5-(2-Bromo-acetyl)-nicotinic acid methyl ester | 60699-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(2-Bromo-acetyl)-nicotinic acid methyl ester
• 英文别名: Methyl 5-(2-bromoacetyl)pyridine-3-carboxylate
• CAS: 60699-65-2
• 化学式: C₉H₈BrNO₃
• 分子量: 258.071
• InChiKey: ABBYOGNAPSAFBG-UHFFFAOYSA-N

物化性质

• 沸点：
  359.6±32.0 °C(Predicted)
• 密度：
  1.561±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-Bromo-acetyl)-nicotinic acid methyl ester 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 5.0h， 生成 N-[4-(5-Chloromethyl-pyridin-3-yl)-thiazol-2-yl]-guanidine
  参考文献：
  名称：

  Studies on antiulcer drugs. 7. 2-Guanidino-4-pyridylthiazoles as histamine H2-receptor antagonists with potent gastroprotective effects against nonsteroidal antiinflammatory drug-induced injury

  摘要：

  A series of 2-guanidino-4-pyridylthiazole derivatives were synthesized and evaluated for anti-aspirin-ulcer, gastric antisecretory, and histamine-H-2-receptor-antagonist activities. Several compounds showed superior anti-aspirin-ulcer activity to that of clinically used H-2-antagonists in the rat. Among them, 4-[6-(acetamidomethyl)pyridin-2-yl]-2-guanidinothiazole (8) demonstrated potent inhibitory activities against gastric lesions caused by two kinds of nonsteroidal antiinflammatory drugs, aspirin and indomethacin, respectively, in addition to strong antisecretory activity. Compound 8 possessed a preventable ability for the aspirin-induced reduction of the gastric mucosal blood flow at an intragastric administration of 32 mg/kg in the rat. On the other hand, famotidine (32 mg/kg) exhibited no significant effect and ranitidine (100 mg/kg) aggravated the blood flow in this system.

  DOI：

  10.1021/jm00027a007
• 作为产物：
  描述：

  5-乙酰基烟酸甲酯 在 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 5-(2-Bromo-acetyl)-nicotinic acid methyl ester
  参考文献：
  名称：

  Studies on antiulcer drugs. 7. 2-Guanidino-4-pyridylthiazoles as histamine H2-receptor antagonists with potent gastroprotective effects against nonsteroidal antiinflammatory drug-induced injury

  摘要：

  A series of 2-guanidino-4-pyridylthiazole derivatives were synthesized and evaluated for anti-aspirin-ulcer, gastric antisecretory, and histamine-H-2-receptor-antagonist activities. Several compounds showed superior anti-aspirin-ulcer activity to that of clinically used H-2-antagonists in the rat. Among them, 4-[6-(acetamidomethyl)pyridin-2-yl]-2-guanidinothiazole (8) demonstrated potent inhibitory activities against gastric lesions caused by two kinds of nonsteroidal antiinflammatory drugs, aspirin and indomethacin, respectively, in addition to strong antisecretory activity. Compound 8 possessed a preventable ability for the aspirin-induced reduction of the gastric mucosal blood flow at an intragastric administration of 32 mg/kg in the rat. On the other hand, famotidine (32 mg/kg) exhibited no significant effect and ranitidine (100 mg/kg) aggravated the blood flow in this system.

  DOI：

  10.1021/jm00027a007

文献信息

• New thiazole derivatives, processes for the preparation thereof and pharmaceutical compositon comprising the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0417751A2

  公开（公告）日：1991-03-20

  A compound of the formula : wherein R' is amino which may have suitable substituent ( s). hydroxy. halogen, cyano, acyl, heterocyclic thio, heterocyclic group or a group of the formula : in which R4 is hydrogen, cyano or acyl. and R5 is amino or lower alkoxy. R2 and R3 are each hydrogen, acyl or lower alkyl which may have halogen: or R2 and R3 are linked together to form lower alkylene. in which R6 is hydrogen or halogen, and A is bond or lower alkylene, provided that when R1 is amino which may have suitable substituent(s) and A is bond; or R1 is lower alkylthioureido and A is lower alkylene, then and pharmaceutically acceptable salt thereof, processes for their preparation and pharmaceutical compositions comprising them as an active. ingredient.

  式中的化合物 其中 R'为氨基，可具有合适的取代基（s）、羟基、卤素、氰基、酰基、杂环硫基、杂环基团或式......的基团： 其中 R4 是氢、氰基或酰基。 R5 是氨基或低级烷氧基。 R2 和 R3 各为氢、酰基或低级烷基，其中可含卤素：或 R2 和 R3 连接在一起形成低级亚烷基。 其中 R6 是氢或卤素，以及 A 是键或低级亚烷基、 条件是 当 R1 是氨基，可有适当的取代基，且 A 为键；或 R1 为低级烷基硫脲基，且 A 为低级亚烷基时 且 A 为低级亚烷基，则 以及它们的药学上可接受的盐、它们的制备方法和含有它们作为活性成分的药物组合物。
• [DE] NEUE THIAZOL-DERIVATE MIT PHOSPHODIESTERASE INHIBIERENDER WIRKUNG<br/>[EN] NEW THIAZOLE DERIVATIVES WITH PHOSPHODIESTERASE-INHIBITING EFFECT<br/>[FR] NOUVEAUX DERIVES DE THIAZOL A EFFET INHIBANT LA PHOSPHODIESTERASE
  申请人：BYK GULDEN LOMBERG CHEMISCHE FABRIK GMBH

  公开号：WO1998008841A1

  公开（公告）日：1998-03-05

  (DE) Verbindungen der Formel (I), worin R1, R2, R3, R4, R5 und n die in der Beschreibung angegebenen Bedeutungen haben, sind neue wirksame Bronchialtherapeutika (Inhibitoren der Phosphodiesterase IV).(EN) Compounds having the formula (I), in which R1, R2, R3, R4 and n have the meanings given in the description, are new effective bronchotherapeutic agents (phosphodiesterase IV inhibitors).(FR) L'invention concerne des composés de la formule (I) dans laquelle R1, R2, R3, R4 et R5 et n ont la signification donnée dans la description. Ces composés sont de nouveaux agents thérapeutiques pour les bronches efficaces.

  以下是对英文文本的准确翻译： (DE) Verbindungen der Formel (I), worin R1, R2, R3, R4, R5 und n die in der Beschreibung angegebenen Bedeutungen haben, sind neue wirksame Bronchialtherapeutika (Inhibitoren der Phosphodiesterase IV). 翻译：其中，(I)形式的化合物，其中R1、R2、R3、R4、R5和n具有描述中给出的意义，都是新的有效的支气管药物（磷酸酯酶IV抑制剂）。 (EN) Compounds having the formula (I), in which R1, R2, R3, R4 and n have the meanings given in the description, are new effective bronchotherapeutic agents (phosphodiesterase IV inhibitors). 翻译：其中，化合物有公式(I)，R1、R2、R3、R4和n具有描述中给出的意义，都是新的有效的支气管治疗药物（磷酸酯酶IV抑制剂）。 (FR) L'invention concerne des composés de la formule (I) dans laquelle R1, R2, R3, R4 et R5 et n ont la signification donnée dans la description. Ces composés sont de nouveaux agents thérapeutiques pour les bronches efficaces. 翻译：这些化合物涉及公式(I)，其中R1、R2、R3、R4和R5以及n具有描述中给出的意义。这些化合物是新的有效的支气管治疗药物。
• THIAZOLE DERIVATIVES
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0575614A1

  公开（公告）日：1993-12-29
• NEUE THIAZOL-DERIVATE MIT PHOSPHODIESTERASE INHIBIERENDER WIRKUNG
  申请人：ALTANA Pharma AG

  公开号：EP0920426B1

  公开（公告）日：2003-10-01
• US5364871A
  申请人：——

  公开号：US5364871A

  公开（公告）日：1994-11-15