2-[2-(2-Chloro-phenoxy)-ethyl]-isoindole-1,3-dione | 727368-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[2-(2-Chloro-phenoxy)-ethyl]-isoindole-1,3-dione
• 英文别名: 2-[2-(2-chlorophenoxy)ethyl]-2,3-dihydro-1H-isoindole-1,3-dione；2-[2-(2-chlorophenoxy)ethyl]isoindole-1,3-dione
• CAS: 727368-76-5
• 化学式: C₁₆H₁₂ClNO₃
• 分子量: 301.729
• InChiKey: RQRFJWZCYBTJAU-UHFFFAOYSA-N

物化性质

• 沸点：
  455.9±25.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)
• 溶解度：
  3.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(2-Chloro-phenoxy)-ethyl]-isoindole-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以39%的产率得到2-(2-氯苯氧基)乙胺
  参考文献：
  名称：

  新型吡咯烷-2,4-二酮衍生物的设计，合成，晶体结构和除草活性

  摘要：

  为了发现具有新型分子支架的绿色除草剂，使用天然四酸作为先导化合物来设计和合成四种结合了链状烷氧基烷基部分（4a–4d）和十九种吡咯烷-2,4-的吡咯烷-2,4-二酮衍生物。通过取代，酰化，环化和酸化反应掺入取代的苯氧乙基部分（10a-10s）的二酮衍生物。通过FT-IR，1 H NMR，13 C NMR和HRMS光谱分析确认了合成的目标化合物。化合物10a的单晶结构X-射线衍射分析表明，1-羟基亚乙烯基通过具有Z-构型的双键连接吡咯烷杂环的第三位置。通过培养皿培养法，以bar草（Echinochloa crus-galli）和油菜（Brassica campestris）为模型植物来评价除草活性。发现大多数目标化合物在100μgmL -1时对植物生长具有中等至良好的抑制活性。其中，化合物10q和10n对草和油菜幼苗的根系表现出最高的除草活性，相应的抑制率分别为65.6％和84.0％。该结果

  DOI：

  10.1039/d1nj00119a
• 作为产物：
  描述：

  邻氯苯酚 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2-[2-(2-Chloro-phenoxy)-ethyl]-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α_1d Adrenergic Receptor

  摘要：

  In the present study, more than 75 compounds structurally related to BMY 7378 have been designed and synthesized. Structural variations of each part of the reference molecule have been introduced, obtaining highly selective ligands for the aid adrenergic receptor. The molecular determinants for selectivity at this receptor are essentially, held by the phenyl substituent in the phenylpiperazine moiety. The integration of an extensive SAR analysis with docking simulations using the rhodopsin-based models of the three alpha(1)-AR subtypes and of the 5-HT1A receptor provides significant insights into the characterization of the receptor binding sites as well as into the molecular determinants of ligand selectivity at the alpha(1d)-AR and the 5-HT1A receptors. The results of multiple copies simultaneous search (MCSS) on the substituted phenylpiperazines together with those of manual docking of compounds BAN 7378 and 69 into the putative binding sites of the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptors suggest that the phenylpiperazine moiety would dock into a site formed by amino acids in helices 3, 4, 5, 6 and extracellular loop 2, (E2), whereas the spirocyclic ring of the ligand docks into a site formed by amino acids of helices 1, 2, 3, and 7. This docking mode is consistent with the SAR data produced in this work. Furthermore, the binding site of the imide moiety does not allow for the simultaneous involvement of the two carbonyl oxygen atoms in H-bonding, interactions, consistent with the SAR data, in particular with the results obtained with the lactam derivative 128. The results of docking simulations also suggest that the second and third extracellular loops may act as selectivity filters for the substituted phenylpiperazines. The most potent and selective compounds for alpha(1d) adrenergic receptor, i.e., 69 (Rec 26D/038) and 128 (Rec 26D/073), are characterized by the presence of the 2,5-dichlorophenylpiperazine moiety.

  DOI：

  10.1021/jm030944+

文献信息

• Phenoxypropanol connected with phenylpiperazine and phenoxyalkylamine terminal in its side chain
  申请人：——

  公开号：US20030055066A1

  公开（公告）日：2003-03-20

  The invention disclosed some 1,4-dihydropiridine derivative chemically have pharmacologically with adrenoceptor blocking and calcium channel blocker is now emerging. The compound of 1,4-dihydropiridine derivative wherein has the formula I, wherein R selected from four group as follow 1 whetherin R present R 1 selected from halogen(X), hydrogen(H), saturated C 1 -C 6 alkyl chain, saturated C 1 -C 6 alkyoxyl chain, R 2 selected from 2 R 3 selected from halogen(X), hydrogen(H), saturated C 1 -C 6 alkyl chain, saturated C 1 -C 6 alkyoxyl chain, and O—(C 1 -C 3 )—CF 3 .

  该发明披露了一些具有肾上腺素受体阻滞和钙通道阻滞药理作用的1,4-二氢吡啶衍生物化合物正在出现。其中1,4-二氢吡啶衍生物化合物的化学式为I，其中R选自以下四个基团之一：1. 在R存在时，R1选自卤素（X），氢（H），饱和C1-C6烷基链，饱和C1-C6烷氧基链，R2选自2，R3选自卤素（X），氢（H），饱和C1-C6烷基链，饱和C1-C6烷氧基链，和O-(C1-C3)-CF3。
• alpha/beta-adrenoceptors blockers and angiotensin converting enzyme inhibitors derived from hydroxyphenyl carboxylic acid and alcohol
  申请人：——

  公开号：US20030040485A1

  公开（公告）日：2003-02-27

  The invention disclosed some derivative chemically with Hydroxyphenyl carboxylic acid and Alcohol based phenoxypropanolamine and associated alanyl-proline peptide derivatives. The compounds shown as formula I, 1 whether R is a number selected from the group of hydrogen, unsaturated 2-6 straight chain carbon atoms, saturated 1-6 straight chain carbon atoms, unsaturated 2-6 straight chain of alkoxyl group, saturated 1-6 straight chain of alkoxyl group, halogen, and —NO 2 ; R 1 is selected from the groups of —R 2 OH, —R 2 OR 3 , —R 2 COCOOR 4 , —R 2 COOR4 and R 2 CH(COR 4 )-alanylproline, R 2 CH(COOR 4 )-alanylproline; R 2 is selected from the groups of unsaturated 2-6 straight chain carbon atoms, saturated 1-6 straight chain carbon atoms; R 3 is selected from the ester groups consisting of proline and alanylproline; R 4 is selected from the groups of hydrogen, unsaturated 2-6 straight chain carbon atoms, saturated 1-6 straight chain carbon atoms; R 5 is selected from the groups of hydrogen, unsaturated 2-6 straight chain carbon atoms, saturated 1-6 straight chain carbon atoms, and 2 R may be on the meta, ortho, or para position with ethoxyl group on the bezene ring. Through in vivo experiment to prove those compounds have new generation &agr;/&bgr;-adrenoceptor antagonist with vasorelaxant activity or angiotensin converting enzyme inhibitory activities.

  该发明揭示了一些衍生物，其化学结构基于羟基苯甲酸和醇基苯氧丙胺以及相关的丙氨酰-脯氨酸肽衍生物。化合物的结构如公式I所示，其中1，R是从氢、不饱和的2-6直链碳原子、饱和的1-6直链碳原子、不饱和的2-6直链烷氧基、饱和的1-6直链烷氧基、卤素和—NO2中选择的数字；R1是从—R2OH、—R2OR3、—R2COCOOR4、—R2COOR4和R2CH（COR4）-丙氨酰脯氨酸、R2CH（COOR4）-丙氨酰脯氨酸中选择的基团；R2是从不饱和的2-6直链碳原子、饱和的1-6直链碳原子中选择的基团；R3是由脯氨酸和丙氨酰脯氨酸组成的酯基团；R4是从氢、不饱和的2-6直链碳原子、饱和的1-6直链碳原子中选择的基团；R5是从氢、不饱和的2-6直链碳原子、饱和的1-6直链碳原子、2R可以位于苯环上的甲氧基的间位、邻位或对位中选择的基团。通过体内实验证明这些化合物具有新一代α/β肾上腺素受体拮抗剂和血管松弛活性或血管紧张素转换酶抑制活性。
• US6846826B2
  申请人：——

  公开号：US6846826B2

  公开（公告）日：2005-01-25
• Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α_1d Adrenergic Receptor
  作者：Amedeo Leonardi、Daniela Barlocco、Federica Montesano、Giorgio Cignarella、Gianni Motta、Rodolfo Testa、Elena Poggesi、Michele Seeber、Pier G. De Benedetti、Francesca Fanelli

  DOI：10.1021/jm030944+

  日期：2004.4.1

  In the present study, more than 75 compounds structurally related to BMY 7378 have been designed and synthesized. Structural variations of each part of the reference molecule have been introduced, obtaining highly selective ligands for the aid adrenergic receptor. The molecular determinants for selectivity at this receptor are essentially, held by the phenyl substituent in the phenylpiperazine moiety. The integration of an extensive SAR analysis with docking simulations using the rhodopsin-based models of the three alpha(1)-AR subtypes and of the 5-HT1A receptor provides significant insights into the characterization of the receptor binding sites as well as into the molecular determinants of ligand selectivity at the alpha(1d)-AR and the 5-HT1A receptors. The results of multiple copies simultaneous search (MCSS) on the substituted phenylpiperazines together with those of manual docking of compounds BAN 7378 and 69 into the putative binding sites of the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptors suggest that the phenylpiperazine moiety would dock into a site formed by amino acids in helices 3, 4, 5, 6 and extracellular loop 2, (E2), whereas the spirocyclic ring of the ligand docks into a site formed by amino acids of helices 1, 2, 3, and 7. This docking mode is consistent with the SAR data produced in this work. Furthermore, the binding site of the imide moiety does not allow for the simultaneous involvement of the two carbonyl oxygen atoms in H-bonding, interactions, consistent with the SAR data, in particular with the results obtained with the lactam derivative 128. The results of docking simulations also suggest that the second and third extracellular loops may act as selectivity filters for the substituted phenylpiperazines. The most potent and selective compounds for alpha(1d) adrenergic receptor, i.e., 69 (Rec 26D/038) and 128 (Rec 26D/073), are characterized by the presence of the 2,5-dichlorophenylpiperazine moiety.
• Design, synthesis, crystal structure, and herbicidal activity of novel pyrrolidine-2,4-dione derivatives incorporating an alkyl ether pharmacophore with natural tetramic acids as lead compounds
  作者：Min Chen、Chun-Wen Geng、Ling Han、Yu Liu、Yong-Kai Yu、Ai-Min Lu、Chun-Long Yang、Guo-Hua Li

  DOI：10.1039/d1nj00119a

  日期：——

  Z-configuration. The herbicidal activity was evaluated using barnyard grass (Echinochloa crus-galli) and rape (Brassica campestris) as model plants by a Petri dish culture method. Most target compounds were found to possess moderate to good inhibitory activities against the plant growth at 100 μg mL−1. Among them, the compounds 10q and 10n showed the highest herbicidal activities against the roots of

  为了发现具有新型分子支架的绿色除草剂，使用天然四酸作为先导化合物来设计和合成四种结合了链状烷氧基烷基部分（4a–4d）和十九种吡咯烷-2,4-的吡咯烷-2,4-二酮衍生物。通过取代，酰化，环化和酸化反应掺入取代的苯氧乙基部分（10a-10s）的二酮衍生物。通过FT-IR，1 H NMR，13 C NMR和HRMS光谱分析确认了合成的目标化合物。化合物10a的单晶结构X-射线衍射分析表明，1-羟基亚乙烯基通过具有Z-构型的双键连接吡咯烷杂环的第三位置。通过培养皿培养法，以bar草（Echinochloa crus-galli）和油菜（Brassica campestris）为模型植物来评价除草活性。发现大多数目标化合物在100μgmL -1时对植物生长具有中等至良好的抑制活性。其中，化合物10q和10n对草和油菜幼苗的根系表现出最高的除草活性，相应的抑制率分别为65.6％和84.0％。该结果