerhard Eisenbrand、Jürgen Fischer、Karl Mühlbauer、Georg Schied、Joachim Schreiber、Weici Tang、Otto Zelezny

  DOI：10.1002/ardp.19893221206

  日期：——

  Syntheses of steroid‐linked N‐[N′‐(2‐chloroethyl)‐N′‐nitrosocarbamoyl]‐(CNC‐) amino acid esters and ‐amides with potential antineoplastic activity are described. The esters are prepared by reaction of CNC‐amino acids with steroids using N,N′‐carbonyldiimidazole and N,N′‐dicyclohexylcarbodiimide. The corresponding amides are prepared by reaction of 1‐(CNC‐amino acyloxy)‐pyrrolidine‐2, 5‐diones with

  描述了具有潜在抗肿瘤活性的类固醇连接的 N-[N'-(2-氯乙基)-N'-亚硝基氨基甲酰基]-(CNC-)氨基酸酯和-酰胺的合成。这些酯是通过 CNC - 氨基酸与类固醇使用 N, N' - 羰基二咪唑和 N, N' - 二环己基碳二亚胺反应制备的。相应的酰胺是通过 1-(CNC-氨基酰氧基)-吡咯烷-2, 5-二酮与 17β-氨基-3-羟基-1,3,5(10)-雌三烯或 17β-O-反应制备的 [4] - (6-氨基己基氨基)-1, 4-二氧代-丁基]-雌二醇。雌二醇 - 17β - 半琥珀酸酯与 N- (2 - 羟乙基) -N ' - (2 - 氯乙基) -N' - 亚硝基脲 (HECNU) 酯化。给出了光谱特征和对类固醇受体的相对结合亲和力。
• Synthesis of Potentially Antineoplastic Derivatives of N-[N-(2-Chloroethyl)-N-nitrosocarbamoyl]amino Acids
  作者：Wei-Ci Tang、Gerhard Eisenbrand

  DOI：10.1002/ardp.19813141104

  日期：——

  The synthesis of N‐[N‐(2‐chloroethyl)‐N‐nitrosocarbamoyl]amino acids and their anilides, congeners of N‐(2‐chloroethyl)‐N‐nitrosoureas, as potential antineoplastic substances is reported. N‐[N‐(2‐chloroethyl)‐N‐nitrosocarbamoyl]amino acids are prepared by reaction of amino acids with N‐(2‐chloroethyl)‐N‐nitrosocarbamoyl azide. Corresponding anilides and toluidides are obtained by condensation of the

  据报道，合成 N-[N-(2-氯乙基)-N-亚硝基氨基甲酰基]氨基酸及其苯胺，N-(2-氯乙基)-N-亚硝基脲的同系物，作为潜在的抗肿瘤物质。N-[N-(2-氯乙基)-N-亚硝基氨基甲酰基]氨基酸通过氨基酸与N-(2-氯乙基)-N-亚硝基氨基甲酰基叠氮化物反应制备。相应的苯胺和甲苯胺是通过初级反应产物与苯胺和甲苯胺使用二环己基碳二亚胺 (DCC) 缩合获得的。
• N-Substituted alkyl-N-nitrosocarbamoyl azides
  申请人：——

  公开号：US04228086A1

  公开（公告）日：1980-10-14

  The invention relates to the preparation of novel N-substituted alkyl-N-nitrosocarbamoyl azides and to the compounds obtained thereby. The novel N-substituted alkyl-N-nitrosocarbamoyl azides can be reacted with amines, diamines, aminoalcohols, aminoacids or aminoacid derivatives to prepare unsymmetrically 1,3-disubstituted nitrosoureas which show therapeutical activity.

  本发明涉及制备新型N-取代烷基-N-亚硝基氨基甲酰叠氮化物以及由此得到的化合物。新型N-取代烷基-N-亚硝基氨基甲酰叠氮化物可与胺、二胺、氨基醇、氨基酸或氨基酸衍生物反应，制备出具有治疗活性的不对称1,3-二取代亚硝基脲。
• Novel nitrosourea derivatives and process for their production
  申请人：Kowa Co., Ltd.

  公开号：US04335247A1

  公开（公告）日：1982-06-15

  The specification describes a nitrosourea derivative having the general formula: Cl--(CH.sub.2).sub.2 --N(NO)CO--NHR, wherein --NHR represents a 2-(1,3,4-thiadiazolyl)amino group, an amino residue of a neutral .alpha.-amino acid, or an amino residue of a neutral .alpha.-amino acid whose carboxyl group is amidated with 2-(1,3,4-thiadiazolyl)amine, or a pharmaceutically acceptable acid addition salt thereof. The above nitrosourea derivative and its salt are useful as antitumor drugs. The above nitrosourea derivative may be prepared either by nitrosating a urea derivative of the general formula: Cl--(CH.sub.2).sub.2 NHCONHR or by reacting N-(2-chloroethyl)-N-nitrosocarbamic acid or a reactive derivative thereof with an amino compound of the general formula: R--NH.sub.2.

  该规格说明书描述了一种亚硝基脲衍生物，其一般式为：Cl--(CH.sub.2).sub.2 --N(NO)CO--NHR，其中--NHR表示2-(1,3,4-噻二唑基)氨基基团，中性α-氨基酸的氨基残基，或其羧基被2-(1,3,4-噻二唑基)胺酰化的中性α-氨基酸的氨基残基，或其药物可接受的酸盐。上述亚硝基脲衍生物及其盐可用作抗肿瘤药物。上述亚硝基脲衍生物可通过亚硝化一般式为Cl--(CH.sub.2).sub.2 NHCONHR的脲衍生物或通过反应N-(2-氯乙基)-N-亚硝基氨基甲酸或其活性衍生物与一般式为R--NH.sub.2的氨基化合物制备。
• Analogs of 1-(2-chloroethyl)-1-nitroso-3-(cycloheyl)-urea substituted by
  申请人：Stiftung Deutsches Krebsforschungszentrum

  公开号：US04377687A1

  公开（公告）日：1983-03-22

  This invention relates to compounds having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, acyl, trifluoroacetyl, straight chained and branched alkyl groups with up to 6 carbon atoms, such alkyl groups with up to 3 substituents selected from the group consisting of OH, OSO.sub.2 CH.sub.3, COOH, COOR, CONH.sub.2 and Hal, where R is an alkyl group with up to 6 carbon atoms, and R.sub.1 and R.sub.2 together form a heterocyclic ring containing 4 to 6 carbon atoms and optionally further heteroatoms and such rings with up to 3 substituents selected from the group consisting of lower alkyl, OH, COOH, COOR, CONH.sub.2, where R has the above meaning, the chloroethyl nitrosoureido group and Hal, and Hal is selected from the group consisting of chlorine and fluorine, which heterocyclic ring is not the para-methyl piperazine group, said nitroso ureas having a tumor inhibiting effect. This invention also related to a method of inhibiting transplanted tumors which comprises treating a tumor-afflicted subject with one of the foregoing 1,3 - disubstituted nitroso ureas. It also involves a method of preparing such new compounds by reacting N-(2-halogenethyl)-N-nitrosocarbamoylazide with hydrazine or a monocyclic N-amino heterocyclic or their derivatives.

  本发明涉及具有以下结构式的化合物：##STR1## 其中R.sub.1和R.sub.2选自羟基、酰基、三氟乙酰基、直链和支链烷基，其碳原子数最多为6，这种烷基还可以有最多3个取代基，所述取代基选自羟基、OSO.sub.2 CH.sub.3、COOH、COOR、CONH.sub.2和Hal，其中R是碳原子数最多为6的烷基，而R.sub.1和R.sub.2一起形成含有4到6个碳原子的杂环环，可选地还含有其他杂原子，这种环还可以有最多3个取代基，所述取代基选自较低的烷基、羟基、COOH、COOR、CONH.sub.2，其中R具有上述含义，氯乙基亚硝基脲基团和Hal，而Hal选自氯和氟，所述杂环环不是对甲苯基哌嗪基团，这些亚硝基脲具有抑制肿瘤的作用。本发明还涉及一种抑制移植肿瘤的方法，该方法包括用上述1,3-二取代亚硝基脲之一治疗患有肿瘤的受试者。它还涉及一种制备这种新化合物的方法，该方法通过将N-(2-卤乙基)-N-亚硝基甲酰肼与肼或单环N-氨基杂环或其衍生物反应。