1-(2-氯乙基)-3-(2,6-二甲基苯基)脲 | 13908-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2-氯乙基)-3-(2,6-二甲基苯基)脲
• 英文名称: N-(2-chloro-ethyl)-N'-(2,6-dimethyl-phenyl)-urea
• 英文别名: N-(2-Chlor-aethyl)-N'-(2,6-dimethyl-phenyl)-harnstoff；Urea, 1-(2-chloroethyl)-3-(2,6-xylyl)-；1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea
• CAS: 13908-40-2
• 化学式: C₁₁H₁₅ClN₂O
• mdl: MFCD01676556
• 分子量: 226.706
• InChiKey: QURAGLSSZNXFCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  1-(2-氯乙基)-3-(2,6-二甲基苯基)脲 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 4.5h， 生成 1-{2-[1-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-4-yl]-ethyl}-3-(2,6-dimethyl-phenyl)-imidazolidin-2-one
  参考文献：
  名称：

  New Substituted 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidin-4-yl Derivatives with α₂-Adrenoceptor Antagonist Activity

  摘要：

  The emergence of a novel theory concerning the role of noradrenaline in the progression and the treatment of neurodegenerative diseases such as Parkinson's and Alzheimer's diseases has provided a new impetus toward the discovery of novel compounds acting at alpha(2)-adrenoceptors. A series of substituted 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl) piperidin-4-yl derivatives bearing an amide, urea, or imidazolidinone moiety was studied. Some members of this series of compounds proved to be potent alpha(2)-adrenoceptor antagonists with good selectivity versus alpha(1)-adrenergic and D(2)-dopamine receptors. Particular emphasis is given to compound 33g which displays potent alpha(2)-adrenoceptor binding affinity in vitro and central effects in vivo following oral administration.

  DOI：

  10.1021/jm991121g
• 作为产物：
  描述：

  氯乙基异氰酸酯 、 2,6-二甲基苯胺 以67%的产率得到1-(2-氯乙基)-3-(2,6-二甲基苯基)脲
  参考文献：
  名称：

  抗有丝分裂抗肿瘤剂：N-芳基-N'-（2-氯乙基）脲作为新型选择性烷基化剂的合成，构效关系和生物学表征。

  摘要：

  合成了一系列的N-芳基-N'-（2-氯乙基）脲（CEU）及其衍生物，并评估了其对多种肿瘤细胞系的抗增殖活性。系统结构-活性关系（SAR）研究表明：（i）苯环或芴基/茚满基4位上的支链烷基链或卤素，（ii）外环脲官能团，和（iii） ）需要N'-2-氯乙基部分以确保明显的细胞毒性。诸如免疫荧光显微镜等生物学实验证实，这些有前途的化合物通过β-微管蛋白的选择性烷基化诱导微管解聚，从而改变了细胞骨架。随后的评估表明，有效的CEU是弱烷基化剂，是非DNA破坏剂，并且不与谷胱甘肽或谷胱甘肽还原酶的硫醇功能相互作用。因此，CEU是新型抗有丝分裂剂的一部分。最后，在评估的一系列CEU中，选择了化合物12、15、16和27用于进一步的体内试验。

  DOI：

  10.1021/jm0010264

文献信息

• Antimitotic Antitumor Agents: Synthesis, Structure−Activity Relationships, and Biological Characterization of <i>N</i>-Aryl-<i>N</i>‘-(2-chloroethyl)ureas as New Selective Alkylating Agents
  作者：Emmanuelle Mounetou、Jean Legault、Jacques Lacroix、René C-Gaudreault

  DOI：10.1021/jm0010264

  日期：2001.3.1

  series of N-aryl-N'-(2-chloroethyl)ureas (CEUs) and derivatives were synthesized and evaluated for antiproliferative activity against a wide panel of tumor cell lines. Systematic structure--activity relationship (SAR) studies indicated that: (i) a branched alkyl chain or a halogen at the 4-position of the phenyl ring or a fluorenyl/indanyl group, (ii) an exocyclic urea function, and (iii) a N'-2-chloroethyl

  合成了一系列的N-芳基-N'-（2-氯乙基）脲（CEU）及其衍生物，并评估了其对多种肿瘤细胞系的抗增殖活性。系统结构-活性关系（SAR）研究表明：（i）苯环或芴基/茚满基4位上的支链烷基链或卤素，（ii）外环脲官能团，和（iii） ）需要N'-2-氯乙基部分以确保明显的细胞毒性。诸如免疫荧光显微镜等生物学实验证实，这些有前途的化合物通过β-微管蛋白的选择性烷基化诱导微管解聚，从而改变了细胞骨架。随后的评估表明，有效的CEU是弱烷基化剂，是非DNA破坏剂，并且不与谷胱甘肽或谷胱甘肽还原酶的硫醇功能相互作用。因此，CEU是新型抗有丝分裂剂的一部分。最后，在评估的一系列CEU中，选择了化合物12、15、16和27用于进一步的体内试验。
• Najer et al., Bulletin de la Societe Chimique de France, 1959, p. 352,355
  作者：Najer et al.

  DOI：——

  日期：——
• Synthesis and cytotoxic activity of new alkyl[3-(2-chloroethyl)ureido]benzene derivatives
  作者：P Béchard、J Lacroix、P Poyet、R C-Gaudreault

  DOI：10.1016/0223-5234(94)90196-1

  日期：1994.1

  Several alkyl[3-(2-chloroethyl)ureido] (CEU) benzene derivatives were prepared as potential anticancer agents. These new compounds were readily prepared in good yields by addition of anilines to 2-chloroethylisocyanate. Their cytotoxic activity was evaluated on human breast cancer (MDA-MB-231), human colon adenocarcinoma (LoVo) and mouse lymphocytic leukemia (P388D(1),) tumor cell lines. Several new CEUs were significantly more cytotoxic than the nitrogen mustard chlorambucil. The biological activity of these aromatic urea derivatives seems to be related to the nature and position of the alkyl substituents on the aromatic ring. Substitution by branched alkyl groups on position 4 of the aromatic ring led to cytotoxic molecules which are up to 5 times more potent than the standard chlorambucil.
• The Synthesis of Potential Anticancer Agents. XXXVI. N-Nitrosoureas.¹ II. Haloalkyl Derivatives
  作者：Thomas P. Johnston、George S. McCaleb、Pamela S. Opliger、John A. Montgomery

  DOI：10.1021/jm00324a026

  日期：1966.11
• New Substituted 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidin-4-yl Derivatives with α₂-Adrenoceptor Antagonist Activity
  作者：Patrice Mayer、Pascale Brunel、Céline Chaplain、Christel Piedecoq、Francis Calmel、Philippe Schambel、Philippe Chopin、Thierry Wurch、Petrus J. Pauwels、Marc Marien、Jean-Louis Vidaluc、Thierry Imbert

  DOI：10.1021/jm991121g

  日期：2000.10.1

  The emergence of a novel theory concerning the role of noradrenaline in the progression and the treatment of neurodegenerative diseases such as Parkinson's and Alzheimer's diseases has provided a new impetus toward the discovery of novel compounds acting at alpha(2)-adrenoceptors. A series of substituted 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl) piperidin-4-yl derivatives bearing an amide, urea, or imidazolidinone moiety was studied. Some members of this series of compounds proved to be potent alpha(2)-adrenoceptor antagonists with good selectivity versus alpha(1)-adrenergic and D(2)-dopamine receptors. Particular emphasis is given to compound 33g which displays potent alpha(2)-adrenoceptor binding affinity in vitro and central effects in vivo following oral administration.