2-[3-methoxy-4-(3-phenylpropoxy)phenyl]ethanamine

• 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-[3-methoxy-4-(3-phenylpropoxy)phenyl]ethanamine
• 英文别名: 2-[3-methoxy-4-(3-phenylpropoxy)phenyl]ethan-1-amine；2-[3-Methoxy-4-(3-phenyl-propoxy)-phenyl]-ethylamine
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: DKZFGWYKPGGSBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[3-methoxy-4-(3-phenylpropoxy)phenyl]ethanamine 、 (2S)-(+)-1-(3',4'-dibenzyloxyphenoxy)-2,3-epoxypropane 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 7.5h， 生成 (S)-4-(2-hydroxy-3-((3-methoxy-4-(3-phenylpropoxy)phenethyl)amino)propoxy)benzene-1,2-diol hydrochloride
  参考文献：
  名称：

  Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias

  摘要：

  Starting from the beta-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gas, while they only show weak or even no beta-arrestin-2 recruitment at both beta(1)- and beta(2)-AR Molecular dynamics simulations suggest that the difference in G protein efficacy and beta-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the beta(2)-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser(5.46) and Asn(6.55), and the aromatic head group of the ligands.

  DOI：

  10.1021/acs.jmedchem.9b00349
• 作为产物：
  描述：

  N-Carbobenzoxy-homovanillylamin 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 21.0h， 生成 2-[3-methoxy-4-(3-phenylpropoxy)phenyl]ethanamine
  参考文献：
  名称：

  Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias

  摘要：

  Starting from the beta-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gas, while they only show weak or even no beta-arrestin-2 recruitment at both beta(1)- and beta(2)-AR Molecular dynamics simulations suggest that the difference in G protein efficacy and beta-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the beta(2)-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser(5.46) and Asn(6.55), and the aromatic head group of the ligands.

  DOI：

  10.1021/acs.jmedchem.9b00349

文献信息

• Structure-guided development of dual β2 adrenergic/dopamine D2 receptor agonists
  作者：Dietmar Weichert、Markus Stanek、Harald Hübner、Peter Gmeiner

  DOI：10.1016/j.bmc.2016.04.028

  日期：2016.6

  adrenergic/dopamine D2 receptor ligands, a structure-guided approach for the evolution of GPCR agonists that address multiple targets was elaborated. Starting from GPCR crystal structures, we describe the design, synthesis and biological investigation of a defined set of compounds leading to the identification of the benzoxazinone (R)-3, which shows agonist properties at the adrenergic β2 receptor and substantial

  旨在发现双重作用的β 2肾上腺素/多巴胺d 2受体配体，该地址多个目标进行详细阐述了GPCR受体激动剂演变的结构为导向的做法。从GPCR晶体结构开始，我们描述了设计，合成和定义的一组化合物导致苯并恶嗪酮的标识（的生物调查- [R ）- 3，其示出了在肾上腺素能β激动剂性质2受体和大量的G蛋白促进D 2受体的活化。这种直接的方法产生了具有双重活性的分子探针。在同类DES OH- 3不含苄基羟基官能团的被证明是一个β 2肾上腺素能拮抗剂/ d 2受体激动剂与ķ我在低纳摩尔范围内的值。这些化合物可以作为神经疾病研究和治疗的有希望的起点。
• Alpha-sulfin-and alpha-sulfonamino acid amides
  申请人：——

  公开号：US20020099241A1

  公开（公告）日：2002-07-25

  The invention relates to &agr;-sulfin- and &agr;-sulfonamino acid amides of the general formula I 1 including the optical isomers thereof and mixtures of such isomers, wherein n is a number zero or one; R 1 is C 1 -C 12 alkyl, C 1 -C 12 alkyl substituted with C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, C 3 -C 8 cycloalkyl, cyano, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl or C 3 -C 6 alkynyloxycarbonyl; C 3 -C 8 cycloalkyl; C 2 -C 12 alkenyl; C 2 -C 12 alkynyl; C 1 -C 12 haloalkyl; or a group NR 12 R 13 wherein R 12 and R 13 are each independently of the other hydrogen or C 1 -C 6 -alkyl, or together are tetra- or penta-methylene; R 2 and R 3 are each independently hydrogen; C 1 -C 8 alkyl; C 1 -C 8 alkyl substituted with hydroxy, mercapto, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 cycloalkyl; C 3 -C 8 cycloalkyl-C 1 -C 4 alkyl; or the two groups R 2 and R 3 together with the carbon atom to which they are bonded form a three- to eight-membered hydrocarbon ring; R 4 , R 5 , R 6 and R 7 are each independently hydrogen or C 1 -C 4 alkyl; R 8 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; R 9 , R 10 , R 14 , R 15 , R 16 and R 17 are each independently hydrogen or C 1 -C 4 alkyl; A is optionally substituted phenyl, and to the preparation of those substances and to agrochemical compositions comprising at least one of those compounds as active ingredient. The invention relates also to the preparation of the said compositions and to the use of the compounds or of the compositions in controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.

  该发明涉及一般式I1的α-亚砜基和α-磺酰氨基酸酰胺，包括其光学异构体和混合物，其中n是零或一；R1是C1-C12烷基，C1-C12烷基取代C1-C4烷氧基，C1-C4烷硫基，C1-C4烷磺基，C3-C8环烷基，氰基，C1-C6烷氧羰基，C3-C6烯氧羰基或C3-C6炔氧羰基；C3-C8环烷基；C2-C12烯基；C2-C12炔基；C1-C12卤代烷基；或基团NR12R13，其中R12和R13各自独立地为氢或C1-C6-烷基，或者一起为四甲基或五亚甲基；R2和R3各自独立地为氢；C1-C8烷基；C1-C8烷基取代羟基，巯基，C1-C4烷氧基或C1-C4烷硫基；C3-C8烯基；C3-C8炔基；C3-C8环烷基；C3-C8环烷基-C1-C4烷基；或两个基团R2和R3与它们连接的碳原子一起形成三至八元环烃环；R4、R5、R6和R7各自独立地为氢或C1-C4烷基；R8是C1-C6烷基，C3-C6烯基或C3-C6炔基；R9、R10、R14、R15、R16和R17各自独立地为氢或C1-C4烷基；A是可选取代的苯基，以及制备这些物质和包含至少一种这些化合物作为活性成分的农药组合物。该发明还涉及所述组合物的制备以及化合物或组合物在控制或预防植物受植物病原微生物，特别是真菌侵害方面的应用。
• &agr;-sulfin-and &agr;-sulfonamino acid amides
  申请人：Syngenta Participations AG

  公开号：US06538159B2

  公开（公告）日：2003-03-25

  The invention relates to &agr;-sulfin- and &agr;-sulfonamino acid amides of the general formula I including the optical isomers thereof and mixtures of such isomers, wherein n is a number zero or one; R1 is C1-C12alkyl, C1-C12alkyl substituted with C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C3-C8cycloalkyl, cyano, C1-C6alkoxycarbonyl, C3-C6alkenyloxycarbonyl or C3-C6alkenyloxycarbonyl; C3-C8cycloalkyl; C2-C12alkenyl; C2-C12alkynyl; C1-C12haloalkyl; or a group NR12R13 wherein R12 and R13 are each independently of the other hydrogen or C1-C6-alkyl, or together are tetra- or penta-methylene; R2 and R3 are each independently hydrogen; C1-C8alkyl; C1-C8alkyl substituted with hydroxy, mercapto, C1-C4alkoxy or C1-C4alkylthio; C3-C8alkenyl; C3-C8alkynyl; C3-C8cycloalkyl; C3-C8cycloalkyl-C1-C4alkyl; or the two groups R2 and R3 together with the carbon atom to which they are bonded form a three- to eight-membered hydrocarbon ring; R4, R5, R6 and R7 are each independently hydrogen or C1-C4alkyl; R8 is C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl; R9, R10, R14, R15, R16 and R17 are each independently hydrogen or C1-C4alkyl; A is optionally substituted phenyl, and to the preparation of those substances and to agrochemical compositions comprising at least one of those compounds as active ingredient. The invention relates also to the preparation of the said compositions and to the use of the compounds or of the compositions in controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.

  本发明涉及一般式I的α-磺酰基和α-磺酰氨基酸酰胺，包括其光学异构体和混合物，其中n是零或一；R1是C1-C12烷基，C1-C12烷基取代C1-C4烷氧基，C1-C4烷硫基，C1-C4烷基磺酰基，C3-C8环烷基，氰基，C1-C6烷氧羰基，C3-C6烯氧羰基或C3-C6烯烃氧羰基；C3-C8环烷基；C2-C12烯基；C2-C12炔基；C1-C12卤代烷基；或一个NR12R13基团，其中R12和R13各自独立地为氢或C1-C6烷基，或一起为四亚甲基或五亚甲基；R2和R3各自独立地为氢；C1-C8烷基；C1-C8烷基取代羟基，巯基，C1-C4烷氧基或C1-C4烷硫基；C3-C8烯基；C3-C8炔基；C3-C8环烷基；C3-C8环烷基-C1-C4烷基；或两个R2和R3基团连同它们连接的碳原子形成一个三到八元环烃环；R4、R5、R6和R7各自独立地为氢或C1-C4烷基；R8是C1-C6烷基，C3-C6烯基或C3-C6炔基；R9、R10、R14、R15、R16和R17各自独立地为氢或C1-C4烷基；A是可选取代的苯基，以及制备这些物质和包含至少一种这些化合物作为活性成分的农药组合物。本发明还涉及所述组合物的制备以及化合物或组合物在控制或预防植物受植物病原微生物，特别是真菌侵染方面的用途。
• ALPHA-SULFIN- AND ALPHA-SULFONAMINO ACID AMIDES
  申请人：Syngenta Participations AG

  公开号：EP1135369A2

  公开（公告）日：2001-09-26
• US6538159B2
  申请人：——

  公开号：US6538159B2

  公开（公告）日：2003-03-25