8-(2'-chloroethanoxy)quinoline | 54149-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-(2'-chloroethanoxy)quinoline
• 英文别名: 8-(2-chloroethyloxy)quinoline；8-(2-chloroethoxy)quinoline
• CAS: 54149-31-4
• 化学式: C₁₁H₁₀ClNO
• 分子量: 207.659
• InChiKey: NHZAYGYJDNCWHH-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C(Solv: chloroform (67-66-3); ethyl ether (60-29-7))
• 沸点：
  344.1±17.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-(2'-chloroethanoxy)quinoline 以 苯 为溶剂， 生成 2,3-Dihydropyrido[1,2,3-de]-1,4-benzoxazinium chloride
  参考文献：
  名称：

  2,3-二氢[1,4]恶嗪基[2,3,4-ij]溴化喹啉鎓的合成及其与氢氧化钠的反应

  摘要：

  喹啉-8-醇与1,2-二溴乙烷在二甲基甲酰胺中的反应生成2,3-二氢[1,4]-恶嗪基[2,3,4- ij ]溴化喹啉鎓，与氢氧化钠水溶液反应得到2， 3,4,5-四氢[1,4]恶嗪[2,3,4- ij ]喹啉，2,3,4,5-四氢[1,4]恶嗪[2,3,4- ij ]喹啉- 5-醇和2,3,4,5-四氢[1,4]恶嗪基[2,3,4- ij ]喹啉-5-酮。

  DOI：

  10.1134/s1070363218010218
• 作为产物：
  描述：

  2-(8-quinolinyloxy)ethanol 在 氯化亚砜 作用下， 生成 8-(2'-chloroethanoxy)quinoline
  参考文献：
  名称：

  2,3-二氢[1,4]恶嗪基[2,3,4-ij]溴化喹啉鎓的合成及其与氢氧化钠的反应

  摘要：

  喹啉-8-醇与1,2-二溴乙烷在二甲基甲酰胺中的反应生成2,3-二氢[1,4]-恶嗪基[2,3,4- ij ]溴化喹啉鎓，与氢氧化钠水溶液反应得到2， 3,4,5-四氢[1,4]恶嗪[2,3,4- ij ]喹啉，2,3,4,5-四氢[1,4]恶嗪[2,3,4- ij ]喹啉- 5-醇和2,3,4,5-四氢[1,4]恶嗪基[2,3,4- ij ]喹啉-5-酮。

  DOI：

  10.1134/s1070363218010218

文献信息

• Synthesis, Anticonvulsant and Antihypertensive Activities of 8-Substituted Quinoline Derivatives
  作者：Nithyanantham Muruganantham、Ramaiah Sivakumar、Navaneetharaman Anbalagan、Vedachalam Gunasekaran、Joseph Thomas Leonard

  DOI：10.1248/bpb.27.1683

  日期：——

  A series of 8-substituted quinolines were synthesized and tested against seizures induced by maximal electro shock (MES), pentylenetetrazole (scMet) and antihypertensive activities. Neurologic deficit was evaluated by the rotarod test. Among the newly synthesized derivatives, several compounds with a 2-hydroxypropyloxyquinoline moiety displayed excellent anticonvulsant and antihypertensive activities. Compound 20 (8-(3′-(4″-phenylpiperazino)-2′-hydroxypropyloxy)quinoline) was potent in both series as an anticonvulsive agent. 13 (8-(3′-piperazino)-2′-hydroxypropyloxyquinoline) and 14 (8-(3′-imidazolo)-2′-hydroxypropyloxyquinoline) showed very good anticonvulsant activities in the propanol series of compound, whereas in the ethane series, 1 (8-(2′-piperazino-ethanoxy)quinoline) and 2 (8-(2′-imidazolo-ethanoxy)quinoline) were the most active as anticonvulsive agents. Compounds 20 (8-(3′-(4″-phenylpiperazino)-2′-hydroxypropyloxy)quinoline), 13 (8-(3′-piperazino)-2′-hydroxypropyloxyquinoline) and 19 (8-(3′-(4″-ethylpiperazino)-2′-hydroxypropyloxy)quinoline) have shown excellent antihypertensive activity. They have significantly antagonized the pressor response elicited by adrenaline. These pharmacological results suggest that their anticonvulsant and antihypertensive effects may be correlated to the presence of β-blocking properties, and that those properties depend on the presence of aryloxypropanolamine.

  合成了一系列 8-取代喹啉并测试其对最大电击 (MES)、戊四唑 (scMet) 和抗高血压活性引起的癫痫发作的作用。通过转棒试验评估神经功能缺损。在新合成的衍生物中，几种带有2-羟丙氧基喹啉部分的化合物表现出优异的抗惊厥和抗高血压活性。化合物 20（8-（3'-（4''-苯基哌嗪）-2'-羟丙氧基）喹啉）在这两个系列中均作为有效的抗惊厥剂。 13(8-(3'-哌嗪)-2'-羟丙氧基喹啉)和14(8-(3'-咪唑基)-2'-羟丙氧基喹啉)在丙醇系列化合物中表现出很好的抗惊厥活性，而在乙烷系列中表现出很好的抗惊厥活性，1（8-（2'-哌嗪基-乙氧基）喹啉）和2（8-（2'-咪唑基-乙氧基）喹啉）是最有效的抗惊厥剂。化合物20(8-(3'-(4'-苯基哌嗪基)-2'-羟基丙氧基)喹啉)、13(8-(3'-哌嗪基)-2'-羟基丙氧基喹啉)和19(8-(3'-( 4'-乙基哌嗪基）-2'-羟丙氧基）喹啉）显示出优异的抗高血压活性。它们显着拮抗肾上腺素引起的升压反应。这些药理学结果表明，它们的抗惊厥和抗高血压作用可能与β-阻断特性的存在相关，并且这些特性取决于芳氧基丙醇胺的存在。
• Azacyclic carboxylic acid derivatives, their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0342635A1

  公开（公告）日：1989-11-23

  Novel O-alkylated oximes of the general formula I wherein R¹ and R² are optionally substituted aromatic or heteroaromatic rings, R³ is hydrogen or lower alkyl, R⁴ is a nitrogen containing, substituted ring or an amino group carrying a substituted ring, and n and m indepen­dently are 0, 1 or 2, are potent inhibitors of GABA re­uptake from the synaptic cleft.

  通式 I 的新型 O-烷基肟 其中 R¹ 和 R² 是任选取代的芳香族或杂芳环，R³ 是氢或低级烷基，R⁴ 是含氮的取代环或带有取代环的氨基，n 和 m 独立地为 0、1 或 2。
• Novel aryloxy-8-azabicyclo[3.2.1]oct-3-enes with 5-HT transporter and 5-HT1A affinity
  作者：Adam M. Gilbert、Thomas Coleman、Jason Kodah、Richard E. Mewshaw、Rosemary Scerni、Lee E. Schechter、Deborah L. Smith、Terrance H. Andree

  DOI：10.1016/j.bmcl.2004.08.030

  日期：2004.11

  Joining aryl 8-azabicyclo[3.2.1]oct-3-enes with aryloxyethanes and aryloxypropanes produces novel series of compounds 11 and 12 with potent 5-HT-T affinity and moderately potent 5-HT1A affinity. Moreover, several of these compounds possess functional 5-HT1A antagonism. Optimal compounds are, 4-indolyloxyethane 21, 4-indolyloxypropanes 25, and 27, which possess potent 5-HT-T affinity (5-HT-T K-i: 21: 1.2 nM, 25: 0.54 nM, 27: 0.38 nM) and good 5-HT1A affinity/antagonism (5-HT1A K-i, [S-35]GTPgammaS: E-max (%): 21: 111.1 nM, 0% 25: 173.2 nM, 0%; 27: 107 nM, 0%). (C) 2004 Elsevier Ltd. All rights reserved.
• Manufacture synthesis of 2,3-dihydropyrido[1,2,3-de]-1,4-benzoxazinium chlorides
  作者：I. P. Kovel'man、A. I. Tochilkin、O. A. Volkova、V. Z. Dubinskii

  DOI：10.1007/bf02219412

  日期：1994.12
• Kowelman I. R., Totschilkin A. I., Wolkowa O. A., Dubinskiii W. S., Khim.-farmach. zh., 29 (1995) N 5, S 48-49
  作者：Kowelman I. R., Totschilkin A. I., Wolkowa O. A., Dubinskiii W. S.

  DOI：——

  日期：——