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2-methyl-4-(4-(trifluoromethoxy)penoxy)phenylboronic acid | 1312077-90-9

中文名称
——
中文别名
——
英文名称
2-methyl-4-(4-(trifluoromethoxy)penoxy)phenylboronic acid
英文别名
[2-Methyl-4-[4-(trifluoromethoxy)phenoxy]phenyl]boronic acid
2-methyl-4-(4-(trifluoromethoxy)penoxy)phenylboronic acid化学式
CAS
1312077-90-9
化学式
C14H12BF3O4
mdl
——
分子量
312.053
InChiKey
QQJLTKPMGRGDIW-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

物化性质

  • 沸点:
    388.3±52.0 °C(Predicted)
  • 密度:
    1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.37
  • 重原子数:
    22
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.14
  • 拓扑面积:
    58.9
  • 氢给体数:
    2
  • 氢受体数:
    7

反应信息

  • 作为反应物:
    描述:
    8-bromo-3,4-dihydro-1H-thiopyrano[4,3-b]quinolin-10(5H)-one2-methyl-4-(4-(trifluoromethoxy)penoxy)phenylboronic acid2-双环己基膦-2',6'-二甲氧基联苯tris-(dibenzylideneacetone)dipalladium(0) 、 sodium carbonate 作用下, 以 N,N-二甲基甲酰胺 为溶剂, 以56%的产率得到7-(2-methyl-4-(4-(trifluoromethoxy)phenyl)phenyl)-1,3,4,10-tetrahydro-2-thia-10-azaanthracen-9-one
    参考文献:
    名称:
    Optimization of 1,2,3,4-Tetrahydroacridin-9(10H)-ones as Antimalarials Utilizing Structure–Activity and Structure–Property Relationships
    摘要:
    Antimalarial activity of 1,2,3,4-tetrahydroacridin-9(10H)-ones (THAs) has been known since the 1940s and has garnered more attention with the development of the acridinedione floxacrine (1) in the 1970s and analogues thereof such as WR 243251 (2a) in the 1990s. These compounds failed just prior to clinical development because of suboptimal activity, poor solubility, and rapid induction of parasite resistance. Moreover, detailed structure-activity relationship (SAR) studies of the THA core scaffold were lacking and SPR studies were nonexistent. To improve upon initial findings, several series of 1,2,3,4-tetrahydroacridin-9(10H)-ones were synthesized and tested in a systematic fashion, examining each compound for antimalarial activity, solubility, and permeability. Furthermore, a select set of compounds was chosen for microsomal stability testing to identify physicochemical liabilities of the THA scaffold. Several potent compounds (EC50 < 100 nM) were identified to be active against the clinically relevant isolates W2 and TM90-C2B while possessing good physicochemical properties and little to no cross-resistance.
    DOI:
    10.1021/jm200015a
  • 作为产物:
    参考文献:
    名称:
    Optimization of 1,2,3,4-Tetrahydroacridin-9(10H)-ones as Antimalarials Utilizing Structure–Activity and Structure–Property Relationships
    摘要:
    Antimalarial activity of 1,2,3,4-tetrahydroacridin-9(10H)-ones (THAs) has been known since the 1940s and has garnered more attention with the development of the acridinedione floxacrine (1) in the 1970s and analogues thereof such as WR 243251 (2a) in the 1990s. These compounds failed just prior to clinical development because of suboptimal activity, poor solubility, and rapid induction of parasite resistance. Moreover, detailed structure-activity relationship (SAR) studies of the THA core scaffold were lacking and SPR studies were nonexistent. To improve upon initial findings, several series of 1,2,3,4-tetrahydroacridin-9(10H)-ones were synthesized and tested in a systematic fashion, examining each compound for antimalarial activity, solubility, and permeability. Furthermore, a select set of compounds was chosen for microsomal stability testing to identify physicochemical liabilities of the THA scaffold. Several potent compounds (EC50 < 100 nM) were identified to be active against the clinically relevant isolates W2 and TM90-C2B while possessing good physicochemical properties and little to no cross-resistance.
    DOI:
    10.1021/jm200015a
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文献信息

  • Synthesis, Antimalarial Activity, and Structure–Activity Relationship of 7-(2-Phenoxyethoxy)-4(1<i>H</i>)-quinolones
    作者:R. Matthew Cross、Niranjan K. Namelikonda、Tina S. Mutka、Lisa Luong、Dennis E. Kyle、Roman Manetsch
    DOI:10.1021/jm200718m
    日期:2011.12.22
    resistant P. falciparum. Optimal activity with low cross-resistance indexes (RI) to atovaquone was achieved by introducing ortho-substituted aryl moieties at the 3-position of the 7-(2-phenoxyethoxy)-4(1H)-quinolone core.
    ICI 56,780 ( 5 ) 在啮齿动物疟疾模型中显示出因果预防和血液分裂活性(ED 50 = 0.05 mg/kg),但在感染伯氏疟原虫的小鼠中迅速获得了寄生虫学抗性。在此,我们描述了针对多药耐药恶性疟原虫的 EC 50低至 0.15 nM的5类似物的合成。通过在 7-(2-phenoxyethoxy)-4(1 H )-quinolone 核心的 3 位引入邻位取代的芳基部分,实现了对 atovaquone 的低交叉阻力指数 (RI) 的最佳活性。
  • 4(1H)-Quinolones Having Antimalarial Activity With Reduced Chemical Resistance
    申请人:Manetsch Roman
    公开号:US20130123258A1
    公开(公告)日:2013-05-16
    Provided are 4(1H)-quinolone derivatives effective in inhibiting or eliminating the viability of at least one of the stages in the life-cycle of the malarial parasite, and to show a reduced propensity to induce resistance to the compound by the target parasite. In particular, the compounds can be derivatives of phenoxyethoxy-quinolones, and including, but not only, 7-(2-phenoxyethoxy)quinolin derivatives. These compounds may be administered by themselves, with at least one other derivative compound, or with other antimalarial compounds, to an animal or human subject. The therapeutic compositions can be and formulated to reduce the extent of a Plasmodium infection in the recipient subject, or to reduce the likelihood of the onset or establishment of a Plasmodium infection if administered prior to the parasite contacting the subject. The therapeutic compositions can be formulated to provide an effective single dose amount of an antimalarial compound or multiple doses for administering over a period of time.
    提供了4(1H)-喹啉酮衍生物,能有效抑制或消除疟原虫生命周期中至少一个阶段的生存能力,并且显示出减少目标寄生虫对化合物产生抗药性的倾向。具体来说,这些化合物可以是苯氧乙氧基喹啉酮的衍生物,包括但不限于7-(2-苯氧乙氧基)喹啉衍生物。这些化合物可以单独或与至少另一种衍生物化合物或其他抗疟疾化合物一起,向动物或人类受试者施用。治疗组合物可以配制成减少受试者体内疟原虫感染程度的程度,或者在寄生虫接触受试者之前施用,以减少疟原虫感染的可能性。治疗组合物可以配制成提供有效的单剂量抗疟疾化合物或多剂量,以在一段时间内施用。
  • Orally Bioavailable 6-Chloro-7-methoxy-4(1<i>H</i>)-quinolones Efficacious against Multiple Stages of <i>Plasmodium</i>
    作者:R. Matthew Cross、David L. Flanigan、Andrii Monastyrskyi、Alexis N. LaCrue、Fabián E. Sáenz、Jordany R. Maignan、Tina S. Mutka、Karen L. White、David M. Shackleford、Ian Bathurst、Frank R Fronczek、Lukasz Wojtas、Wayne C. Guida、Susan A. Charman、Jeremy N. Burrows、Dennis E. Kyle、Roman Manetsch
    DOI:10.1021/jm500942v
    日期:2014.11.13
    The continued proliferation of malaria throughout temperate and tropical regions of the world has promoted a push for more efficacious treatments to combat the disease. Unfortunately, more recent remedies such as artemisinin combination therapies have been rendered less effective due to developing parasite resistance, and new drugs are required that target the parasite in the liver to support the disease elimination efforts. Research was initiated to revisit antimalarials developed in the 1940s and 1960s that were deemed unsuitable for use as therapeutic agents as a result of poor understanding of both physicochemical properties and parasitology. Structure-activity and structure-property relationship studies were conducted to generate a set of compounds with the general 6-chloro-7-methoxy-2-methyl-4(1H)-quinolone scaffold which were substituted at the 3-position with a variety of phenyl moieties possessing various properties. Extensive physicochemical evaluation of the quinolone series was carried out to downselect the most promising 4(1H)-quinolones, 7, 62, 66, and 67, which possessed low-nanomolar EC50 values against W2 and TM90-C2B as well as improved microsomal stability. Additionally, in vivo Thompson test results using Plasmodium berghei in mice showed that these 4(1H)-quinolones were efficacious for the reduction of parasitemia at >99% after 6 days.
  • Optimization of 1,2,3,4-Tetrahydroacridin-9(10<i>H</i>)-ones as Antimalarials Utilizing Structure–Activity and Structure–Property Relationships
    作者:R. Matthew Cross、Jordany R. Maignan、Tina S. Mutka、Lisa Luong、Justin Sargent、Dennis E. Kyle、Roman Manetsch
    DOI:10.1021/jm200015a
    日期:2011.7.14
    Antimalarial activity of 1,2,3,4-tetrahydroacridin-9(10H)-ones (THAs) has been known since the 1940s and has garnered more attention with the development of the acridinedione floxacrine (1) in the 1970s and analogues thereof such as WR 243251 (2a) in the 1990s. These compounds failed just prior to clinical development because of suboptimal activity, poor solubility, and rapid induction of parasite resistance. Moreover, detailed structure-activity relationship (SAR) studies of the THA core scaffold were lacking and SPR studies were nonexistent. To improve upon initial findings, several series of 1,2,3,4-tetrahydroacridin-9(10H)-ones were synthesized and tested in a systematic fashion, examining each compound for antimalarial activity, solubility, and permeability. Furthermore, a select set of compounds was chosen for microsomal stability testing to identify physicochemical liabilities of the THA scaffold. Several potent compounds (EC50 < 100 nM) were identified to be active against the clinically relevant isolates W2 and TM90-C2B while possessing good physicochemical properties and little to no cross-resistance.
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