4,6-dichloro-2-(octylthio)pyrimidine | 86627-14-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,6-dichloro-2-(octylthio)pyrimidine
• 英文别名: 2-octylthio-4,6-dichloropyrimidine；4,6-Dichloro-2-(octylsulfanyl)pyrimidine；4,6-dichloro-2-octylsulfanylpyrimidine
• CAS: 86627-14-7
• 化学式: C₁₂H₁₈Cl₂N₂S
• 分子量: 293.26
• InChiKey: UGJZFWLNPIRHPT-UHFFFAOYSA-N

物化性质

• 沸点：
  369.8±22.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-dichloro-2-(octylthio)pyrimidine 、 2,3-二甲基苯胺 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以49.3%的产率得到2-octylthio-4-chloro-6-(2,3-xylidino)-pyrimidine
  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：

  1-碘辛烷 在 四丁基氢氧化铵 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 反应 16.17h， 生成 4,6-dichloro-2-(octylthio)pyrimidine
  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

• Design, Synthesis, and Structure−Activity Relationship Studies of Novel 2,4,6-Trisubstituted-5-pyrimidinecarboxylic Acids as Peroxisome Proliferator-Activated Receptor γ (PPARγ) Partial Agonists with Comparable Antidiabetic Efficacy to Rosiglitazone
  作者：Shigeki Seto、Kyoko Okada、Koichi Kiyota、Shigeki Isogai、Maki Iwago、Takehiro Shinozaki、Yoshiaki Kitamura、Yasushi Kohno、Koji Murakami

  DOI：10.1021/jm100443s

  日期：2010.7.8

  series of novel 2,4,6-trisubstitutedpyrimidine-5-carboxylic acid derivatives were designed and synthesized with the intent of producing a peroxisome proliferator-activated receptor γ (PPARγ) partial agonist for antidiabetic agents. A pharmacophore-driven approach of in-house screening identified compound 7, which led to the identification of compound 9 featuring a 2,4,6-trisubstituted pyrimidine-5-carboxylic

  设计和合成了一系列新颖的2,4,6-三取代嘧啶-5-羧酸衍生物，目的是生产抗糖尿病药的过氧化物酶体增殖物激活受体γ（PPARγ）部分激动剂。药效团驱动的内部筛选方法可鉴定出化合物7，从而鉴定出具有2,4,6-三取代嘧啶-5-羧酸核的化合物9。9的构效关系研究确定了4,6-双苄硫基-2-甲基硫基嘧啶-5-羧酸（50）是所有筛选化合物中最有吸引力的。X射线共晶结构为50PPARγ上的键揭示了与激活功能2（AF-2）位点无关的关键氢键相互作用与完全激动剂的氢键相互作用不同。化合物50在PPARγ-GAL4功能试验中显示出典型的PPARγ部分激动剂特性，并且与罗格列酮相比在3T3-L1细胞中的脂肪细胞分化更弱。此外，尽管有50种药效比罗格列酮弱10倍，但在db / db小鼠中有50种与罗格列酮具有相当的抗糖尿病功效。
• 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