2,6-dichloro-N-(2-methoxyethyl)pyrimidin-4-ylamine | 879609-73-1

• 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: 2,6-dichloro-N-(2-methoxyethyl)pyrimidin-4-ylamine
• 英文别名: 2,6-dichloro-N-(2-methoxyethyl)pyrimidin-4-amine
• CAS: 879609-73-1
• 化学式: C₇H₉Cl₂N₃O
• 分子量: 222.074
• InChiKey: PIUWRBXZLZJOSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dichloro-N-(2-methoxyethyl)pyrimidin-4-ylamine 、 3-氨基-1-丙醇 在 N,N-二异丙基乙胺 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以72%的产率得到2-(3-aminopropoxy)-6-chloro-N-(2-methoxyethyl)pyrimidin-4-ylamine
  参考文献：
  名称：

  De Novo Design of Nonpeptidic Compounds Targeting the Interactions between Interferon-α and its Cognate Cell Surface Receptor

  摘要：

  Type 1 interferons (IFN) bind specifically to the corresponding receptor, IFNAR. Agonists and antagonists for IFNAR have potential therapeutic value in the treatment of viral infections and systemic lupus erythematosus, respectively. Specific sequences on the surface of IFN, IFN receptor recognition peptides (IRRPs) mediate the binding and signal transduction when IFN interacts with IFNAR. Structural features of two such IRRPs, IRRP-1 and IRRP-3, were used as templates to design small molecule mimetics. In silico screening was used to identify the molecular structural features mimicking their surface characteristics. A set of 26 compounds were synthesized and their ability to interfere with IFN-IFNAR interactions was investigated. Two compounds exhibited antagonist activity, specifically, blocking IFN-inducible Stat phosphorylation Stat complex-DNA binding. Design principles revealed here pave the way toward a novel series of small molecules as antagonists for IFN-IFNAR interactions.

  DOI：

  10.1021/jm701182y
• 作为产物：
  描述：

  2,4,6-三氯嘧啶 、 2-甲氧基乙胺 生成 4,6-dichloro-N-(2-methoxyethyl)pyrimidin-2-amine 、 2,6-dichloro-N-(2-methoxyethyl)pyrimidin-4-ylamine
  参考文献：
  名称：

  Vanilloid receptor ligands and their use in treatments

  摘要：

  取代吡啶和嘧啶以及含有它们的组合物，用于治疗急性、炎症性和神经痛、牙痛、普通头痛、偏头痛、集簇头痛、混合血管和非血管综合征、紧张性头痛、一般炎症、关节炎、风湿性疾病、骨关节炎、炎症性肠道疾病、炎症性眼部疾病、炎症性或不稳定的膀胱疾病、牛皮癣、具有炎症成分的皮肤问题、慢性炎症症状、炎症性疼痛及相关的痛觉过敏和触痛、神经痛及相关的痛觉过敏和触痛、糖尿病性神经病痛、烧灼性神经痛、交感神经维持性疼痛、去神经症候群、哮喘、上皮组织损伤或功能障碍、单纯疱疹、呼吸系统、泌尿系统、消化系统或血管区域内脏动力障碍、伤口、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠道障碍、胃溃疡、十二指肠溃疡、腹泻、由坏死性药剂引起的胃损伤、毛发生长、血管运动性或过敏性鼻炎、支气管疾病或膀胱疾病。

  公开号：

  US20060058308A1

文献信息

• US7335672B2
  申请人：——

  公开号：US7335672B2

  公开（公告）日：2008-02-26
• Vanilloid receptor ligands and their use in treatments
  申请人：Norman H. Mark

  公开号：US20060058308A1

  公开（公告）日：2006-03-16

  Substituted pyridines and pyrimidines and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

  取代吡啶和嘧啶以及含有它们的组合物，用于治疗急性、炎症性和神经痛、牙痛、普通头痛、偏头痛、集簇头痛、混合血管和非血管综合征、紧张性头痛、一般炎症、关节炎、风湿性疾病、骨关节炎、炎症性肠道疾病、炎症性眼部疾病、炎症性或不稳定的膀胱疾病、牛皮癣、具有炎症成分的皮肤问题、慢性炎症症状、炎症性疼痛及相关的痛觉过敏和触痛、神经痛及相关的痛觉过敏和触痛、糖尿病性神经病痛、烧灼性神经痛、交感神经维持性疼痛、去神经症候群、哮喘、上皮组织损伤或功能障碍、单纯疱疹、呼吸系统、泌尿系统、消化系统或血管区域内脏动力障碍、伤口、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠道障碍、胃溃疡、十二指肠溃疡、腹泻、由坏死性药剂引起的胃损伤、毛发生长、血管运动性或过敏性鼻炎、支气管疾病或膀胱疾病。
• De Novo Design of Nonpeptidic Compounds Targeting the Interactions between Interferon-α and its Cognate Cell Surface Receptor
  作者：Angelica M. Bello、Tanushree Bende、Lianhu Wei、Xiaoyang Wang、Beata Majchrzak-Kita、Eleanor N. Fish、Lakshmi P. Kotra

  DOI：10.1021/jm701182y

  日期：2008.5.1

  Type 1 interferons (IFN) bind specifically to the corresponding receptor, IFNAR. Agonists and antagonists for IFNAR have potential therapeutic value in the treatment of viral infections and systemic lupus erythematosus, respectively. Specific sequences on the surface of IFN, IFN receptor recognition peptides (IRRPs) mediate the binding and signal transduction when IFN interacts with IFNAR. Structural features of two such IRRPs, IRRP-1 and IRRP-3, were used as templates to design small molecule mimetics. In silico screening was used to identify the molecular structural features mimicking their surface characteristics. A set of 26 compounds were synthesized and their ability to interfere with IFN-IFNAR interactions was investigated. Two compounds exhibited antagonist activity, specifically, blocking IFN-inducible Stat phosphorylation Stat complex-DNA binding. Design principles revealed here pave the way toward a novel series of small molecules as antagonists for IFN-IFNAR interactions.