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1-丁基-4-氯-3-硝基喹啉-2-酮 | 133306-31-7

中文名称
1-丁基-4-氯-3-硝基喹啉-2-酮
中文别名
——
英文名称
1-butyl-4-chloro-3-nitroquinolin-2(1H)-one
英文别名
1-n-Butyl-4-chloro-3-nitro-2(1H)-quinolone;1-butyl-4-chloro-3-nitroquinolin-2-one
1-丁基-4-氯-3-硝基喹啉-2-酮化学式
CAS
133306-31-7
化学式
C13H13ClN2O3
mdl
——
分子量
280.711
InChiKey
GPBMDSQCSRJXBX-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.2
  • 重原子数:
    19
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.31
  • 拓扑面积:
    66.1
  • 氢给体数:
    0
  • 氢受体数:
    3

SDS

SDS:dd4a48277de820948229c4f5c57ab70e
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上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    • 1
    • 2

反应信息

  • 作为反应物:
    描述:
    1-丁基-4-氯-3-硝基喹啉-2-酮platinum(IV) oxide 、 palladium on activated charcoal 氢气 作用下, 以 四氢呋喃乙醇三氟乙酸 为溶剂, 25.0~110.0 ℃ 、413.69 kPa 条件下, 反应 137.0h, 生成 5-butyl-1-methyl-6,7,8,9-tetrahydro-1H-imidazo<4,5-c>quinolin-4(5H)-one
    参考文献:
    名称:
    New bronchodilators. 1. 1,5-Substituted 1H-imidazo[4,5-c]quinolin-4(5H)-ones
    摘要:
    A series of novel xanthine-based tricyclic heterocycles in 1H-imidazo[4,5-c]quinolin-4(5H)-ones was designed, synthesized, and tested as potential active bronchodilators. Inhibition of the Schulz-Dale (SD) reaction-induced contraction in trachea and inhibition of antigen inhalation-induced bronchospasm in passively sensitized guinea pigs served as primary in vitro and in vivo assays, respectively. Simultaneous measurement of acute lethal toxicity (minimum lethal dose; MLD, po) in mice allowed determination of a safety margin. The bronchodilatory activity of these heterocycles was considerably varied with the nature of substituents at the 5-position. The most active substituents at the 2- and 5-positions and on the aromatic ring were found to be hydrogen, n-butyl, and hydrogen, respectively. There was a bulk tolerance for lipophilic substituents at the 1-position. 5-Butyl-substituted compounds appeared to be less toxic than theophylline on the basis of MLD data. Thus 5-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4(5H)-one (10) (IC50 value of the SD assay = 0.25 muM, MLD > 300 mg/kg) was selected for further studies. Compound 10 (KF15570) reduced bronchoconstriction produced by antigen (Konzett-Rossler preparation in anesthetized guinea pigs, ED50 = 0.42 mg/kg, iv) more effectively than aminophylline (ethylenediamine salt of theophylline, ED50 = 7.8 mg/kg, iv) but had fewer side effects on the heart and CNS than theophylline. Compound 10 and its derivatives showed weak adenosine antagonism and phosphodiesterase (PDE) inhibition which could not account for their potent bronchodilation. Although their precise mechanism of action remains unclear, this series of novel tricyclic heterocycles represents a new class of bronchodilator.
    DOI:
    10.1021/jm00100a009
  • 作为产物:
    描述:
    1-butyl-4-hydroxy-3-nitroquinolin-2(1H)-one 在 三氯氧磷 作用下, 反应 1.0h, 生成 1-丁基-4-氯-3-硝基喹啉-2-酮
    参考文献:
    名称:
    New bronchodilators. 1. 1,5-Substituted 1H-imidazo[4,5-c]quinolin-4(5H)-ones
    摘要:
    A series of novel xanthine-based tricyclic heterocycles in 1H-imidazo[4,5-c]quinolin-4(5H)-ones was designed, synthesized, and tested as potential active bronchodilators. Inhibition of the Schulz-Dale (SD) reaction-induced contraction in trachea and inhibition of antigen inhalation-induced bronchospasm in passively sensitized guinea pigs served as primary in vitro and in vivo assays, respectively. Simultaneous measurement of acute lethal toxicity (minimum lethal dose; MLD, po) in mice allowed determination of a safety margin. The bronchodilatory activity of these heterocycles was considerably varied with the nature of substituents at the 5-position. The most active substituents at the 2- and 5-positions and on the aromatic ring were found to be hydrogen, n-butyl, and hydrogen, respectively. There was a bulk tolerance for lipophilic substituents at the 1-position. 5-Butyl-substituted compounds appeared to be less toxic than theophylline on the basis of MLD data. Thus 5-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4(5H)-one (10) (IC50 value of the SD assay = 0.25 muM, MLD > 300 mg/kg) was selected for further studies. Compound 10 (KF15570) reduced bronchoconstriction produced by antigen (Konzett-Rossler preparation in anesthetized guinea pigs, ED50 = 0.42 mg/kg, iv) more effectively than aminophylline (ethylenediamine salt of theophylline, ED50 = 7.8 mg/kg, iv) but had fewer side effects on the heart and CNS than theophylline. Compound 10 and its derivatives showed weak adenosine antagonism and phosphodiesterase (PDE) inhibition which could not account for their potent bronchodilation. Although their precise mechanism of action remains unclear, this series of novel tricyclic heterocycles represents a new class of bronchodilator.
    DOI:
    10.1021/jm00100a009
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文献信息

  • Imidazoquinolone derivatives
    申请人:Kyowa Hakko Kogyo Co., Ltd.
    公开号:US04994468A1
    公开(公告)日:1991-02-19
    Novel imidazoquinolone derivative represented by the formula (I); ##STR1## wherein R.sup.1 represents hydrogen, alkyl, cycloalkyl, alkenyl aralkyl, aralkenyl or substituted or unsubstituted aryl; X represents nitrogen or ##STR2## where R.sup.2 is hydrogen, hydroxyl, alkyl, cycloalkyl, alkenyl, aralkyl, aralkenyl, substituted or unsubstituted aryl, thiol, halogen, substituted or unsubstituted aromatic heterocyclic group, or --(CH.sub.2).sub.m CO.sub.2 R.sup.6 where R.sup.6 is hydrogen or lower alkyl and m is an integer of 0 to 3; Y represents oxygen or sulfur; R.sup.3 represents alkyl, cycloalkyl, alkoxyalkly, alkenyl, aralkyl, aralkenyl, --(CH.sub.2).sub.n -- Het where Het is substituted or unsubstituted aromatic heterocyclic group and n is an integer of 1 to 3 or --(CH.sub.2).sub.n CO.sub.2 R.sup.6a where n has the same meaning as defined above and R.sup.6a has the same meaning as defined as to R.sup.6 ; each of R.sup.4 and R.sup.5 independently represents hydrogen, lower alkyl, trifluoromethyl, cycloalkyl, halogen, hydroxyl, lower alkoxyl, lower alkylthio, nitro, amino, lower alkylamino, lower alkanoylamino, aroylamino, lower alkanoyl or aroyl; and a pharmaceutically acceptable salt thereof. The Compound (I) and a pharmaceutically acceptable salt thereof show bronchodilatory and antiallergic activities, and are useful for treating respiratory disorders such as bronchial asthma.
    新型咪唑喹酮衍生物的化学式(I)所代表的是:其中R.sup.1代表氢、烷基、环烷基、烯基芳基、烯基芳基或取代或未取代芳基;X代表氮或##STR2##其中R.sup.2为氢、羟基、烷基、环烷基、烯基、芳基、硫醇、卤素、取代或未取代芳香杂环基,或--(CH.sub.2).sub.m CO.sub.2 R.sup.6,其中R.sup.6为氢或较低烷基,m为0到3的整数;Y代表氧或硫;R.sup.3代表烷基、环烷基、烷氧基烷基、烯基、芳基、烯基芳基、--(CH.sub.2).sub.n -- Het,其中Het为取代或未取代芳香杂环基,n为1到3的整数,或--(CH.sub.2).sub.n CO.sub.2 R.sup.6a,其中n具有上述定义的相同含义,R.sup.6a具有与R.sup.6相同的定义;R.sup.4和R.sup.5中的每一个独立地代表氢、较低烷基、三氟甲基、环烷基、卤素、羟基、较低烷氧基、较低烷基硫基、硝基、氨基、较低烷基氨基、较低烷酰胺基、芳酰胺基、较低烷酰基或芳酰基;以及其药学上可接受的盐。化合物(I)及其药学上可接受的盐具有支气管扩张和抗过敏活性,并且可用于治疗支气管哮喘等呼吸系统疾病。
  • New Bronchodilators. II. 3H-Imidazo(4,5-c)quinolin-4(5H)-ones.
    作者:Fumio SUZUKI、Takeshi KURODA、Hiroaki HAYASHI、Yoshisuke NAKASATO、Haruhiko MANABE、Kenji OHMORI、Shigeto KITAMURA
    DOI:10.1248/cpb.40.3245
    日期:——
    A series of novel 3-substituted imidazo[4, 5-c]quinolin-4(5H)-ones (2a-w) was prepared by the reaction of imidazo[4, 5-c]quinolin-4(5H)-ones (6) with several electrophiles under basic conditions. The bronchodilatory activity of these compounds was evaluated on the basis of their protective effects against antigen-induced contraction (the Schultz-Dale reaction) of guinea-pig trachea (in vitro) and antigen inhalation-induced bronchospasm in passively sensitized guinea-pigs (in vivo). Although correlations between in vitro and in vivo activities were not clear, short alkyl chains such as the methyl and ethyl groups at the 3-position were important for potent activity, especially in vivo. Substituents at the 5-position were more tolerant of the activity than those at the 3-position. 5-Ethyl-3-methyl-3H-imidazo[4, 5-c]quinolin-4(5H)-one (21) exhibits the most potent bronchodilatory activity among our tested compounds and is at least 5-fold more active than theophylline in vivo.
    一系列新型3-取代咪唑并[4,5-c]喹啉-4(5H)-酮(2a-w)是通过咪唑并[4,5-c]喹啉-4(5H)-酮(6)与几种电化合物的反应在碱性条件下制备的。这些化合物的支气管扩张活性是根据它们对豚鼠气管(体外)抗原诱导收缩(舒尔茨-戴尔反应)和被动致敏豚鼠(体内)抗原吸入诱导支气管痉挛的保护作用来评估的。虽然体外和体内活性之间的相关性尚不清楚,但3位上的甲基和乙基等短烷基链对于有效活性非常重要,特别是在体内。5位上的取代基比
  • US4994468A
    申请人:——
    公开号:US4994468A
    公开(公告)日:1991-02-19
  • New bronchodilators. 1. 1,5-Substituted 1H-imidazo[4,5-c]quinolin-4(5H)-ones
    作者:Fumio Suzuki、Takeshi Kuroda、Yoshisuke Nakasato、Haruhiko Manabe、Kenji Ohmori、Shigeto Kitamura、Shunji Ichikawa、Tetsuji Ohno
    DOI:10.1021/jm00100a009
    日期:1992.10
    A series of novel xanthine-based tricyclic heterocycles in 1H-imidazo[4,5-c]quinolin-4(5H)-ones was designed, synthesized, and tested as potential active bronchodilators. Inhibition of the Schulz-Dale (SD) reaction-induced contraction in trachea and inhibition of antigen inhalation-induced bronchospasm in passively sensitized guinea pigs served as primary in vitro and in vivo assays, respectively. Simultaneous measurement of acute lethal toxicity (minimum lethal dose; MLD, po) in mice allowed determination of a safety margin. The bronchodilatory activity of these heterocycles was considerably varied with the nature of substituents at the 5-position. The most active substituents at the 2- and 5-positions and on the aromatic ring were found to be hydrogen, n-butyl, and hydrogen, respectively. There was a bulk tolerance for lipophilic substituents at the 1-position. 5-Butyl-substituted compounds appeared to be less toxic than theophylline on the basis of MLD data. Thus 5-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4(5H)-one (10) (IC50 value of the SD assay = 0.25 muM, MLD > 300 mg/kg) was selected for further studies. Compound 10 (KF15570) reduced bronchoconstriction produced by antigen (Konzett-Rossler preparation in anesthetized guinea pigs, ED50 = 0.42 mg/kg, iv) more effectively than aminophylline (ethylenediamine salt of theophylline, ED50 = 7.8 mg/kg, iv) but had fewer side effects on the heart and CNS than theophylline. Compound 10 and its derivatives showed weak adenosine antagonism and phosphodiesterase (PDE) inhibition which could not account for their potent bronchodilation. Although their precise mechanism of action remains unclear, this series of novel tricyclic heterocycles represents a new class of bronchodilator.
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