(+/-)-1-(2-aminoethylamino)-3-(naphthylen-1-yloxy)propan-2-ol | 60145-65-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-1-(2-aminoethylamino)-3-(naphthylen-1-yloxy)propan-2-ol
• 英文别名: N-[2-hydroxy-3-(1-naphthoxy)propyl]ethylenediamine；1-β-aminoethylamino-3-α-naphthoxypropan-2-ol；1-beta-Aminoethylamino-3-alpha-naphthyloxypropan-2-ol；1-(2-aminoethylamino)-3-naphthalen-1-yloxypropan-2-ol
• CAS: 60145-65-5
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: ZXYQCRKQZAFPHH-UHFFFAOYSA-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：

  ethyl β-(3,5-diamino-6-chloropyrazine-2-carboxamido)propionate 、 (+/-)-1-(2-aminoethylamino)-3-(naphthylen-1-yloxy)propan-2-ol 生成 3,5-diamino-6-chloro-{N-β-[N-(2-hydroxy-3-α-naphthoxy-propylamino)ethylcarbamoyl]-ethyl}pyrazine-2-carboxamide hydrogen oxalate
  参考文献：
  名称：

  Alkanolamine derivatives

  摘要：

  新型烷醇胺衍生物的通式为：##STR1## 其中Ar为苯基或萘基，未取代或带有一个或两个选自卤素、三氟甲基、羟基、氨基、硝基、氨甲酰基、氨甲酰甲基和氰基的取代基，以及最多含有6个碳原子的烷基、烯基、烷氧基、烯氧基、烷硫基、烷酰基和烷酰胺基；或者Ar为4-吲哚基、4-苯并[b]噻吩基、5-苯并[1,4]二氧六环基、4-或5-茚满基、5-或6-1,2,3,4-四氢萘基、2,3-二羟基-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.sup.1为含有2至6个碳原子的亚烷基；其中A.sup.2为含有1至7个碳原子的亚烷基，未取代或带有苯基、羟基或氨甲酰基取代基，或者A.sup.2为含有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β-肾上腺素能阻滞活性或利尿活性或两者兼有，可用于治疗心脏病或高血压。还公开了这些化合物的制备方法以及含有它们的药物组合物。

  公开号：

  US04399138A1
• 作为产物：
  描述：

  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 (+/-)-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

• Dihydropyridine alkanol amines, process for their preparation and pharmaceutical compositions containing them
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0194752A1

  公开（公告）日：1986-09-17

  A dihydropyridine of the formula:- wherein R' and R2 each is alkyl or alkoxyalkyl, wherein R3 is alkyl, wherein benzene ring A bears one or more substituents selected from halogeno, cyano, nitro, trifluoromethyl and alkyl or bears the substituent =N-0-N= attached to the 2- and 3-positions; wherein Ar is phenyl, naphthul, tetrahydronaphthyl, indanyl or indenyl which is unsubstituted or which bears one or more substituents or Ar is a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from oxygen, nitrogen and sulphur, which ring is saturated or unsaturated, and which ring is unsubstituted or bears one or more substituents, wherein p is 0 or 1; wherein q is 1, 2, 3 or 4; wherein X is -0-, -NH-, -NHCO- or -CONH-; and wherein Y is straight-or branched-chain alkylene which may optionally be interrupted by one or two groups selected from oxygen, sulphur, imino, substituted imino, phenylene, substituted phenylene, pyridylene, cycloalkylene, 1,4-piperazinediyl, 1,4-piperidinediyl and amido groups; or an acid-addition salt thereof, processes for their manufacture and pharmaceutical compositions containing them. The compounds possess either beta-adrenergic blocking or calcium ion slow channel blocking properties or both such properties, and may be used in the treatment of hypertension.

  式中的一种二氢吡啶：- 其中 R' 和 R2 各为烷基或烷氧基烷基、 其中 R3 为烷基，苯环 A 具有一个或多个选自卤素、氰基、硝基、三氟甲基和烷基的取代基，或在 2 位和 3 位上具有取代基 =N-0-N= ； 其中 Ar 是苯基、萘基、四氢萘基、茚基或未取代的茚基，或带有一个或多个取代基 或 Ar 是含有 1、2 或 3 个选自氧、氮和硫的杂原子的 5 或 6 元杂环，该环饱和或不饱和，且该环未被取代或带有一个或多个取代基，其中 p 为 0 或 1； 其中 q 为 1、2、3 或 4； 其中 X 为-0-、-NH-、-NHCO-或-CONH-； 其中 Y 为直链或支链亚烷基，可任选被一个或两个选自氧、硫、亚氨基、取代亚氨基、亚苯基、取代亚苯基、吡啶基、环亚烷基、1,4-哌嗪二基、1,4-哌啶二基和氨基基团的基团打断；或其酸加成盐、其制造工艺和含有它们的药物组合物。这些化合物具有β-肾上腺素能阻断特性或钙离子慢通道阻断特性，或同时具有这两种特性，可用于治疗高血压。
• DE2745222
  申请人：——

  公开号：——

  公开（公告）日：——
• ——
  作者：Donatella Boschi、Antonella Di Stilo、Clara Cena、Marco Lolli、Roberta Fruttero、Alberto Gasco

  DOI：10.1023/a:1012136030849

  日期：——

  Purpose. A series of derivatives having a propranolol-like moiety linked to NO-donor furoxan substructures were synthesized. The main objective of this investigation was to obtain agents with mixed No-dependent vasodilating and beta-blocking activities.Methods. Most of the target compounds were synthesized from the appropriate furoxans bearing XCH2CH2NH2 (X = O, S, SO2) chains at the 4 position of the ring, using AI(C2H5)(3) in methylene chloride solution and (+/-)2,3-epoxypropyl 1-naphtyl ether. Two of the final products (X = CONH) were obtained by coupling the appropriate furoxancarboxylic acids with N-[2-hydroxy-3-(1-naphthoxy)propyl]ethylenediamine. beta(1)- and beta(2)-blocking activities were examined on isolated guinea pig right atria and on guinea pig trachea respectively. Vasodilating properties were assessed on endothelium denuded strips of rat aortaResult. Some derivatives behave as well balanced "hybrids" displaying NO-dependent vasodilating and beta-blocking properties in the same concentration range. Some others display either prevalent beta-blocking or vasodilating activity. Generally speaking hybrid formation lowers the affinity for beta-receptors, in particular for beta(2)-type, to give an increase in beta(1)/beta(2) selectivity.Conclusions. The furoxan system is a flexible tool in designing analogues of propranolol whose NO-donating and beta-blocking properties are modulated over a wide range.
• US4399138A
  申请人：——

  公开号：US4399138A

  公开（公告）日：1983-08-16
• US4550111A
  申请人：——

  公开号：US4550111A

  公开（公告）日：1985-10-29