5-(2-hydroxyethyl)-6-methyl-2-methylthiopyrimidin-4(3H)-one | 98489-83-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(2-hydroxyethyl)-6-methyl-2-methylthiopyrimidin-4(3H)-one
• 英文别名: 5-(2-hydroxy-ethyl)-6-methyl-2-methylsulfanyl-3H-pyrimidin-4-one；5-(2-Hydroxy-aethyl)-6-methyl-2-methylmercapto-3H-pyrimidin-4-on；5-(2-hydroxyethyl)-6-methyl-2-(methylthio)-4(3H)-pyrimidinone；2-methylthio-5-(2-hydroxyethyl)-6-methyl-3H-pyrimidin-4-one；5-(2-hydroxyethyl)-6-methyl-2-(methylsulfanyl)-4(3H)-pyrimidinone；5-(2-hydroxyethyl)-4-methyl-2-methylsulfanyl-1H-pyrimidin-6-one
• CAS: 98489-83-9
• 化学式: C₈H₁₂N₂O₂S
• 分子量: 200.261
• InChiKey: YZKGFQOBXIGBEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-hydroxyethyl)-6-methyl-2-methylthiopyrimidin-4(3H)-one 在 三氯氧磷 作用下， 反应 2.0h， 以77%的产率得到4-chloro-5-(2-chloroethyl)-6-methyl-2-methylthiopyrimidine
  参考文献：
  名称：

  某些新型嘧啶和相关稠环系统的合成和体外评价作为潜在的抗癌药

  摘要：

  几种新的嘧啶6-11，18-20，呋喃并，噻吩并，和吡咯并[2,3- d ]嘧啶3，8，12，三唑并- [4,3-一个]嘧啶14，15，16和四唑由已知的中间体5-（2-羟乙基）-6-甲基-2-硫尿嘧啶（2）制备[1，5- a ]嘧啶17。化合物7（4-氯-5-（2-氯乙基）-2-甲硫基-6-甲基-嘧啶）在体外表现出较弱的抗肿瘤活性。

  DOI：

  10.1002/jhet.5570330202
• 作为产物：
  描述：

  2-(2-hydroxy-ethyl)-acetoacetic acid ethyl ester 在 sodium ethanolate 作用下， 生成 5-(2-hydroxyethyl)-6-methyl-2-methylthiopyrimidin-4(3H)-one
  参考文献：
  名称：

  Kawanishi, Tanabe seiyaku kenkyu nenpo = Annual report of Gohei Tanabe Co., 1958, vol. 3, # 1, p. 4,7

  摘要：

  DOI：

文献信息

• 2-aminopyrimidinone derivatives
  申请人：Janssen Pharmaceutica N.V.

  公开号：US05140029A1

  公开（公告）日：1992-08-18

  2-Amino-pyrimidininone derivatives possessing serotonin-antagonistic and antihistaminic properties. Compositions containing these compounds as the active ingredient. Method of treating subjects suffering from diseases and/or disorders associated with the release of neurotransmitters, in particular, a method of treating subjects suffering from sleep disorders with 2-aminopyrimidinone derivatives substituted with a 4-bis(aryl)methylene-1-piperidinyl group; and a method of treating subjects suffering from psychotic diseases and/or disorders with 2-aminopyrimidinone derivatives substituted with a 4-arylcarbonyl-1-piperidinyl, 4-benzazoyl-1-piperidinyl, 4-benzazolyl-1-piperazinyl or 4-indolyl-1-piperidinyl, 4-benzo[b]furanyl-1-piperidinyl or 4-benzo[b]thienyl-1-piperidinyl group.

  2-氨基嘧啶酮衍生物具有5-羟色胺拮抗和抗组胺性能。含有这些化合物作为活性成分的组合物。治疗患有与神经递质释放相关的疾病和/或障碍的受试者的方法，特别是一种使用取代有4-双(芳基)亚甲基-1-哌啶基的2-氨基嘧啶酮衍生物治疗患有睡眠障碍的受试者的方法；以及一种使用取代有4-芳基甲酰基-1-哌啶基、4-苯并咪唑基-1-哌啶基、4-苯并咪唑基-1-哌啶基、4-吲哚基-1-哌啶基、4-苯并[b]呋喃基-1-哌啶基或4-苯并[b]噻吩基-1-哌啶基的2-氨基嘧啶酮衍生物治疗患有精神疾病和/或障碍的受试者的方法。
• Tetrahydropyridin-4-yl indoles with a combination of affinity for dopamine-D2 receptors and serotonin reuptake sites
  申请人：Hes van Roelof

  公开号：US20060122206A1

  公开（公告）日：2006-06-08

  The present invention relates to a group of novel tetrahydropyridin-4-yl indoles with a dual mode of action: serotonin reuptake inhibition and affinity for dopamine-D 2 receptors, to methods for the preparation of these compounds and to novel intermediates useful for the synthesis of said tetrahydropyridin-4-yl indoles. The invention also relates to the use of a compound disclosed herein for the manufacture of a medicament giving a beneficial effect. The invention relates to novel tetrahydropyridin-4-yl indoles of the formula. and tautomers, stereoisomers, prodrugs, N-oxides, pharmacologically acceptable salts, hydrates and solvates thereof, wherein: R 1 is hydrogen, halogen, alkyl(C 1-3 ) or alkoxy(C 1-3 ), CN or CF 3 , R 2 is hydrogen or alkyl(C 1-3 ), R 3 is hydrogen or alkyl(C 1-3 ), Z is hydrogen or alkyl(C 1-3 ), alkoxy(C 1-3 ) or alkylthio(C 1-3 ), A is hydrogen or alkyl(C 1-3 ), or A and Z together form a saturated or (partly) unsaturated 5- or 6-membered ring which may be substituted with halogen, alkyl (C 1-3 ) or phenyl, in which ring Z represents carbon, sulfur of nitrogen.

  本发明涉及一组具有双重作用机制的新型四氢吡啶-4-基吲哚化合物：血清素再摄取抑制和对多巴胺-D2受体的亲和力，以及用于制备这些化合物的方法和用于合成所述四氢吡啶-4-基吲哚的有用新中间体。该发明还涉及利用本文披露的化合物制备具有有益效果的药物。该发明涉及公式中的新型四氢吡啶-4-基吲哚及其互变异构体、立体异构体、前药、N-氧化物、药理学上可接受的盐、水合物和溶剂合物，其中：R1为氢、卤素、烷基（C1-3）或烷氧基（C1-3）、CN或CF3，R2为氢或烷基（C1-3），R3为氢或烷基（C1-3），Z为氢或烷基（C1-3）、烷氧基（C1-3）或烷硫基（C1-3），A为氢或烷基（C1-3），或A和Z共同形成饱和或（部分）不饱和的5-或6-成员环，该环可用卤素、烷基（C1-3）或苯基取代，其中环Z代表碳、硫或氮。
• TETRAHYDROPYRIDIN-4-YL INDOLES WITH A COMBINATION OF AFFINITY FOR DOPAMINE-D2 RECEPTORS AND SEROTONIN REUPTAKE SITES
  申请人：Hes Roelof van

  公开号：US20070066634A2

  公开（公告）日：2007-03-22

  The present invention relates to a group of novel tetrahydropyridin-4-yl indoles with a dual mode of action: serotonin reuptake inhibition and affinity for dopamine-D 2 receptors, to methods for the preparation of these compounds and to novel intermediates useful for the synthesis of said tetrahydropyridin-4-yl indoles. The invention also relates to the use of a compound disclosed herein for the manufacture of a medicament giving a beneficial effect. The invention relates to novel tetrahydropyridin-4-yl indoles of the formula. and tautomers, stereoisomers, prodrugs, N-oxides, pharmacologically acceptable salts, hydrates and solvates thereof, wherein: R 1 is hydrogen, halogen, alkyl(C 1-3 ) or alkoxy(C 1-3 ), CN or CF 3 , R 2 is hydrogen or alkyl(C 1-3 ), R 3 is hydrogen or alkyl(C 1-3 ), Z is hydrogen or alkyl(C 1-3 ), alkoxy(C 1-3 ) or alkylthio(C 1-3 ), A is hydrogen or alkyl(C 1-3 ), or A and Z together form a saturated or (partly) unsaturated 5- or 6- membered ring which may be substituted with halogen, alkyl (C 1-3 ) or phenyl, in which ring Z represents carbon, sulfur of nitrogen.

  本发明涉及一组新型四氢吡啶-4-基吲哚化合物，具有双重作用模式：抑制血清素再摄取和亲和力对多巴胺-D2受体，以及用于制备这些化合物的方法和用于合成该四氢吡啶-4-基吲哚的新型中间体。本发明还涉及使用此处披露的化合物制造有益效果药物。本发明涉及式中的新型四氢吡啶-4-基吲哚和互变异构体、立体异构体、前药、N-氧化物、药学上可接受的盐、水合物和溶剂化物，其中：R1为氢、卤素、烷基（C1-3）或烷氧基（C1-3）、CN或CF3，R2为氢或烷基（C1-3），R3为氢或烷基（C1-3），Z为氢或烷基（C1-3）、烷氧基（C1-3）或烷硫基（C1-3），A为氢或烷基（C1-3），或A和Z一起形成饱和或（部分）不饱和的5-或6-成员环，该环可能被卤素、烷基（C1-3）或苯基取代，在该环中Z代表碳、硫或氮。
• Svab,A. et al., Collection of Czechoslovak Chemical Communications, 1967, vol. 32, # 4, p. 1582 - 1587
  作者：Svab,A. et al.

  DOI：——

  日期：——
• 2-Aminopyrimidinone derivatives
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0378254B1

  公开（公告）日：1994-06-22