2-((bis(4-bromophenyl)methyl)thio)acetic acid | 1253944-20-5

• 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-((bis(4-bromophenyl)methyl)thio)acetic acid
• 英文别名: 2-(bis(4-bromophenyl)methylthio)acetic acid；2-((Bis(4-bromophenyl)methyl)thio)acetic acid；2-[bis(4-bromophenyl)methylsulfanyl]acetic acid
• CAS: 1253944-20-5
• 化学式: C₁₅H₁₂Br₂O₂S
• 分子量: 416.133
• InChiKey: RBAZHUVGVFUTFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((bis(4-bromophenyl)methyl)thio)acetic acid 在 双氧水 、 溶剂黄146 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 26.0h， 生成 2-(bis(4-bromophenyl)methylsulfinyl)-N-methylacetamide
  参考文献：
  名称：

  新型系列莫达非尼（2-[（（二苯甲基）亚磺酰基]乙酰胺）类似物在单胺转运蛋白上的结构-活性关系。

  摘要：

  合成了一系列莫达非尼（1）类似物，其中1）将对卤代取代基添加到芳环上，2）除去亚砜官能团，3）伯酰胺基被仲和叔酰胺和胺取代，得到研究这些化学修饰对DAT，SERT和NET结合的影响。另外，将（+/-）-莫达非尼（1），其R-和S-对映异构体及其对氯亚磺酰基乙酰胺类似物（5c）对小鼠的运动刺激作用与可卡因进行了比较。

  DOI：

  10.1021/ml1002025
• 作为产物：
  描述：

  4,4'-二溴二苯甲酮 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 生成 2-((bis(4-bromophenyl)methyl)thio)acetic acid
  参考文献：
  名称：

  新型系列莫达非尼（2-[（（二苯甲基）亚磺酰基]乙酰胺）类似物在单胺转运蛋白上的结构-活性关系。

  摘要：

  合成了一系列莫达非尼（1）类似物，其中1）将对卤代取代基添加到芳环上，2）除去亚砜官能团，3）伯酰胺基被仲和叔酰胺和胺取代，得到研究这些化学修饰对DAT，SERT和NET结合的影响。另外，将（+/-）-莫达非尼（1），其R-和S-对映异构体及其对氯亚磺酰基乙酰胺类似物（5c）对小鼠的运动刺激作用与可卡因进行了比较。

  DOI：

  10.1021/ml1002025

文献信息

• POTENT AND SELECTIVE INHIBITORS OF MONOAMINE TRANSPORTERS; METHOD OF MAKING; AND USE THEREOF
  申请人：THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY DEPARTMENT OF HEALTH AND HUMAN SERVICE

  公开号：US20160009644A1

  公开（公告）日：2016-01-14

  Disclosed herein are bisarylmethylthioacetamides and bisarylmethylthioethylamines useful as inhibitors of monoamine transporters. The compounds are potent and/or selective inhibitors of dopamine (DA), serotonin (5-HT), and/or norepinephrine (NE) reuptake via their respective transporters, DAT, SERT and NET. Also disclosed are methods for eliciting a wake-promoting or cognitive or attention enhancing effect and for treating substance use disorders, attention deficit (hyperactivity) disorder, depressive disorders, bipolar disorder or other neuropsychiatric disorders sleep disorders or cognitive impairment using the compounds.

  本文揭示了双芳基甲硫基乙酰胺和双芳基甲硫基乙胺作为单胺转运体抑制剂的用途。这些化合物是通过它们各自的转运体DAT、SERT和NET对多巴胺（DA）、5-羟色胺（5-HT）和/或去甲肾上腺素（NE）的再摄取具有强效和/或选择性抑制作用。还揭示了利用这些化合物引发促醒、认知或注意力增强效应以及治疗物质使用障碍、注意缺陷（多动）障碍、抑郁障碍、双相障碍或其他神经精神障碍、睡眠障碍或认知障碍的方法。
• Potent and selective inhibitors of monoamine transporters; method of making; and use thereof
  申请人：THE UNITED STATES OF AMERICA, as represented by the Secretary, Department of Health and Human Services, Office of Technology Transfer, National Institutes of Health

  公开号：US10590074B2

  公开（公告）日：2020-03-17

  Disclosed herein are bisarylmethylthioacetamides and bisarylmethylthioethylamines useful as inhibitors of monoamine transporters. The compounds are potent and/or selective inhibitors of dopamine (DA), serotonin (5-HT), and/or norepinephrine (NE) reuptake via their respective transporters, DAT, SERT and NET. Also disclosed are methods for eliciting a wake-promoting or cognitive or attention enhancing effect and for treating substance use disorders, attention deficit (hyperactivity) disorder, depressive disorders, bipolar disorder or other neuropsychiatric disorders sleep disorders or cognitive impairment using the compounds.

  本文公开了可用作单胺转运体抑制剂的双芳基甲硫基乙酰胺和双芳基甲硫基乙胺。这些化合物是多巴胺（DA）、5-羟色胺（5-HT）和/或去甲肾上腺素（NE）通过各自的转运体 DAT、SERT 和 NET 再摄取的强效和/或选择性抑制剂。此外，还公开了利用这些化合物激发促进觉醒或认知或注意力增强效应以及治疗药物使用障碍、注意力缺陷（多动）症、抑郁症、双相情感障碍或其他神经精神疾病睡眠障碍或认知障碍的方法。
• Elucidation of Structural Elements for Selectivity across Monoamine Transporters: Novel 2-[(Diphenylmethyl)sulfinyl]acetamide (Modafinil) Analogues
  作者：Oluyomi M. Okunola-Bakare、Jianjing Cao、Theresa Kopajtic、Jonathan L. Katz、Claus J. Loland、Lei Shi、Amy Hauck Newman

  DOI：10.1021/jm401754x

  日期：2014.2.13

  2-[(Diphenylmethyl)sulfinyl]acetamide (modafinil, (+/-)-1) is a unique dopamine uptake inhibitor that binds the dopamine transporter (DAT) differently than cocaine and may have potential for the treatment of psychostimulant abuse. To further investigate structural requirements for this divergent binding mode, novel thio- and sulfinylacetamide and ethanamine analogues of (+/-)-1 were synthesized wherein (1) the diphenyl rings were substituted with methyl, trifluoromethyl, and halogen substituents and (2) substituents were added to the terminal amide/amine nitrogen. Halogen substitution of the diphenyl rings of (+/-)-1 gave several amide analogues with improved binding affinity for DAT and robust selectivity over the serotonin transporter (SERT), whereas affinity improved at SERT over DAT for the p-halo-substituted amine analogues. Molecular docking studies, using a subset of analogues with DAT and SEAT homology models, and functional data obtained with DAT (A480T) and SERT (T497A) mutants defined a role for TM10 in the substrate/inhibitor S1 binding sites of DAT and SERT.
• US9862679B2
  申请人：——

  公开号：US9862679B2

  公开（公告）日：2018-01-09
• [EN] POTENT AND SELECTIVE INHIBITORS OF MONOAMINE TRANSPORTERS; METHOD OF MAKING; AND USE THEREOF<br/>[FR] INHIBITEURS PUISSANTS ET SÉLECTIFS DE TRANSPORTEURS DE MONOAMINE; PROCÉDÉ DE FABRICATION; ET LEUR UTILISATION
  申请人：US HEALTH

  公开号：WO2014138518A2

  公开（公告）日：2014-09-12

  Disclosed herein are bisarylmethylthioacetamides and bisarylmethylthioethylamines useful as inhibitors of monoamine transporters. The compounds are potent and/or selective inhibitors of dopamine (DA), serotonin (5-HT), and/or norepinephrine (NE) reuptake via their respective transporters, DAT, SERT and NET. Also disclosed are methods for eliciting a wake-promoting or cognitive or attention enhancing effect and for treating substance use disorders, attention deficit (hyperactivity) disorder, depressive disorders, bipolar disorder or other neuropsychiatric disorders sleep disorders or cognitive impairment using the compounds.