ethyl 2-amino-4,6-diphenyl-3,4-dihydropyrimidine-5-carboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 2-amino-4,6-diphenyl-3,4-dihydropyrimidine-5-carboxylate
• 英文别名: Ethyl 2-amino-4,6-diphenyl-1,4-dihydropyrimidine-5-carboxylate
• 化学式: C₁₉H₁₉N₃O₂
• 分子量: 321.379
• InChiKey: TYFQHKOTSQXNMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-4,6-diphenyl-3,4-dihydropyrimidine-5-carboxylate 在 盐酸 、 4-二甲氨基吡啶 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 0.5h， 生成 ethyl 8-(1H-indol-2-yl)-2,4-diphenyl-4H-pyrimido[1,2-a]pyrimidine-3-carboxylate
  参考文献：
  名称：

  Condensation reactions of guanidines with bis-electrophiles: formation of highly nitrogenous heterocycles

  摘要：

  2-Amino-1,4-dihydropyrimidines were reacted with bis-electrophiles to produce novel fused bipyrimidine, pyrimidoaminotriazine, and pyrimidosulfonamide scaffolds. In addition, a quinazoline library was constructed using a guanidine Atwal-Biginelli reaction with 1-(quinazolin-2-yl)guanidines. The product heterocycles have novel constitutions with high nitrogen atom counts and represent valuable additions to screening libraries for the discovery of new modulators of biological targets. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.127
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 哌啶 、 碳酸氢钠 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 ethyl 2-amino-4,6-diphenyl-3,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  2-氨基二氢-5-嘧啶乙基羧酸酯衍生物和3,7-二乙氧基羰基-4,6-二氢-2,4,6,8-四芳基-1 H-嘧啶[1,2- a ]嘧啶的合成

  摘要：

  已经研究了3-芳基-2-苯甲酰基丙烯酸乙酯1与胍和N-烷基（或苄基）胍的反应。2-氨基二氢-5-嘧啶羧酸乙酯衍生物3、4或5和3,7-二乙氧基羰基-4,6-二氢-2,4,6,8-四芳基-1 H-嘧啶[1,2- a已经合成了嘧啶6。

  DOI：

  10.1002/jhet.5570340152

文献信息

• Efficient Biginelli Synthesis of 2-Aminodihydropyrimidines under Microwave Irradiation
  作者：Fulvia Felluga、Fabio Benedetti、Federico Berti、Sara Drioli、Giorgia Regini

  DOI：10.1055/s-0036-1591900

  日期：2018.5

  A practical and general method for the Biginelli cyclocondensation of guanidine with aldehydes and β-dicarbonyl compounds is described and illustrated with the synthesis of a set of 26 functionalized 2-amino-3,4-dihydropyrimidines. The simple protocol involves the ­microwave-mediated reaction of a twofold excess of guanidine hydrochloride with the required reaction partners in an alcohol at 120 °C

  用一组 26 个功能化的 2-氨基-3,4-二氢嘧啶的合成描述和说明了胍与醛和 β-二羰基化合物的 Biginelli 环缩合反应的实用和通用方法。简单的协议涉及双倍过量的盐酸胍与所需的反应伙伴在 120 °C 的酒精中的微波介导反应。收率通常良好，反应时间短，后处理简单。其范围比在常规加热下进行的类似反应要广泛得多。
• Microwave-mediated regioselective synthesis of novel pyrimido[1,2- a ]pyrimidines under solvent-free conditions
  作者：Jean Jacques Vanden Eynde、Nancy Hecq、Olga Kataeva、C.Oliver Kappe

  DOI：10.1016/s0040-4020(00)01157-1

  日期：2001.2

  Ethyl 2-amino-4-aryl-1,4-dihydro-6-phenylpyrimidine-5-carboxylates readily react, under microwave irradiation and solvent-free conditions, with 3-formylchromone or diethyl (ethoxymethylene)malonate to yield novel pyrimido[1,2-a]pyrimidines. The structure of the final products, deduced from the spectral data and confirmed by X-ray analysis, allows us to suggest reaction pathways.

  2-氨基-4-芳基-1,4-二氢-6-苯基嘧啶-5-羧酸乙酯在微波辐射和无溶剂条件下，很容易与3-甲酰基色酮或丙二酸二乙酯（乙氧基亚甲基）反应生成新的嘧啶基[1]。 ，2- a ]嘧啶。从光谱数据推导并通过X射线分析确认的最终产品结构，使我们能够提出反应途径。
• 10.1021/acsmedchemlett.4c00173
  作者：Russo, Christopher M.、Boyer, Zachary W.、Scheunemann, Kaitlyn、Farren, Jonathan、Minich, Alexandra、Wenthur, Cody J.、O’Reilly, Matthew C.

  DOI：10.1021/acsmedchemlett.4c00173

  日期：——

  libraries were prepared and screened for bacterial growth inhibition, and these compounds provided additional insights into the structure–activity relationships, allowing for the preparation of compounds that inhibited all strains of Staphylococcus aureus with an MIC of 2 μg/mL. After eliminating the proposed mechanism of dihydrofolate reductase inhibition, trifluoromethyl diazirine photoaffinity probes were

  抗生素耐药性细菌是一个全球性的健康问题，因此需要开发通过新的或未充分利用的机制发挥作用的抗生素。功能化氨基二氢嘧啶先前已被证明具有作为抗菌剂的潜力，但它们的效力有限，并且其生物学机制尚不清楚。为了进一步评估它们的潜力，我们制备了重点文库并筛选了细菌生长抑制作用，这些化合物为结构-活性关系提供了额外的见解，从而可以制备抑制所有金黄色葡萄球菌菌株的化合物，其 MIC 为 2 μg/毫升。在消除了所提出的二氢叶酸还原酶抑制机制后，合成了三氟甲基二氮丙啶光亲和探针以研究其机制，并对这些探针进行测试以确保光不稳定基团不会影响抗菌活性。最后，筛选化合物的溶血性和哺乳动物细胞毒性。虽然它们缺乏非特异性膜破裂活性，但许多化合物表现出显着的哺乳动物细胞毒性，表明需要进一步开发才能使它们对细菌具有选择性。
• Antibacterial Activity of Functionalized Dihydropyrimidines
  申请人：WiSys Technology Foundation, Inc.

  公开号：US20220220082A1

  公开（公告）日：2022-07-14

  Emmacin-related substituted dihydropyrimidine compounds demonstrate potency at low concentrations and inhibit Methicillin-resistant S. aureus growth. One such compound is:
• Condensation reactions of guanidines with bis-electrophiles: formation of highly nitrogenous heterocycles
  作者：David M. Arnold、Matthew G. LaPorte、Shelby M. Anderson、Peter Wipf

  DOI：10.1016/j.tet.2013.04.127

  日期：2013.9

  2-Amino-1,4-dihydropyrimidines were reacted with bis-electrophiles to produce novel fused bipyrimidine, pyrimidoaminotriazine, and pyrimidosulfonamide scaffolds. In addition, a quinazoline library was constructed using a guanidine Atwal-Biginelli reaction with 1-(quinazolin-2-yl)guanidines. The product heterocycles have novel constitutions with high nitrogen atom counts and represent valuable additions to screening libraries for the discovery of new modulators of biological targets. (C) 2013 Elsevier Ltd. All rights reserved.