5-bromo-4-(furan-2-yl)pyrimidin-2-amine | 357285-97-3

• 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: 5-bromo-4-(furan-2-yl)pyrimidin-2-amine
• 英文别名: 5-Bromo-4-(2-furyl)-2-pyrimidinylamine
• CAS: 357285-97-3
• 化学式: C₈H₆BrN₃O
• 分子量: 240.059
• InChiKey: KIMSQHCTXKUJBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  411.6±53.0 °C(Predicted)
• 密度：
  1.685±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-4-(furan-2-yl)pyrimidin-2-amine 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 7.0h， 生成 5-(8-chloro-4-methylquinazolin-6-yl)-4-(furan-2-yl)pyrimidin-2-amine
  参考文献：
  名称：

  2-胺基嘧啶类衍生物、其制备方法及其在医药上的应用

  摘要：

  本发明涉及2‑胺基嘧啶类衍生物、其制备方法及其在医药上的应用。具体而言，本发明涉及一种通式(D‑I)所示的2‑胺基嘧啶类衍生物、其制备方法及含有该衍生物的药物组合物以及其作为治疗剂，特别是作为A2a受体和/或A2b受体拮抗剂的用途和在制备用于治疗通过对A2a受体和/或A2b受体的抑制而改善的病况或病症的药物中的用途，其中通式(D‑I)的各取代基与说明书中的定义相同。

  公开号：

  CN110655509B
• 作为产物：
  描述：

  4-(2-呋喃基)嘧啶-2-胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 生成 5-bromo-4-(furan-2-yl)pyrimidin-2-amine
  参考文献：
  名称：

  作为潜在抗菌剂的新型磺酰脲类衍生物：化学合成、生物学评价和计算研究。

  摘要：

  耐甲氧西林金黄色葡萄球菌 (MRSA) 是一种全球性的健康威胁，在其悠久的历史中已经折磨着人类，因此迫切需要开发新型抗菌剂。本研究设计并合成了 21 种含有苯基-5-乙烯基和嘧啶基-4-芳基部分的新型磺酰脲类衍生物，其中 9 种化合物对革兰氏阳性菌具有抑制作用：MRSA（朝阳临床分离株）、金黄色葡萄球菌 ATCC6538、耐万古霉素肠球菌 309 (VRE-309) 和枯草芽孢杆菌 ATCC 6633。尤其是，9i 和 9q 对四种细菌菌株表现出抑制活性，最低抑菌浓度 (MIC) 为 0.78-1.56 μg/mL ，以及相当多的其他 MRSA 临床菌株，MIC 为 0.78 μg/mL，优于阳性对照万古霉素（MIC 为 1 μg/mL）和甲氧西林（MIC >200 μg/mL）。这是磺酰脲类衍生物首次被确定为针对不同 MRSA 临床分离株的有希望的抑制剂。此外，所有合成化合物对白色念珠菌的

  DOI：

  10.3390/antibiotics12020323

文献信息

• Design, synthesis and SAR study of novel sulfonylurea derivatives containing arylpyrimidine moieties as potential anti-phytopathogenic fungal agents
  作者：Wei Chen、Yuxin Li、Yunyun Zhou、Yi Ma、Zhengming Li

  DOI：10.1016/j.cclet.2019.04.072

  日期：2019.12

  Abstract Acetohydroxyacid synthase (AHAS) was considered as a promising target for antifungal agents. Herein, three series of novel sulfonylureas (SUs) 9−11 containing aromatic-substituted pyrimidines were designed and synthesized according to pharmacophore-combination and bioisosterism strategy. The in vitro fungicidal activities against ten phytopathogenic fungi indicated that most of the title compounds

  摘要乙酰羟酸合酶（AHAS）被认为是抗真菌药物的有希望的靶标。在这里，根据药效团结合和生物立体异构策略，设计并合成了三类含有芳香族取代的嘧啶的新型磺酰脲类（SUs）9-11。对十种植物病原真菌的体外杀真菌活性表明，大多数标题化合物均表现出广谱和优异的杀真菌活性。基于初步的杀真菌活性，构建了CoMFA模型，并通过3D-QSAR分析表明，嘧啶环5位附近的大基团或苯环2位附近的正电基团都有利于杀真菌活动。为了研究互动机制，10k自动停靠在酵母AHAS中，这进一步表明在嘧啶环上带有大量基团的芳基对于增强抗真菌活性至关重要。结果表明，衍生物9-11的抗真菌活性可能是由于真菌AHAS的抑制作用所致。因此，本结果有力地表明，SU应被认为是开发新型抗植物病原性真菌剂的先导化合物或模型分子。
• Adenosine receptor ligands and their use in the treatment of disease
  申请人：——

  公开号：US20010027196A1

  公开（公告）日：2001-10-04

  The invention relates to cyclic heteroaromatic compounds, containing at least one nitrogen atom, and to their use in the manufacture of medicaments for the treatment of diseases, related to adenosine receptor modulators, such as Alzheimer's disease, Parkinson's disease, neuroprotection, schizophrenia, anxiety, pain, respiration deficits, depression, asthma, allergic responses, hypoxia, ischaemia, seizure, substance abuse, sedation and they may be active as muscle relaxants, antipsychotics, anti epileptics, anticonvulsants and cardiaprotective agents.

  这项发明涉及含有至少一个氮原子的环状杂芳化合物，以及它们在制造用于治疗与腺苷受体调节剂相关的疾病的药物中的应用，如阿尔茨海默病、帕金森病、神经保护、精神分裂症、焦虑、疼痛、呼吸功能障碍、抑郁症、哮喘、过敏反应、缺氧、缺血、癫痫、物质滥用、镇静，它们可能作为肌肉松弛剂、抗精神病药、抗癫痫药、抗惊厥药和心脏保护剂而具有活性。
• Pyrimidine compound and medicinal composition thereof
  申请人：Harada Hitoshi

  公开号：US20050004149A1

  公开（公告）日：2005-01-06

  The present invention provides a novel pyrimidine compound having an excellent adenosine receptor (A 1 , A 2A , A 2B receptor) antagonistic action. More specifically, it provides a compound represented by the following formula, a salt thereof or a solvate of them. In the formula, R 1 and R 2 are the same as or different from each other and each represents a hydrogen atom, an alkyl group having one to six carbon atoms which may be substituted, an alkenyl group having two to six carbon atoms which may be substituted, an alkynyl group having two to six carbon atoms which may be substituted, a cycloalkyl group having three to eight carbon atoms which may be substituted, a cycloalkenyl group having three to eight carbon atoms which may be substituted, a 5 to 14-membered non-aromatic heterocyclic group which may be substituted, an aromatic hydrocarbon cyclic group having six to fourteen carbon atoms which may be substituted, a 5 to 14-membered aromatic heterocyclic group which may be substituted, an acyl group having one to six carbon atoms which may be substituted or an alkylsulfonyl group having one to six carbon atoms which may be substituted; R 3 represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having one to six carbon atoms which may be substituted, an alkenyl group having two to six carbon atoms which may be substituted, an alkynyl group having two to six carbon atoms which may be substituted, an aromatic hydrocarbon cyclic group having six to fourteen carbon atoms which may be substituted, a 5 to 14-membered aromatic heterocyclic group which may be substituted, a nitrogen atom which may be substituted, an oxygen atom which may be substituted or a sulfur atom which may be substituted; R 4 represents an aromatic hydrocarbon cyclic group having six to fourteen carbon atoms which may be substituted, a 5 to 14-membered aromatic heterocyclic group which may be substituted or a 5 to 14-membered non-aromatic heterocyclic group having at least one or more unsaturated bonds which may be substituted; and R 5 represents an aromatic hydrocarbon cyclic group having six to fourteen carbon atoms which may be substituted or a 5 to 14-membered aromatic heterocyclic group which may be substituted.

  本发明提供了一种新型嘧啶化合物，具有优异的腺苷受体（A1、A2A、A2B受体）拮抗作用。更具体地，提供了下式所示的化合物、其盐或其溶剂化物。其中，R1和R2相同或不同，分别代表氢原子、可被取代的具有1至6个碳原子的烷基、可被取代的具有2至6个碳原子的烯基、可被取代的具有2至6个碳原子的炔基、可被取代的具有3至8个碳原子的环烷基、可被取代的具有3至8个碳原子的环烯基、可被取代的5至14个成员的非芳香杂环基、可被取代的具有6至14个碳原子的芳香烃环基、可被取代的5至14个成员的芳香杂环基、可被取代的具有1至6个碳原子的酰基或可被取代的具有1至6个碳原子的烷基磺酰基；R3代表氢原子、卤素原子、氰基、可被取代的具有1至6个碳原子的烷基、可被取代的具有2至6个碳原子的烯基、可被取代的具有2至6个碳原子的炔基、可被取代的具有6至14个碳原子的芳香烃环基、可被取代的5至14个成员的芳香杂环基、可被取代的氮原子、可被取代的氧原子或可被取代的硫原子；R4代表可被取代的具有6至14个碳原子的芳香烃环基、可被取代的5至14个成员的芳香杂环基或可被取代的具有至少一个或多个不饱和键的5至14个成员的非芳香杂环基；而R5代表可被取代的具有6至14个碳原子的芳香烃环基或可被取代的5至14个成员的芳香杂环基。
• PYRIMIDINE COMPOUNDS AND MEDICINAL COMPOSITION THEREOF
  申请人：Harada Hitoshi

  公开号：US20090030023A1

  公开（公告）日：2009-01-29

  A compound represented by the following formula (I), a salt, or a solvate thereof: wherein, R 1 and R 2 are the same as or different from each other and each represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a non-aromatic heterocyclic group, an aromatic hydrocarbon cyclic group, an aromatic heterocyclic group, an acyl group or an alkylsulfonyl group all of which may be substituted and wherein one, or both, of R 1 or R 2 is an aromatic, or non-aromatic, heterocyclic group which may be substituted; R 3 represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon cyclic group, an aromatic heterocyclic group, a nitrogen atom, an oxygen atom or a sulfur atom all of which may be substituted if possible; and R 4 is a pyridyl group which may be substituted.

  以下是化合物（I）的化学式，盐或其溶剂化物： 其中，R1和R2相同或不同，每个代表氢原子，烷基，烯基，炔基，环烷基，环烯基，非芳香杂环基，芳香烃环基，芳香杂环基，酰基或烷基磺酰基，所有这些基团都可以被取代，其中R1或R2中的一个或两个是可能被取代的芳香或非芳香杂环基；R3代表氢原子，卤素原子，氰基，烷基，烯基，炔基，芳香烃环基，芳香杂环基，氮原子，氧原子或硫原子，所有这些基团都可以被取代；R4是可能被取代的吡啶基团。
• Pyrimidine compounds and medicinal composition thereof
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP2246344A1

  公开（公告）日：2010-11-03

  The present invention provides a novel pyrimidine compound having an excellent adenosine receptor (A1, A2A, A2B receptor) antagonistic action. More specifically, it provides a compound represented by the following formula, a salt thereof or a solvate of them. In the formula, R1 and R2 are the same as or different from each other and each represents a hydrogen atom, an alkyl group having one to sixcarbon atoms which maybe substituted, an alkenyl group having two to six carbon atoms which may be substituted, an alkynyl group having two to six carbon atoms which may be substituted, a cycloalkyl group having three to eight carbon atoms which may be substituted, a cycloalkenyl group having three to eight carbon atoms which may be substituted, a 5 to 14-membered non-aromatic heterocyclic group which may be substituted, an aromatic hydrocarbon cyclic group having six to fourteen carbon atoms which may be substituted, a 5 to 14-membered aromatic heterocyclic group which may be substituted, an acyl group having one to six carbon atoms which may be substituted or an alkylsulfonyl group having one to six carbon atoms which may be substituted; R3 represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having one to six carbon atoms which may be substituted, an alkenyl group having two to six carbon atoms which may be substituted, an alkynyl group having two to six carbon atoms which may be substituted, an aromatic hydrocarbon cyclic group having six to fourteen carbon atoms which may be substituted, a 5 to 14-membered aromatic heterocyclic group which may be substituted, a nitrogen atom which may be substituted, an oxygen atom which may be substituted or a sulfur atom which may be substituted; R4 represents a 4-pyridyl group which may have one or two substituents; and R5 represents an aromatic hydrocarbon cyclic group having six to fourteen carbon atoms which may be substituted or a 5 to 14-membered aromatic heterocyclic group which may be substituted.

  本发明提供了一种新型嘧啶化合物，它具有优异的腺苷受体（A1、A2A、A2B 受体）拮抗作用。更具体地说，本发明提供了由下式代表的化合物、其盐或它们的溶液。 式中，R1 和 R2 彼此相同或不同，各自代表氢原子、具有一至六个碳原子且可能被取代的烷基、具有二至六个碳原子且可能被取代的烯基、具有二至六个碳原子且可能被取代的炔基、具有三至八个碳原子且可能被取代的环烷基、具有三至八个碳原子并可被取代的环烯基、具有五至十四个碳原子并可被取代的非芳香杂环基、具有六至十四个碳原子并可被取代的芳香烃环基、具有五至十四个碳原子并可被取代的芳香杂环基、具有一至六个碳原子并可被取代的酰基或具有一至六个碳原子并可被取代的烷基磺酰基；R3 代表氢原子、卤素原子、氰基、具有 1 至 6 个碳原子且可被取代的烷基、具有 2 至 6 个碳原子且可被取代的烯基、具有 2 至 6 个碳原子且可被取代的炔基、具有 6 至 14 个碳原子且可被取代的芳香烃环基、具有 5 至 14 个元的芳香杂环基、可被取代的氮原子、可被取代的氧原子或可被取代的硫原子；R4 代表可具有一个或两个取代基的 4-吡啶基；以及 R5 代表可被取代的具有 6 至 14 个碳原子的芳香烃环基或可被取代的 5 至 14 元芳香杂环基。