1,3-dimethyl-5-nitro-6-styryl-1H-pyrimidine-2,4-dione | 59119-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-dimethyl-5-nitro-6-styryl-1H-pyrimidine-2,4-dione
• 英文别名: 1,3-dimethyl-5-nitro-6-((E)-styryl)-1H-pyrimidine-2,4-dione；1,3-Dimethyl-5-nitro-6-styryluracil；1,3-dimethyl-5-nitro-6-[(E)-2-phenylethenyl]pyrimidine-2,4-dione
• CAS: 59119-41-4
• 化学式: C₁₄H₁₃N₃O₄
• 分子量: 287.275
• InChiKey: LKYSNWSHWDHNJX-CMDGGOBGSA-N

物化性质

• 熔点：
  196-198 °C(Solv: acetic acid (64-19-7); water (7732-18-5))
• 沸点：
  406.3±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-5-nitro-6-styryl-1H-pyrimidine-2,4-dione 在 甲酸 、 sodium dithionite 作用下， 以66%的产率得到1,3-dimethyl-6-phenylpyrrolo<3,2-d>pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  [EN] NEW-4-(PYRROLOPYRIMIDIN-6-YL)BENZENESULPHONAMIDE DERIVATIVES
  [FR] NOUVEAUX DERIVES DE 4-(PYRROLOPYRIMIDIN-6-YL)BENZENESULPHONAMIDE

  摘要：

  这项发明是针对新型高效选择性A2A和/或A2B腺苷受体拮抗剂的，其具有通用公式（I），用于其制备的过程；包含它们的药物组合物；以及它们在治疗中的应用。

  公开号：

  WO2003082873A1
• 作为产物：
  描述：

  1,3,6-三甲基-5-硝基-2,4(1H,3H)-嘧啶二酮 、 苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以60%的产率得到1,3-dimethyl-5-nitro-6-styryl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  [EN] NEW-4-(PYRROLOPYRIMIDIN-6-YL)BENZENESULPHONAMIDE DERIVATIVES
  [FR] NOUVEAUX DERIVES DE 4-(PYRROLOPYRIMIDIN-6-YL)BENZENESULPHONAMIDE

  摘要：

  这项发明是针对新型高效选择性A2A和/或A2B腺苷受体拮抗剂的，其具有通用公式（I），用于其制备的过程；包含它们的药物组合物；以及它们在治疗中的应用。

  公开号：

  WO2003082873A1

文献信息

• New-4-pyrrolopyrimidin-6-YL)benzenesulphonamide derivatives
  申请人：Vidal Juan Bernat

  公开号：US20050261248A1

  公开（公告）日：2005-11-24

  This invention is directed to selective antagonists of A 2A and/or A 2B adenosine receptors having the general formula (I); to processes for their preparation; to pharmaceutical compositions comprising them; and to their use in therapy.

  本发明涉及选择性A2A和/或A2B腺苷受体拮抗剂，其具有一般式（I）；它们的制备方法；包括它们的药物组合物；以及它们在治疗中的使用。
• Substituted-4-(pyrrolo pyrimidin-6-yl)benzenesulphonamide derivatives
  申请人：Laboratorios Almirall S.A.

  公开号：US07504398B2

  公开（公告）日：2009-03-17

  This invention is directed to selective antagonists of A2A and/or A2B adenosine receptors having the general formula (I); to processes for their preparation; to pharmaceutical compositions comprising them; and to their use in therapy.

  本发明涉及选择性A2A和/或A2B腺苷受体拮抗剂，其具有一般公式（I）；它们的制备过程；包括它们的制药组合物；以及它们在治疗中的应用。
• New pyrrolopyrimidin-6-yl benzenesulfonamides: Potent A2B adenosine receptor antagonists
  作者：Cristina Esteve、Arsenio Nueda、José Luis Díaz、Jorge Beleta、Alvaro Cárdenas、Estrella Lozoya、Maria Isabel Cadavid、Maria Isabel Loza、Hamish Ryder、Bernat Vidal

  DOI：10.1016/j.bmcl.2006.04.074

  日期：2006.7

  A new series of 4-(1,3-dialkyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)benzenesulfonamides has been identified as potent AZB adenosine receptor antagonists. The products have been evaluated for their binding affinities for the human A(2B), A(1) and A(3) adenosine receptors. 6-(4-[4-(4-Bromobenzyl)piperazin-1-yl]sulfonyl}phenyl)-1,3-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (16) showed a high affinity for the AZB adenosine receptor (IC50 = 1 nM) and selectivity (A(1): 183x; A(30): 12660x). Synthesis and SAR of this novel class of compounds showing improved absorption properties is presented herein. (c) 2006 Elsevier Ltd. All rights reserved.
• 8-Substituted-9-deazaxanthines as adenosine receptor ligands: design, synthesis and structure-affinity relationships at A2B
  作者：Angelo Carotti、Angela Stefanachi、Enrique Raviña、Eddy Sotelo、Maria Isabel Loza、Maria Isabel Cadavid、Nuria B. Centeno、Orazio Nicolotti

  DOI：10.1016/j.ejmech.2004.07.008

  日期：2004.10

  A number of 8-substituted-9-deazaxanthine derivatives (1,3-dialkyl-6-substituted-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-diones) were prepared and tested for their antagonistic activity at the recombinant human adenosine receptors, in particular at the A(2B) and A(2A) receptor subtypes. Compounds endowed with micromolar to nanomolar binding affinities, but with poor A(2B)/A(2A) selectivity, were obtained. Preliminary quantitative structure-affinity relationships suggested that the binding potency at the A(2B) receptor is mainly modulated by the electronic and lipophilic properties of the ligands. (C) 2004 Elsevier SAS. All rights reserved.
• HIROTA K.; YAMADA Y.; ASAO T.; SENDA S., J. CHEM. SOC. PERKIN TRANS., 1981, PART 1, NO 7, 1896-1899
  作者：HIROTA K.、 YAMADA Y.、 ASAO T.、 SENDA S.

  DOI：——

  日期：——