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3-[5-(2-benzo[b]thiophenecarboxamido)pentyl]-6-(3-ethyl-4-methylanilino)uracil

中文名称
——
中文别名
——
英文名称
3-[5-(2-benzo[b]thiophenecarboxamido)pentyl]-6-(3-ethyl-4-methylanilino)uracil
英文别名
N-[5-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1H-pyrimidin-3-yl]pentyl]-1-benzothiophene-2-carboxamide
3-[5-(2-benzo[b]thiophenecarboxamido)pentyl]-6-(3-ethyl-4-methylanilino)uracil化学式
CAS
——
化学式
C27H30N4O3S
mdl
——
分子量
490.626
InChiKey
BEOMKTDBFIGDSI-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    5.5
  • 重原子数:
    35
  • 可旋转键数:
    10
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.3
  • 拓扑面积:
    119
  • 氢给体数:
    3
  • 氢受体数:
    5

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    参考文献:
    名称:
    Synthesis and Antibacterial Activity of 3-Substituted-6-(3-ethyl-4-methylanilino)uracils
    摘要:
    Numerous 3-substituted-6-(3-ethyl-4-methylanilino)uracils (EMAU) have been synthesized and screened for their capacity to inhibit the replication-specific bacterial DNA polymerase IIIC (pol IIIC) and the growth of Gram+ bacteria in culture. Direct alkylation of 2-methoxy-6-amino-4-pyrimidone produced the N3-substituted derivatives, which were separated from the byproduct 4-alkoxy analogues. The N3-substituted derivatives were heated with a mixture of 3-ethyl-4-methylaniline and its hydrochloride to effect displacement of the 6-amino group and simultaneous demethylation of the 2-methoxy group to yield target compounds in good yields. Certain intermediates, e.g. the 3-(iodoalkyl) compounds, were converted to a variety of (3-substituted-alkyl)-EMAUs by displacement. Most compounds were potent competitive inhibitors of pol IIIC (K(i)s 0.02-0.5 mu M), and those with neutral, moderately polar 3-substituents had potent antibacterial activity against Gram+ organisms in culture (MICs 0.125-10 mu g/mL). Several compounds protected mice from lethal intraperitoneal (ip) infections with S. aureus (Smith) when given by the ip route. A water soluble derivative, 3-(4-morpholinylbutyl)-EMAU hydrochloride, given subcutaneously, prolonged the life of infected mice in a dose dependent manner.
    DOI:
    10.1021/jm050517r
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文献信息

  • N3-substituted 6-anilinopyrimidines and methods to treat-Gram-positive bacterial and mycoplasmal infections
    申请人:——
    公开号:US20030114445A1
    公开(公告)日:2003-06-19
    Compounds useful for treating Gram-positive bacterial and mycoplasmal infections are disclosed. The compounds have the general formulae shown below. 1
    本发明揭示了用于治疗革兰氏阳性细菌和支原体感染的化合物。该化合物具有下面所示的一般式。1
  • [EN] N3-SUBSTITUTED 6-ANILINOPYRIMIDINES AND METHODS TO TREAT GRAM-POSITIVE BACTERIAL AND MYCOPLASMAL INFECTIONS<br/>[FR] 6-ANILINOPYRIMIDINES N3-SUBSTITUEES ET METHODES DE TRAITEMENT D'INFECTIONS GRAM-POSITIF BACTERIENNES ET MYCOPLASMIQUES
    申请人:UNIV MASSACHUSETTS
    公开号:WO2003011297A1
    公开(公告)日:2003-02-13
    Compounds useful for treating Gram-positive bacterial and mycoplasmal infections are disclosed. The compounds have the general formulae (I) and (II).
  • [EN] MAMMALIAN GENES INVOLVED IN INFECTION<br/>[FR] GÈNES DE MAMMIFÈRE IMPLIQUÉS DANS L'INFECTION
    申请人:ZIRUS INC
    公开号:WO2010134939A2
    公开(公告)日:2010-11-25
    The present invention relates to nucleic acid sequences and cellular proteins encoded by these sequences that are involved in infection or are otherwise associated with the life cycle of one or more pathogens.
  • Synthesis and Antibacterial Activity of 3-Substituted-6-(3-ethyl-4-methylanilino)uracils
    作者:Chengxin Zhi、Zheng-yu Long、Andrzej Manikowski、Neal C. Brown、Paul M. Tarantino,、Karsten Holm、Edward J. Dix、George E. Wright、Kim A. Foster、Michelle M. Butler、William A. LaMarr、Donna J. Skow、Irina Motorina、Serge Lamothe、Richard Storer
    DOI:10.1021/jm050517r
    日期:2005.11.1
    Numerous 3-substituted-6-(3-ethyl-4-methylanilino)uracils (EMAU) have been synthesized and screened for their capacity to inhibit the replication-specific bacterial DNA polymerase IIIC (pol IIIC) and the growth of Gram+ bacteria in culture. Direct alkylation of 2-methoxy-6-amino-4-pyrimidone produced the N3-substituted derivatives, which were separated from the byproduct 4-alkoxy analogues. The N3-substituted derivatives were heated with a mixture of 3-ethyl-4-methylaniline and its hydrochloride to effect displacement of the 6-amino group and simultaneous demethylation of the 2-methoxy group to yield target compounds in good yields. Certain intermediates, e.g. the 3-(iodoalkyl) compounds, were converted to a variety of (3-substituted-alkyl)-EMAUs by displacement. Most compounds were potent competitive inhibitors of pol IIIC (K(i)s 0.02-0.5 mu M), and those with neutral, moderately polar 3-substituents had potent antibacterial activity against Gram+ organisms in culture (MICs 0.125-10 mu g/mL). Several compounds protected mice from lethal intraperitoneal (ip) infections with S. aureus (Smith) when given by the ip route. A water soluble derivative, 3-(4-morpholinylbutyl)-EMAU hydrochloride, given subcutaneously, prolonged the life of infected mice in a dose dependent manner.
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