5-Bromomethyl-1H-quinolin-2-one | 103702-28-9

• 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-Bromomethyl-1H-quinolin-2-one
• 英文别名: 5-(Bromomethyl)quinolin-2(1H)-one；5-(bromomethyl)-1H-quinolin-2-one
• CAS: 103702-28-9
• 化学式: C₁₀H₈BrNO
• 分子量: 238.084
• InChiKey: CFJLYEFMSQAECF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Bromomethyl-1H-quinolin-2-one 在 sodium 作用下， 以 乙醇 为溶剂， 以79%的产率得到2-Acetylamino-2-(2-oxo-1,2-dihydro-quinolin-5-ylmethyl)-malonic acid diethyl ester
  参考文献：
  名称：

  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.

  摘要：

  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。

  DOI：

  10.1248/cpb.33.3775
• 作为产物：
  描述：

  2-氧代-1H-喹啉-5-羧酸甲酯 在 lithium aluminium tetrahydride 、 氢溴酸 作用下， 以 四氢呋喃 为溶剂， 生成 5-Bromomethyl-1H-quinolin-2-one
  参考文献：
  名称：

  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.

  摘要：

  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。

  DOI：

  10.1248/cpb.33.3775

文献信息

• Hydroxamic acids substituted by heterocycles useful for inhibition of tumor necrosis factor
  申请人：ZENECA LIMITED

  公开号：US20020040002A1

  公开（公告）日：2002-04-04

  1 Compounds of formula (I), wherein: n is 1 to 6; Het is a nitrogen containing ring fused to the benzene ring on two adjacent carbon atoms to form a bicyclic ring system which ring system may be optionally substituted; R 1 is hydrogen, C 1-8 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-8 cycloalkyl, aryl, heteroaryl, heterocyclyl, arylC 1-6 alkyl, heteroarylC 1-6 alkyl, heterocyclylC 1-6 alkyl or C 3-8 cycloalkylC 1-6 alkyl; R 2 is C 1-6 alkyl, C 2-6 alkenyl, arylC 1-6 alkyl, heteroarylC 1-6 alkyl or the side-chain of a naturally occurring amino acid; R 3 is hydrogen, C 1-6 alkyl, C 3-8 cycloalkyl, C 4-8 cycloalkenyl, arylC 1-6 alkyl, heteroarylC 1-6 alkyl or heterocyclylC 1-6 alkyl; R 4 is hydrogen or C 1-6 alkyl; or R 3 and R 4 together with the nitrogen atom to which they are joined form a heterocyclic ring; wherein any group or ring, in R 1 -R 4 , is optionally substituted; and pharmceutically acceptable salts and in vivo hydrolysable esters thereof, are described as inhibitors of the production of Tumour Necrosis Factor and/or one or more matrix metalloproteinase enzymes. Compositions containing them and their preparation are also described.

  化合物的式子(I)，其中：n为1至6；Het是一个氮含环，在苯环上的两个相邻碳原子上融合形成一个双环系统，该环系统可以选择性地被取代；R1为氢、C1-8烷基、C2-6烯基、C2-6炔基、C3-8环烷基、芳基、杂芳基、杂环基、芳基C1-6烷基、杂芳基C1-6烷基、杂环基C1-6烷基或C3-8环烷基C1-6烷基；R2为C1-6烷基、C2-6烯基、芳基C1-6烷基、杂芳基C1-6烷基或天然氨基酸的侧链；R3为氢、C1-6烷基、C3-8环烷基、C4-8环烯基、芳基C1-6烷基、杂芳基C1-6烷基或杂环基C1-6烷基；R4为氢或C1-6烷基；或者R3和R4与它们连接的氮原子一起形成一个杂环；其中R1-R4中的任何基团或环都可以选择性地被取代；并且其药学上可接受的盐和体内可水解的酯被描述为肿瘤坏死因子和/或一个或多个基质金属蛋白酶酶的生产抑制剂。还描述了含有它们的组合物及其制备方法。
• UCHIDA, MINORU;TABUSA, FUJIO;KOMATSU, MAKOTO;MORITA, SEIJI;KANBE, TOSHIMI+, CHEM. AND PHARM. BULL., 1985, 33, N 9, 3775-3786
  作者：UCHIDA, MINORU、TABUSA, FUJIO、KOMATSU, MAKOTO、MORITA, SEIJI、KANBE, TOSHIMI+

  DOI：——

  日期：——
• HYDROXAMIC ACIDS SUBSTITUTED BY HETEROCYCLES USEFUL FOR INHIBITION OF TUMOR NECROSIS FACTOR
  申请人：ZENECA LIMITED

  公开号：EP0971895A1

  公开（公告）日：2000-01-19
• [EN] HYDROXAMIC ACIDS SUBSTITUTED BY HETEROCYCLES USEFUL FOR INHIBITION OF TUMOR NECROSIS FACTOR<br/>[FR] ACIDES HYDROXAMIQUES SUBSTITUES PAR DES COMPOSES HETEROCYCLIQUES POUVANT INHIBER LE FACTEUR DE NECROSE TUMORALE
  申请人：ZENECA LIMITED

  公开号：WO1998043959A1

  公开（公告）日：1998-10-08

  (EN) Compounds of formula (I), wherein: n is 1 to 6; Het is a nitrogen containing ring fused to the benzene ring on two adjacent carbon atoms to form a bicyclic ring system which ring system may be optionally substituted; R1 is hydrogen, C1-8alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, aryl, heteroaryl, heterocyclyl, arylC1-6alkyl, heteroarylC1-6alkyl, heterocyclylC1-6alkyl or C3-8cycloalkylC1-6alkyl; R2 is C1-6alkyl, C2-6alkenyl, arylC1-6alkyl, heteroarylC1-6alkyl or the side-chain of a naturally occurring amino acid; R3 is hydrogen, C1-6alkyl, C3-8cycloalkyl, C4-8cycloalkenyl, arylC1-6alkyl, heteroarylC1-6alkyl or heterocyclylC1-6alkyl; R4 is hydrogen or C1-6alkyl; or R3 and R4 together with the nitrogen atom to which they are joined form a heterocyclic ring; wherein any group or ring, in R1-R4, is optionally substituted; and pharmceutically acceptable salts and $i(in vivo) hydrolysable esters thereof, are described as inhibitors of the production of Tumour Necrosis Factor and/or one or more matrix metalloproteinase enzymes. Compositions containing them and their preparation are also described.(FR) L'invention concerne des composés de la formule (I) dans laquelle n est compris entre 1 et 6; Het est un azote contenant un noyau lié par fusion au noyau benzénique sur deux atomes de carbone adjacents pour former un système bicyclique pouvant être éventuellement substitué; R1 est hydrogène, alkyle C1-8, alcényle C2-6, alkynyle C2-6, cycloalkyle C3-8, aryle, hétéroaryle, hétérocyclyle, aryle C1-6 alkyle, hétéroaryle C1-6 alkyle, hétérocyclyle C1-6 alkyle ou C3-8 cycloalkyle C1-6 alkyle; R2 est alkyle C1-6, alcényle C2-6, aryle C1-6 alkyle, hétéroaryle C1-6 alkyle, ou la chaîne latérale d'un amino-acide naturel; R3 est hydrogène, alkyle C1-6, cycloalkyle C3-8, cycloalcényle C4-8, aryle C1-6 alkyle, hétéroaryle C1-6 alkyle ou hétérocyclyle C1-6 alkyle; R4 est hydrogène ou alkyle C1-6; ou R3 et R4 forment ensemble, avec l'atome d'azote auquel ils sont liés, un noyau hétérocyclique. Dans ladite formule, chaque groupe ou noyau compris entre R1 et R2 est éventuellement substitué. L'invention concerne en outre des sels pharmaceutiquement acceptables et des esters hydrolysables desdits sels obtenus $i(in vivo), qui peuvent inhiber la production du facteur de nécrose tumorale et/ou une ou plusieurs enzymes métalloprotéases matricielles. Elle concerne enfin des compositions contenant ces éléments et leur préparation.
• 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。