2-(2,6-dimethylphenylimino)imidazolidine | 4859-06-7

• 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-(2,6-dimethylphenylimino)imidazolidine
• 英文别名: 2-<(2,6-dimethylphenyl)imino>imidazolidine；(4,5-dihydro-1H-imidazol-2-yl)-(2,6-dimethyl-phenyl)-amine；1H-Imidazol-2-amine, N-(2,6-dimethylphenyl)-4,5-dihydro-；N-(2,6-dimethylphenyl)-4,5-dihydro-1H-imidazol-2-amine
• CAS: 4859-06-7
• 化学式: C₁₁H₁₅N₃
• 分子量: 189.26
• InChiKey: IVCKBWZBJVLCDH-UHFFFAOYSA-N

物化性质

• 熔点：
  143 °C
• 沸点：
  290.0±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,6-dimethylphenylimino)imidazolidine 、 苯甲酰乙酸乙酯 生成 8-(2,6-dimethyl-phenyl)-5-phenyl-2,8-dihydro-3H-imidazo[1,2-a]pyrimidin-7-one
  参考文献：
  名称：

  HAERTER H. P.; LICHTL H.; STAUSS U.; SCHINDLER O., HELV. CHIM. ACTA , 1976, 59, NO 4, 1203-1212

  摘要：

  DOI：
• 作为产物：
  描述：

  生成 2-(2,6-dimethylphenylimino)imidazolidine
  参考文献：
  名称：

  Three-dimensional quantitative structure–activity studies of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera

  摘要：

  The quantitative structure-activity relationship (QSAR) of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera, was analyzed using physicochemical parameters, molecular shape analysis (MSA), molecular field analysis (MFA), and receptor surface model (RSM), respectively. The dose-response studies were performed in vitro analyzing the effect of these compounds on intracellular cAMP production in the presence of pheromone biosynthesis activating neuropeptide (PBAN) at 1 pmol/intersegment. Six active derivatives were identified in the order of decreasing pheromonostatic activity: 2-(2,6-dimethylanilino)imidazolide (6) > 2-(2-methyl-4-chloroanilino)oxazolidine (1) > clonidine (5) > 2-(2,6-diethylanilino)thiazolidine (8) > 2-(3,5-dichlorobenzylamino)-2-oxazoline (4) > tolazoline (10) which were all active in the nanomolar range in inhibition of cAMP production by 1 pmol PBAN/intersegment. Four other compounds were less active having K-i in the micromolar range. An MSA was tried to obtain QSAR equation that incorporates spatial molecular similarity data of those compounds. MFA on the training set of those compounds evaluated effectively the energy between a probe and a molecular model at a series of points defined by a rectangular or spherical grid. An RSM was generated using some subset of the most active structures. Three-dimensional energetics descriptors were calculated from RSM/ligand interaction and these three-dimensional descriptors were used in QSAR analysis. These results indicate that these derivatives could provide useful information in the characterization and differentiation of octopaminergic receptor types and subtypes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00189-3

文献信息

• Method for treating central nervous system disorders with substituted 2-imidazoline derivatives
  申请人：Hoener Marius

  公开号：US20070197569A1

  公开（公告）日：2007-08-23

  The present invention relates to a method for treating depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders which comprises administering to an individual a therapeutically effective amount of a compound of formula I wherein R, X, A, and n are as defined in the specification and pharmaceutically active salts, racemic mixtures, enantiomers, optical isomers and tautomeric forms thereof.

  本发明涉及一种治疗抑郁症、焦虑障碍、双相情感障碍、注意力缺陷多动障碍（ADHD）、与压力相关的障碍、如精神分裂症等精神障碍、帕金森病等神经系统疾病、阿尔茨海默病等神经退行性疾病、癫痫、偏头痛、高血压、物质滥用和代谢性疾病，如进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍、心血管疾病的方法，包括向个体施用化合物I的治疗有效量，其中R、X、A和n如规范中所定义，以及其药用活性盐、外消旋混合物、对映体、光学异构体和互变异构体形式。
• Propargyl-substituted 2-phenylamino-2-imidazolines and salts thereof
  申请人：Boehringer Ingelheim GmbH

  公开号：US04025607A1

  公开（公告）日：1977-05-24

  Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3, which may be identical to or different from each other, are each hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy or trifluoromethyl, and R.sub.4 and R.sub.5 are each hydrogen or propargyl, but other than both hydrogen or both propargyl at the same time, And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as the salts are useful as analgesics and hypotensives.

  公式为##STR1##的化合物，其中R.sub.1、R.sub.2和R.sub.3可以相同也可以不同，分别为氢、氟、氯、溴、甲基、乙基、甲氧基或三氟甲基，R.sub.4和R.sub.5分别为氢或丙炔基，但不能同时为两个氢或两个丙炔基，以及其非毒性、药理学上可接受的酸盐；这些化合物及其盐可用作镇痛药和降压药。
• Process for the manufacture of 2-arylamino-2-imidazoline derivatives and
  申请人：Boehringer Ingelheim GmbH

  公开号：US03931216A1

  公开（公告）日：1976-01-06

  A process for the preparation of the known and valuable 2-aryl-amino-2-imidazoline derivatives which comprises condensing an appropriately substituted aniline with a 1-acyl-imidazolidin-2-one to produce an intermediate compound which on neutralisation in an aqueous medium is converted into a N-acyl derivative of the 2-aryl-amino-2-imidazoline, and splitting the intermediate compound or the said N-acyl derivative to give the corresponding free arylamino-2-imidazoline derivative or a salt thereof.

  一种制备已知和有价值的2-芳基氨基-2-咪唑啉衍生物的方法，包括将适当取代的苯胺与1-酰基咪唑啉-2-酮缩合，产生一个中间化合物，在水性介质中中和后转化为2-芳基氨基-2-咪唑啉的N-酰基衍生物，然后分解中间化合物或所述的N-酰基衍生物，得到相应的游离芳基氨基-2-咪唑啉衍生物或其盐。
• Poultry feeds containing and methods of using anovulatory compounds, and novel anovulatory imidazolines
  申请人：Merck & Co., Inc.

  公开号：EP0035393A1

  公开（公告）日：1981-09-09

  2-(Substituted phenylimino)imidazolidines of formula: and their non-toxic salts in which R is C1-4 alkyl, C2-5 alkenyl, or halo, is hydrogen, C1-4 alkyl, or halo, is C1-4 alkanoyl, carboxy, (C1-3 alkoxy)carbonyl, C1-4 alkylthio, phenoxy, (C1-3 alkoxy)-phenoxy, halophenoxy, phenylthio, (C1-3 alkyl)-phenylthio, (C1-3 alkoxy)-phenylthio, halophenylthio, C1-4 hydroxyalkyl, (C1-3 alkoxy)-(C1-4 alkyl, di (C1-3 alkyl)amino-(C1-4 alkyl), C5-5 alkenyl, or di(C1-3 alkyl)amino are novel. Compunds of formula: and their non-toxic salts where R is defined above, each of R1 and R2 is independently a radical as defined for either of and or a nitro, amino, C1-3 alkylamino, di(C1-3 alkyl) amino, hydroxy, trifluormethylthio, C1-4 aminoalkyl or (C1- 3 alkyl)amino-(C1-4 alkyl) radical, are administered to poultry to delay the onset of egg production in young pullets and interrupt egg production in mature hens and are useful in producing an artificial moult. They are included in feeds, feed concentrates and additives for drinking water.

  式中的 2-(取代的苯基亚氨基)咪唑啉： 及其无毒盐，其中 R 是 C1-4 烷基、C2-5 烯基或卤代，是氢、C1-4 烷基或卤代，是 C1-4 烷酰基、羧基、(C1-3 烷氧基)羰基、C1-4 烷硫基、苯氧基、(C1-3 烷氧基)-苯氧基、卤代苯氧基、苯硫基、(C1-3 烷基)-苯硫基、(C1-3 烷氧基)-苯氧基、卤苯氧基、苯硫基、(C1-3 烷基)-苯硫基、(C1-3 烷氧基)-苯硫基、卤苯硫基、C1-4 羟基烷基、(C1-3 烷氧基)-(C1-4 烷基)、二(C1-3 烷基)氨基-(C1-4 烷基)、C5-5 烯基或二(C1-3 烷基)氨基是新型的。 式的化合物： 及其无毒盐 其中 R 定义如上，R1 和 R2 中的每一个独立地是定义为和 或硝基、氨基、C1-3 烷基氨基、二(C1-3 烷基)氨基、羟基、三氟甲硫基、C1-4 氨基烷基或 (C1- 3 烷基)氨基-(C1-4烷基)基的基团。它们可用于饲料、浓缩饲料和饮用水添加剂。
• Three-Dimensional common-Feature hypotheses for octopamine agonist 2-(arylimino)imidazolidines
  作者：Akinori Hirashima、Masako Morimoto、Eiichi Kuwano、Eiji Taniguchi、Morifusa Eto

  DOI：10.1016/s0968-0896(01)00247-4

  日期：2002.1

  Three-dimensional pharmacophore hypotheses were built from a set of 10 octopamine (OA) agonist 2-(Arylimino)imidazolidines (AIIs), 2-(Arylimino)thiazolidines (AITs) and 2-(Arylimino)oxazolidines (AIOs). Among the 10 common-featured models generated by program Catalyst/HipHop, a hypothesis including a ring aromatic (RA), a positive ionizable (PI) and three hydrophobic aliphatic (HpAl) features was considered to be important in evaluating the OA-agonist activity. Active OA agonist 2,6-Et-2 All mapped well onto all the RA, PI and HpAl features of the hypothesis. On the other hand, less active compounds were shown to be difficult to achieve the energetically favorable conformation which is found in the active molecules in order to fit the 3-D common-feature pharmacophore models. Taken together, 2,6-Et-2-Ph and foramidine structures are important as OA agonists. The present studies on OA agonists demonstrate that a RA, a PI and three HpAl sites located on the molecule seem to be essential for OA-agonist activity. (C) 2001 Elsevier Science Ltd. All rights reserved.