1-[(4-氯苯基)苯基甲基]六氢-1H-1,4-二氮杂卓 | 24342-60-7

• 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-[(4-氯苯基)苯基甲基]六氢-1H-1,4-二氮杂卓
• 英文名称: 1-<(4-chlorophenyl)phenylmethyl>homopiperazine
• 英文别名: 1-((4-chlorophenyl)(phenyl)methyl)-1,4-diazepane；1-((4-chlorophenyl)(phenyl)methyl)-1,4-diazepan；1-(4-chlorobenzhydryl)homopiperazine；1-[(4-Chlorophenyl)phenylmethyl]hexahydro-1H-1,4-diazepine；1-[(4-chlorophenyl)-phenylmethyl]-1,4-diazepane
• CAS: 24342-60-7
• 化学式: C₁₈H₂₁ClN₂
• 分子量: 300.831
• InChiKey: RMTYMEIZBKIWGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(4-氯苯基)苯基甲基]六氢-1H-1,4-二氮杂卓 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 2-[3-[4-(4-chlorobenzhydryl)homopiperazino)propyl]amino-4-methylphenol
  参考文献：
  名称：

  抗氧化剂邻氨基苯酚衍生物的合成及其局部抗炎和抗过敏活性。

  摘要：

  为了开发具有抗过敏和抗炎活性的新型局部用化合物，合成了一系列带有H1-抗组胺结构的邻氨基苯酚衍生物，并研究了它们对大鼠脑匀浆脂质过氧化，抗炎作用花生四烯酸和12-O-十四烷酰佛波醇-13-乙酸盐诱导的小鼠耳水肿及对大鼠48小时同源被动皮肤过敏反应的抗过敏作用。此外，检查了这些化合物对小鼠迟发型超敏反应的影响。在所有这些测定中，发现了几种N-单取代的氨基-4-甲基苯酚发挥有效的抑制活性。在这些化合物中，选择4m作为AD0261进行进一步开发。

  DOI：

  10.1021/jm00039a010
• 作为产物：
  描述：

  在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 1-[(4-氯苯基)苯基甲基]六氢-1H-1,4-二氮杂卓
  参考文献：
  名称：

  Hybrid approach for the design of highly affine and selective dopamine D3 receptor ligands using privileged scaffolds of biogenic amine GPCR ligands

  摘要：

  A series of compounds containing privileged scaffolds of the known histamine H-1 receptor antagonists cetirizine, mianserin, ketotifen, loratadine, and bamipine were synthesized for further optimization as ligands for the related biogenic amine binding dopamine D-3 receptor. A pharmacological screening was carried out at dopamine D-2 and D-3 receptors. In the preliminary testing various ligands have shown moderate to high affinities for dopamine D-3 receptors, for example, N-(4-{4-[benzyl(phenyl)amino]piperidin-1-yl} butylnaphthalen-2-carboxamide (19a) (hD(3) K-i = 0.3 nM; hD(2) K-i = 703 nM), leading to a selectivity ratio of 2343. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.034

文献信息

• Synthesis, Structure−Activity Relationship, and Mode-of-Action Studies of Antimalarial Reversed Chloroquine Compounds
  作者：Steven J. Burgess、Jane X. Kelly、Shawheen Shomloo、Sergio Wittlin、Reto Brun、Katherine Liebmann、David H. Peyton

  DOI：10.1021/jm1006484

  日期：2010.9.9

  moiety and a resistance reversal-like moiety, can overcome chloroquine resistance in P. falciparum (Burgess, S. J.; Selzer, A.; Kelly, J. X.; Smilkstein, M. J.; Riscoe, M. K.; Peyton, D. H. J. Med. Chem. 2006, 49, 5623. Andrews, S.; Burgess, S. J.; Skaalrud, D.; Kelly, J. X.; Peyton, D. H. J. Med. Chem. 2010, 53, 916). Here, we present an investigation into the structure−activity relationship of the RCQ

  我们先前已经证明了“反向氯喹（RCQ）”分子，的氯喹等构成部分和耐药性逆转样部分，可以克服在氯喹抗性的恶性疟原虫（伯吉斯，SJ；塞尔泽，A.；凯利，JX；斯米尔克斯坦，MJ；里斯科，MK；佩顿，卫生署 J. 医学。化学 2006年，49，5623。安德鲁斯，S。伯吉斯，SJ；斯卡尔鲁德，D.；凯利，JX；佩顿，卫生署 J. 医学。化学 2010 , 53 , 916)。在这里，我们对 RCQ 结构的构效关系进行了研究，从而产生了一种具有良好体外和体内抗疟活性的口服活性分子。我们还提供了作用方式的证据，表明 RCQ 分子以类似于氯喹的方式抑制寄生虫消化液泡中血红素的形成。
• Substituted or unsubstituted benzhydryl heteroalkyl-substituted
  申请人：Green Cross Corporation

  公开号：US05308840A1

  公开（公告）日：1994-05-03

  Aminophenol derivatives of the following formula (I) ##STR1## wherein X is hydrogen atom, lower alkyl or a protecting group for phenolic hydroxy, Y is hydrogen atom or lower alkyl, Z is hydrogen atom, lower alkyl, halogen atom or trifluoromethyl, A is hydrogen atom or lower alkyl, t is an integer of 1 to 5, l and m are respectively an integer of 2 to 4, E and W are nitrogen atoms, F is a direct bond or oxygen atom, P and Q are each hydrogen atom, halogen atom, lower alkyl or lower alkoxy, and R.sup.8 is hydrogen atom, hydroxy or a hydroxy-protecting group, and their pharmcologically acceptable salts. Since the aminophenol derivatives (I) of the present invention have excellent antioxidative action and antiinflammatory and antiallergic action in mammalian animals including human, they are extremely useful as pharmaceuticals such as an antiinflammatory or an antiallergic.

  具有以下结构式(I)的氨基酚衍生物 其中X是氢原子、较低的烷基或苯酚羟基的保护基，Y是氢原子或较低的烷基，Z是氢原子、较低的烷基、卤原子或三氟甲基，A是氢原子或较低的烷基，t是1到5的整数，l和m分别是2到4的整数，E和W是氮原子，F是直接键或氧原子，P和Q分别是氢原子、卤原子、较低的烷基或较低的烷氧基，R.sup.8是氢原子、羟基或羟基保护基，以及其药学上可接受的盐。由于本发明的氨基酚衍生物(I)在哺乳动物动物中，包括人类，具有出色的抗氧化作用、抗炎和抗过敏作用，因此它们作为药物，如抗炎或抗过敏药物，非常有用。
• Novel aminophenol derivatives and pharmaceutical compositions thereof
  申请人：THE GREEN CROSS CORPORATION

  公开号：EP0508334A2

  公开（公告）日：1992-10-14

  Aminophenol derivatives of the following formula (I) wherein X is hydrogen atom, lower alkyl or a protecting group for phenolic hydroxy, Y is hydrogen atom or lower alkyl, Z is hydrogen atom, lower alkyl, halogen atom or trifluoromethyl, A is hydrogen atom or lower alkyl, t is an integer of 1 to 5, l and m are respectively an integer of 2 to 4, E and W are nitrogen atoms, F is a direct bond or oxygen atom, P and Q are each hydrogen atom, halogen atom, lower alkyl or lower alkoxy, and R⁸ is hydrogen atom, hydroxy or a hydroxy-protecting group, and their pharmcologically acceptable salts. Since the aminophenol derivatives (I) of the present invention have excellent antioxidative action and antiinflammatory and antiallergic action in mammalian animals including human, they are extremely useful as pharmaceuticals such as an antiinflammatory or an antiallergic.

  下式（I）的氨基苯酚衍生物 其中 X 为氢原子、低级烷基或酚羟基保护基，Y 为氢原子或低级烷基，Z 为氢原子、低级烷基、卤素原子或三氟甲基，A 为氢原子或低级烷基，t 为 1 至 5 的整数，l 和 m 分别为 2 至 4 的整数、E和W是氮原子，F是直接键或氧原子，P和Q分别是氢原子、卤素原子、低级烷基或低级烷氧基，R⁸是氢原子、羟基或羟基保护基团，以及它们的药学上可接受的盐。由于本发明的氨基苯酚衍生物（I）在哺乳动物（包括人类）中具有优异的抗氧化作用、抗炎作用和抗过敏作用，因此它们作为抗炎或抗过敏等药物非常有用。
• Synthesis and bradykinin inhibitory activity of novel non-peptide compounds, and evaluation of in vivo analgesic activity
  作者：Yoo Lim Kam、Hee-Kyung Rhee、Hwa-Jung Kim、Seung Keun Back、Heung Sik Na、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2010.01.050

  日期：2010.3

  A series of novel non-peptide diamide compounds was synthesized and evaluated as antibradykinin agents by utilizing guinea-pig ileum smooth muscle. Among the final compounds, (Z)-4-(4-(bis(4-fluorophenyl) methyl)piperazin-1-yl)-4-oxo-N-(4-phenylbutan-2-yl)but-2-enamide showed most favorable bradykinin inhibitory activity and demonstrated analgesic efficacies in the rat models of inflammatory and neuropathic pain. (C) 2010 Published by Elsevier Ltd.
• WO2007/142431
  申请人：——

  公开号：——

  公开（公告）日：——