7-(bromomethyl)-4-ethoxycoumarin | 75590-54-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(bromomethyl)-4-ethoxycoumarin
• 英文别名: 7-bromomethyl-4-ethoxy-chromen-2-one；7-bromomethyl-4-ethoxycoumarin；7-(bromomethyl)-4-ethoxychromen-2-one
• CAS: 75590-54-4
• 化学式: C₁₂H₁₁BrO₃
• 分子量: 283.122
• InChiKey: SEOHSSGSTLQOSF-UHFFFAOYSA-N

物化性质

• 熔点：
  152-155 °C(Solv: ethanol (64-17-5))
• 沸点：
  424.7±45.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(bromomethyl)-4-ethoxycoumarin 在 盐酸 、 硝酸 、 potassium carbonate 作用下， 以 氯仿 、 溶剂黄146 、 氯苯 为溶剂， 反应 21.5h， 生成 1-(4-chlorobenzyl)-4-[(4-hydroxy-3-nitrocoumarin-7-yl)methyl]piperazine
  参考文献：
  名称：

  N-Benzylpiperazino derivatives of 3-nitro-4-hydroxycoumarin with H1 antihistamine and mast cell stabilizing properties

  摘要：

  In a small range finding study a number of N-benzylpiperazino derivates of 3-nitro-4-hydroxycoumarin have been shown to combine potent H1-antihistamine activity with that of mast cell stabilization as demonstrated by their activity as antagonists of histamine on guinea pig ileum and by their inhibition of the release of histamine in rat passive peritoneal anaphylaxis (PPA). The most potent compound, 1-[2-hydroxy-3-[(4-hydroxy-3-nitrocoumarin-7-yl)oxy]propyl]-4- (4-chlorobenzyl)piperazine, 30, had a pA2 of 9.0 against histamine on guinea pig ileum and inhibited histamine release in the rat PPA test with a potency similar to that of disodium cromoglycate.

  DOI：

  10.1021/jm00377a013
• 作为产物：
  描述：

  4-羟基-7-甲基香豆素 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 1.5h， 生成 7-(bromomethyl)-4-ethoxycoumarin
  参考文献：
  名称：

  N-Benzylpiperazino derivatives of 3-nitro-4-hydroxycoumarin with H1 antihistamine and mast cell stabilizing properties

  摘要：

  In a small range finding study a number of N-benzylpiperazino derivates of 3-nitro-4-hydroxycoumarin have been shown to combine potent H1-antihistamine activity with that of mast cell stabilization as demonstrated by their activity as antagonists of histamine on guinea pig ileum and by their inhibition of the release of histamine in rat passive peritoneal anaphylaxis (PPA). The most potent compound, 1-[2-hydroxy-3-[(4-hydroxy-3-nitrocoumarin-7-yl)oxy]propyl]-4- (4-chlorobenzyl)piperazine, 30, had a pA2 of 9.0 against histamine on guinea pig ileum and inhibited histamine release in the rat PPA test with a potency similar to that of disodium cromoglycate.

  DOI：

  10.1021/jm00377a013

文献信息

• Antagonists of melanin concentrating hormone effects on the melanin concentrating hormone receptor
  申请人：Lynch K. John

  公开号：US20050209274A1

  公开（公告）日：2005-09-22

  The present invention is directed to compounds of formula (I), which antagonize of the effects of melanin-concentrating hormone (MCH) through the melanin concentrating hormone receptor which is useful for the prevention or treatment of eating disorders, weight gain, obesity, abnormalities in reproduction and sexual behavior, thyroid hormone secretion, diuresis and water/electrolyte homeostasis, sensory processing, memory, sleeping, arousal, anxiety, depression, seizures, neurodegeneration and psychiatric disorders.

  本发明涉及式(I)的化合物，通过对抗黑素浓集激素（MCH）的作用，通过对抗黑素浓集激素受体，有助于预防或治疗进食障碍、体重增加、肥胖、生殖和性行为异常、甲状腺激素分泌、利尿和水/电解质稳态、感觉处理、记忆、睡眠、觉醒、焦虑、抑郁、癫痫、神经退行性疾病和精神障碍。
• Heterocyclic coumarin derivatives
  申请人：Beecham Group Limited

  公开号：US04263299A1

  公开（公告）日：1981-04-21

  A compound of formula (I): ##STR1## and pharmaceutically acceptable salts thereof, wherein R is hydrogen or an alkyl group containing up to 6 carbon atoms; X is a bond or oxygen; Y is --(CH.sub.2).sub.n -- where n is 0 or an integer from 1 to 5 wherein one carbon atom not bound to the nitrogen atom may be optionally substituted with a hydroxy group; and Z is hydrogen or halogen; may be used in the prophylaxis and treatment of diseases whose symptoms are controlled by the mediators of the allergic response, for example asthma, hay-fever, rhinitis and allergic eczema.

  化合物的结构式（I）：##STR1##及其药学上可接受的盐，其中R是氢或含有最多6个碳原子的烷基基团；X是键或氧；Y是--(CH.sub.2).sub.n--，其中n为0或1至5的整数，其中一个未与氮原子结合的碳原子可以选择性地被羟基取代；Z是氢或卤素；可用于预防和治疗由过敏反应介质控制症状的疾病，例如哮喘、花粉症、鼻炎和过敏性湿疹。
• Heterocyclic coumarin derivatives, their preparation and pharmaceutical compositions comprising said derivatives
  申请人：BEECHAM GROUP PLC

  公开号：EP0010392A1

  公开（公告）日：1980-04-30

  A compound of formula (I): and pharmaceutically acceptable salts thereof, wherein R is hydrogen or an alkyl group containing up to 6 carbon atoms; X is a bond or oxygen; Y is -(CH2)n -where n is 0 or an integer from 1 to 5 wherein one carbon atom not bound to the nitrogen atom may be optionally substituted with a hydroxy group; and Z is hydrogen or halogen; e.g. 1-(4-chlorobenzyl) -4-[3-(4-hydroxy-3-nitro- coumarin-7-yloxy) propyl] piperazine; may be used in the prophylaxis and treatment of diseases whose symptoms are controlled by the mediators of the allergic response, for example asthma, hay-fever, rhinitis and allergic eczema. A compound of formula (I) is prepared by reacting a compound of formula (II) or a salt thereof wherein R, X, Y, and Z are defined with respect to formula (i) with a nitrating agent

  式(I)化合物 及其药学上可接受的盐类，其中 R 是氢或最多含有 6 个碳原子的烷基；X 是键或氧；Y 是-(CH2)n -其中 n 是 0 或 1 至 5 的整数，其中未与氮原子结合的一个碳原子可任选被羟基取代；Z 是氢或卤素；例如：1-(4-氯苄基)-4-[3-(4-羟基-3-硝基香豆素-7-氧基)丙基]哌啶。g. 1-(4-氯苄基)-4-[3-(4-羟基-3-硝基香豆素-7-氧基)丙基]哌嗪；可用于预防和治疗其症状受过敏反应介质控制的疾病，例如哮喘、花粉症、鼻炎和过敏性湿疹。 式（I）化合物是通过式（II）化合物或其盐反应制备的 其中 R、X、Y 和 Z 的定义见式 (i)。
• Neue alpha-(Pyridyl-2-oxy-phenoxy)-propionsäurederivate, Verfahren zu deren Herstellung, sowie deren Verwendung als Herbizide und/oder Pflanzenwachstumsregulatoren
  申请人：CIBA-GEIGY AG

  公开号：EP0050097A1

  公开（公告）日：1982-04-21

  Verbindungen der Formel 1 worin X für Wasserstoff, Halogen oder Pseudohalogen steht; R1 Wasserstoff oder eine unsubstituierte oder durch Halogen, Hydroxy oder C1-C3-Alkoxy substituierte C1-C6-Alkyl- oder Phenylgruppe bedeutet; R2 eine unsubstituierte oder eine durch Halogen, Hydroxy oder C1-C3-Alkoxy substituierte C1-C6-Alkyl-, C2-Ce-Alkenyl-, C2-C6-Alkinyl- oder Phenylgruppe bedeutet; oder R1 und R2 zusammen für eine unsubstituierte oder eine durch C1-C3-Alkyl substituierte Tetramethylen-, Pentamethylen- oder Hexamethylenbrücke stehen, sowie deren Herstellung. Die neuen Wirkstoffe der Formel I lassen sich in Form entsprechender Mittel zur Regulierung des Pflanzenwachstums und oder zur Bekämpfung von Unkräutern in Kulturpflanzen einsetzen.

  式 1 的化合物 其中 X 是氢、卤素或假卤素； R1 是氢或未被卤素、羟基或 C1-C3 烷氧基取代或取代的 C1-C6 烷基或苯基；R2 是未被卤素、羟基或 C1-C3 烷氧基取代或被卤素、羟基或 C1-C3 烷氧基取代的 C1-C6 烷基、C2-Ce 烯基、C2-C6 炔基或苯基；或 R1 和 R2 一起是未被 C1-C3 烷基取代或被 C1-C3 烷基取代的四亚甲基、五亚甲基或六亚甲基桥，及其制备方法。式 I 的新活性物质可以相应制剂的形式用于调节植物生长和/或控制栽培植物中的杂草。
• Coumarin intermediates
  申请人：BEECHAM GROUP PLC

  公开号：EP0050396A1

  公开（公告）日：1982-04-28

  Compounds of the formula (II): or a salt thereof, wherein R is hydrogen or an alkyl group containing up to 6 carbon atoms; X is a covalent bond or oxygen; Y is -(CH2)n- where n is 0 or an integer from 1 to 5 wherein one carbon atom not bound to the nitrogen atom may be optionally substituted with a hydroxy group; and Z is hydrogen or halogen are useful intermediates in the preparation of pharmacologically active compounds described in European Patent Application No 79302141.

  式 (II) 的化合物：或其盐，其中 R 是氢或最多含有 6 个碳原子的烷基；X 是共价键或氧；Y 是-(CH2)n-，其中 n 是 0 或 1 至 5 的整数，其中未与氮原子结合的一个碳原子可任选被羟基取代；Z 是氢或卤素，是制备欧洲专利申请第 79302141 号所述药理活性化合物的有用中间体。