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3-(2-hydroxyethyl)-1,2,4-benzotriazine 1-oxide | 507477-05-6

中文名称
——
中文别名
——
英文名称
3-(2-hydroxyethyl)-1,2,4-benzotriazine 1-oxide
英文别名
3-(2-hydroxyethyl)-1,2,4-benzotriazine-1-oxide;2-(1-oxido-1,2,4-benzotriazin-1-ium-3-yl)ethanol
3-(2-hydroxyethyl)-1,2,4-benzotriazine 1-oxide化学式
CAS
507477-05-6
化学式
C9H9N3O2
mdl
——
分子量
191.189
InChiKey
SPLPGUFTJBHEKS-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):
    -0.2
  • 重原子数:
    14
  • 可旋转键数:
    2
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.22
  • 拓扑面积:
    71.5
  • 氢给体数:
    1
  • 氢受体数:
    4

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
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Benzoazine mono-N-oxides and benzoazine 1,4 dioxides and compositions therefrom for the therapeutic use in cancer treatments
    摘要:
    本发明涉及一种协同作用的组合物,包括一种或多种苯并噁唑-单-N-氧化物,以及一种或多种苯并噁唑1,4-二氧化物,用于癌症治疗。 该发明还提供了一系列新颖的1,2,4-苯并噁唑-单-N-氧化物及相关类似物。这些可以用作增强现有抗癌药物的细胞毒性和癌症治疗的治疗剂。
    公开号:
    US20040192686A1
  • 作为产物:
    参考文献:
    名称:
    New and versatile syntheses of 3-alkyl- and 3-aryl-1,2,4-benzotriazine 1,4-dioxides: preparation of the bioreductive cytotoxins SR 4895 and SR 4941
    摘要:
    Palladium-mediated coupling of 3-chloro-1,2,4-benzotriazine 1-oxide with a variety of stannanes in the presence of Pd(PPh3)(4) gives 3-alkyl derivatives in good yields. Suzuki reaction of the 3-chloro compound with phenylboronic acids gives 3-aryl-1,2,4-benzotriazine 1-oxides. Oxidation of I-oxides with trifluoroperacetic acid gives the 1,4-dioxides. This method provides a better route to the potential anti-cancer agents SR 4895 and SR 4941. (C) 2002 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0040-4039(02)02417-6
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文献信息

  • Hypoxia-Selective 3-Alkyl 1,2,4-Benzotriazine 1,4-Dioxides: The Influence of Hydrogen Bond Donors on Extravascular Transport and Antitumor Activity
    作者:Michael P. Hay、Karin Pchalek、Frederik B. Pruijn、Kevin O. Hicks、Bronwyn G. Siim、Robert F. Anderson、Sujata S. Shinde、Victoria Phillips、William A. Denny、William R. Wilson
    DOI:10.1021/jm701037w
    日期:2007.12.27
    Tirapazamine (TPZ) and related 1,2,4-benzotriazine 1,4 dioxides (BTOs) are selectively toxic under hypoxia, but their ability to kill hypoxic cells in tumors is generally limited by their poor extravascular transport. Here we show that removing hydrogen bond donors by replacing the 3-NH2 group of TPZ with simple alkyl groups increased their tissue diffusion coefficients as measured in multicellular layer cultures. This advantage was largely retained using solubilizing 3-alkylaminoalkyl substituents provided these were sufficiently lipophilic at pH 7.4. The high reduction potentials of such compounds resulted in rates of metabolism too high for optimal penetration into hypoxic tissue, but electron-donating 6- and 7-substituents moderated metabolism. Pharmacokinetic/pharmacodynamic model-guided screening was used to select BTOs with optimal extravascular transport and hypoxic cytotoxicity properties for evaluation against HT29 human tumor xenografts in combination with radiation. This identified four novel 3-alkyl BTOs providing greater clonogenic killing of hypoxic cells than TPZ at equivalent host toxicity, with the 6-morpholinopropyloxy-BTO 22 being 3-fold more active.
  • Benzoazine mono-N-oxides and benzoazine 1,4 dioxides and compositions therefrom for the therapeutic use in cancer treatments
    申请人:Auckland Uniservices Limited
    公开号:EP1468688A2
    公开(公告)日:2004-10-20
    The present invention relates to a synergetistic composition comprising one or more benzoazine-mono-N-oxides, and one or more benzoazine 1,4 dioxides for use in cancer therapy. The invention also provides a range of novel 1,2,4 benzoazine-mono-N-oxides and related analogues. These can be used as potentiators of the cytotoxicity of existing anticancer drugs and therapies for cancer treatment.
    本发明涉及一种协同组合物,包括一种或多种苯并噁唑-单-N-氧化物,以及一种或多种苯并噁唑1,4-二氧化物,用于癌症治疗。 该发明还提供了一系列新颖的1,2,4苯并噁唑-单-N-氧化物及相关类似物。这些可以用作增强现有抗癌药物的细胞毒性和癌症治疗的治疗剂。
  • New and versatile syntheses of 3-alkyl- and 3-aryl-1,2,4-benzotriazine 1,4-dioxides: preparation of the bioreductive cytotoxins SR 4895 and SR 4941
    作者:Michael P Hay、William A Denny
    DOI:10.1016/s0040-4039(02)02417-6
    日期:2002.12
    Palladium-mediated coupling of 3-chloro-1,2,4-benzotriazine 1-oxide with a variety of stannanes in the presence of Pd(PPh3)(4) gives 3-alkyl derivatives in good yields. Suzuki reaction of the 3-chloro compound with phenylboronic acids gives 3-aryl-1,2,4-benzotriazine 1-oxides. Oxidation of I-oxides with trifluoroperacetic acid gives the 1,4-dioxides. This method provides a better route to the potential anti-cancer agents SR 4895 and SR 4941. (C) 2002 Elsevier Science Ltd. All rights reserved.
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