2-(pyridin-3-yl)thieno[3,2-d]pyrimidin-4(3H)-one | 214417-11-5

• 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-(pyridin-3-yl)thieno[3,2-d]pyrimidin-4(3H)-one
• 英文别名: 2-(3-Pyridinyl)thieno[3,2-d]pyrimidin-4(3h)-one；2-pyridin-3-yl-3H-thieno[3,2-d]pyrimidin-4-one
• CAS: 214417-11-5
• 化学式: C₁₁H₇N₃OS
• 分子量: 229.262
• InChiKey: SFMNELLPLFFCFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(pyridin-3-yl)thieno[3,2-d]pyrimidin-4(3H)-one 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 90.5h， 生成 Benzyl-(2-pyridin-3-yl-thieno[3,2-d]pyrimidin-4-yl)-amine
  参考文献：
  名称：

  Design, Synthesis, and Biological Activities of New Thieno[3,2-d]pyrimidines as Selective Type 4 Phosphodiesterase Inhibitors

  摘要：

  A common pharmacophore for compounds structurally related to nitraquazone has been derived. Using this pharmacophore, new structures have been designed, synthesized, and evaluated for their inhibitory potencies against cyclic adenosine 5'-monophosphate (cAMP) specific phosphodiesterase (PDE 4). From these compounds, 4-benzylamino-2-butylthieno[3,2-d]-pyrimidine (4) was selected for optimization. The effects of changes to the lipophilic groups and the amino linkage on the PDE 4 activity have been investigated. As a result, some potent PDE 4 inhibitors, selective with respect to PDE 3, have been identified. A selected group of compounds have been further evaluated for their ability to displace [H-3]rolipram from its binding site and also to potentiate isoprenaline-induced cAMP accumulation in isolated guinea pig eosinophils. Of these, 2-butyl-4-cyclohexylaminothieno[3,2-d]pyrimidine (33) has an interesting profile, with an important improvement in PDE 4/[H-3]rolipram ratio with respect to reference drugs, and good activity in cAMP potentiation, consistent with efficient cell penetration.

  DOI：

  10.1021/jm981012m
• 作为产物：
  描述：

  3-[(3-pyridinylcarbonyl)amino]-2-thiophenecarboxylic acid methyl ester 在 氨 、 水 作用下， 反应 6.0h， 以26%的产率得到2-(pyridin-3-yl)thieno[3,2-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  WO2008/92862

  摘要：

  公开号：

文献信息

• [EN] NOVEL QUINAZOLINONES THAT INHIBIT THE FORMATION OF TAU OLIGOMERS AND THEIR METHOD OF USE<br/>[FR] NOUVELLES QUINAZOLINONES INHIBANT LA FORMATION D'OLIGOMÈRES TAU ET LEUR PROCÉDÉ D'UTILISATION
  申请人：OLIGOMERIX INC

  公开号：WO2018118791A9

  公开（公告）日：2019-08-22
• NOVEL QUINAZOLINONES THAT INHIBIT THE FORMATION OF TAU OLIGOMERS AND THEIR METHOD OF USE
  申请人：Oligomerix, Inc.

  公开号：EP3558950A2

  公开（公告）日：2019-10-30
• [EN] BICYCLIC DERIVATIVES AS EP4 AGONISTS<br/>[FR] DÉRIVÉS BICYCLIQUES UTILISÉS COMME AGONISTES DE EP4
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2008092862A1

  公开（公告）日：2008-08-07

  [EN] The present invention relates to a compound of formula (I) including any stereochemical isomeric form thereof, wherein A represents a 5 or 6-membered aromatic optionally substituted heterocycle containing 1, 2 or 3 heteroatoms; ring E represents a partially saturated or aromatic 5-membered heterocycle wherein the dotted lines represent an optional double bond and wherein B, C and D each independently represent CH₂, CH, N, NH, S or O and F represents N or C, provided that the 5-membered ring contains 1, 2 or 3 heteroatoms; X represents a direct bond or C_1-4alkanediyl; Y represents N or CH; R¹ represents hydrogen or fluoro; R² represents hydrogen, halo, cyano, C_1-6alkyl, C_1-6alkyloxy, C_1-6alkylcarbonyl or C_1-6alkylcarbonylamino; R³ represents hydrogen, halo, C_1-6alkyl, C_1-6alkyloxy, cyano, nitro, amino or mono-or di(C_1-6alkyl)amino; n represents an integer of value 1, 2 or 3; a N-oxide thereof, a pharmaceutically acceptable salt thereof or a solvate thereof. The claimed compounds are useful for the treatment of a disease by activating the EP4 receptor.
  [FR] L'invention concerne un composé représenté par la formule (I) comprenant une forme isomère stéréo chimique quelconque de ce composé, un N-oxyde de celui-ci, un sel pharmaceutiquement acceptable de celui-ci ou un solvate de celui-ci. Dans cette formule, A représente un composé hétérocyclique aromatique éventuellement substitué à 5 ou 6 éléments contenant 1, 2 ou 3 hétéroatomes; un noyau E représente un composé hétérocyclique à 5 éléments aromatique ou partiellement saturé, les lignes en pointillé représentant une liaison double facultative, B, C et D représentant chacun indépendamment CH₂, CH, N, NH, S ou O, et F représentant N ou C, à condition que le noyau à 5 éléments contienne 1, 2 ou 3 hétéroatomes; X représente représente une liaison directe ou C_1-4alkanédiyle; Y représente N ou CH; R¹ représente hydrogène ou fluoro; R² représente hydrogène, halo, cyano, C_1-6alkyle, C_1-6alkyloxy, C_1-6alkylcarbonyle ou C_1-6alkylcarbonylamino; R³ représente hydrogène, halo, C_1-6alkyle, C_1-6alkyloxy, cyano, nitro, amino ou mono- ou di(C_1-6alkyl)amino; n représente un nombre entier de valeur 1, 2 ou 3. Les composés précités sont utilisés pour traiter une maladie par activation du récepteur EP4.
• WO2008/92862
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, Synthesis, and Biological Activities of New Thieno[3,2-<i>d</i>]pyrimidines as Selective Type 4 Phosphodiesterase Inhibitors
  作者：María I. Crespo、Lluís Pagès、Armando Vega、Victor Segarra、Manel López、Teresa Doménech、Montserrat Miralpeix、Jordi Beleta、Hamish Ryder、José M. Palacios

  DOI：10.1021/jm981012m

  日期：1998.10.1

  A common pharmacophore for compounds structurally related to nitraquazone has been derived. Using this pharmacophore, new structures have been designed, synthesized, and evaluated for their inhibitory potencies against cyclic adenosine 5'-monophosphate (cAMP) specific phosphodiesterase (PDE 4). From these compounds, 4-benzylamino-2-butylthieno[3,2-d]-pyrimidine (4) was selected for optimization. The effects of changes to the lipophilic groups and the amino linkage on the PDE 4 activity have been investigated. As a result, some potent PDE 4 inhibitors, selective with respect to PDE 3, have been identified. A selected group of compounds have been further evaluated for their ability to displace [H-3]rolipram from its binding site and also to potentiate isoprenaline-induced cAMP accumulation in isolated guinea pig eosinophils. Of these, 2-butyl-4-cyclohexylaminothieno[3,2-d]pyrimidine (33) has an interesting profile, with an important improvement in PDE 4/[H-3]rolipram ratio with respect to reference drugs, and good activity in cAMP potentiation, consistent with efficient cell penetration.