2-(Tetrahydro-thiophen-2-yl)-pyrazine | 82081-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(Tetrahydro-thiophen-2-yl)-pyrazine
• 英文别名: 2-Pyrazinyltetrahydrothiophen；2-(thiolan-2-yl)pyrazine
• CAS: 82081-53-6
• 化学式: C₈H₁₀N₂S
• 分子量: 166.247
• InChiKey: SMTXCNOUCDVZKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(Tetrahydro-thiophen-2-yl)-pyrazine 、 异硫氰酸甲酯 在 正丁基锂 、 二异丙胺 作用下， 生成 N-Methyl-2-(pyrazin-2-yl)-tetrahydrothiophene-2-carbothioamide
  参考文献：
  名称：

  Synthesis and antisecretory and antiulcer activities of derivatives and analogs of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide

  摘要：

  New thioamide derivatives of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (29) and related compounds (in which the tetrahydrothiophene ring was replaced by tetrahydrothiopyran, tetrahydrofuran, 1,3-dithiane, or 1,3-oxathiane and where the pyridine ring was replaced by other nitrogen heterocycles) were synthesized and tested for their antisecretory and antiulcer activities. These thioamides were prepared according to one of the following methods: reaction of an isothiocyanate with the carbanion of the corresponding cyclic precursor (for secondary thioamides); reaction of ammonia or an amine with the dithio ester prepared from the same precursor (for primary, secondary, and tertiary thioamides). These thioamides were evaluated by the Shay method to measure their antisecretory activity and by the stress-induced-ulcer method to test their antiulcer activity. Structure-activity relationships are discussed. N-Methyl-2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (R.P. 40749, 30) exhibited activities that were at least 10 times higher than those reported for cimetidine.

  DOI：

  10.1021/jm00384a004
• 作为产物：
  描述：

  2-巯甲基吡嗪 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 2-(Tetrahydro-thiophen-2-yl)-pyrazine
  参考文献：
  名称：

  Synthesis and antisecretory and antiulcer activities of derivatives and analogs of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide

  摘要：

  New thioamide derivatives of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (29) and related compounds (in which the tetrahydrothiophene ring was replaced by tetrahydrothiopyran, tetrahydrofuran, 1,3-dithiane, or 1,3-oxathiane and where the pyridine ring was replaced by other nitrogen heterocycles) were synthesized and tested for their antisecretory and antiulcer activities. These thioamides were prepared according to one of the following methods: reaction of an isothiocyanate with the carbanion of the corresponding cyclic precursor (for secondary thioamides); reaction of ammonia or an amine with the dithio ester prepared from the same precursor (for primary, secondary, and tertiary thioamides). These thioamides were evaluated by the Shay method to measure their antisecretory activity and by the stress-induced-ulcer method to test their antiulcer activity. Structure-activity relationships are discussed. N-Methyl-2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (R.P. 40749, 30) exhibited activities that were at least 10 times higher than those reported for cimetidine.

  DOI：

  10.1021/jm00384a004

文献信息

• Thiocarboxamide derivatives and their use as pharmaceuticals
  申请人：Rhone-Poulenc Sante

  公开号：US04379154A1

  公开（公告）日：1983-04-05

  Thioformamide derivatives of the formula: ##STR1## wherein R represents hydrogen or alkyl of 1 through 4 carbon atoms, and (i) Het represents a heterocyclic radical selected from pyrid-3-yl, pyrid-4-yl, pyridazinyl, pyrazinyl, pyrimidinyl, quinolyl, imidazolyl, naphthyridinyl, quinoxalinyl and quinazolinyl, X represents sulphur or oxygen and Y represents sulphur or oxygen, a valency bond or methylene, or (ii) Het represents pyrid-2-yl, X represents sulphur or oxygen and Y represents sulphur or oxygen or methylene, or (iii) Het represents pyrid-2-yl, X represents oxygen and Y represents a valency bond, are new compounds possessing useful pharmacological properties. They are particularly useful in the treatment of gastrointestinal ulcers and in the treatment of hypertension, depending on the definition of the symbol Het.

  式为：##STR1## 其中R代表氢或1至4个碳原子的烷基，(i)Het代表从吡啶-3-基、吡啶-4-基、吡嗪基、吡咯嗪基、嘧啶基、喹啉基、咪唑基、萘啶基、喹喔啉基和喹唑啉基中选出的杂环基，X代表硫或氧，Y代表硫或氧、一个价键或亚甲基，或者(ii) Het代表吡啶-2-基，X代表硫或氧，Y代表硫或氧或亚甲基，或者(iii) Het代表吡啶-2-基，X代表氧，Y代表一个价键的新化合物具有有用的药理学性质。它们在治疗胃肠溃疡和高血压方面特别有用，具体取决于符号Het的定义。
• Nouveaux dérivés de la thioformamide, leur préparation et les médicaments qui les contiennent
  申请人：RHONE-POULENC SANTE

  公开号：EP0046417A1

  公开（公告）日：1982-02-24

  Nouveaux dérivés de la thioformamide de formule générale (1) dans laquelle R est hydrogène ou alcoyle (1 à 4 C) et, - soit Het est pyridyle-3 ou 4, pyridazinyle, pyrazinyle, pyrimidinyle, quinolyle, imidazolyle, naphtyridinyle, quinoxalinyle ou quinazolinyle, X représente un soufre ou un oxygène et Y représente un soufre, un oxygène, une liaison de valence ou un radical méthylène, - soit Het représente pyridyle-2, X représente un soufre ou un oxygène et Y est un soufre, un oxygène ou un radical méthylène, - soit Het représente pyridyle-2, X est un oxygène et Y une liaison de valence. Ces nouveaux dérivés sont particulièrement utiles comme anti-ulcères et anti-hypertenseurs.

  通式（1）的新型硫代甲酰胺衍生物，其中 R 是氢或烷基（1-4 C），--或者 Het 是吡啶基-3 或 4、哒嗪基、吡嗪基、嘧啶基、喹啉基、咪唑基、萘啶基、喹喔啉基或喹唑啉基，X 代表硫或氧，Y 代表硫、氧、价键或亚甲基基，--或者 Het 代表吡啶基-2，X 代表硫或氧，Y 是硫、氧或亚甲基基，--或者 Het 代表吡啶基-2，X 是氧，Y 是价键 这些新型衍生物特别适用于抗溃疡和抗高血压药物。
• ALOUP J. C.; BOUCHAUDON J.; FARGE D.; JAMES C.; DEREGNAUCOURT J.; HARDY-H+, J. MED. CHEM., 30,(1987) N 1, 24-29
  作者：ALOUP J. C.、 BOUCHAUDON J.、 FARGE D.、 JAMES C.、 DEREGNAUCOURT J.、 HARDY-H+

  DOI：——

  日期：——
• US4379154A
  申请人：——

  公开号：US4379154A

  公开（公告）日：1983-04-05
• Synthesis and antisecretory and antiulcer activities of derivatives and analogs of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide
  作者：Jean-Claude Aloup、Jean Bouchaudon、Daniel Farge、Claude James、Jean Deregnaucourt、Monique Hardy-Houis

  DOI：10.1021/jm00384a004

  日期：1987.1

  New thioamide derivatives of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (29) and related compounds (in which the tetrahydrothiophene ring was replaced by tetrahydrothiopyran, tetrahydrofuran, 1,3-dithiane, or 1,3-oxathiane and where the pyridine ring was replaced by other nitrogen heterocycles) were synthesized and tested for their antisecretory and antiulcer activities. These thioamides were prepared according to one of the following methods: reaction of an isothiocyanate with the carbanion of the corresponding cyclic precursor (for secondary thioamides); reaction of ammonia or an amine with the dithio ester prepared from the same precursor (for primary, secondary, and tertiary thioamides). These thioamides were evaluated by the Shay method to measure their antisecretory activity and by the stress-induced-ulcer method to test their antiulcer activity. Structure-activity relationships are discussed. N-Methyl-2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (R.P. 40749, 30) exhibited activities that were at least 10 times higher than those reported for cimetidine.