3-pyridylcyclohexanone thioamide | 124034-07-7

• 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: 3-pyridylcyclohexanone thioamide
• 英文别名: (-)-N-methyl-2-oxo-1-(pyridin-3-yl)cyclohexanecarbothioamide；N-methyl-2-oxo-1-(pyrid-3-yl)-cyclohexanecarbothioamide；(+/-)-N-methyl-2-oxo-1-(3-pyridyl)cyclohexanecarbothioamide；N-methyl-2-oxo-1-pyridin-3-ylcyclohexane-1-carbothioamide
• CAS: 124034-07-7
• 化学式: C₁₃H₁₆N₂OS
• 分子量: 248.349
• InChiKey: PYJPFPWAYOYUMI-UHFFFAOYSA-N

物化性质

• 沸点：
  408.7±55.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-pyridylcyclohexanone thioamide 在 吡啶 、 4-二甲氨基吡啶 、 钾硼氢 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 [1R,2S]-trans-2-benzoyloxy-N-methyl-1-(pyrid-3-yl)cyclohexanecarbothioamide
  参考文献：
  名称：

  The synthesis of RP 65479 a novel, potent potassium channel opener.

  摘要：

  The potent potassium channel opener, 4, RP 65479, has been synthesised from the key intermediate, 2-(3-pyridyl)cyclohexanone, 8.

  DOI：

  10.1016/s0040-4039(00)61206-6
• 作为产物：
  描述：

  2-甲氧基环己酮 在 正丁基锂 、 硫酸 、 oxonium 、 水 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 3-pyridylcyclohexanone thioamide
  参考文献：
  名称：

  The synthesis of RP 66471. A potent potassium channel opener.

  摘要：

  The potent, homochiral, potassium channel opener, PP 66471, has been synthesised and shown to possess the (1R, 2S) configuration.

  DOI：

  10.1016/s0040-4039(00)60875-4

文献信息

• Derivatives of thioformamide
  申请人：Rhone-Poulenc Sante

  公开号：US05151436A1

  公开（公告）日：1992-09-29

  Therapeutically useful thioformamide derivatives of the formula: ##STR1## wherein R represents alkyl, Het represents pyrid-3-yl, isoquinolin-4-yl, tetrahydroquinolin-3-yl, quinolin-3-yl, pyridazin-4-yl, pyrimid-5-yl, thiazol-5-yl, thieno[2,3-b]-pyridin-5-yl, pyrazin-2-yl, indol-3-yl and thieno[3,2-b]-pyridin-6-yl, Y represents ethylene, methylene or a valency bond, and X represents carbonyl, hydroxymethylene, >C.dbd.NOR.sup.1, >C.dbd.NN(R.sup.1).sub.2 or >C.dbd.NN(R.sup.1)CON(R.sup.1).sub.2 in which R.sup.1 represents hydrogen or optionally substituted alkyl, benzyl, phenethyl, 1-naphthylmethyl, 2-naphthylmethyl or pyrid-3-ylmethyl, or two R.sup.1 substituents on the same nitrogen atom may together form an optionally substituted alkylene radical chain and salts thereof, processes for their preparation and compositions containing them are described.

  公式为：##STR1## 其中R代表烷基，Het代表吡啶-3-基，异喹啉-4-基，四氢喹啉-3-基，喹啉-3-基，吡啶并嗪-4-基，嘧啶-5-基，噻唑-5-基，噻吩[2,3-b]-吡啶-5-基，吡嗪-2-基，吲哚-3-基和噻吩[3,2-b]-吡啶-6-基，Y代表乙烯，亚甲基或一个价键，X代表羰基，羟甲基，>C.dbd.NOR.sup.1，>C.dbd.NN(R.sup.1).sub.2或>C.dbd.NN(R.sup.1)CON(R.sup.1).sub.2，其中R.sup.1代表氢或可选择地取代的烷基，苄基，苯乙基，1-萘甲基，2-萘甲基或吡啶-3-甲基，或同一氮原子上的两个R.sup.1取代基可能共同形成一个可选择地取代的烷基链，以及它们的盐，描述了其制备方法和含有它们的组合物。
• Thioformamide derivatives
  申请人：Rhone-Poulenc Sante

  公开号：US05246950A1

  公开（公告）日：1993-09-21

  Thioformamide derivatives of the formula (I) ##STR1## wherein R represents an alkyl group; A represents either: (1) a phenyl group which is optionally substituted; or (2) heteroaromatic group (e.g. pyrid-3-yl, quinolin-3-yl); Y represents: an ethylene or methylene group or a direct bond; and B represents either: a) a phenyl, pyridyl, furyl or thienyl group, each of which may be optionally substituted, or b) a straight- or branched-chain alkyl, alkenyl, or cycloalkyl group, each of which may be optionally substituted. These compounds may be formulated into pharmaceutical preparations and have utility in the treatment of disorders associated with smooth muscle contraction.

  Thioformamide衍生物的化学式(I) ##STR1## 其中R代表烷基; A代表：(1) 可选择取代的苯基; 或(2) 杂芳基(例如吡啶-3-基，喹啉-3-基); Y代表：乙烯基或亚甲基或直接键; B代表：a) 可选择取代的苯基，吡啶基，呋喃基或噻吩基，或b) 直链或支链烷基，烯基或环烷基，每种均可选择取代。这些化合物可以制成药物制剂，并在治疗与平滑肌收缩有关的疾病中发挥作用。
• Syntheses and biological activities of potent potassium channel openers derived from (.+-.)-2-oxo-1-pyridin-3-yl-cyclohexanecarbothioic acid methylamide: new potassium channel openers
  作者：Thomas J. Brown、Robert F. Chapman、Jonathan S. Mason、Malcolm N. Palfreyman、Nigel Vicker、Roger J. A. Walsh

  DOI：10.1021/jm00063a010

  日期：1993.5

  K(+)-channel opening activity are presented. These new series of potassium channel openers so derived are best exemplified by (+/-)-2-[2-(phenylsulfanyl)ethylidene]-1-pyridin-3-ylcyclohexan ecarbothioic acid methylamide (13d, RP 66266) and trans-(+/-)-2-[2-[(phenylsulfonyl)amino]ethyl]-1-pyridin-3- ylcyclohexanecarbothioic acid methylamide (25a, RP 66784), which have IC90 values of 3 and 0.3 nM, respectively

  （+/-）-2-（氰基亚甲基）-1-吡啶-3-基环己烷甲硫基++ +酸甲酰胺（6）和反式（+/-）-2-（氰基甲基）-1-吡啶-的合成及生物活性据报道衍生自（+/-）-2-氧代-1-吡啶-3-基环己烷甲硫代甲酸甲基酰胺（4）的3-基环己烷甲硫代甲酸甲基酰胺（14）。测试化合物对钾诱导的去内皮化大鼠主动脉收缩的拮抗作用。提出了6和14修饰对体外K（+）通道开放活性的影响。如此衍生的这些新系列的钾通道开放剂最好以（+/-）-2- [2-（苯基硫烷基）亚乙基] -1-吡啶-3-基环己基硫代硫代甲酸甲酰胺（13d，RP 66266）和反式-（ +/-）-2- [2-[（[苯磺酰基）氨基]乙基] -1-吡啶-3-基环己烷硫代甲酸甲酰胺（25a，RP 66784），其IC90值分别为3和0.3 nM。最具活性的化合物的效力表明在额外的结合位点可能发生相互作用。本文所述的化合物是潜在的抗高血压药和抗心绞痛药。
• Pyrid-3-yl thioformamide compounds which have useful pharmaceutical
  申请人：Rhone-Poulenc Sante

  公开号：US05064843A1

  公开（公告）日：1991-11-12

  This invention relates to a thioformamide derivative of the formula I ##STR1## wherein: R and R.sup.1 each independently represent an alkyl group; A represents either: (1) a phenyl group which is optionally substituted; or (2) a heteroaromatic group (e.g. pyrid-3-yl, quinolin-3-yl); and Y represents: an ethylene or methylene group or a direct bond. These compounds may be formulated as pharmaceutical preparations and have utility for the treatment of disorders associated with smooth muscle contraction.

  这项发明涉及式I的硫代甲酰胺衍生物，其中：R和R.sup.1分别独立代表烷基基团；A表示：(1) 一个苯基团，可以是可选取代的；或(2) 一个杂环芳基团（例如吡啶-3-基，喹啉-3-基）；Y表示：一个乙烯基或亚甲基基团或直接键。这些化合物可以制备为药物制剂，并用于治疗与平滑肌收缩相关的疾病。
• Thioformamide derivative, process for its preparation, pharmaceutical
  申请人：Rhone-Poulenc Sante

  公开号：US05276045A1

  公开（公告）日：1994-01-04

  A thioformamide derivative of the formula: ##STR1## wherein R represents alkyl, A represents optionally substituted pyrid-3-yl, isoquinolin-4-yl, tetrahydroquinolin-3-yl, quinolin-3-yl, pyridazin-4-yl, pyrimid-5-yl, thiazol-5-yl, thieno[2,3-b]pyridin-5-yl, pyrazin-2-yl, indol-3-yl and thieno[3,2-b]pyridin-6-yl, or phenyl and Y represents a valency bond, methylene or ethylene, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, aryloxyalkyl, aromatic heterocyclylalkyl or aromatic heterocyclyloxyalkyl group or a group ZC(.dbd.O)-- in which Z represents optionally substituted alkyl, aryl, or aromatic heterocyclic, n represents 0 or 1, and when n represents 0, R.sup.1 may represent a hydrogen atom, optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, aryloxyalkyl, aromatic heterocyclylalkyl or aromatic heterocyclyloxyalkyl group or a group ZC(.dbd.O)-- or ZSO.sub.2 --, and when n represents 1, R.sup.1 represents optionally substituted alkyl, benzyl, phenethyl, 1-naphthylmethyl, 2-naphthylmethyl or pyrid-3-ylmethyl radical and pharmaceutically acceptable salts thereof possess pharmacological properties.

  一种硫代甲酰胺衍生物，其化学式为：##STR1## 其中R代表烷基，A代表可选取代的吡啶-3-基，异喹啉-4-基，四氢喹啉-3-基，喹啉-3-基，吡嗪-4-基，嘧啶-5-基，噻唑-5-基，噻吩[2,3-b]吡啶-5-基，吡嗪-2-基，吲哚-3-基和噻吩[3,2-b]吡啶-6-基，或苯基，Y代表价键，亚甲基或乙烯基，R.sup.2代表氢，可选取代的烷基，环烷基，环烷基烷基，芳基，芳基烷基，芳基氧烷基，芳基杂环烷基或芳基杂环氧烷基或ZC(.dbd.O)--基团，其中Z代表可选取代的烷基，芳基或芳基杂环，n代表0或1，当n代表0时，R.sup.1可以代表氢原子，可选取代的烷基，环烷基，环烷基烷基，芳基，芳基烷基，芳基氧烷基，芳基杂环烷基或芳基杂环氧烷基或ZC(.dbd.O)--或ZSO.sub.2 --基团，当n代表1时，R.sup.1代表可选取代的烷基，苄基，苯乙基，1-萘甲基，2-萘甲基或吡啶-3-基甲基基团及其药学上可接受的盐具有药理特性。