5-ethoxy-3,4-dihydroquinolin-2(1H)-one | 34685-03-5

• 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: 5-ethoxy-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 5-ethoxy-3,4-dihydro-1H-quinolin-2-one
• CAS: 34685-03-5
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: TZTZXWWQOGBZSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-ethoxy-3,4-dihydroquinolin-2(1H)-one 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  3,4-Dihydro-2(1H)-quinolinone as a Novel Antidepressant Drug:  Synthesis and Pharmacology of 1-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-3,4- dihydro-5-methoxy-2(1H)-quinolinone and Its Derivatives

  摘要：

  To develop a novel antidepressant drug with central nervous system-stimulating activity, me prepared a series of 1-[w-(4-substituted phenyl-1-piperazinyl)alkyl]-3,4-dihydro-2(1H)-quinlinone derivatives and examined their activities by their effects at 30 and 100 mg/kg po on the sleeping time of mice anesthetized with halothane and on the time required for recovery from coma induced in mice by cerebral concussion. We examined their binding affinities for a receptors by evaluating their ability to inhibit [H-3]-1,3-di(o-tolyl)guanidine ([H-3]DTG) binding to the rat whole brain membrane in comparison with three putative a receptor agonists: 1,3-di(o-tolyl)guanidine (DTG, 66), (+)-1,2,3,4,5,6-hexahydro-6,11-dimethylmethano-3-benzazecin-8-ol (SKF10,047, 67), and (+)-1,2,3,4,5,6-hexahydro-6, 11-dimethyl-3(3 -methyl-2-butenyl)-2,6-methano-3-benzazecin-8-ol (pentazocine, 68). Among the series of derivatives, 1-3-[4-(3-chlorophenyl)-1-piperazinyl]-3p linone hydrochloride (34b) and its mesylate (34c), at a dose of 30 mg/kg po, reduced the sleeping time and the time for recovery from coma and they inhibited [H-3]DTG binding for a receptors. The putative a receptor agonists reduced the sleeping time and the time for recovery from coma whereas two a receptor antagonists, alpha-(4-fluorophenyl)-4-(5-fluoro-2-pyrimidinyl) piperazinebutanol hydrochloride (BMY14802, 69) and cis-9-[3-(3,5-dimethyl-1-piperazinyl)propyl]carbazole dihydrochloride (rimcazole, 70), were inactive in the two tests. Preadministration of the putative a receptor antagonists 69 (3 mg/kg po) and 70 (30 mg/kg po) completely antagonized the actions of 34b and the a receptor agonists in the test for recovery from coma. These results suggested that 34b and 34c are a receptor agonists. Furthermore, a single administration of 1 and 10 mg/kg po 34b and 34c showed antidepressant-like activity by reducing the immobility time in the forced-swimming test with mice, while a tricyclic antidepressant, 10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine hydrochloride (imipramine, 1) (10 and 30 mg/kg po), did not reduce the time after a single administration. 1 reduced the time after repeated administration of 30 mg/kg po once a day for 4 days. The structure-activity relationship of the series of compounds is also discussed.

  DOI：

  10.1021/jm980333v
• 作为产物：
  描述：

  溴乙烷 、 5-羟基-3,4-二氢-2-喹啉酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以98%的产率得到5-ethoxy-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  的3,4-二氢喹啉-2（1氧化芳ħ） -酮向喹啉-2（1个H ^） -酮使用过渡金属活化过硫酸盐

  摘要：

  无机过硫酸盐被确定为通过活化容易获得的过渡金属（如铁和铜）活化3,4-二氢喹啉-2（1 H）-的一种有效的氧化芳香化试剂。利用符合绿色化学要求的可行方案，以100 g的规模，以80％的分离产率制备了brexpiprazole的关键中间体（7-（4-氯丁氧基）喹啉-2（1 H）-one 2） ，并以52–89％的产率证明了具有各种官能团的不同quinolin-2（1 H）-one衍生物。

  DOI：

  10.1021/acs.joc.9b00756

文献信息

• Oxidative Aromatization of 3,4-Dihydroquinolin-2(1<i>H</i>)-ones to Quinolin-2(1<i>H</i>)-ones Using Transition-Metal-Activated Persulfate Salts
  作者：Weiming Chen、Changliang Sun、Yan Zhang、Tianwen Hu、Fuqiang Zhu、Xiangrui Jiang、Melkamu Alemu Abame、Feipu Yang、Jin Suo、Jing Shi、Jingshan Shen、Haji A. Aisa

  DOI：10.1021/acs.joc.9b00756

  日期：2019.7.5

  of 3,4-dihydroquinolin-2(1H)-ones through the activation of readily available transition metals, such as iron and copper. The feasible protocol conforming to the requirement of green chemistry was utilized in the preparation of the key intermediate (7-(4-chlorobutoxy)quinolin-2(1H)-one 2) of brexpiprazole in 80% isolated yield on a 100 g scale, and different quinolin-2(1H)-one derivatives with various

  无机过硫酸盐被确定为通过活化容易获得的过渡金属（如铁和铜）活化3,4-二氢喹啉-2（1 H）-的一种有效的氧化芳香化试剂。利用符合绿色化学要求的可行方案，以100 g的规模，以80％的分离产率制备了brexpiprazole的关键中间体（7-（4-氯丁氧基）喹啉-2（1 H）-one 2） ，并以52–89％的产率证明了具有各种官能团的不同quinolin-2（1 H）-one衍生物。
• 4-Amino-5-Cyanopyrimidine Derivatives
  申请人：Kato Masaya

  公开号：US20080182854A1

  公开（公告）日：2008-07-31

  The present invention provides 4-amino-5-cyanopyrimidine derivatives of the formula: wherein R 1 , R 2 and R 3 are defined herein, or pharmaceutically acceptable salts thereof, having a safe and potent adenosine A2a receptor agonistic activity; and also provides an adenosine A2a receptor agonist, an intraocular pressure reducing agent, or a medicine for treating glaucoma, etc., which comprises the compound as an active ingredient.

  本发明提供了式子如下的4-氨基-5-氰基嘧啶衍生物：其中R1、R2和R3如本文所定义，或其药学上可接受的盐，具有安全有效的腺苷A2a受体激动活性；同时还提供了一种腺苷A2a受体激动剂、降眼压剂或治疗青光眼等药物，其包含该化合物作为活性成分。
• Pyrimidine Compounds and Use Thereof
  申请人：Geneste Herve

  公开号：US20080161322A1

  公开（公告）日：2008-07-03

  The invention relates to pyrimidine compounds of general formula (I), and to the use of these compounds of general formula (I) and of the physiologically compatible acid addition salts of compounds (I) for producing a pharmaceutical agent for treating diseases, which respond to the influence of dopamine D 3 receptor antagonists or agonists.

  本发明涉及一般式（I）的嘧啶化合物，以及使用这些一般式（I）化合物和化合物（I）的生理兼容酸加合盐来生产用于治疗对多巴胺D3受体拮抗剂或激动剂产生反应的疾病的制药剂。
• PYRIMIDINE COMPOUNDS AND USE THEREOF
  申请人：Geneste Hervè

  公开号：US20110118232A1

  公开（公告）日：2011-05-19

  The invention relates to novel pyrimidine compounds of general formula (I), in which: A represents a group C═W or CR f R g ; B represents a chemical bond or a group CR h R i ; X represents O, S, a group N—R k or a group CR m R n ; D represents C═O or a chemical bond; E represents a linear or branched 2- to 10-membered alkylene chain that, as members of a chain, can have 1 or 2 non-adjacent heteroatom group(s) K, which is selected among O, S, S(O), S(O) 2 and N—R p and which can comprise a carbonyl group and/or a cycloalkanediyl group and/or a double or triple bond; W represents oxygen or sulfur; Z, together with the carbon atoms, to which it is bound, represents a condensed, optionally substituted 5-, 6- or 7-membered carbocyclic compound or heterocyclic compound that has 1, 2, 3 or 4 heteroatoms, which are selected among N, O and S; J represents CH 2 , CH 2 —CH 2 or CH 2 —CH 2 —CH 2 ; M represents CH or N; Y represents CH 2 , CH 2 —CH 2 or CH 2 —CH 2 —CH 2 or M-X, together, represent CH═C or CH 2 —CH═C; n is 0 or 1, and; R a , R b , R c , R d , R e , R f , R g , R h , R i , R k , R p , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meanings cited in the claims and in the description. The invention also relates to the physiologically compatible acid addition salts of the aforementioned compounds, and to the use of these compounds of general formula (I) and of the physiologically compatible acid addition salts of compounds (I) for producing a pharmaceutical agent for treating diseases, which respond to the influence of dopamine D 3 receptor antagonists or agonists.

  本发明涉及一种新的嘧啶化合物，其通式为（I），其中：A代表C═W或CRfRg基团；B代表化学键或CRhRi基团；X代表O、S、N—Rkor CRmRn基团；D代表C═O或化学键；E代表线性或支链2-10位碳原子的烷基链，作为链的成员，可以有1或2个非相邻杂原子基团K，该基团从O、S、S（O）、S（O）2和N—Rp中选择，并且可以包含一个羰基基团和/或一个环烷二基基团和/或一个双键或三键；W代表氧或硫；Z与其结合的碳原子一起表示一种紧凑的、可选地取代的5、6或7位成员的碳环化合物或杂环化合物，其中有1、2、3或4个杂原子，选择自N、O和S；J代表CH2、CH2—CH2或CH2—CH2—CH2；M代表CH或N；Y代表CH2、CH2—CH2或CH2—CH2—CH2或M-X，共同表示CH═C或CH2—CH═C；n为0或1；Ra、Rb、Rc、Rd、Re、Rf、Rg、Rh、Ri、Rk、Rp、R1、R2、R3、R4、R5和R6在权利要求书和说明书中所述。本发明还涉及上述化合物的生理相容性酸盐以及使用通式（I）化合物和化合物（I）的生理相容性酸盐制备用于治疗对多巴胺D3受体拮抗剂或激动剂有反应的疾病的药物的用途。
• NITROGEN-CONTAINING COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF ATRIAL FIBRILLATION
  申请人：Oshima Kunio

  公开号：US20120225866A1

  公开（公告）日：2012-09-06

  The present invention provides a novel diazepine compound that blocks the I Kur current or the Kv1.5 channel potently and more selectively than other K + channels. The present invention relates to a diazepine compound represented by General Formula (1) or a salt thereof, wherein R 1 , R 2 , R 3 , and R 4 are each independently hydrogen, lower alkyl, cyclo lower alkyl or lower alkoxy lower alkyl; R 2 and R 3 may be linked to form lower alkylene; A 1 is lower alkylene optionally substituted with one or more substituents selected from the group consisting of hydroxyl and oxo; Y 1 and Y 2 are each independently —N═ or —CH═; and R 5 is group represented by wherein R 6 and R 7 are each independently hydrogen or organic group; R 6 and R 7 may be linked to form a ring together with the neighboring group —X A —N—X B —; X A and X B are each independently a bond, lower alkylene, etc.

  本发明提供了一种新型的二氮杂环化合物，它可以有效地阻断IKur电流或Kv1.5通道，并比其他K+通道更具选择性。本发明涉及一种由通式（1）表示的二氮杂环化合物或其盐，其中R1、R2、R3和R4各自独立地表示氢、低碳基、环状低碳基或低烷氧基低碳基；R2和R3可以连接形成低碳烷基；A1是低碳烷基，可选地取代一个或多个羟基和氧代基；Y1和Y2各自独立地表示—N═或—CH═；R5是由下式表示的基：其中R6和R7各自独立地表示氢或有机基团；R6和R7可以与相邻的基团—XA—N—XB—一起形成环；XA和XB各自独立地表示键、低碳烷基等。