6-(oxiran-2-ylmethoxy)-3,4-dihydroquinolin-2(1H)-one | 51780-90-6

• 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: 6-(oxiran-2-ylmethoxy)-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 6-(2,3-epoxy)propoxy-3,4-dihydrocarbostyril；6-(oxiran-2-ylmethoxy)-3,4-dihydro-1H-quinolin-2-one
• CAS: 51780-90-6
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: DYLLIXGCEBNMDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(oxiran-2-ylmethoxy)-3,4-dihydroquinolin-2(1H)-one 在 溶剂黄146 、 pyridinium chlorochromate 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 6-(3-bromo-2-oxopropoxy)-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  [EN] SELECTIVE NR2B ANTAGONISTS
  [FR] ANTAGONISTES SÉLECTIFS DU NR2B

  摘要：

  该披露通常涉及到式(I)的化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物是配体，NR2B受体的拮抗剂，可能对治疗中枢神经系统的各种疾病有用。

  公开号：

  WO2013049119A1
• 作为产物：
  描述：

  6-羟基-3,4-二氢-2(1H)-喹诺酮 、 环氧氯丙烷 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 6-(oxiran-2-ylmethoxy)-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Novel Carvedilol Analogues That Suppress Store-Overload-Induced Ca²⁺ Release

  摘要：

  Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the beta-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.

  DOI：

  10.1021/jm401090a

文献信息

• Cardiotonic and antithrombotic sulfur-containing derivatives of
  申请人：Boehringer Ingelheim GmbH

  公开号：US04329347A1

  公开（公告）日：1982-05-11

  Compounds of the formula ##STR1## wherein W is vinylene, methyl-vinylene, methylene or ethylene; m is 0, 1 or 2; D is straight or branched alkylene of 2 to 6 carbon atoms, straight or branched hydroxy-alkylene of 3 to 6 carbon atoms, or xylylene; R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms; R.sub.2 is cycloalkyl of 3 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 11 carbon atoms, heteroaryl, heteroarlkyl, 1,2,4-triazolyl, triphenylmethyl, 4,5-bis-(p-chlorophenyl)-oxazol-2-yl, N-methyl-cyclohexylamino-carbonylmethyl,-amino-iminomethyl or, when m is 1 or D is hydroxyalkylene or xylylene, also alkyl of 1 to 6 carbon atoms; and R.sub.3 and R.sub.4 are each hydrogen, halogen, alkyl of 1 to 4 carbon atoms, amino, acetylamino or nitro. The compounds of the invention are useful as cardiotonics and as antithrombotics.

  式为##STR1##的化合物，其中W为乙烯基、甲基乙烯基、亚甲基或乙烯基；m为0、1或2；D为2至6个碳原子的直链或支链烷基、3至6个碳原子的直链或支链羟基烷基，或二甲苯基；R.sub.1为氢或1至3个碳原子的烷基；R.sub.2为3至6个碳原子的环烷基、6至10个碳原子的芳基、7至11个碳原子的芳基烷基、杂环芳基、杂环芳基烷基、1,2,4-三唑基、三苯甲基、4,5-双-(对氯苯基)-噁唑-2-基、N-甲基环己基氨基甲酰甲基、氨基亚甲基或当m为1或D为羟基烷基或二甲苯基时，也为1至6个碳原子的烷基；以及R.sub.3和R.sub.4分别为氢、卤素、1至4个碳原子的烷基、氨基、乙酰氨基或硝基。本发明的化合物可用作心力衰竭药和抗血栓药。
• Synthesis and evaluation of N -(4-benzylphenyl)piperazines as VGF inducers
  作者：Tetsuya Toba、Ryosuke Suzuki、Junko Futamura-Takahashi、Yoshito Kawamoto、Shigeki Tamura、Mariko Kuroda、Yoshiari Shimmyo、Michinori Kadokura、Kazumichi Goto、Teruyoshi Inoue、Tsuyoshi Muto、Hirokazu Annoura

  DOI：10.1016/j.bmcl.2018.05.047

  日期：2018.8

  A series of compounds was discovered that induce the production of VGF mRNA in SH-SY5Y cells and exhibit cytoprotection under tunicamycin induced endoplasmic reticulum (ER) stress. The aminophenol ring and linker chain of the template SUN N8075 (1) was modified to yield compounds with higher efficacy and lower propensity for adverse effects.

  发现了一系列化合物，这些化合物在SH-SY5Y细胞中诱导VGF mRNA的产生，并在衣霉素诱导的内质网（ER）胁迫下表现出细胞保护作用。对模板SUN N8075（1）的氨基苯酚环和连接链进行了修饰，以产生具有更高功效和更低不良反应倾向的化合物。
• [EN] SUBSTITUTED OCTAHYDROPYRROLO[1,2-a]PYRAZINES AS CALCIUM CHANNEL BLOCKERS<br/>[FR] OCTAHYDROPYRROLO[1,2-A]PYRAZINES SUBSTITUÉES UTILISÉES EN TANT QU'INHIBITEURS DES CANAUX CALCIQUES
  申请人：ABBVIE INC

  公开号：WO2013049164A1

  公开（公告）日：2013-04-04

  The present application relates to: (a) compounds of Formula (I): (I), and salts thereof, wherein Z1, Z2, Z3, Z4, R1, R2, and R3 are as defined in the specification; (b) compositions comprising such compounds and salts; and (c) methods of use of such compounds, salts, and compositions, particularly use as calcium channel inhibitors.

  本申请涉及：(a) 公式(I)的化合物：(I)，以及其盐，其中Z1、Z2、Z3、Z4、R1、R2和R3如规范中定义；(b) 包含这些化合物和盐的组合物；以及(c) 使用这些化合物、盐和组合物的方法，特别是作为钙通道抑制剂的用途。
• Pharmaceutically useful carbostyril derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04734416A1

  公开（公告）日：1988-03-29

  Carbostyril derivatives having antihistamic action and central nervous controlling action are useful as antihistamic agents or central nervous controlling agents. The derivatives are represented by the general formula, ##STR1## wherein R.sup.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenylalkyl group having an alkylene group containing 1 to 4 carbon atoms; R.sup.2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group; R.sup.3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanolyoxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R.sup.4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R.sup.5 is a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group (which may have 1 to 3 substituted groups selected from the group consisting of halogen atoms, alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms), an alkyl group having 1 to 4 carbon atoms (having one substituted group such as a hydroxy group, a phenyl group or an alkanoyloxy group having 1 to 4 carbon atoms), an alkanoyl group having 1 to 4 carbon atoms or benzoyl group; X is a halogen atom; n is 0, or an integer of 1 or 2; Q is an integer of 2 or 3, l and m are respectively an integer of 0 or 1-6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; and the substituted position of the side chain of ##STR2## is any one of the 4-, 5-, 6-, 7- or 8-positions.

  羧基苯基丙酰衍生物具有抗组胺作用和中枢神经调节作用，可用作抗组胺剂或中枢神经调节剂。 衍生物由通式##STR1##表示，其中R.sup.1是氢原子，具有1到6个碳原子的烷基，具有2到4个碳原子的烯基，具有2到4个碳原子的炔基或具有含有1到4个碳原子的碳链的苯基烷基; R.sup.2是氢原子，具有1到4个碳原子的烷基或苯基; R.sup.3是氢原子，羟基，具有1到4个碳原子的烷基，具有1到4个碳原子的烷氧基或3,4,5-三甲氧基苯甲酰氧基; R.sup.4是氢原子或具有1到4个碳原子的烷基; R.sup.5是具有3到8个碳原子的环烷基，苯基（可以具有1到3个取代基，所述取代基选择自卤原子，具有1到4个碳原子的烷基和具有1到4个碳原子的烷氧基），具有1到4个碳原子的烷基（具有一个取代基，例如羟基，苯基或具有1到4个碳原子的烷酰氧基），具有1到4个碳原子的烷酰基或苯甲酰基; X是卤原子; n为0或1或2的整数; Q为2或3的整数，l和m分别为0或1-6的整数，但是l和m的总和不应超过6; 在羧基苯基丙酰骨架的3-和4-位的碳-碳键是单键或双键; 以及##STR2##的侧链的取代位置是4-, 5-, 6-, 7-或8-位中的任何一个。
• Carbostyril derivatives and pharmaceutical preparations containing same
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04824840A1

  公开（公告）日：1989-04-25

  Carbostyril derivatives having antihistaminic action and central nervous controlling action are useful as antihistaminic agents or central nervous controlling agents. The derivatives are represented by the general formula, ##STR1## wherein R.sup.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenylalkyl group, an alkylene group containing 1 to 4 carbon atoms; R.sup.2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group; R.sup.3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R.sup.4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R.sup.5 is a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group (which may have 1 to 3 substituted groups selected from the group consisting of halogen atoms, alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms), an alkyl group having 1 to 4 carbon atoms (having one substituted group such as a hydroxy group, a phenyl group or an alkanoyloxy group having 1 to 4 carbon atoms), an alkanoyl group having 1 to 4 carbon atoms or benzoyl group; X is a halogen atom; n is 0, or an integer of 1 or 2; Q is an integer of 2 or 3, l and m are respectively an integer of 0 to 1-6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond and; the substituted position of the side chain of ##STR2## is any one of the 4-, 5-, 6-, 7- or 8-positions.

  羧基苯基吡啶衍生物具有抗组胺作用和中枢神经控制作用，可用作抗组胺剂或中枢神经控制剂。该衍生物由通式## STR1 ##表示，其中R.sup.1是氢原子，具有1至6个碳原子的烷基，具有2至4个碳原子的烯基，具有2至4个碳原子的炔基或苯基烷基，含有1至4个碳原子的烷基，R.sup.2是氢原子，具有1至4个碳原子的烷基或苯基，R.sup.3是氢原子，羟基，具有1至4个碳原子的烷基，具有1至4个碳原子的烷酰氧基或3,4,5-三甲氧基苯甲酰氧基，R.sup.4是氢原子或具有1至4个碳原子的烷基，R.sup.5是具有3至8个碳原子的环烷基，苯基（可能具有1至3个取代基，所述取代基选自卤原子，具有1至4个碳原子的烷基和具有1至4个碳原子的烷氧基），具有1至4个碳原子的烷基（具有一个取代基，例如羟基，苯基或具有1至4个碳原子的烷酰氧基），具有1至4个碳原子的烷酰基或苯甲酰基; X是卤原子; n为0或1或2的整数; Q为2或3的整数，l和m分别为0至1-6的整数，但l和m的总和不应超过6;羧基吡啶骨架中3-和4-位置的碳-碳键是单键或双键; ## STR2 ##的侧链的取代位置是4-，5-，6-，7-或8-位置之一。