(1S)-5-甲氧基-1,2,3,4-四氢萘-1-基)胺 | 103834-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (1S)-5-甲氧基-1,2,3,4-四氢萘-1-基)胺
• 英文名称: (S)-(+)-5-methoxy-1,2,3,4-tetrahydro-1-naphthalenamine
• 英文别名: (S)-5-methoxy-1,2,3,4-tetrahydro-1-naphthylamine；(1S)-5-Methoxy-1,2,3,4-tetrahydronaphthylamine；(1S)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-amine
• CAS: 103834-50-0
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: WGLJGXBRZQHFBR-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S)-5-甲氧基-1,2,3,4-四氢萘-1-基)胺 在 sodium tetrahydroborate 、 三溴化硼 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 (S)-5-[(S)-1-(4,5-Diphenyl-oxazol-2-yl)-4-hydroxy-butylamino]-5,6,7,8-tetrahydro-naphthalen-1-ol
  参考文献：
  名称：

  Discovery of new diphenyloxazole derivatives containing a pyrrolidine ring: Orally active prostacyclin mimetics. Part 2

  摘要：

  Synthetic and biological evaluation of novel diphenyloxazole derivatives containing a pyrrolidine ring, as a prostacyclin mimetic without the PG skeleton, are described. Asymmetric reduction of a ketone using a chiral Ru complex and reductive amination by NaBH4 produces four isomers of the tetrahydronaphthalene ring and the pyrrolidine ring with high stereoselectivity. FR193262 (4), (R,R)-diphenyloxazolyl pyrrolidine derivative, displays high potency and agonist efficacy at the IP receptor and has good bioavailability in rats and dogs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.042
• 作为产物：
  描述：

  5-甲氧基-1-四氢萘胺 生成 (1S)-5-甲氧基-1,2,3,4-四氢萘-1-基)胺
  参考文献：
  名称：

  1-Aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)alkyl]piperazines and Their Analogues:  Influence of the Stereochemistry of the Tetrahydronaphthalen-1-yl Nucleus on 5-HT_1A Receptor Affinity and Selectivity versus α₁ and D₂ Receptors. 5

  摘要：

  Some 1-aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazines and their alkylamino and alkylamido analogues, previously studied as 5-HT1A ligands, were prepared in enantiomerically pure form, and their absolute configuration was det;ermined by chemical correlation or by chiroptical properties. They were evaluated for in vitro 5-HT1A, D-2, and alpha(1) receptor affinity by radioligand binding assays, to study the influence of the chiral carbon atom of the tetrahydronaphthalene nucleus on the 5-HT1A affinity and selectivity. Results indicated that, as regarding the 5-HT1A receptor affinity, there was no difference in affinity between (-)- and (+)-enantiomers as well as the racemate of each compound. The stereochemistry, instead, influenced the selectivity: all (-)-enantiomers displayed affinity values higher than those of (+)-isomers at D-2 receptors, and conversely, all (+)-enantiomers displayed affinity values higher than those of (-)-isomers at alpha(1) receptors. As a result of this trend, it is not possible to predict the isomer with a better selectivity profile. However, compounds (S)-(+)-2, (S)-(+)-4, and (R)-(+)-6 displayed high affinity for the 5-HT1A receptor (IC50 values ranging between 7.0 and 2.3 nM) and good selectivity (greater than or equal to 250-fold) versus both D-2 and alpha(1) receptors. Furthermore, compounds (S)-(+)-4 and (R)-(-)-4 were submitted to the [S-35]GTP gamma S binding assay for a preliminary evaluation of their intrinsic activity on the 5-HT1A receptor.

  DOI：

  10.1021/jm980420n

文献信息

• 一种肌球蛋白抑制剂及其制备方法和用途
  申请人：上海先行医药开发有限公司

  公开号：CN110698415B

  公开（公告）日：2023-05-09

  本发明涉及药物化学领域，特别是涉及一种肌球蛋白抑制剂及其制备方法和用途。本发明提供一种化合物或其药学上可接受的盐、异构体、前药、多晶型物或溶剂化物，所述化合物的化学结构式如式I所示。本发明所提供的化合物或其药学上可接受的盐、异构体、前药、多晶型物或溶剂化物相较于现有技术中其他同类药物具有更优的活性和更理想的药代动力学特性。
• 一种手性化合物的制备方法
  申请人：王际菊

  公开号：CN106397225A

  公开（公告）日：2017-02-15

  本发明公开了一种手性化合物S‑5‑甲氧基‑1‑萘满胺的制备方法,本发明的具体方法是以5‑甲氧基‑1‑萘满酮为原料，与羟胺反应成肟，肟再经催化剂催化加氢还原得5‑甲氧基‑1‑萘满胺，所得胺再经生物酶催化的动态动力学拆分反应，即可得S‑5‑甲氧基‑1‑萘满胺；本发明具备操作简单、产品收率好、拆分产品光学纯度高等特点，在S‑5‑甲氧基‑1‑萘满胺的制备工艺中，具有极大的指导和应用价值。
• Analogues of σ Receptor Ligand 1-Cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28) with Added Polar Functionality and Reduced Lipophilicity for Potential Use as Positron Emission Tomography Radiotracers
  作者：Carmen Abate、Mauro Niso、Enza Lacivita、Philip D. Mosier、Annamaria Toscano、Roberto Perrone

  DOI：10.1021/jm1013133

  日期：2011.2.24

  1-Cyclohexyl-4[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine 1 (PB28) represents an excellent lead candidate for therapeutic and/or diagnostic applications in oncology. However, because its utility is limited by its relatively high degree of lipophilicity, novel analogues of 1 with reduced lipophilic character were designed by substituting methylene groups with more polar functional groups in the propylene linker and at the tetralin C4 position. For the chiral analogues, separate enantiomers exhibited substantial and roughly equal affinities within a given receptor subtype, with the greatest difference observed for compound 9 at sigma(1) (7.5-fold; (-)-(S)-9 K(i) = 94.6 nM, (+)-(R)-9 K(i) = 12.6 nM). Compound (-)-(S)-9 was also found to be the most sigma(2)-selective agent (sigma(2) K(i) = 5.92 nM), to possess a lipophilicity consistent with entry into tumor cells (log D(7.4) = 2.38), and to show minimal antiproliferative activity. However, (-)-(S)-9 exhibited moderate activity (EC(50) = 8.1 mu M) at the P-gp efflux pump.
• TRIVEDI, BHARAT K.;MOOS, WALTER;HAMILTON, HARRIET W.;PATT, WILLIAM C.
  作者：TRIVEDI, BHARAT K.、MOOS, WALTER、HAMILTON, HARRIET W.、PATT, WILLIAM C.

  DOI：——

  日期：——
• N6-substituted adenosines
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0179667B1

  公开（公告）日：1989-12-27