(R)-2-(3',4'-dichlorophenyl)pent-4-enoic acid | 223905-68-8

• 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: (R)-2-(3',4'-dichlorophenyl)pent-4-enoic acid
• 英文别名: (R)-2-(3,4-Dichlorophenyl)pent-4-enoic acid；(2R)-2-(3,4-dichlorophenyl)pent-4-enoic acid
• CAS: 223905-68-8
• 化学式: C₁₁H₁₀Cl₂O₂
• 分子量: 245.105
• InChiKey: KPZNUENYSGBIBF-MRVPVSSYSA-N

物化性质

• 沸点：
  352.3±37.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-(3',4'-dichlorophenyl)pent-4-enoic acid 在 四氧化锇 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 40.0h， 生成 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methyl butanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, Synthesis, and Optimization of Balanced Dual NK₁/NK₃Receptor Antagonists

  摘要：

  In connection with a program directed at potent and balanced dual NK1/NK3 receptor ligands, a focused exploration of an original class of peptidomimetic derivatives was performed. The rational design and molecular hybridization of a novel phenylalanine core series was achieved to maximize the in vitro affinity and antagonism at both human NK1 and NK3 receptors. This study led to the identification of a new potent dual NK1/NK3 antagonist with pK(i) values of 8.6 and 8.1, respectively.

  DOI：

  10.1021/ml400528y
• 作为产物：
  描述：

  2-(3,4-dichlorophenyl)-pent-4-enoic acid 在 R(+)-alpha-甲基苄胺 、 盐酸 作用下， 生成 (R)-2-(3',4'-dichlorophenyl)pent-4-enoic acid
  参考文献：
  名称：

  Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 2: structure–activity relationships for substituted 2-aryl-1-[ N -(methyl)- N -(phenylsulfonyl)amino]-4-(piperidin-1-yl)butanes

  摘要：

  (2S)-2-(3,4-二氯苯基)-1-[N-(甲基)-N-(苯基亚砜)氨基]-4-[螺(2,3-二氢苯并噻吩-3,4'-哌啶-1'-基)]丁烷 S-氧化物 (3) 已被鉴定为一种具有强效 CCR5 拮抗活性的先导结构化合物，其 IC50 值为 35 nM。本文中，我们描述了针对 C-2 苯基片段的需求和优化的结构-活性关系研究。研究发现，苯基对于 CCR5 拮抗活性至关重要，取代基仅限于在 3 位引入小型基团（如 13 和 16，当 X=H、3-F、3-Cl、3-Me 时）。(C) 2001 Elsevier Science Ltd. 出版。

  DOI：

  10.1016/s0960-894x(00)00639-9

文献信息

• Aryl and biaryl compounds having MCH modulatory activity
  申请人：SCHERING CORPORATION

  公开号：US20030092715A1

  公开（公告）日：2003-05-15

  In one embodiment, this invention provides a novel class of compounds as antagonists of the MCH receptor, methods of preparing such compounds, pharmaceutical compositions containing one or more of the compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention or amelioration or one or more of diseases associated with the MCH receptor. An illustrative inventive compound is shown below: 1

  本发明的其中一个实施例提供了一类新颖的化合物，作为MCH受体的拮抗剂，制备这类化合物的方法，包含一个或多个此类化合物的药物组合物，制备包含一个或多个此类化合物的药物制剂的方法，以及治疗、预防或改善与MCH受体相关的一个或多个疾病的方法。下面展示了一个说明性的创新化合物：1
• [EN] ARYL AND BIARYL COMPOUNDS HAVING MCH MODULATORY ACTIVITY<br/>[FR] COMPOSES D'ARYLE ET DE BIARYLE AYANT UNE ACTIVITE MODULATRICE DE MCH
  申请人：PHARMACOPEIA INC

  公开号：WO2002076929A1

  公开（公告）日：2002-10-03

  In one embodiment, this invention provides a novel class of compounds as antagonists of the MCH receptor, methods of preparing such compounds, pharmaceutical compositions containing one or more of the compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention or amelioration or one or more of diseases associated with the MCH receptor. An illustrative inventive compound is shown here.

  在一种实施方式中，本发明提供了一类新型化合物作为MCH受体拮抗剂，制备这种化合物的方法，含有一种或多种这种化合物的药物组合物，制备包含一种或多种这种化合物的药物配方的方法，以及治疗、预防或改善与MCH受体相关的一种或多种疾病的方法。这里展示了一种有创造性的化合物。
• Azepines and Piperidines with Dual Norepinephrine Dopamine Uptake Inhibition and Antidepressant Activity
  作者：Dean G. Brown、Peter R. Bernstein、Ye Wu、Rebecca A. Urbanek、Christopher W. Becker、Scott R. Throner、Bruce T. Dembofsky、Gary B. Steelman、Lois A. Lazor、Clay W. Scott、Michael W. Wood、Steven S. Wesolowski、David A. Nugiel、Stephanie Koch、Jian Yu、Donald E. Pivonka、Shuang Li、Carol Thompson、Anna Zacco、Charles S. Elmore、Patricia Schroeder、JianWei Liu、Christopher A. Hurley、Stuart Ward、Hazel J. Hunt、Karen Williams、Joseph McLaughlin、Valerie Hoesch、Simon Sydserff、Donna Maier、David Aharony

  DOI：10.1021/ml300262e

  日期：2013.1.10

  Herein, we describe the discovery of inhibitors of norepinephrine (NET) and dopamine (DAT) transporters with reduced activity relative to serotonin transporters (SERT). Two compounds, 8b and 21a, along with nomifensine were tested in a rodent receptor occupancy study and demonstrated dose-dependent displacement of radiolabeled NET and DAT ligands. These compounds were efficacious in a rat forced swim assay (model of depression) and also had activity in rat spontaneous locomotion assay.
• Azepinone as a conformational constraint in the design of κ-opioid receptor agonists
  作者：Paul A. Tuthill、Pamela R. Seida、William Barker、Joel A. Cassel、Serge Belanger、Robert N. DeHaven、Michael Koblish、Susan L. Gottshall、Patrick J. Little、Diane L. DeHaven-Hudkins、Roland E. Dolle

  DOI：10.1016/j.bmcl.2004.08.041

  日期：2004.11

  A new class of kappa-opioid receptor agonists is described. The design of these agents was based upon energy minimization and structural overlay studies of the generic azepin-2-one structure 3 with the crystal structure of arylacetamide kappa agonist 1, ICI 199441. The most active compound identified was ligand 4a (K-i = 0.34 nM), which demonstrated potent antinociceptive activity after oral administration in rodents. (C) 2004 Elsevier Ltd. All rights reserved.
• ARYL AND BIARYL COMPOUNDS HAVING MCH MODULATORY ACTIVITY
  申请人：PHARMACOPEIA, INC.

  公开号：EP1370520A1

  公开（公告）日：2003-12-17