1-(2-氨基-1H-咪唑-5-基)乙酮 | 67560-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-氨基-1H-咪唑-5-基)乙酮
• 英文名称: 5-acetyl-2-aminoimidazole
• 英文别名: 1-(2-amino-1H-imidazol-4-yl)ethan-1-one；2-Amino-4(5)-acetylimidazol；1-(2-amino-1(3)H-imidazol-4-yl)-ethanone；1-(2-amino-1H-imidazol-5-yl)ethanone
• CAS: 67560-27-4
• 化学式: C₅H₇N₃O
• 分子量: 125.13
• InChiKey: TUHILCSTOZCXEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-氨基-1H-咪唑-5-基)乙酮 在 氢溴酸 、 溴 作用下， 反应 1.0h， 生成 1-(2-Amino-1H-imidazol-4-yl)-2-bromo-ethanone
  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：

  1-(咪唑并[1,2-A]嘧啶-3-基)乙酮 在 肼 作用下， 以 水 为溶剂， 反应 0.5h， 以56%的产率得到1-(2-氨基-1H-咪唑-5-基)乙酮
  参考文献：
  名称：

  Nocarimidazoles C和D，来自珊瑚的放线菌Kocuria sp。的抗菌烷氨基咪唑：1JC，H偶联常数在确定微生物代谢物中取代咪唑的确定性和前异烷基链立体化学多样性中的应用

  摘要：

  从该属的海洋来源的放线菌菌株的次级代谢产物的化学调查Kocuria，从石珊瑚分离Mycedium属，导致了两个新alkanoylimidazoles的鉴定，nocarimidazoles C（1）和d（2），以及三个已知同类物，诺卡咪唑A（3）和B（4）和灯泡咪唑A（5）。1和2的结构分析NMR和MS分析表明，它们都是分别具有6-甲基辛酰基或癸酰基链的4-烷酰基-5-氨基咪唑。咪唑环上两个氨基的可能位置（C-2和C-5）对结构研究提出了挑战，该问题通过测量1 J C，H偶联常数与合成模型比较来解决。咪唑。本anteisoalkanoyl组中的绝对构型1，4和5分别由标与手性蒽试剂，其显示该降解产物的低温HPLC分析测定1是的混合物[R -和小号-比例为73:27的对映体，其中4是纯的（S）对映体，5是具有98％ee的（S）对映体。本研究说明了细菌代谢产物中前异分支的立体化学的多样性。化合物1

  DOI：

  10.3762/bjoc.16.222

文献信息

• The reaction of 5-acetyl-2-aminooxazole with amines: an approach to 1H-5-acetyl-2-aminoimidazoles
  作者：John L. LaMattina、Christian J. Mularski

  DOI：10.1016/s0040-4039(01)81336-8

  日期：1984.1
• LAMATTINA, J. L.;MULARSKI, CH. J., TETRAHEDRON LETT., 1984, 25, N 28, 2957-2960
  作者：LAMATTINA, J. L.、MULARSKI, CH. J.

  DOI：——

  日期：——
• 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：——
• 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.
• Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete <i>Kocuria</i> sp.: application of ¹<i>J</i>_C,H coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites
  作者：Md Rokon Ul Karim、Enjuro Harunari、Amit Raj Sharma、Naoya Oku、Kazuaki Akasaka、Daisuke Urabe、Mada Triandala Sibero、Yasuhiro Igarashi

  DOI：10.3762/bjoc.16.222

  日期：——

  low-temperature HPLC analysis of the degradation products labeled with a chiral anthracene reagent, which revealed that 1 is a mixture of the R- and S-enantiomers with a ratio of 73:27, 4 is the pure (S)-enantiomer, and 5 is the (S)-enantiomer with 98% ee. The present study illustrates the diversity in the stereochemistry of anteiso branching in bacterial metabolites. Compounds 1−4 were moderately antimicrobial

  从该属的海洋来源的放线菌菌株的次级代谢产物的化学调查Kocuria，从石珊瑚分离Mycedium属，导致了两个新alkanoylimidazoles的鉴定，nocarimidazoles C（1）和d（2），以及三个已知同类物，诺卡咪唑A（3）和B（4）和灯泡咪唑A（5）。1和2的结构分析NMR和MS分析表明，它们都是分别具有6-甲基辛酰基或癸酰基链的4-烷酰基-5-氨基咪唑。咪唑环上两个氨基的可能位置（C-2和C-5）对结构研究提出了挑战，该问题通过测量1 J C，H偶联常数与合成模型比较来解决。咪唑。本anteisoalkanoyl组中的绝对构型1，4和5分别由标与手性蒽试剂，其显示该降解产物的低温HPLC分析测定1是的混合物[R -和小号-比例为73:27的对映体，其中4是纯的（S）对映体，5是具有98％ee的（S）对映体。本研究说明了细菌代谢产物中前异分支的立体化学的多样性。化合物1