2-(5-chloroquinolin-8-yloxy)ethanol | 82488-72-0

• 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: 2-(5-chloroquinolin-8-yloxy)ethanol
• 英文别名: 2-(5-chloro-[8]quinolyloxy)-ethanol；2-(5-Chlor-[8]chinolyloxy)-aethanol；2-[(5-Chloro-8-quinolinyl)oxy]-1-ethanol；8-(2-hydroxyethyl)oxy-5-chloroquinoline；2-(5-Chloroquinolin-8-yl)oxyethanol
• CAS: 82488-72-0
• 化学式: C₁₁H₁₀ClNO₂
• 分子量: 223.659
• InChiKey: QNEJISASQSRCCJ-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C(Solv: ethanol (64-17-5))
• 沸点：
  400.9±30.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 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：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氯-8-羟基喹啉 以48%的产率得到2-(5-chloroquinolin-8-yloxy)ethanol
  参考文献：
  名称：

  Certain aryl-aliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases

  摘要：

  通式（I）的化合物： 其中变量如规范中定义的那样，对于预防或治疗人类或动物中与血清素相关，特别是5-HT2受体相关的疾病是有用的，特别是与5-HT2c受体相关的疾病，尤其是与进食障碍、记忆障碍、精神分裂症、情绪障碍、焦虑障碍、疼痛、性功能障碍和尿液障碍等疾病相关的疾病。

  公开号：

  US06465467B1

文献信息

• Substituted oxines inhibit endothelial cell proliferation and angiogenesis
  作者：Shridhar Bhat、Joong Sup Shim、Feiran Zhang、Curtis Robert Chong、Jun O. Liu

  DOI：10.1039/c2ob06978d

  日期：——

  Two substituted oxines, nitroxoline (5) and 5-chloroquinolin-8-yl phenylcarbamate (22), were identified as hits in a high-throughput screen aimed at finding new anti-angiogenic agents. In a previous study, we have elucidated the molecular mechanism of antiproliferative activity of nitroxoline in endothelial cells, which comprises of a dual inhibition of type 2 human methionine aminopeptidase (MetAP2)

  两个取代的oxines， 硝基氧( 5 ) 和5-氯喹啉-8-基苯基氨基甲酸酯( 22 )，在旨在寻找新的抗血管生成剂的高通量筛选中被鉴定为命中。在先前的研究中，我们阐明了抗增殖活性的分子机制硝基氧 在内皮细胞中，包括对 2 型人的双重抑制 蛋氨酸氨肽酶 (MetAP2) 和 Sirtuin 1 (SIRT1)。构效关系研究 (SAR)硝基氧提供了许多惊喜，其中微小的修改产生了对人脐静脉内皮细胞 (HUVEC) 效力增加的 oxine 衍生物，但具有完全不同的未知机制。例如，5-nitrosoquinolin-8-ol( 33 ) 以亚微摩尔 IC 50抑制 HUVEC 生长，但不影响 MetAP2 或 MetAP1，仅对 SIRT1 显示出微弱的抑制作用。其他亚微摩尔抑制剂是5-aminoquinolin-8-ol( 34 ) 和8-磺胺喹啉( 32 )。氨基磺酸盐衍生物硝基氧( 48 )
• CERTAIN ARYLALIPHATIC AND HETEROARYL-ALIPHATIC PIPERAZINYL PYRAZINES AND THEIR USE IN THE TREATMENT OF SEROTONIN-RELATED DISEASES
  申请人：Biovitrum, AB, a Stockholm, Sweden corporation

  公开号：US20040242554A1

  公开（公告）日：2004-12-02

  The invention relates to compounds of the general formula (I): 1 wherein Ar is optionally substituted aryl or heteroaryl; A is (i) —O—, —S—, —SO 2 —, —NH—, (ii) a C 1-4 -alkyl- or C 1-6 -acyl-substituted nitrogen atom or (iii) a C 1-8 -alkylene chain or a heteroalkylene chain having 2 to 8 chain atoms, which optionally contains at least one unsaturation, and which may be substituted and/or contain a bridge to form a saturated or partially or fully unsaturated ring having 3-8 ring members; B is —C(R 4 )(R 5 )—, —OC(R 4 )(R 5 )—, —N(R 6 )C(R 4 )(R 5 )—, —N(R 6 )—, —O—, —S— or —SO 2 —; R is optionally substituted C 3-8 -cycloalkyl, aryl or heteroaryl; R 1 is (i) a saturated or unsaturated azacyclic or aminoazacyclic ring, or a saturated diazacyclic or aminodiazacyclic ring, which has 4 to 7 ring members, or a saturated aminoazabicyclic, azabicyclic or diazabicyclic ring which has 7 to 10 ring members, which rings optionally are substituted in one or more positions, or a group —[C(R 4 )(R 5 )] x N(R 2a )(R 3a )]; R 2a , R 3a , R 4 , R 5 , R 6 and x are as defined in the claims, and n is 0 or 1; and pharmaceutically acceptable salts, hydrates and prodrug forms thereof. The compounds may be prepared by per se conventional methods and can be used for treating a human or animal subject suffering from a serotonin-related disorder, such as eating disorders, especially obesity, memory, disorders, schizophrenia, mood disorders, anxiety disorders, pain, sexual dysfunctions, and urinary disorders. The invention also relates to such use as well as to pharmaceutical compositions comprising a compound of formula (I).

  本发明涉及通式（I）的化合物：其中Ar是可选取代的芳基或杂芳基；A是（i）—O—，—S—，—SO2—，—NH—，（ii）C1-4烷基或C1-6酰基取代的氮原子，或（iii）C1-8烷基链或具有2-8链原子的杂烷基链，其可选包含至少一个不饱和度，并且可以取代和/或含有桥接以形成具有3-8环成员的饱和或部分或完全不饱和环；B是—C（R4）（R5）—，—OC（R4）（R5）—，—N（R6）C（R4）（R5）—，—N（R6）—，—O—，—S—或—SO2—；R是可选取代的C3-8环烷基，芳基或杂芳基；R1是（i）饱和或不饱和的氮杂环或氨基氮杂环，或饱和的二氮杂环或氨基二氮杂环，其具有4-7环成员，或饱和的氨基氮杂双环、氮杂双环或二氮杂双环，其具有7-10环成员，这些环在一个或多个位置上可选取代，或者是一个组—[C（R4）（R5）]xN（R2a）（R3a）；R2a，R3a，R4，R5，R6和x如权利要求中所定义，n为0或1；以及其药学上可接受的盐、水合物和前药形式。这些化合物可以通过常规方法制备，并可用于治疗患有血清素相关疾病的人或动物，例如进食障碍，尤其是肥胖症，记忆障碍，精神分裂症，情绪障碍，焦虑障碍，疼痛，性功能障碍和泌尿系统疾病。本发明还涉及这种用途以及包含通式（I）化合物的制药组合物。
• Certain arylaliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases
  申请人：Biovitrum, AB, a Stockholm, Sweden corporation

  公开号：US20030092694A1

  公开（公告）日：2003-05-15

  The invention relates to compounds of the general formula (I): 1 wherein Ar is optionally substituted aryl or heteroaryl; A is (i) —O—, —S—, —SO 2 —, —NH—, (ii) a C 1-4 -alkyl- or C 1-6 -acyl-substituted nitrogen atom or (iii) a C 1-8 -alkylene chain or a heteroalkylene chain having 2 to 8 chain atoms, which optionally contains at least one unsaturation, and which may be substituted and/or contain a bridge to form a saturated or partially or fully unsaturated ring having 3-8 ring members; B is —C(R 4 )(R 5 )—, —OC(R 4 )(R 5 )—, —N(R 6 )C(R 4 )(R 5 )—, —N(R 6 )—, —O—, —S— or —SO 2 —; R is optionally substituted C 3-8 -cycloalkyl, aryl or heteroaryl; R 1 is (i) a saturated or unsaturated azacyclic or aminoazacyclic ring, or a saturated diazacyclic or aminodiazacyclic ring, which has 4 to 7 ring members, or a saturated aminoazabicyclic, azabicyclic or diazabicyclic ring which has 7 to 10 ring members, which rings optionally are substituted in one or more positions, or a group —[C(R 4 )(R 5 )] x N(R 2a )(R 3a )]; R 2a , R 3a , R 4 , R 5 , R 6 and x are as defined in the claims, and n is 0 or 1; and pharmaceutically acceptable salts, hydrates and prodrug forms thereof The compounds may be prepared by per se conventional methods and can be used for treating a human or animal subject suffering from a serotonin-related disorder, such as eating disorders, especially obesity, memory disorders, schizophrenia, mood disorders, anxiety disorders, pain, sexual dysfunctions, and urinary disorders The invention also relates to such use as well as to pharmaceutical compositions comprising a compound of formula (I)

  本发明涉及一般式（I）的化合物：其中Ar是可选取代的芳基或杂环芳基；A是（i）-O-，-S-，-SO2-，-NH-，（ii）C1-4-烷基或C1-6-酰基取代的氮原子或（iii）C1-8-烷基链或具有2至8个链原子的杂烷基链，可选地含有至少一个不饱和度，并且可以取代和/或包含桥以形成具有3-8个环成员的饱和或部分或完全不饱和的环；B是-C（R4）（R5）-，-OC（R4）（R5）-，-N（R6）C（R4）（R5）-，-N（R6）-，-O-，-S-或-SO2-；R是可选取代的C3-8-环烷基，芳基或杂环芳基；R1是（i）饱和或不饱和的氮杂环或氨基氮杂环环，或具有4至7个环成员的饱和二氮杂环或氨基二氮杂环环，或具有7至10个环成员的饱和氨基氮杂双环、氮杂双环或二氮杂双环环，这些环可选地在一个或多个位置上取代，或一个组-［C（R4）（R5）］xN（R2a）（R3a）；其中R2a，R3a，R4，R5，R6和x如所述，n为0或1；以及其药学上可接受的盐、水合物和前药形式。这些化合物可以通过常规方法制备，并可用于治疗患有血清素相关疾病的人类或动物受试者，例如进食障碍，特别是肥胖，记忆障碍，精神分裂症，情绪障碍，焦虑症，疼痛，性功能障碍和泌尿系统疾病。本发明还涉及这种用途以及包含式（I）化合物的药物组合物。
• QUINOLINE COMPOUNDS AS INHIBITORS OF ANGIOGENESIS, HUMAN METHIONINE AMINOPEPTIDASE, AND SIRT1, AND METHODS OF TREATING DISORDERS
  申请人：Liu Jun O.

  公开号：US20110301163A1

  公开（公告）日：2011-12-08

  Described herein are methods of inhibiting methionine aminopeptidase or SirT1, inhibiting angiogenesis, and treating disorders (or symptoms thereof) associated with methionine aminopeptidase, SirT1 and/or angiogenesis, wherein a compound of the invention is administered to a subject.

  本文描述了抑制甲硫氨酸氨肽酶或SirT1，抑制血管生成以及治疗与甲硫氨酸氨肽酶、SirT1和/或血管生成有关的疾病（或其症状）的方法，其中将本发明的化合物给予受试者。
• Herbicidal composition
  申请人：Syngenta Participations AG

  公开号：EP1842426A2

  公开（公告）日：2007-10-10

  A herbicidal composition, comprising a) a compound of formula I or an agronomically acceptable salt of that compound, and b) a synergistically effective amount of one or more compounds selected from ametryn, simazine, terbutryn, foramsulfuron, trifloxysulfuron, metolachlor, S-metolachlor, alachlor, acetochlor, flufenacet, dimethenamid, S-dimethenamid, pethoxamid, flumetsulam, metosulam, pyridate, pyridafol, dicamba and salts thereof, procarbazone, glufosinate, fluthiacet, imazamox, imazethapyr, nicosulfuron, primisulfuron-methyl, rimsulfuron, halosulfuron, cloransulam, clomazone, diclosulam, 2,4-D, florasulam, flumiclorac, bromoxynil, sethoxydim, ioxynil, tepraloxydim, carfentrazone, clethodim, sulfentrazone, imazaquin, sulcotrione, imazapyr, mesotrione, thifensulfuron, isoxaflutole, prosulfuron, isoxachlortole, bentazone, iodosulfuron, prohexadione, diflufenzopyr, flurtamone, butylate, flumioxazin, fentrazamide, benzfendizone, isopropazole, fluazolate, aclonifen, tritosulfuron, cinidon-ethyl, mesotrione + terbuthylazine, metolachlor + terbuthylazine, S-metolachlor + terbuthylazine, paraquat, ketospiradox, aminopyralid, amicarbazone and azafenidin. The compositions according to the invention may also comprise a safener.

  一种除草组合物，包括 a) 式 I 的化合物 或该化合物的农艺学上可接受的盐，以及 b) 增效有效量的一种或多种化合物，选自莠去津，西玛津，特丁净，福来嘧磺隆，三氟磺隆，甲草胺，S-甲草胺，甲草胺，乙草胺，氟草胺，二甲戊草胺，S-二甲戊草胺，醚菊酯，氟磺胺草醚、甲磺隆、吡啶甲酸盐、哒螨醇、麦草畏及其盐类、丙溴磷、草铵膦、氟噻草胺、咪鲜胺、咪鲜胺、烟嘧磺隆、甲基吡嘧磺隆、嘧磺隆、氟磺隆、氯磺隆、氯马宗、双氯磺隆、2,4-D、氟磺胺草醚、氟虫腈、溴虫腈、噻虫嗪、噻虫嗪、噻嗪酮、噻虫嗪、噻虫嗪、噻虫啉、异噁唑禾草灵、丙磺隆、异噁唑禾草灵、苄嘧磺隆、碘苯磺隆、丙溴磷、氟唑禾草灵、丁酯氟噻草胺、戊唑醇、苯醚甲环唑、异丙唑醇、氟唑醇、烯唑醇、三唑磺隆、西尼隆、甲磺隆＋特丁硫嗪、甲草胺＋特丁硫嗪、S-甲草胺＋特丁硫嗪、百草枯、Ketospiradox、氨吡啉酮、脒草酮和唑草酮。根据本发明的组合物还可以包含一种安全剂。