4-(4-pyridyl)-5-methyl-2-mercaptoimidazole | 103851-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(4-pyridyl)-5-methyl-2-mercaptoimidazole
• 英文别名: 4-methyl-5-pyridin-4-yl-1,3-dihydroimidazole-2-thione
• CAS: 103851-90-7
• 化学式: C₉H₉N₃S
• 分子量: 191.257
• InChiKey: ORNPJKGHOLXYNV-UHFFFAOYSA-N

物化性质

• 熔点：
  >270 °C
• 沸点：
  337.7±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-pyridyl)-5-methyl-2-mercaptoimidazole 在 硝酸 作用下， 反应 1.0h， 以49%的产率得到5-methyl-4-(4'-piridyl)imidazole
  参考文献：
  名称：

  Bioisosteric prototype design of biaryl imidazolyl and triazolyl competitive histamine H2-receptor antagonists

  摘要：

  The structural relationship of the competitive histamine H2-receptor antagonist 3-amino-5-(2-amino-4-pyridyl)-1,2,4-triazole (1) to the agonist histamine and to antagonists of the cimetidine type was explored by the design and synthesis of four series of bioisosterically designed prototypes. Biological data from these series was best interpreted as indicating a similarity between the imidazole moiety of histamine and cimetidine and the 2-amino-4-pyridyl moiety of 1. On the basis of this data, sequential replacement of 2-amino-4-pyridyl by 2-[(dimethylamino)methyl]-5-furyl and 2-guanidino-4-triazolyl moieties led to a structurally more potent series of biaryl histamine H2-receptor antagonists. The best of these, 2-methyl-4-(2-guanidino-4-thiazolyl)imidazole (29, CP-57,361-1) was 120 times more potent as a histamine H2-receptor antagonist than 1.

  DOI：

  10.1021/jm00161a005
• 作为产物：
  描述：

  potassium thioacyanate 、 2-amino-1-(4-pyridyl)propanone hydrochloride 以 水 为溶剂， 反应 1.0h， 以3.92 g的产率得到4-(4-pyridyl)-5-methyl-2-mercaptoimidazole
  参考文献：
  名称：

  Bioisosteric prototype design of biaryl imidazolyl and triazolyl competitive histamine H2-receptor antagonists

  摘要：

  The structural relationship of the competitive histamine H2-receptor antagonist 3-amino-5-(2-amino-4-pyridyl)-1,2,4-triazole (1) to the agonist histamine and to antagonists of the cimetidine type was explored by the design and synthesis of four series of bioisosterically designed prototypes. Biological data from these series was best interpreted as indicating a similarity between the imidazole moiety of histamine and cimetidine and the 2-amino-4-pyridyl moiety of 1. On the basis of this data, sequential replacement of 2-amino-4-pyridyl by 2-[(dimethylamino)methyl]-5-furyl and 2-guanidino-4-triazolyl moieties led to a structurally more potent series of biaryl histamine H2-receptor antagonists. The best of these, 2-methyl-4-(2-guanidino-4-thiazolyl)imidazole (29, CP-57,361-1) was 120 times more potent as a histamine H2-receptor antagonist than 1.

  DOI：

  10.1021/jm00161a005

文献信息

• Dérivés de pipéridine, leur préparation et leur application en thérapeutique
  申请人：SYNTHELABO

  公开号：EP0507650A1

  公开（公告）日：1992-10-07

  Composés répondant à la formule générale (I) dans laquelle R1 représente soit un atome d'hydrogène, soit un groupe (C₁₋₆)alkyle droit ou ramifié, soit un groupe cyclo(C₃₋₈)alkyle, X représente soit un atome d'oxygène, soit un atome de soufre soit un groupe de formule générale N-R3 dans laquelle R3 est un atome d'hydrogène, un groupe (C₁₋₈)alkyle droit ou ramifié, cyclo(C₃₋₆)alkyle, cyclo(C₃₋₆)alkylméthyle, C₁₋₄)alcoxy(C₁₋₄)alkyle, phényle, pyridin-4-yle, pyridin-3-yle, Z représente un atome d'hydrogène ou de fluor ainsi que leurs sels d'addition à des acides pharmaceutiquement acceptables. Application en thérapeutique.

  通式(I)对应的化合物 其中 R1 代表氢原子，或直链或支链 (C₁₋₆)烷基，或环(C₃₋₈)烷基、 X 代表氧原子、硫原子或通式 N-R3 的基团，其中 R3 为氢原子、直链或支链(C₁₋₈)烷基、环(C₃₋₆)烷基、环(C₃₋₆)烷甲基、C₁₋₄)烷氧基(C₁₋₄)烷基、苯基、吡啶-4-基、吡啶-3-基、 Z 代表氢原子或氟原子，以及它们与药学上可接受的酸的加成盐。 治疗应用。
• LIPINSKI C. A.; LAMATTINA J. L.; OATES P. J., J. MED. CHEM., 29,(1986) N 11, 2154-2163
  作者：LIPINSKI C. A.、 LAMATTINA J. L.、 OATES P. J.

  DOI：——

  日期：——
• US5280030A
  申请人：——

  公开号：US5280030A

  公开（公告）日：1994-01-18
• Bioisosteric prototype design of biaryl imidazolyl and triazolyl competitive histamine H2-receptor antagonists
  作者：Christopher A. Lipinski、John L. LaMattina、P. J. Oates

  DOI：10.1021/jm00161a005

  日期：1986.11

  The structural relationship of the competitive histamine H2-receptor antagonist 3-amino-5-(2-amino-4-pyridyl)-1,2,4-triazole (1) to the agonist histamine and to antagonists of the cimetidine type was explored by the design and synthesis of four series of bioisosterically designed prototypes. Biological data from these series was best interpreted as indicating a similarity between the imidazole moiety of histamine and cimetidine and the 2-amino-4-pyridyl moiety of 1. On the basis of this data, sequential replacement of 2-amino-4-pyridyl by 2-[(dimethylamino)methyl]-5-furyl and 2-guanidino-4-triazolyl moieties led to a structurally more potent series of biaryl histamine H2-receptor antagonists. The best of these, 2-methyl-4-(2-guanidino-4-thiazolyl)imidazole (29, CP-57,361-1) was 120 times more potent as a histamine H2-receptor antagonist than 1.