3-溴-5-氯-2,6-二甲氧基苯甲酸 | 73219-92-8

• 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: 3-溴-5-氯-2,6-二甲氧基苯甲酸
• 英文名称: 3-bromo-5-chloro-2,6-dimethoxybenzoic acid
• CAS: 73219-92-8
• 化学式: C₉H₈BrClO₄
• 分子量: 295.517
• InChiKey: VOIBMJIPLSKRQL-UHFFFAOYSA-N

物化性质

• 熔点：
  95-97°C
• 沸点：
  379.7±42.0 °C(Predicted)
• 密度：
  1.659±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  3-溴-5-氯-2,6-二甲氧基苯甲酸 在 氯化亚砜 作用下， 以 丁酮 为溶剂， 反应 1.5h， 生成 3-溴-5-氯-N-[(1-乙基吡咯烷-2-基)甲基]-2,6-二甲氧基苯甲酰胺
  参考文献：
  名称：

  Potential neuroleptic agents. 2,6-Dialkoxybenzamide derivatives with potent dopamine receptor blocking activities

  摘要：

  A series of some novel N-(l-ethyl-2-pyrrolidinylmethyl)benzamides was synthesized and tested for dopamine receptor blockade in vivo by the ability to block the apomorphine syndrome in the rat. Several compounds were considerably more potent than sulpiride as dopamine receptor blockers and displayed low liability to induce extrapyramidal side effects (catalepsy) in the rat. The blockade of dopamine receptor activity in vivo was mainly confined to the levorotatory isomers having the S absolute configuration. The structure-activity relationships are discussed.

  DOI：

  10.1021/jm00353a003
• 作为产物：
  描述：

  2,6-二甲氧基苯甲酸 在 磺酰氯 、 溴 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 14.75h， 生成 3-溴-5-氯-2,6-二甲氧基苯甲酸
  参考文献：
  名称：

  Potential neuroleptic agents. 2,6-Dialkoxybenzamide derivatives with potent dopamine receptor blocking activities

  摘要：

  A series of some novel N-(l-ethyl-2-pyrrolidinylmethyl)benzamides was synthesized and tested for dopamine receptor blockade in vivo by the ability to block the apomorphine syndrome in the rat. Several compounds were considerably more potent than sulpiride as dopamine receptor blockers and displayed low liability to induce extrapyramidal side effects (catalepsy) in the rat. The blockade of dopamine receptor activity in vivo was mainly confined to the levorotatory isomers having the S absolute configuration. The structure-activity relationships are discussed.

  DOI：

  10.1021/jm00353a003

文献信息

• Potential neuroleptic agents. 4. Chemistry, behavioral pharmacology, and inhibition of [3H]spiperone binding of 3,5-disubstituted N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxysalicylamides
  作者：Tomas De Paulis、Yatendra Kumar、Lars Johansson、Sten Raemsby、Haakan Hall、Maria Saellemark、Kristina Aengeby-Moeller、Sven Ove Oegren

  DOI：10.1021/jm00151a010

  日期：1986.1

  methyl]-6-methoxysalicylamides was synthesized, starting from the 2,6-dimethoxybenzoic acids, by boron tribromide demethylation of the corresponding 3,5-disubstituted 2,6-dimethoxybenzamides and separation of the two positional isomers. The correct structure assignments were based on selective decoupling studies on their 13C NMR spectra. The salicylamide derivatives were tested for antidopamine activity in vivo

  从2,6-二甲氧基苯甲酸开始，通过相应的3,5-硼的三溴化硼脱甲基，合成了一系列的3,5-二取代的N-[（（1-乙基-2-吡咯烷基）甲基] -6-甲氧基水杨酰胺。二取代2，6-二甲氧基苯甲酰胺和两个位置异构体的分离。正确的结构分配基于对它们的13C NMR光谱进行的选择性去偶联研究。水杨酰胺衍生物通过在大鼠中抑制阿扑吗啡综合征的能力在体内进行了抗多巴胺活性的测试，并在体外从大鼠脑纹状体制剂中置换了[3H]哌酮的能力进行了体外抗多巴胺活性的测试。该活性似乎仅存在于S对映异构体中。几种化合物比氟哌啶醇更有效，特别是在芳环的3-位具有乙基且在5-位具有卤原子的那些。相应的5-烷基-3-卤素取代的化合物的活性低得多。发现最有效的化合物的急性毒性低。一些水杨酰胺在阻止阿扑吗啡诱导的过度活跃和阻止阿朴吗啡引起的刻板印象的剂量之间显示出10-20倍的间隔。一种化合物S-（-）-3,5-二氯-N-[（（1-乙基-2-吡咯烷基）甲基]
• 2,6-Dialkoxybenzamides, intermediates, pharamaceutical compositions and
  申请人：Astra Lakemedel Aktiebolag

  公开号：US04232037A1

  公开（公告）日：1980-11-04

  A compound of the formula ##STR1## wherein R.sup.1 is an alkyl group with 1-3 carbon atoms, R.sup.2 and R.sup.3 are the same or different and each is hydrogen, chlorine or bromine; and pharmaceutically acceptable salts and optical isomers thereof; methods and intermediates for the preparation of the compounds; pharmaceutical preparations containing them and their medical use for the treatment of psychoses.

  一种化合物的分子式为##STR1##，其中R.sup.1是含有1-3个碳原子的烷基基团，R.sup.2和R.sup.3相同或不同，且每个都是氢、氯或溴；以及其药用可接受盐和光学异构体；制备该化合物的方法和中间体；含有它们的药物制剂以及它们用于治疗精神病的医疗用途。
• Aryl and heteroaryl compounds, compositions, and methods of use
  申请人：Mjalli M.M. Adnan

  公开号：US20050059713A1

  公开（公告）日：2005-03-17

  This invention provides aryl and heteroaryl compounds of Formula (I) as described herein, and methods of their preparation. Also provided are pharmaceutical compositions made with the compounds of Formula (I) and methods for making such compositions. Compounds of Formula (I) may be useful for treating viral infections including orthopox viruses, either alone or in combination with other therapeutic agents.

  本发明提供了公式(I)所描述的芳基和杂环芳基化合物，以及它们的制备方法。还提供了由公式(I)化合物制成的制药组合物和制备这种组合物的方法。公式(I)化合物可能有助于治疗包括正痘病毒在内的病毒感染，可以单独使用或与其他治疗剂联合使用。
• 2,6-Dialkoxybenzamides, process for their preparation, compositions and these compounds for use in the treatment of psychotic disordes
  申请人：Astra Läkemedel Aktiebolag

  公开号：EP0004831B1

  公开（公告）日：1983-02-16
• FLORVALL, L.;OEGREN, S. -O., J. MED. CHEM., 1982, 25, N 11, 1280-1286
  作者：FLORVALL, L.、OEGREN, S. -O.

  DOI：——

  日期：——