4-chlorobutyl 2-pyridylmethyl sulfide | 82081-46-7

• 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: 4-chlorobutyl 2-pyridylmethyl sulfide
• 英文别名: Pyrid-2-ylmethyl 4-chlorobutyl sulphide；2-(4-chlorobutylsulfanylmethyl)pyridine
• CAS: 82081-46-7
• 化学式: C₁₀H₁₄ClNS
• 分子量: 215.747
• InChiKey: SPOJMJGNESDJGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  311.2±27.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chlorobutyl 2-pyridylmethyl sulfide 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 1.0h， 以79%的产率得到2-(2-pyridyl)tetrahydrothiopyran
  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-(2-pyridylmethyl)isothiourea dihydrochloride 在 sodium hydroxide 作用下， 反应 0.33h， 生成 4-chlorobutyl 2-pyridylmethyl sulfide
  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

• Synthesis and biological activity of trans-(.+-.)-N-methyl-2-(3-pyridyl)-2-tetrahydrothiopyrancarbothioamide 1-oxide (RP 49356) and analogs: a new class of potassium channel opener
  作者：Thomas J. Brown、Robert F. Chapman、David C. Cook、Terance W. Hart、Iain M. McLay、Roy Jordan、Jonathan S. Mason、Malcolm N. Palfreyman、Roger J. A. Walsh

  DOI：10.1021/jm00098a004

  日期：1992.10

  othioamid+ ++ e 1-oxide (8a, RP 49356) and analogues is reported. These compounds constitute a new structural class of K(+)-channel opener. The effects of changes in pyridyl group, thioamide, and thiane ring on in vitro K(+)-channel opening reactivity are discussed. A 3-pyridyl or 3-quinolyl group, a small N-alkyl thioamide function, and a thiane oxide ring, in which the sulfoxide is in a trans relationship

  报道了反式-（+-）-N-甲基-2-（3-吡啶基）-2-四氢硫代吡喃氨基甲磺酰胺+++ e 1-氧化物（8a，RP 49356）和类似物的合成和生物活性。这些化合物构成K（+）通道开放剂的新结构类。讨论了吡啶基，硫代酰胺和硫杂环上的变化对体外K（+）通道开放反应性的影响。为了活性，优选3-吡啶基或3-喹啉基，小的N-烷基硫代酰胺官能团和氧化亚砜环，其中亚砜与硫代酰胺具有反式关系。选择的化合物在降压麻醉的大鼠中静脉内测试降压作用，其活性反映了其体外K（+）通道的开放活性。
• 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。
• 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
• US4680303A
  申请人：——

  公开号：US4680303A

  公开（公告）日：1987-07-14