2-methylsulfanyl-5-pyridin-2-ylmethyl-3H-pyrimidin-4-one | 64107-52-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methylsulfanyl-5-pyridin-2-ylmethyl-3H-pyrimidin-4-one
• 英文别名: 5-(pyridin-2-ylmethyl)-2-methylthio-4-pyrimidone；5-(2-pyridylmethyl)-2-methylthio-4-pyrimidone；5-<2>Pyridylmethyl-2-methylthio-4-pyrimidon；2-methylsulfanyl-5-(pyridin-2-ylmethyl)-1H-pyrimidin-6-one
• CAS: 64107-52-4
• 化学式: C₁₁H₁₁N₃OS
• 分子量: 233.294
• InChiKey: DADQIFJRAOADQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(((5-二甲基氨基)甲基)-2-呋喃基)甲基)硫代乙胺 、 2-methylsulfanyl-5-pyridin-2-ylmethyl-3H-pyrimidin-4-one 以 吡啶 为溶剂， 反应 24.0h， 生成 2-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethylamino]-5-(pyridin-2-ylmethyl)-1H-pyrimidin-6-one
  参考文献：
  名称：

  Dérivés de l'isocytosine antagonistes des récepteurs H2 de l'histamine. III. Synthèse et activité biologique de la lupitidine (SK&F 93479) et de composés apparentés

  摘要：

  DOI：

  10.1016/0223-5234(90)90204-g
• 作为产物：
  描述：

  5-<2>Pyridylmethyl-2-thiouracil 、 碘甲烷 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 生成 2-methylsulfanyl-5-pyridin-2-ylmethyl-3H-pyrimidin-4-one
  参考文献：
  名称：

  Substituted isocytosines having histamine H.sub.2 -antagonist activity

  摘要：

  这些化合物是取代的异胞嘧啶，是组织胺H.sub.2-拮抗剂。本发明的两种具体化合物是2-[2-(5-甲基-4-咪唑基甲硫基)乙基]氨基-5-(3-吡啶甲基)-4-吡咯酮和2-[2-(3-溴-2-吡啶甲硫基)乙基]氨基-5-(4-吡啶甲基)-4-吡咯酮。

  公开号：

  US04154834A1

文献信息

• Synthesis of 2-Substituted Pyrimido[5,4-b]indolizine Derivatives from Acetates of Baylis-Hillman Adducts
  作者：Chunhao Yang、Yuyuan Xie、Min Jiang、Qian He

  DOI：10.3987/com-08-11428

  日期：——

  synthesized conveniently in two steps. The key intermediates 2-substituted 5-[(pyridin-2-yl)methyl]pyrimidin-4(3H)-ones 2 were obtained by facile cyclization of the acetate of Baylis-Hillman adduct 3 and various amidine hydrochlorides 4 in the presence of sodium ethoxide. Treatment of 5-[(pyridin-2-yl)methyl]pyrimidin-4(3H)-ones 2 with phosphoryl chloride by reflux afforded fused 2-substituted pyrimido[5

  - 新型三环杂环嘧啶并[5,4-b]中氮茚衍生物1通过两步方便地合成。关键中间体 2-取代的 5-[(pyridin-2-yl)methyl]pyrimidin-4(3H)-ones 2 由 Baylis-Hillman 加合物 3 和各种脒盐酸盐 4 在乙醇钠。通过回流用磷酰氯处理 5-[(pyridin-2-yl)methyl]pyrimidin-4(3H)-ones 2 以高产率提供稠合的 2-取代的嘧啶并 [5,4-b] 中氮茚 1。
• Heterocyclic alkyl 4-pyrimidones
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04216318A1

  公开（公告）日：1980-08-05

  The compounds are substituted isocytosines which are histamine H.sub.2 -antagonists. Two specific compounds of the present invention are 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-py rimidone and 2-[2-(3-bromo-2-pyridylmethylthio)-ethylamino]-5-(4-pyridylmethyl)-4-pyrim idone.

  这些化合物是取代的异胞嘧啶，它们是组胺H.sub.2-拮抗剂。本发明的两种特定化合物是2-[2-(5-甲基-4-咪唑基甲硫基)乙基氨基]-5-(3-吡啶甲基)-4-吡咯酮和2-[2-(3-溴-2-吡啶甲硫基)-乙基氨基]-5-(4-吡啶甲基)-4-吡咯酮。
• Iso(thio)ureas, processes for their preparation and compositions containing them
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0007232A1

  公开（公告）日：1980-01-23

  Isoureas and isothioureas which are histamine H2- antagonists and also have histamine H1-antagonist activity and antiinflammatory activity having the structure in which R' and R2 are hydrogen, lower alkyl, or together with the carbon and two nitrogen atoms shown form a dihydroimidazolyl or tetrahydropyrimidyl group, Y is sulphur or oxygen, n is from 3 to 8, X is oxygen or sulphur, Z is hydrogen or lower alkyl, A is C1-C3 alkylene or -(CH2)pW(CH2)q- where W is oxygen or sulphur and the sum of p and q is 1 to4, and B is methyl, cycloalkyl, heteroaryl, aryl or, when A is alkylene, hydrogen, are prepared by a process in which a compound of structure where D is HY- or a leaving group is reacted with: (a) when D is HY-, an isothiourea where A is lower alkyl or aryl (lower alkyl), or a cyanamide R1HNCN or a carbodiimide R1N=C=NR2 or (b) when D is a leaving group, a urea or thiourea or, when Y is oxyen a compound of structure where G is a lower alkylthio, chlorine, bromine or NO2NH-, is reacted with an isothiourea of Structure

  异脲类和异硫脲类是组胺 H2-拮抗剂，也具有组胺 H1-拮抗剂活性和抗炎活性，其结构为 其中 R' 和 R2 为氢、低级烷基或与所示的碳原子和两个氮原子一起形成二氢咪唑基或四氢嘧啶基，Y 为硫或氧，n 为 3 至 8，X 为氧或硫，Z 为氢或低级烷基、A 为 C1-C3 亚烷基或-(CH2)pW(CH2)q-，其中 W 为氧或硫，p 和 q 之和为 1 至 4，B 为甲基、环烷基、杂芳基、芳基或（当 A 为亚烷基时）氢，通过以下工艺制备结构如下的化合物 其中 D 为 HY- 或离去基团，并与之反应： (a) 当 D 为 HY- 时，异硫脲 其中 A 为低级烷基或芳基（低级烷基），或氰胺 R1HNCN 或碳化二亚胺 R1N=C=NR2 或 (b) 当 D 为离去基团时，脲或硫脲 或当 Y 为氧烯时，结构如下的化合物 其中 G 为低级烷硫基、氯、溴或 NO2NH- 时，与结构式如下的异硫脲反应
• Pyrimidinone derivatives, processes for preparing them and pharmaceutical compositions containing them
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0013071A1

  公开（公告）日：1980-07-09

  The invention provides new histamine H2- antagonist compounds of Structure 1 in which R' is hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen, trifluoromethyl, nitro, amino, lower alkylamino, lower alkanoylamino, di(lower alkyl)amino or cyano; R2 is in the 3-, 4- or 5- position and is hydrogen, or R2 is lower alkyl substituted by amino, lower alkylamino, di(lower alkyl)amino, N-piperidino or N-pyrollidino, or R2 is ethoxy or propoxy w-substituted by amino, lower alkylamino, di(lower alkyl)amino, N-piperidino or N-pyrollidino; Y is methylene or oxygen and X is methylene or sulphur provided that one or two of the groups X and Y is methylene; Z is hydrogen or lower alkyl; A is C1-C5 alkylene or-(CH2)pW-(CH2)q-where W is oxygen or sulphur and p and q are such that their sum is from 1 to4, and B is hydrogen, methyl, C3-C6 cycloalkyl, a heteroaryl group optionally substituted by one or more of the groups lower alkyl, lower alkoxy, halo, hydroxy and amino, or B is a naphthyl, 6-(2,3-dihydro-1,4-benzodioxinyl), a 4- or 5-(1,3-benzodioxolyl) group, or a phenyl group optionally substituted with one or more lower alkyl, lower alkoxy, halogen, aryl(lower alkoxy), hydroxy, lower alkoxy-lower alkoxy, trifluoromethyl, di(lower alkyl)amino, phenoxy, halophenoxy, lower alkoxyphenoxy, phenyl, halophenyl or lower alkoxyphenyl groups and pharmaceutical compositions containing them. A compound of Structure 1 can be prepared by reacting a compound of Structure 3 in which Q is nitroamino, loweralkylthio, benzylthio or halogen with an amine of Structure 2, in which R3 is in the 3-, 4- or 5p position and is hydrogen, lower alkyl substituted by a group R4, or is R4CH2CH2O-or R4CH2CH2CH2O-, where R' is di(lower alkyl)amino, N-piperidino, N-pyrrollidino, a protected amino group or a protected lower alkylamino group, and where necessary any amino-protecting group present in the substituent R3 is removed.

  本发明提供了结构 1 的新型组胺 H2- 拮抗剂化合物 其中R'是氢、低级烷基、低级烷氧基、羟基、卤素、三氟甲基、硝基、氨基、低级烷基氨基、低级烷酰氨基、二（低级烷基）氨基或氰基；R2 位于 3-、4-或 5-位且为氢，或 R2 为被氨基、低级烷基氨基、二（低级烷基）氨基、N-哌啶基或 N-吡咯烷基取代的低级烷基，或 R2 为被氨基、低级烷基氨基、二（低级烷基）氨基、N-哌啶基或 N-吡咯烷基取代的乙氧基或丙氧基；Y 为亚甲基或氧，X 为亚甲基或硫，条件是 X 和 Y 中的一个或两个基团为亚甲基；Z 为氢或低级烷基；A是C1-C5亚烷基或-(CH2)pW-(CH2)q-其中W是氧或硫，p和q的和为1至4，B是氢、甲基、C3-C6环烷基、任选被一个或多个基团低级烷基、低级烷氧基、卤代、羟基和氨基取代的杂芳基，或者B是萘基、6-(2,3-二氢-1,4-苯并二噁烷基)、4-或5-(1、3-苯并二恶茂基）基团，或任选被一个或多个低级烷基、低级烷氧基、卤素、芳基（低级烷氧基）、羟基、低级烷氧基-低级烷氧基、三氟甲基、二（低级烷基）氨基、苯氧基、卤代苯氧基、低级烷氧基苯氧基、苯基、卤代苯基或低级烷氧基苯基基团取代的苯基基团以及含有它们的药物组合物。结构 1 的化合物可通过结构 3 的化合物（其中 Q 为硝基氨基、低级烷硫基、苄硫基或卤素） 与结构 2 的胺反应制备，其中 R3 位于 3-、4-或 5p 位，是氢、被基团 R4 取代的低级烷基或 R4CH2CH2O- 或 R4CH2CH2CH2O-，其中 R' 是二（低级烷基）氨基、N-哌啶基、N-吡咯烷基、受保护的氨基或受保护的低级烷基氨基，必要时去除取代基 R3 中存在的任何氨基保护基。
• Pyrimidone derivatives, processes for their preparation and pharmaceutical derivatives containing them
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0049173A2

  公开（公告）日：1982-04-07

  Compounds (1) in which R1 and R2 are C1-C4 alkyl or together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino group; Y is methylene or sulphur; X is methylene or oxygen provided that X is methylene when Y is sulphur; Z is hydrogen or C1-C4 alkyl; and R5 is hydrogen, C1-4 alkyl or -A-B where A is C1-C4 alkylene and B is optionally substituted heteroaryl or phenyl are histamine H2-antagonists. Processes for their preparation and pharmaceutical compositions containing them are also described.

  其中 R1 和 R2 是 C1-C4 烷基或与它们连接的氮原子一起形成吡咯烷基或哌啶基；Y 是亚甲基或硫；X 是亚甲基或氧，条件是当 Y 是硫时 X 是亚甲基；Z 是氢或 C1-C4 烷基；R5 是氢、C1-4 烷基或 -A-B 其中 A 是 C1-C4 亚烷基，B 是任选取代的杂芳基或苯基的化合物 (1) 是组胺 H2-拮抗剂。 还描述了它们的制备方法和含有它们的药物组合物。