1-(2-Hydroxy-ethyl)-3-(3-methoxy-benzyl)-thiourea | 366786-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-Hydroxy-ethyl)-3-(3-methoxy-benzyl)-thiourea
• 英文别名: 1-(2-Hydroxyethyl)-3-[(3-methoxyphenyl)methyl]thiourea
• CAS: 366786-85-8
• 化学式: C₁₁H₁₆N₂O₂S
• 分子量: 240.326
• InChiKey: PQBGLFIBFGSHKN-UHFFFAOYSA-N

物化性质

• 沸点：
  401.0±55.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  85.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-Hydroxy-ethyl)-3-(3-methoxy-benzyl)-thiourea 在 三氟乙酸 作用下， 反应 2.0h， 以75%的产率得到(4,5-Dihydro-thiazol-2-yl)-(3-methoxy-benzyl)-amine
  参考文献：
  名称：

  Synthesis of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas and evaluation as modulators of the isoforms of nitric oxide synthase

  摘要：

  Inhibition of the isoforms of nitric oxide synthase (NOS) has important applications in therapy of several diseases, including cancer. Using 1400W [N-(3-aminomethylbenzyl)acetamidme], thiocitrulline and N-delta-(4,5-dihydrothiazol-2-yl)ornithine as lead compounds, series of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas were designed as inhibitors of NOS. Ring-substituted benzyl and phenyl isothiocyanates were synthesised by condensation of the corresponding amines with thiophosgene and addition of ammonia gave the corresponding thioureas in high yields. The substituted 2-amino-4,5-dihydrothiazoles were approached by two routes. Treatment of simple benzylamines with 2-methylthio-4,5-dihydrothiazole at 180degreesC afforded the corresponding 2-benzylamino-4,5-dihydrothiazoles. For less nucleophilic amines and those carrying more thermally labile substituents, the 4,5-dihydrothiazoles were approached by acid-catalysed cyclisation of N-(2-hydroxyethyl)thioureas. This cyclisation was shown to proceed by an S(N)2-like process. Modest inhibitory activity was shown by most of the thioureas and 4,5-dihydrothiazoles, with N-(3-aminomethylphenyl)thiourea (IC50 = 13 muM vs rat neuronal NOS and IC50 = 23 muM vs rat inducible NOS) and 2-(3-aminomethylphenylamino)-4,5-dihydrothiazole (IC50 - 13 muM vs rat neuronal NOS and IC50 = 19 muM vs human inducible NOS) being the most potent. Several thioureas and 4,5-dihydrothiazoles were found to stimulate the activity of human inducible NOS in a time-dependent manner. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00451-6
• 作为产物：
  描述：

  3-甲氧基苄胺 在 calcium carbonate 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 20.0h， 生成 1-(2-Hydroxy-ethyl)-3-(3-methoxy-benzyl)-thiourea
  参考文献：
  名称：

  Synthesis of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas and evaluation as modulators of the isoforms of nitric oxide synthase

  摘要：

  Inhibition of the isoforms of nitric oxide synthase (NOS) has important applications in therapy of several diseases, including cancer. Using 1400W [N-(3-aminomethylbenzyl)acetamidme], thiocitrulline and N-delta-(4,5-dihydrothiazol-2-yl)ornithine as lead compounds, series of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas were designed as inhibitors of NOS. Ring-substituted benzyl and phenyl isothiocyanates were synthesised by condensation of the corresponding amines with thiophosgene and addition of ammonia gave the corresponding thioureas in high yields. The substituted 2-amino-4,5-dihydrothiazoles were approached by two routes. Treatment of simple benzylamines with 2-methylthio-4,5-dihydrothiazole at 180degreesC afforded the corresponding 2-benzylamino-4,5-dihydrothiazoles. For less nucleophilic amines and those carrying more thermally labile substituents, the 4,5-dihydrothiazoles were approached by acid-catalysed cyclisation of N-(2-hydroxyethyl)thioureas. This cyclisation was shown to proceed by an S(N)2-like process. Modest inhibitory activity was shown by most of the thioureas and 4,5-dihydrothiazoles, with N-(3-aminomethylphenyl)thiourea (IC50 = 13 muM vs rat neuronal NOS and IC50 = 23 muM vs rat inducible NOS) and 2-(3-aminomethylphenylamino)-4,5-dihydrothiazole (IC50 - 13 muM vs rat neuronal NOS and IC50 = 19 muM vs human inducible NOS) being the most potent. Several thioureas and 4,5-dihydrothiazoles were found to stimulate the activity of human inducible NOS in a time-dependent manner. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00451-6

文献信息

• Alpha-2B adrenergic receptor agonist and serotonin-norepinephrine reuptake inhibitor compositions for treating chronic pain
  申请人：Allergan, Inc.

  公开号：EP2428207A1

  公开（公告）日：2012-03-14

  Disclosed herein is a pharmaceutical composition comprising serotonin-norepinephrine reuptake inhibitor and an alpha-2B receptor agonist. The composition is effective for treating chronic pain, and methods of treating pain using the composition and compounds comprising it are also disclosed.

  本文公开了一种药物组合物，其中包含血清素-去甲肾上腺素再摄取抑制剂和α-2B受体激动剂。该组合物对治疗慢性疼痛有效，还公开了使用该组合物和包含该组合物的化合物治疗疼痛的方法。
• ALPHA-2B RECEPTOR AGONIST AND 5HT4 SEROTONIN RECEPTOR COMPOSITIONS FOR TREATING GASTROINTESTINAL MOTILITY DISORDERS
  申请人：Brooks Gregory F.

  公开号：US20080153825A1

  公开（公告）日：2008-06-26

  Disclosed herein is a pharmaceutical composition comprising a 5-HT4 serotonin receptor agonist and an alpha-2B receptor agonist. The composition is effective for treating gastrointestinal motility disorders, and methods of treating such disorders using the composition and compounds comprising it are also disclosed.
• ALPHA-2B RECEPTOR AGONIST AND ANTICONVULSANT COMPOSITIONS FOR TREATING CHRONIC PAIN
  申请人：Gil Daniel W.

  公开号：US20080153874A1

  公开（公告）日：2008-06-26

  Disclosed herein is a pharmaceutical composition comprising a pain-relieving anticonvulsant and an alpha-2B receptor agonist. The composition is effective for treating chronic pain, and methods of treating chronic pain using the composition and the compounds comprising it are also disclosed.
• ALPHA-2B RECEPTOR AGONIST AND ACID REDUCER COMPOSITIONS FOR TREATING GASTROINTESTINAL MOTILITY DISORDERS
  申请人：Brooks Gregory F.

  公开号：US20080153881A1

  公开（公告）日：2008-06-26

  Disclosed herein is a pharmaceutical composition comprising an acid reducer and an alpha-2B receptor agonist. The composition is effective for treating gastrointestinal motility disorders, and methods of treating such disorders using the composition and compounds comprising it are also disclosed.
• ALPHA-2B RECEPTOR AGONIST AND RELAXANT COMPOSITIONS FOR TREATING GASTROINTESTINAL MOTILITY DISORDERS
  申请人：Brooks Gregory F.

  公开号：US20080153927A1

  公开（公告）日：2008-06-26

  Disclosed herein is a pharmaceutical composition comprising a relaxant and an alpha-2B receptor agonist. The composition is effective for treating gastrointestinal motility disorders, and methods of treating such disorders using the composition and compounds comprising it are also disclosed.