3-trifluoroacetylamino-5-methylpyrazole | 198213-31-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-trifluoroacetylamino-5-methylpyrazole
• 英文别名: 2,2,2-trifluoro-N-(5-methyl-1H-pyrazol-3-yl)-acetamide；2,2,2-trifluoro-N-(5-methyl-1H-pyrazol-3-yl)acetamide
• CAS: 198213-31-9
• 化学式: C₆H₆F₃N₃O
• 分子量: 193.128
• InChiKey: CVGPCNYDFWPKDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-trifluoroacetylamino-5-methylpyrazole 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 生成 N-(4-Chloro-5-methyl-1H-pyrazol-3-yl)-2,2,2-trifluoro-acetamide
  参考文献：
  名称：

  Substituted piperazines

  摘要：

  提供了作为CCR1受体强效拮抗剂的化合物，并且这些化合物在动物炎症测试中进一步得到确认，炎症是CCR1的典型疾病状态之一。这些化合物通常是芳基哌嗪衍生物，在制药组合物、治疗CCR1介导疾病的方法以及用作竞争性CCR1拮抗剂鉴定的检测中是有用的。

  公开号：

  US20040162282A1
• 作为产物：
  描述：

  三氟乙酰氯 、 3-氨基-5-甲基吡唑 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 以99%的产率得到3-trifluoroacetylamino-5-methylpyrazole
  参考文献：
  名称：

  Intermolecular β-Sheet Stabilization with Aminopyrazoles

  摘要：

  3-Aminopyrazole derivatives are the first artificial templates that stabilize the beta-sheet conformation in N/C-protected dipeptides by purely intermolecular interactions. In the complex two aminopyrazole molecules lie exactly above and below the peptide backbone. Binding to the top face of the peptide is strongly favored because it forms three cooperative hydrogen bonds simultaneously to the receptor molecule, whereas the bottom face has only two. Polymerizable 3-amino- and 3-amidopyrazoles have been made accessible in excellent yields by a general route starting from p-toluic acid. With H-1 NMR titrations binding constants for the 1:1 complex of up to 880 M-1 have been determined in chloroform. The association constants are strongly influenced by the electronic character of the aminopyrazole derivative as well as by the steric demand of the peptide residues. Variable temperature studies prove that the complex is formed by dynamic hydrogen bonds and confirmed the preferential binding of the receptor molecules at the top face. By detailed Karplus-analysis of the NH-alpha-CH coupling constants in the complex a remarkable correlation between the dihedral angle theta and the degree of complexation was found, which shows that several amidopyrazoles are capable of forcing the dipeptide into an almost ideal P-sheet conformation. In glycine-containing dipeptides the third hydrogen bond slows down the free rotation around the C-C/C-N bond to almost zero. Intramolecular nuclear Overhauser enhancements (NOE) provide additional evidence for the peptide's extended conformation, while strong reciprocal intermolecular NOEs give the final proof of the existence of the critical third hydrogen bond and the postulated mutual orientation of the complexation partners. First H-1 NMR titrations with tripeptides show very promising results concerning the application of this concept to oligopeptides.

  DOI：

  10.1021/ja972158y

文献信息

• [EN] 1-ARYL-4-SUBSTITUTED PIPERAZINES DERIVATIVES FOR USE AS CCR1 ANTAGONISTS FOR THE TREATMENT OF INFLAMMATION AND IMMUNE DISORDERS<br/>[FR] DERIVES DE PIPERAZINES 1-ARYL-4-SUSBTITUES UTILISES EN TANT QU'ANTAGONISTES DU CCR1 DANS LE TRAITEMENT DE L'INFLAMMATION ET DES TROUBLES IMMUNITAIRES
  申请人：CHEMOCENTRYX INC

  公开号：WO2003105853A1

  公开（公告）日：2003-12-24

  Compounds are provided that act as potent antagonists of the CCR1 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR1. The compounds are generally aryl piperazine derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR1-mediated diseases, and as controls in assays for the identification of competitive CCR1 antagonists.

  提供了作为CCR1受体强效拮抗剂的化合物，并且已经在动物炎症测试中进一步确认，炎症是CCR1的典型疾病状态之一。这些化合物通常是芳基哌嗪衍生物，在制药组合物、治疗CCR1介导疾病的方法以及用于鉴定竞争性CCR1拮抗剂的检测中具有用途。
• SUBSTITUTED PIPERAZINES
  申请人：Pennell Andrew M.K.

  公开号：US20080261987A1

  公开（公告）日：2008-10-23

  Compounds are provided that act as potent antagonists of the CCR1 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR1. The compounds are generally aryl piperazine derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR1-mediated diseases, and as controls in assays for the identification of competitive CCR1 antagonists.

  提供了一种作为CCR1受体强效拮抗剂的化合物，已经在动物炎症测试中进一步确认，这是CCR1标志性疾病状态之一。这些化合物通常是芳基哌嗪衍生物，可用于制药组合物、治疗CCR1介导疾病的方法，以及用作竞争性CCR1拮抗剂鉴定的控制物。
• 1-ARYL-4-SUBSTITUTED PIPERAZINE DERIVATIVES FOR USE AS CCR1 ANTAGONISTS FOR THE TREATMENT OF INFLAMMATION AND IMMUNE DISORDERS
  申请人：Chemocentryx, Inc.

  公开号：EP1531822A1

  公开（公告）日：2005-05-25
• EP1691810A4
  申请人：——

  公开号：EP1691810A4

  公开（公告）日：2009-07-01
• US7157464B2
  申请人：——

  公开号：US7157464B2

  公开（公告）日：2007-01-02