2-amino-4-(4-chlorophenyl)-5H-indeno-[1,2-d]-pyrimidine-5-one

• 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-amino-4-(4-chlorophenyl)-5H-indeno-[1,2-d]-pyrimidine-5-one
• 英文别名: 2-amino-4-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidin-5-one；2-amino-4-(4-chlorophenyl)indeno[1,2-d]pyrimidin-5-one
• 化学式: C₁₇H₁₀ClN₃O
• 分子量: 307.739
• InChiKey: OFUMHZAEMLRAEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  盐酸胍 、 2-(4-chlorobenzylidene)-2H-indene-1,3-dione 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-amino-4-(4-chlorophenyl)-5H-indeno-[1,2-d]-pyrimidine-5-one
  参考文献：
  名称：

  Methylene amine substituted arylindenopyrimidines as potent adenosine A2A/A1 antagonists

  摘要：

  A novel series of arylindenopyrimidines were identified as A(2A) and A(1) receptor antagonists. The series was optimized for in vitro activity by substituting the 8- and 9-positions with methylene amine substituents. The compounds show excellent activity in mouse models of Parkinson's disease when dosed orally. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.042

文献信息

• Ag2O on ZrO2 as a Recyclable Catalyst for Multicomponent Synthesis of Indenopyrimidine Derivatives
  作者：Sandeep Bhaskaruni、Suresh Maddila、Werner van Zyl、Sreekantha Jonnalagadda

  DOI：10.3390/molecules23071648

  日期：——

  We describe the synthesis of silver loaded on zirconia and its use as an efficient catalyst for a one-pot three-component reaction to synthesize 11 indenopyrimidine derivatives, of which 7 are new compounds. The procedure involves substituted benzaldehydes, indane-1,3-dione, and guanidinium hydrochloride, with ethanol as solvent. The proposed green protocol at room temperature is simple and efficient

  我们描述了氧化锆负载银的合成及其作为高效催化剂的一锅三组分反应合成 11 种茚并嘧啶衍生物，其中 7 种是新化合物。该过程涉及取代苯甲醛、茚满-1,3-二酮和盐酸胍，并以乙醇为溶剂。所提出的室温绿色方案简单高效，可在短反应时间（<30 分钟）内提供优异的产率（90^-96%）。该协议按照绿色化学原理运行良好，具有高原子经济性、无需柱分离以及催化剂的可重复使用性等吸引人的特点。采用 XRD、TEM、SEM 和 BET 分析对催化剂材料进行表征。
• Methylene amine substituted arylindenopyrimidines as potent adenosine A2A/A1 antagonists
  作者：Brian C. Shook、Stefanie Rassnick、Daniel Hall、Kenneth C. Rupert、Geoffrey R. Heintzelman、Kristen Hansen、Devraj Chakravarty、James L. Bullington、Robert H. Scannevin、Brian Magliaro、Lori Westover、Karen Carroll、Lisa Lampron、Ronald Russell、Shawn Branum、Kenneth Wells、Sandra Damon、Scott Youells、Xun Li、Mel Osbourne、Keith Demarest、Yuting Tang、Kenneth Rhodes、Paul F. Jackson

  DOI：10.1016/j.bmcl.2010.03.042

  日期：2010.5

  A novel series of arylindenopyrimidines were identified as A(2A) and A(1) receptor antagonists. The series was optimized for in vitro activity by substituting the 8- and 9-positions with methylene amine substituents. The compounds show excellent activity in mouse models of Parkinson's disease when dosed orally. (C) 2010 Elsevier Ltd. All rights reserved.
• Catalytic activity of supra molecular self-assembled Nickel (II) coordination complex in synthesis of indeno-pyrimidine derivatives
  作者：Kranthi Kumar Gangu、Suresh Maddila、Saratchandra Babu Mukkamala、Sreekantha B. Jonnalagadda

  DOI：10.1016/j.poly.2018.11.041

  日期：2019.1

  A supra molecular self-assembled Ni(II) coordination complex, formulated as [Ni-2(2,6-pydc)(2)(mu-4,4'bpy)(H2O)(4)]center dot 2H(2)O (2,6-pydc: pyridine-2,6-dicarboxylic acid, 4,4'bpy:4,4'-bipyridine) was synthesized under hydrothermal condition and characterized by single crystal X-ray diffraction, elemental analysis, FT-IR, powder X-ray diffraction and thermo gravimetric analysis. Single crystal X-ray diffraction analysis reveals that the complex crystallizes in the monoclinic space group P2(1)/c with cell parameters a = 10.5237(6) angstrom, b = 20.1966(10) angstrom, c = 7.2366(4) angstrom, beta = 106.96(1 degrees), V = 1471.22(314) angstrom(3) and displays a 3D supramolecular network through hydrogen bond and C-H center dot center dot center dot pi, C-O center dot center dot center dot pi interactions. Nickel(II) metal species in the structure possess coordinately unsaturated centers, which exhibited viable catalytic properties in the synthesis of five different indeno-pyrimidine derivatives through one-pot reaction involving aldehyde, indane-1,3-dione and guanidinium chloride in a green approach. With the reaction achieved in 15 min time interval in ethanol in excellent yields (87-98%), plus the good recyclability (up to 6 times) provides advantage to this complex in heterogeneous catalysis. (C) 2018 Elsevier Ltd. All rights reserved.
• Synthesis, anti-inflammatory, ulcerogenic and cyclooxygenase activities of indenopyrimidine derivatives
  作者：Santosh S. Undare、Navanath J. Valekar、Ajinkya A. Patravale、Dattatraya K. Jamale、Sunil S. Vibhute、Laxman S. Walekar、Govind B. Kolekar、M.B. Deshmukh、Prashant V. Anbhule

  DOI：10.1016/j.bmcl.2015.12.088

  日期：2016.2

  Objective of the present work was to evaluate the anti-inflammatory, ulcerogenicity and cyclooxygenase activity of indenopyrimidine derivatives. Anti-inflammatory activity of the tested compounds is investigated by carrageenan-induced rat paw edema assay. Compounds A1, A6, A7 and A12 exhibit the comparable anti-inflammatory activity (79.33-81.33%) to the standard drug diclofenac sodium (85.33%), while A6, A7, A9, A12 and A14 show better ulcer index than the reference standard diclofenac sodium. To rationalize the anti-inflammatory activity, docking experiments are performed to study the ability of these compounds to bind into the active site of COX-2 enzyme. (C) 2015 Elsevier Ltd. All rights reserved.