5-butyl-4-chloro-6-methyl-pyrimidin-2-ylamine

• 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-butyl-4-chloro-6-methyl-pyrimidin-2-ylamine
• 英文别名: 5-butyl-4-chloro-6-methylpyrimidine-2-yl amine；2-Amino-4-chlor-5-butyl-6-methyl-pyrimidin；5-Butyl-4-chloro-6-methylpyrimidin-2-amine
• 化学式: C₉H₁₄ClN₃
• mdl: MFCD00460874
• 分子量: 199.683
• InChiKey: OJSWAIOKPQDUQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-氨基戊烷 、 5-butyl-4-chloro-6-methyl-pyrimidin-2-ylamine 在 silica gel 、 甲醇 、 氯仿 作用下， 反应 11.0h， 以to give the object compound (98 mg, 78%) as an oil的产率得到N-(2-Amino-5-butyl-6-methylpyrimidine-4-yl)-N-pentylamine
  参考文献：
  名称：

  Bicyclic pyrimidine compounds and therapeutic use thereof

  摘要：

  公式（1）的嘧啶衍生物或其盐；具有抑制产生Th2型细胞因子如IL-4、IL-5等的活性，可用作过敏性疾病、自身免疫性疾病如系统性红斑狼疮等、获得性免疫缺陷综合症（AIDS）等的治疗剂。

  公开号：

  US06951866B2
• 作为产物：
  描述：

  2-氨基-5-丁基-6-甲基嘧啶-4-醇 在 三氯氧磷 作用下， 以29%的产率得到5-butyl-4-chloro-6-methyl-pyrimidin-2-ylamine
  参考文献：
  名称：

  Bicyclic pyrimidine compounds and therapeutic use thereof

  摘要：

  公式（1）的嘧啶衍生物或其盐；具有抑制Th2型细胞因子（如IL-4、IL-5等）产生的活性，并且对过敏性疾病、系统性红斑狼疮等自身免疫疾病以及获得性免疫缺陷综合征（AIDS）等疾病具有治疗作用。

  公开号：

  US06458798B1

文献信息

• Pyrimidine derivative
  申请人：SUMITOMO PHARMACEUTICALS COMPANY LIMITED

  公开号：US20030105323A1

  公开（公告）日：2003-06-05

  1. A pyrimidine derivative of the formula (1) or a salt thereof; 1 has an inhibitory activity of production of Th2 type cytokines such as IL-4, IL-5, etc., and is useful as an therapeutic agent for allergic diseases, autoimmune diseases such as systemic lupus erythemathosus, etc., and acquired immunodeficiecy syndrome (AIDS) and so on.

  式（1）的嘧啶衍生物或其盐；具有抑制Th2型细胞因子如IL-4，IL-5等的产生的活性，可用作过敏疾病，自身免疫性疾病如系统性红斑狼疮等，以及获得性免疫缺陷综合症（AIDS）等治疗剂。
• PYRIMIDINE DERIVATIVES
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：EP1110951A1

  公开（公告）日：2001-06-27

  1. A pyrimidine derivative of the formula (1) or a salt thereof; has an inhibitory activity of production of Th2 type cytokines such as IL-4, IL-5, etc., and is useful as an therapeutic agent for allergic diseases, autoimmune diseases such as systemic lupus erythemathosus, etc., and acquired immunodeficiecy syndrome (AIDS) and so on.

  1.式（1）的嘧啶衍生物或其盐； 具有抑制 IL-4、IL-5 等 Th2 型细胞因子产生的活性，可作为过敏性疾病、系统性红斑狼疮等自身免疫性疾病和获得性免疫缺陷综合征（艾滋病）等的治疗剂。
• Identification of High-Potency Human TLR8 and Dual TLR7/TLR8 Agonists in Pyrimidine-2,4-diamines
  作者：Mallesh Beesu、Alex C. D. Salyer、Michael J. H. Brush、Kathryn L. Trautman、Justin K. Hill、Sunil A. David

  DOI：10.1021/acs.jmedchem.6b01860

  日期：2017.3.9

  The induction of toll-like receptor 7 (TLR7)-dependent type I interferons (IFN-alpha/beta) from plasmacytoid dendritic cells as well as the production of TLR8-dependent type II interferon (IFN-y), TNF-alpha, and IL-12 in myeloid dendritic cells are of importance in generating T helper-1 biased adaptive immune responses. In an effort to identify novel dual TLR7/TLR8-active compounds, we undertook structure activity relationship studies in pyrimidine 2,4-diamines, focusing on substituents at CS. Several analogues substituted with aminopropyl appendages at CS displayed dominant TLR8-agonistic activity. N4-Butyl-6-methyl-S-(3morpholinopropyl)pyrimidine-2,4-diamine was found to be a very potent dual TLR7/TLR8 agonist. Employing novel cytokine reporter cell assays, we verified that potency at TLR7 correlates with IFN-alpha/beta production in human blood, whereas IFN-y and TNF-a induction is largely TLR8dependent. Dual TLR7/TLR8 agonists markedly upregulate CD80 expression in multiple dendritic cell subsets, providing insight into the immunological basis for the superior adjuvantic properties of such innate immune stimuli.
• US6458798B1
  申请人：——

  公开号：US6458798B1

  公开（公告）日：2002-10-01
• US6951866B2
  申请人：——

  公开号：US6951866B2

  公开（公告）日：2005-10-04