6-chloro-N-(2,3-dimethylphenyl)-2-methylsulfonylpyrimidin-4-amine | 86627-00-1

• 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: 6-chloro-N-(2,3-dimethylphenyl)-2-methylsulfonylpyrimidin-4-amine
• 英文别名: 2-methylsulfonyl-4-chloro-6-(2,3-xylidino)-pyrimidine；6-Chloro-N-(2,3-dimethylphenyl)-2-(methanesulfonyl)pyrimidin-4-amine
• CAS: 86627-00-1
• 化学式: C₁₃H₁₄ClN₃O₂S
• 分子量: 311.792
• InChiKey: KDPZGZPNWFHNMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-N-(2,3-dimethylphenyl)-2-methylsulfonylpyrimidin-4-amine 在 sodium hydroxide 、 sodium hydride 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 18.08h， 生成 阿罗昔尔
  参考文献：
  名称：

  Novel pyrimidine and 1,3,5-triazine hypolipemic agents

  摘要：

  New compounds were synthesized by changing the substituents of a trisubstituted pyrimidine, i.e., [[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]thio] acetic acid, a potent hypolipidemic agent, impaired, however, by a marked hepatomegaly-inducing effect. The structural variations led to the subsidence (14b, i.e., 4-chloro-2-(dimethylamino)-6-[(2,3-dimethylphenyl)amino]pyrimidine) or to the reduction (18b, [[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]amino] acetic acid) of said untoward effect but still maintained the hypolipidemic effect that, although markedly decreased, still proves significant for serum cholesterol and triglycerides (18b) or for serum triglycerides only (14b).

  DOI：

  10.1021/jm00378a016
• 作为产物：
  描述：

  2,3-二甲基苯胺 在 sodium tungstate 、 双氧水 、 sodium carbonate 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 34.0h， 生成 6-chloro-N-(2,3-dimethylphenyl)-2-methylsulfonylpyrimidin-4-amine
  参考文献：
  名称：

  Novel pyrimidine and 1,3,5-triazine hypolipemic agents

  摘要：

  New compounds were synthesized by changing the substituents of a trisubstituted pyrimidine, i.e., [[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]thio] acetic acid, a potent hypolipidemic agent, impaired, however, by a marked hepatomegaly-inducing effect. The structural variations led to the subsidence (14b, i.e., 4-chloro-2-(dimethylamino)-6-[(2,3-dimethylphenyl)amino]pyrimidine) or to the reduction (18b, [[4-chloro-6-[(2,3-dimethylphenyl)amino]-2-pyrimidinyl]amino] acetic acid) of said untoward effect but still maintained the hypolipidemic effect that, although markedly decreased, still proves significant for serum cholesterol and triglycerides (18b) or for serum triglycerides only (14b).

  DOI：

  10.1021/jm00378a016

文献信息

• Tuning Nuclear Receptor Selectivity of Wy14,643 towards Selective Retinoid X Receptor Modulation
  作者：Julius Pollinger、Leonie Gellrich、Simone Schierle、Whitney Kilu、Jurema Schmidt、Lena Kalinowsky、Julia Ohrndorf、Astrid Kaiser、Jan Heering、Ewgenij Proschak、Daniel Merk

  DOI：10.1021/acs.jmedchem.8b01848

  日期：2019.2.28

  The fatty acid sensing nuclear receptor families retinoid X receptors (RXRs) and peroxisome proliferator-activated receptors (PPARs) hold therapeutic potential in neurodegeneration. Valuable pleiotropic activities of Wy14,643 in models of such conditions exceed its known PPAR agonistic profile. Here, we characterize the compound as an RXR agonist explaining the pleiotropic effects and report its systematic

  脂肪酸感应核受体家族类视黄醇X受体（RXRs）和过氧化物酶体增殖物激活受体（PPARs）在神经退行性变中具有治疗潜力。在这种情况下，Wy14,643的有价值的多效性活性超过了其已知的PPAR激动特性。在这里，我们将化合物表征为RXR激动剂，解释了多效性效应，并报告了其系统的结构-活性关系分析，并发现了驱动PPAR和RXR的特定分子决定因素。我们设计了该药物的紧密类似物，包括对RXR和PPAR的选择性和双重激动作用，可以作为研究各种病理学中核受体的作用和相互作用的优良药理学工具。系统优化的高效RXR激动剂揭示了体内活性和脑中活性浓度。与传统的类维生素A相比，由于缺乏RXR /肝X受体介导的副作用和出色的特性，它建立了新型的创新RXR调节剂，以克服针对RXR靶向药物发现的关键挑战。
• Pyrimidine and s-triazine derivatives with antilipidemic activity
  申请人：LBP Istituto Faraceutico S.p.A.

  公开号：US04559345A1

  公开（公告）日：1985-12-17

  Pyrimidine and s-triazine derivatives of formula (I) ##STR1## in which X=CH or N; Y=for example halogen, alkoxy; W=for example --S--CH.sub.2 --COOH, --O--CH.sub.2 --COO alkyl, --NH--CH.sub.2 --CONHCH.sub.2 CH.sub.2 OH; Z=for example 2,3-xylidino, and methods for the preparation thereof are described. The compounds show high antilipemic activity.

  公式(I)的嘧啶和s-三嗪衍生物如下：##STR1## 其中X=CH或N；Y=例如卤素、烷氧基；W=例如--S--CH.sub.2 --COOH、--O--CH.sub.2 --COO烷基、--NH--CH.sub.2 --CONHCH.sub.2 CH.sub.2 OH；Z=例如2,3-二甲苯胺基，以及其制备方法。这些化合物表现出高抗脂质活性。
• Novel pyrimidine and s. triazine derivatives with antilipidemic activity
  申请人：LPB Istituto Farmaceutico s.p.a.

  公开号：EP0073328A1

  公开（公告）日：1983-03-09

  Pyrimidine and s-triazine derivatives of formula (I) in which X = CH or N; Y = for example halogen, alkoxy; W = for example -S-CH2-COOH, -O-CH2-COO alkyl, -NH-CH2-CONHCH2CH2OH; Z = for example 2,3-xylidino, and methods for the preparation thereof are described. The compounds show high antiiipemic activity.

  式(I)的嘧啶和 s-三嗪衍生物 其中 X = CH 或 N；Y = 例如卤素、烷氧基；W = 例如 -S-CH2-COOH、-O- -COO 烷基、-NH- -CONH OH；Z = 例如 2,3-xylidino。这些化合物具有很高的抗血脂活性。
• DATRI, G.;GOMARASCA, P.;RESNATI, G.;TRONCONI, G.;SCOLASTICO, C.;SIRTORI, +, J. MED. CHEM., 1984, 27, N 12, 1621-1629
  作者：DATRI, G.、GOMARASCA, P.、RESNATI, G.、TRONCONI, G.、SCOLASTICO, C.、SIRTORI, +

  DOI：——

  日期：——
• US4559345A
  申请人：——

  公开号：US4559345A

  公开（公告）日：1985-12-17