1-acetyl-N-(2,6-diethylphenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine | 86861-31-6

• 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: 1-acetyl-N-(2,6-diethylphenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine
• 英文别名: 2,6-diethyl-N-[1-acetyl-(2-imidazolidinylidene)]-benzamine；1-[2-(2,6-Diethylanilino)-4,5-dihydroimidazol-1-yl]ethanone
• CAS: 86861-31-6
• 化学式: C₁₅H₂₁N₃O
• 分子量: 259.351
• InChiKey: DTOHSGPCMKTBEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-acetyl-N-(2,6-diethylphenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine 在 palladium on activated charcoal 盐酸 、 超重氢 、 水 、 溴 、 硝酸 、 铁粉 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 、 溶剂黄146 、 三氟乙酸 为溶剂， 反应 10.0h， 生成 3,5-diethyl-4-(imidazolidin-2-ylideneamino)benzen-2,6-t2-amine
  参考文献：
  名称：

  A probe for octopamine receptors. Synthesis of 2-[(4-azido-2,6-diethylphenyl)imino]imidazolidine and its tritiated derivative, a potent reversible irreversible activator of octopamine-sensitive adenylate cyclase

  摘要：

  In order to develop an irreversible ligand for octopamine receptors, a highly potent azido-substituted 2-(phenyl-imino)imidazolidine (NC-5Z, 8) and its tritiated derivative (3H-NC-5Z, 11) have been designed and synthesized. Under reversible-binding conditions, NC-5Z is 50-100-fold more potent than octopamine in activating octopamine-sensitive adenylate cyclase in a variety of tissues. After photolysis, 3H-NC-5Z binds irreversibly to cell membranes, and this binding is reduced by preincubation with octopamine agonists and antagonists but not by norepinephrine, dopamine, serotonin, or histamine. NC-5Z should be useful both as a potent reversible octopamine agonist and as an affinity probe for characterizing and isolating octopamine-receptor proteins.

  DOI：

  10.1021/jm00128a022
• 作为产物：
  描述：

  N-乙酰基-2-咪唑烷酮 、 2,6-二乙基苯胺 在 三氯氧磷 作用下， 反应 3.0h， 以69.9%的产率得到1-acetyl-N-(2,6-diethylphenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine
  参考文献：
  名称：

  A probe for octopamine receptors. Synthesis of 2-[(4-azido-2,6-diethylphenyl)imino]imidazolidine and its tritiated derivative, a potent reversible irreversible activator of octopamine-sensitive adenylate cyclase

  摘要：

  In order to develop an irreversible ligand for octopamine receptors, a highly potent azido-substituted 2-(phenyl-imino)imidazolidine (NC-5Z, 8) and its tritiated derivative (3H-NC-5Z, 11) have been designed and synthesized. Under reversible-binding conditions, NC-5Z is 50-100-fold more potent than octopamine in activating octopamine-sensitive adenylate cyclase in a variety of tissues. After photolysis, 3H-NC-5Z binds irreversibly to cell membranes, and this binding is reduced by preincubation with octopamine agonists and antagonists but not by norepinephrine, dopamine, serotonin, or histamine. NC-5Z should be useful both as a potent reversible octopamine agonist and as an affinity probe for characterizing and isolating octopamine-receptor proteins.

  DOI：

  10.1021/jm00128a022

文献信息

• Method for lowering intraocular pressure using phenylimino-imidazoles
  申请人：Alcon Laboratories, Inc.

  公开号：US04517199A1

  公开（公告）日：1985-05-14

  2-(Trisubstituted phenylimino)-imidazole compounds also known as 2-(trisubstituted anilino)-1,3 diazacyclopentene-(2) compounds are used to lower intraocular pressure.

  2-(三取代苯亚胺基)-咪唑化合物，也称为2-(三取代苯胺基)-1,3-二氮杂环戊烯-(2)化合物，用于降低眼内压。
• Method of lowering intraocular pressure using phenylimino-imidazoles
  申请人：——

  公开号：US04515800A1

  公开（公告）日：1985-05-07

  A method is provided of treating glaucoma in a patient which comprises administering, preferably as eye drops, an effective amount of the compound ##STR1## which is preferably in the form of its hydrochloride. The compound is administered preferably in the form of a sterile pharmacologically acceptable solution which contains from 0.1 to 5, and more preferably 0.1 to 2.0, percent by weight of said compound. The patient preferably obtains the anti-glaucoma agent in the form of a kit which comprises the sterile pharmacologically acceptable solution and an eyedropper for dispensing said sterile pharmacologically acceptable solution to the affected eyes of a patient suffering from glaucoma.

  提供了一种治疗青光眼的方法，包括向患者施用有效量的化合物##STR1##，最好是以眼药水的形式，该化合物最好是其盐酸盐形式。该化合物最好以含有0.1至5％，更好地为0.1至2.0％的所述化合物的重量百分比的无菌药理学可接受的溶液的形式施用。患者最好以一种套装的形式获得抗青光眼药剂，该套装包括无菌药理学可接受的溶液和一个眼滴瓶，用于向患有青光眼的患者的受影响的眼睛中注入所述无菌药理学可接受的溶液。
• Three-dimensional pharmacophore hypotheses of octopamine/tyramine agonists which inhibit [1-14C]acetate incorporation in Plodia interpunctella
  作者：Akinori Hirashima、Tomohiko Eiraku、Yoko Shigeta、Eiichi Kuwano

  DOI：10.1016/s0968-0896(02)00320-6

  日期：2003.1

  Three-dimensional pharmacophore hypotheses were built from a set of 36 octopamine (OA)/tyramine (TA) agonists responsible for the inhibition of sex-pheromone production in Plodia interpunctella. Among the ten chemical-featured models generated by a program Catalyst/Hypo, hypotheses including hydrogen-bond acceptor (HBA), hydrogen-bond acceptor aliphatic (HBAl), hydrophobic (Hp), hydrophobic aromatic (HpAr) and hydrophobic aliphatic (HpAl) features were considered to be important and predictive in evaluating OA/TA agonists. Active agonists mapped well onto all the features of the hypothesis such as HBA, HBAl, Hp, HpAr and HpAl features. On the other hand, inactive compounds were shown to be poorly capable of achieving an energetically favorable conformation shared by the active molecules in order to fit the 3-D chemical-feature pharmacophore models. Those hypotheses are considered to be used in designing new leads for hopefully more active compounds. Further research on the comparison of models from the agonists may help elucidate the mechanisms of OA/TA receptor-ligand interactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Topical compostions for lowering intraocular pressure
  申请人：ALCON LABORATORIES, INC.

  公开号：EP0081924B1

  公开（公告）日：1986-02-19
• US4515800A
  申请人：——

  公开号：US4515800A

  公开（公告）日：1985-05-07