4-(2-hydroxyethyl)quinolin-2-(1H)-one | 5322-08-7

• 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: 4-(2-hydroxyethyl)quinolin-2-(1H)-one
• 英文别名: 4-(2-hydroxyethyl)-2(1H)-quinolinone；4-(2-Hydroxyethyl)-carbostyril；4-(2-hydroxy-ethyl)-1H-quinolin-2-one；4-(2-hydroxyethyl)-1H-quinolin-2-one
• CAS: 5322-08-7
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: SKSTXQZGIMZYNH-UHFFFAOYSA-N

物化性质

• 熔点：
  211-213 °C
• 沸点：
  425.5±45.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxyethyl)quinolin-2-(1H)-one 在 氢溴酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 rac-(1aS,7bS,11aS)-10-benzyl-1,9,10,11a-tetrahydro-1aH-pyrido[4',3':2,3']-cyclobuta[1,2-c]quinoline-2,11(3H,8H)-dione
  参考文献：
  名称：

  Photochemistry of 4-(2‘-Aminoethyl)quinolones:  Enantioselective Synthesis of Tetracyclic Tetrahydro-1aH-pyrido[4‘,3‘:2,3]- cyclobuta[1,2-c] Quinoline-2,11(3H,8H)-diones by Intra- and Intermolecular [2 + 2]-Photocycloaddition Reactions in Solution

  摘要：

  Enantioselective [2 + 2]-photocycloaddition reactions on 4-(2'-aminoethyl) quinolones in solution were studied using the enantiomerically pure complexing agent 1 as source of chirality. The intermolecular reactions of fully N-protected substrates 5a-5c with different 2-alkyl-substituted acrylates 12-15 represent the first systematic study on the diastereoselectivity of their intermolecular [2 + 2]-photocycloadditions to unsymmetrically 1,1-disubstituted olefins (75-91% yield, d.r. = 58/42-95/5). N-Benzylic-protected photoproducts exo-16a/b-19a/b could easily be converted into lactams 20a/b-23a/b by a sequence of Boc deprotection and thermal lactamization (74-98% yield). Identical products 20a-22a were directly accessible by the intramolecular [ 2 + 2]-photocycloaddition of acrylic acid amides 2-4 (41-61% yield). The suitability of both pathways for an enantioselective reaction variant was proven (70-92% ee). Thus, tetracyclic lactams possessing the carbon framework C were obtained with good yields and enantio-selectivities of up to 92% ee in intramolecular reactions. Comparative investigation of both routes showed that quinolone dimerization was the single most decisive factor preventing a complete chirality transfer. Functional group manipulations were successfully conducted with the primary photoproduct exo-17a. Finally, a new and unexpected type of benzylic hydrogen abstraction-radical cyclization reaction was discovered for substrate 5a, which explains the photochemical instability of substrates 2-5 under short wavelength irradiation (lambda = 300 nm).

  DOI：

  10.1021/jo0606608
• 作为产物：
  描述：

  2-羟基-4-甲基喹啉 在 lithium aluminium tetrahydride 、 正丁基锂 、 氯化亚砜 作用下， 生成 4-(2-hydroxyethyl)quinolin-2-(1H)-one
  参考文献：
  名称：

  Photochemistry of 4-(2‘-Aminoethyl)quinolones:  Enantioselective Synthesis of Tetracyclic Tetrahydro-1aH-pyrido[4‘,3‘:2,3]- cyclobuta[1,2-c] Quinoline-2,11(3H,8H)-diones by Intra- and Intermolecular [2 + 2]-Photocycloaddition Reactions in Solution

  摘要：

  Enantioselective [2 + 2]-photocycloaddition reactions on 4-(2'-aminoethyl) quinolones in solution were studied using the enantiomerically pure complexing agent 1 as source of chirality. The intermolecular reactions of fully N-protected substrates 5a-5c with different 2-alkyl-substituted acrylates 12-15 represent the first systematic study on the diastereoselectivity of their intermolecular [2 + 2]-photocycloadditions to unsymmetrically 1,1-disubstituted olefins (75-91% yield, d.r. = 58/42-95/5). N-Benzylic-protected photoproducts exo-16a/b-19a/b could easily be converted into lactams 20a/b-23a/b by a sequence of Boc deprotection and thermal lactamization (74-98% yield). Identical products 20a-22a were directly accessible by the intramolecular [ 2 + 2]-photocycloaddition of acrylic acid amides 2-4 (41-61% yield). The suitability of both pathways for an enantioselective reaction variant was proven (70-92% ee). Thus, tetracyclic lactams possessing the carbon framework C were obtained with good yields and enantio-selectivities of up to 92% ee in intramolecular reactions. Comparative investigation of both routes showed that quinolone dimerization was the single most decisive factor preventing a complete chirality transfer. Functional group manipulations were successfully conducted with the primary photoproduct exo-17a. Finally, a new and unexpected type of benzylic hydrogen abstraction-radical cyclization reaction was discovered for substrate 5a, which explains the photochemical instability of substrates 2-5 under short wavelength irradiation (lambda = 300 nm).

  DOI：

  10.1021/jo0606608

文献信息

• Quinolinone derivatives and their preparation in therapy
  申请人：Synthelabo

  公开号：US04983607A1

  公开（公告）日：1991-01-08

  A quinolinone derivative which is a compound of formula (I): ##STR1## in which: R.sub.1 and R.sub.2 are each, independently of one another, a hydrogen or halogen atom or a (C.sub.1-4)alkyl radical; R.sub.3 is a hydrogen atom or a (C.sub.1-4)alkyl radical; R.sub.4 is an unsubstituted or substituted naphthyl, tetrahydronaphthyl, benzyl, phenyl, pyridyl, isoquinolyl or benzoyl radical; and X and Y are each a hydrogen atom or together form a bond; or a pharmaceutically acceptable acid addition salt thereof and, when X and Y are each a hydrogen atom, the diastereoisomers and enantiomers thereof.

  一种喹啉酮衍生物，其化学式为（I）：##STR1##其中：R.sub.1和R.sub.2分别独立地是氢原子或卤素原子或（C.sub.1-4）烷基基团；R.sub.3是氢原子或（C.sub.1-4）烷基基团；R.sub.4是未取代或取代的萘基、四氢萘基、苄基、苯基、吡啶基、异喹啉基或苯甲酰基基团；X和Y分别是氢原子或一起形成键；或其药学上可接受的酸盐，当X和Y分别是氢原子时，其对映异构体和对映体。
• Studies on 2(1H)-quinolinone derivatives as gastric antiulcer active agents. 2-(4-Chlorobenzoylamino)-3-(2(1H)-quinolinon-4-yl)propionic acid and related compounds.
  作者：MINORU UCHIDA、FUJIO TABUSA、MAKOTO KOMATSU、SEIJI MORITA、TOSHIMI KANBE、KAZUYUKI NAKAGAWA

  DOI：10.1248/cpb.33.3775

  日期：——

  A series of N-acyl amino acid analogues of 2 (1H)-quinolinone was synthesized and tested for antiulcer activity against acetic acid-induced gastric ulcer in rats. These compounds were synthesized by the acylation of amino acid derivatives of 2 (1H)-quinolinone, which were obtained from the reaction of ω-bromoalkyl 2 (1H)-quinolinones and acetamidomalonate in the presence of sodium ethoxide, followed by hydrolysis with diluted hydrochloric acid. Among them, 2-(4-chlorobenzoylamino)-3-[2 (1H)-quinolinon-4-yl] propionic acid (VIIIf) was found to have the most potent activity. The structure-activity relationships are discussed.

  合成了一系列N-酰基氨基酸类似物的2 (1H)-喹啉酮，并测试了它们对醋酸诱导的大鼠胃溃疡的抗溃疡活性。这些化合物是通过酰化2 (1H)-喹啉酮的氨基酸衍生物合成的，这些衍生物是通过ω-溴烷基2 (1H)-喹啉酮和乙酰胺基丙二酸酯在乙醇钠存在下反应，然后与稀盐酸水解得到的。其中，2-(4-氯苯甲酰氨基)-3-[2 (1H)-喹啉酮-4-基]丙酸(VIIIf)显示出最强的活性。讨论了结构活性关系。
• [EN] BARBITURIC ACID DERIVATIVES AS INHIBITORS OF TNF- DOLLAR G(A) CONVERTING ENZYME (TACE) AND/OR MATRIX METALLOPROTEINASES<br/>[FR] DERIVES D'ACIDE BARBITURIQUE UTILISES COMME INHIBITEURS DE L'ENZYME DE CONVERSION DU TNF- DOLLAR G(A) (TACE) ET/OU DE METALLOPROTEINASES MATRICIELLES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003053940A1

  公开（公告）日：2003-07-03

  The present application describes novel barbituric acid derivatives of formula (I), or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, B, L, R1, W, Z, U?a, Xa, Ya, and Za¿ are defined in the present specification, which are useful as TNF-α converting enzyme (TACE) and matrix metalloproteinases (MMP) inhibitors.

  本申请描述了新的巴比妥酸衍生物的公式（I），或其药学上可接受的盐或前药形式，其中A、B、L、R1、W、Z、Ua、Xa、Ya和Za在本说明中有定义，它们可用作TNF-α转化酶（TACE）和基质金属蛋白酶（MMP）抑制剂。
• Synthesis and SAR of 3- and 4-substituted quinolin-2-ones: discovery of mixed 5-HT1B/5-HT2A receptor antagonists
  作者：Gary McCort、Christian Hoornaert、Michel Aletru、Colombe Denys、Olivier Duclos、Caroline Cadilhac、Eric Guilpain、Geneviève Dellac、Philip Janiak、Anne-Marie Galzin、Monique Delahaye、Frédérique Guilbert、Stephen O'Connor

  DOI：10.1016/s0968-0896(01)00118-3

  日期：2001.8

  Quinolin-2-ones bearing a heteroaryl-piperazine linked by a two carbon chain at the 3- or 4-position were synthesised and evaluated as mixed 5-HT1B/5-HT2A receptor antagonists. Potent mixed antagonists were obtained with thieno[3,2-c]pyridine derivatives. In this series, compound 2.1 (SL 65.0472) proved to be functional antagonist at both the 5-HT2A receptor (rat in vivo 5-HT-induced hypertension model) and the 5-HT1B receptor (dog in vitro saphenous vein assay). (C) 2001 Elsevier Science Ltd. All rights reserved.
• MANOURY, PHILIPPE;OBITZ, DANIEL;PEYNOT, MICHEL;FROST, JOHN
  作者：MANOURY, PHILIPPE、OBITZ, DANIEL、PEYNOT, MICHEL、FROST, JOHN

  DOI：——

  日期：——