N-(3-chlorophenyl)-1,2-ethanediamine | 14088-83-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3-chlorophenyl)-1,2-ethanediamine
• 英文别名: N'-(3-chloro-phenyl)-ethane-1,2-diamine；N-(3-chlorophenyl)ethylenediamine；N-(m-chlorophenyl)ethylenediamine；N-(3-chlorophenyl)-1,2-diaminoethane；N'-(3-chlorophenyl)ethane-1,2-diamine
• CAS: 14088-83-6
• 化学式: C₈H₁₁ClN₂
• 分子量: 170.642
• InChiKey: XLYRTRQTLBKLLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-chlorophenyl)-1,2-ethanediamine 以 xylene 为溶剂， 反应 7.33h， 生成 1-(3-chloro-phenyl)-imidazolidine-2-thione
  参考文献：
  名称：

  咪唑啉和含有甲硫基作为可能抗菌剂的咪唑并[2,1-c] [1,2,4]三唑芳基衍生物的合成。

  摘要：

  N-芳基乙二胺与二硫化碳在二甲苯介质中的缩合反应合成了1-Arylimidazolidine-2-thiones（1a-g）。它们与甲基碘的进一步烷基化导致形成一些具有生物活性的1-芳基-2-甲硫基咪唑啉（2a-g）。通过将各自的7-（4）烷基化，获得7-（4-甲基苯基）-3-甲基硫基-5H-6,7-二氢咪唑并[2,1-c] [1,2,4]三唑（4b）。 -甲基苯基）-2,5,6,7-四氢咪唑并[2,1-c] [1,2,4]三唑-3（H）-硫酮（3b）与甲基碘。1-芳基-2-甲硫基咪唑啉（2a-g）和7-（4-甲基苯基）-3-甲硫基-5H-6,7-二氢咪唑啉[2,1-c] [1,2，存在4]三唑（4b）。所有测试的化合物均显示MIC在11.0-89.2 microM的范围内。发现化合物2a，e在体外与氯霉素等效，而化合物2a，c

  DOI：

  10.1016/j.bmc.2006.01.019
• 作为产物：
  描述：

  2-唑烷酮 、 间氯苯胺盐酸盐 以 neat (no solvent) 为溶剂， 以80%的产率得到N-(3-chlorophenyl)-1,2-ethanediamine
  参考文献：
  名称：

  The use of 2-oxazolidinones as latent aziridine equivalents. 2. Aminoethylation of aromatic amines, phenols, and thiophenols

  摘要：

  The utility of 2-oxazolidinones 1 as latent, carboxylated aziridine functionalities was examined. Reaction of 2-oxazolidinone (1a), 3-methyl-2-oxazolidinone (1b), 3-(phenylmethyl)-2-oxazolidinone (1c), 3-phenyl-2-oxazolidinone (1d), 4,4-dimethyl-2-oxazolidinone (1e), and 5-ethyl-2-oxazolidinone (1f) with aromatic amine salts, phenol, or thiophenols at elevated temperatures (> 130-degrees-C) afforded aminoethylated adducts. The aminoethylation occurred with concomitant loss of carbon dioxide to furnish variously substituted N-aryl-1,2-ethanediamines 4, 1-(2-phenoxyethyl)-2-imidazolidinone (8), or 2-(arylthio)ethanamines 9 on reactions of 1 with aromatic amine salts, phenol, and thiophenols, respectively. Imidazolidinone 8 is believed to be a secondary reaction product resulting from the condensation of the initially formed 2-phenoxyethanamine with starting oxazolidinone 1a. The aminoethylation reaction did not proceed with aliphatic amine hydrochlorides or alkyl mercaptans. Preliminary mechanistic pathways for these ring openings were also investigated employing a specific, C-5 deuterium-labeled oxazolidinone 1b-d2. Ring-opening experiments of 1b-d2 with N-methylaniline hydrochloride suggest reaction can occur through either a dioxazolinium 5 and/or an aziridinium 6 intermediate. In contrast, reaction of 1b-d2 with thiophenol suggests ring-opening to proceed only via the dioxazolinium pathway.

  DOI：

  10.1021/jo00049a037

文献信息

• [EN] PYRROLE mTORC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS PYRROLES DE MTORC ET LEURS UTILISATIONS
  申请人：NAVITOR PHARM INC

  公开号：WO2018089493A1

  公开（公告）日：2018-05-17

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用这些化合物的方法。
• Triamine derivatives and their acid-addition salts
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0443862A1

  公开（公告）日：1991-08-28

  A triamine derivative of the formula (I) wherein Ar¹ and Ar² are carbocyclic or heterocyclic single ring or fused ring aromatic groups, R¹, R² and R³ are hydrogen, lower alkyl, aryl aryl-alkyl, aryl-alkyloxycarbonyl, alkyloxycarbonyl or acyl, and A¹ and A² are lower alkylene groups optionally substituted by oxo, exhibits a high N-methyl-D-aspartic acid (NMDA) receptor antagonistic effect and are therefore useful as a medicine for nerve degeneration diseases.

  式(I)的三胺衍生物，其中Ar¹和Ar²是碳环或杂环的单环或融合环芳香基团，R¹、R²和R³是氢、低碳基、芳基芳基-烷基、芳基-烷氧羰基、烷氧羰基或酰基，A¹和A²是可选择地被氧代取代的低碳烯基基团，表现出高N-甲基-D-天冬氨酸（NMDA）受体拮抗作用，因此可用作治疗神经退行性疾病的药物。
• Design, Synthesis, and Evaluation of Chromen-2-ones as Potent and Selective Human Dopamine D4 Antagonists
  作者：Suzanne R. Kesten、Thomas G. Heffner、Stephen J. Johnson、Thomas A. Pugsley、Jonathan L. Wright、Lawrence D. Wise

  DOI：10.1021/jm990266k

  日期：1999.9.1

  The discovery of a series of chromen-2-ones with selective affinity for the dopamine (DA) D4 receptor is described. Target compounds were tested for binding to cloned human DA D2L, D3, and D4.2 receptor subtypes expressed in Chinese hamster ovary K1 cells. Several compounds demonstrated high affinity (<20 nM, K(i)) and greater than 100-fold selectivity for DA D4.2 versus DA D2L receptors. The results

  描述了一系列对多巴胺（DA）D4受体具有选择性亲和力的chromen-2-ones的发现。测试了目标化合物与在中国仓鼠卵巢K1细胞中表达的克隆的人DDA2L，D3和D4.2受体亚型的结合。与DA D2L受体相比，几种化合物对DA D4.2表现出高亲和力（<20 nM，K（i））和超过100倍的选择性。讨论SAR研究的结果。在测量[（3）H]胸苷摄取的DA D4功能测定中，目标化合物对D4.2受体表现出拮抗剂活性。当以20口服时，化合物22，7-[（（2-苯基氨基乙基氨基）甲基] chromen-2-one增加大鼠海马中DOPA（L-3,4-二羟基苯基丙氨酸）的积累51％和纹状体中的23％毫克/千克
• Aminoethylation process
  申请人：The Dow Chemical Company

  公开号：US04381401A1

  公开（公告）日：1983-04-26

  2-Oxazolidinone or N-substituted derivatives thereof are reacted with aromatic amine hydrochlorides at elevated temperatures to produce 1,2-ethanediamines.

  2-噁唑啉酮或其N-取代衍生物在高温下与芳香胺盐酸盐反应，生成1,2-乙二胺。
• Phenylimidazolidin-2-one Derivatives as Selective 5-HT₃ Receptor Antagonists and Refinement of the Pharmacophore Model for 5-HT₃ Receptor Binding
  作者：Franco Heidempergher、Antonio Pillan、Vittorio Pinciroli、Fabrizio Vaghi、Claudio Arrigoni、Giorgio Bolis、Carla Caccia、Luciano Dho、Robert McArthur、Mario Varasi

  DOI：10.1021/jm970060o

  日期：1997.10.1

  metoclopramide, a D2 receptor antagonist with weak 5-HT3 receptor antagonist properties, and zetidoline, a D2 receptor antagonist. Starting from this premise, a series of phenylimidazolidin-2-one derivatives bearing a basic azabicycloalkyl or an imidazolylalkyl moiety were synthesized and evaluated for 5-HT3 receptor radioligand binding affinity ([3H]-GR 43,694). In vitro 5-HT3 receptor antagonist activity was

  根据甲氧氯普胺（一种具有弱的5-HT3受体拮抗剂特性的D2受体拮抗剂）与zeetidoline的相似性，提出了苯甲酰胺基与苯基咪唑啉酮-2-酮部分之间可能存在的生物等排体， D2受体拮抗剂。从这个前提出发，合成了一系列带有碱性氮杂双环烷基或咪唑基烷基部分的苯基咪唑啉二-2-酮衍生物，并评估了其与5-HT3受体放射性配体的结合亲和力（[3H] -GR 43,694）。在豚鼠回肠分析（GPI）中测试了体外5-HT3受体拮抗剂的活性。通过抑制麻醉大鼠的Bezold-Jarisch反射确定了许多高亲和力配体是体内有效的5-HT3受体拮抗剂。一般来说，发现咪唑基烷基衍生物比氮杂双环烷基更具活性。1-（3,5-二氯苯基）-3-[（5-甲基-1H-咪唑-4-基）甲基]咪唑啉丁-2-酮（58）特别显示出对5-HT3的极高亲和力在GPI分析中，其Kb为5.62 nM（Ki为0.038 nM），比测试的参比化