(S)-1-(2-aminoethylamino)-3-(naphthylen-1-yloxy)propan-2-ol | 83860-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(2-aminoethylamino)-3-(naphthylen-1-yloxy)propan-2-ol
• 英文别名: (2S)-1-(2-aminoethylamino)-3-naphthalen-1-yloxypropan-2-ol
• CAS: 83860-54-2
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: ZXYQCRKQZAFPHH-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  BODIPY630/650−X-NHS ester 、 (S)-1-(2-aminoethylamino)-3-(naphthylen-1-yloxy)propan-2-ol 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以78%的产率得到(S)-N-[2-(2-hydroxy-3-(naphthalen-1-yloxy)propylamino)ethyl]-6-(2-(2-(4,4-difluoro-4,4a-dihydro-5-(thiophen-2-yl)-4-bora-3a,4a-diaza-s-indacene-3-yl)vinyl)phenoxyacetamido)hexanamide
  参考文献：
  名称：

  Synthesis and Characterization of High-Affinity 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene-Labeled Fluorescent Ligands for Human β-Adrenoceptors

  摘要：

  The growing practice of exploiting noninvasive fluorescence-based techniques to study G protein-coupled receptor pharmacology at the single cell and single molecule level demands the availability of high-quality fluorescent ligands. To this end, this study evaluated a new series of red-emitting ligands for the human beta-adrenoceptor family. Upon the basis of the orthosteric ligands propranolol, alprenolol, and pindolol, the synthesized linker-modified congeners were coupled to the commercially available fluorophore BODIPY 630/650-X. This yielded high-affinity beta-adrenoceptor fluorescent ligands for both the propranolol and alprenolol derivatives; however, the pindolol-based products displayed lower affinity. A fluorescent diethylene glycol linked propranolol derivative (18a) had the highest affinity (log K-D of -9.53 and -8.46 as an antagonist of functional beta 2- and beta 1-mediated responses, respectively). Imaging studies with this compound further confirmed that it can be employed to selectively label the human beta 2-adrenoceptor in single living cells, with receptor-associated binding prevented by preincubation with the nonfluorescent beta 2-selective antagonist 3-(isopropylamino)-1-[(7-methyl-4-indanyl)oxy]-butan-2-ol (ICI 118551) (J. Cardiovasc. Pharmacol. 1983, 5,430-437.)

  DOI：

  10.1021/jm2008562
• 作为产物：
  描述：

  S-(+)-Alpha-3-(1-萘氧基)-1,2-环氧丙烷 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (S)-1-(2-aminoethylamino)-3-(naphthylen-1-yloxy)propan-2-ol
  参考文献：
  名称：

  Synthesis and Characterization of High-Affinity 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene-Labeled Fluorescent Ligands for Human β-Adrenoceptors

  摘要：

  The growing practice of exploiting noninvasive fluorescence-based techniques to study G protein-coupled receptor pharmacology at the single cell and single molecule level demands the availability of high-quality fluorescent ligands. To this end, this study evaluated a new series of red-emitting ligands for the human beta-adrenoceptor family. Upon the basis of the orthosteric ligands propranolol, alprenolol, and pindolol, the synthesized linker-modified congeners were coupled to the commercially available fluorophore BODIPY 630/650-X. This yielded high-affinity beta-adrenoceptor fluorescent ligands for both the propranolol and alprenolol derivatives; however, the pindolol-based products displayed lower affinity. A fluorescent diethylene glycol linked propranolol derivative (18a) had the highest affinity (log K-D of -9.53 and -8.46 as an antagonist of functional beta 2- and beta 1-mediated responses, respectively). Imaging studies with this compound further confirmed that it can be employed to selectively label the human beta 2-adrenoceptor in single living cells, with receptor-associated binding prevented by preincubation with the nonfluorescent beta 2-selective antagonist 3-(isopropylamino)-1-[(7-methyl-4-indanyl)oxy]-butan-2-ol (ICI 118551) (J. Cardiovasc. Pharmacol. 1983, 5,430-437.)

  DOI：

  10.1021/jm2008562

文献信息

• Alkanolamine derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0057572A1

  公开（公告）日：1982-08-11

  Novel alkanolamine derivatives of the formula: wherein Ar is phenyl or naphthyl which is unsubstituted or which bears one or two substituents selected from halogen, trifluoromethyl, hydroxy, amino, nitro, carbamoyl, carbamoylmethyl and cyano, and alkyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkanoyl and alkanoylamino each of up to 6 carbon atoms, or Ar is 4-indolyl, 4-benzo[b]thienyl, 5-benzo[1,4]dioxanyl, 4-or 5-indanyl, 5- or 6- (1,2,3,4-tetrahydronaphthyl), 2,3-dihydro- xy-1,2,3,4-tetrahydronaphth-5-yl or 4-morpholino-1,2,5-thia- diazol-3-yl; wherein R is halogen; wherein A is alkylene of 2 to 6 carbon atoms; and wherein A2 is alkylene of 1 to 7 carbon atoms which is unsubstituted or bears a phenyl, hydroxy or carbamoyl substituent, or A2 is cycloalkylene of 3 to 6 carbon atoms; or acid-addition salts thereof. The compounds possess either 0-adrenergic blocking activity or diuretic activity or both such activities and may be used in the treatment of heart disease or hypertension. Also disclosed are processes for the manufacture of the compounds and pharmaceutical compositions containing them.

  式中的新型烷醇胺衍生物： 其中 Ar 是未被取代的苯基或萘基，或带有一个或两个选自卤素、三氟甲基、羟基、氨基、硝基、氨基甲酰基、氨基甲酰基甲基和氰基的取代基，以及烷基、烯基、烷氧基、烯氧基、烷硫基、烷酰基和烷酰氨基，每个取代基的碳原子数最多为 6、或 Ar 为 4-吲哚基、4-苯并[b]噻吩基、5-苯并[1,4]二噁烷基、4-或 5-茚基、5-或 6-（1,2,3,4-四氢萘基）、2,3-二氢-xy-1,2,3,4-四氢萘-5-基或 4-吗啉基-1,2,5-噻二唑-3-基； 其中 R 为卤素； 其中 A 为 2 至 6 个碳原子的亚烷基；以及 其中 A2 为未取代的或带有苯基、羟基或氨基甲酰基取代基的 1 至 7 个碳原子的亚烷基，或 A2 为 3 至 6 个碳原子的环亚烷基；或其酸加成盐。 这些化合物具有 0-肾上腺素能阻断活性或利尿活性或两种活性，可用于治疗心脏病或高血压。此外，还公开了制造这些化合物和含有这些化合物的药物组合物的工艺。
• PHOTOAFFINITY PROBES
  申请人：Promega Corporation

  公开号：US20200340982A1

  公开（公告）日：2020-10-29

  Provided herein are compositions and methods for photoaffinity labeling of molecular targets. In particular, probes that specifically interact with cellular targets based on their affinity and are then covalently linked to the cellular target via a photoreactive group (PRG) on the probe.