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2-((2-carboxy-4-chlorophenyl)amino)-3-methoxybenzoic acid | 1221746-46-8

中文名称
——
中文别名
——
英文名称
2-((2-carboxy-4-chlorophenyl)amino)-3-methoxybenzoic acid
英文别名
2-[(2-Carboxy-4-chlorophenyl)amino]-3-methoxybenzoic acid;2-(2-carboxy-4-chloroanilino)-3-methoxybenzoic acid
2-((2-carboxy-4-chlorophenyl)amino)-3-methoxybenzoic acid化学式
CAS
1221746-46-8
化学式
C15H12ClNO5
mdl
——
分子量
321.717
InChiKey
VIIURWCFWOSBGJ-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):
    3.7
  • 重原子数:
    22
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.07
  • 拓扑面积:
    95.9
  • 氢给体数:
    3
  • 氢受体数:
    6

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

  • 作为反应物:
    描述:
    2-((2-carboxy-4-chlorophenyl)amino)-3-methoxybenzoic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺三氯氧磷 作用下, 以 N,N-二甲基甲酰胺乙腈 为溶剂, 反应 5.0h, 生成 2-Chloroelacridar
    参考文献:
    名称:
    Radiosynthesis and in vivo evaluation of 1-[18F]fluoroelacridar as a positron emission tomography tracer for P-glycoprotein and breast cancer resistance protein
    摘要:
    Aim of this study was to label the potent dual P-glycoprotein (Pgp) and breast cancer resistance protein (BCRP) inhibitor elacridar (1) with F-18 to provide a positron emission tomography (PET) radiotracer to visualize Pgp and BCRP. A series of new 1- and 2-halogen- and nitro-substituted derivatives of 1 (4a-e) was synthesized as precursor molecules and reference compounds for radiolabelling and shown to display comparable in vitro potency to 1 in increasing rhodamine 123 accumulation in a cell line overexpressing human Pgp (MDCKII-MDR1). 1-[F-18]fluoroelacridar ([F-18]4b) was synthesized in a decay-corrected radiochemical yield of 1.7 +/- 0.9% by a 1-step no-carrier added nucleophilic aromatic F-18-substitution of 1-nitro precursor 4c. Small-animal PET imaging of [F-18]4b was performed in naive rats, before and after administration of unlabelled 1 (5 mg/kg, n = 3), as well as in wild-type and Mdr1a/b((-/-)) Bcrp1((-/-)) mice (n = 3). In PET experiments in rats, administration of unlabelled 1 increased brain activity uptake by a factor of 9.5 (p = 0.0002, 2-tailed Student's t-test), whereas blood activity levels remained unchanged. In Mdr1a/b((-/-)) Bcrp1((-/-)) mice, the mean brain-to-blood ratio of activity at 60 min after tracer injection was 7.6 times higher as compared to wild-type animals (p = 0.0002). HPLC analysis of rat brain tissue extracts collected at 40 min after injection of [F-18]4b revealed that 93 +/- 7% of total radioactivity in brain was in the form of unchanged [F-18] 4b. In conclusion, the in vivo behavior of [F-18]4b was found to be similar to previously described [C-11]1 suggesting transport of [F-18]4b by Pgp and/or BCRP at the rodent BBB. However, low radiochemical yields and a significant degree of in vivo defluorination will limit the utility of [F-18]4b as a PET tracer. (C) 2011 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2011.02.039
  • 作为产物:
    描述:
    2-氨基-3-甲氧基苯甲酸2-溴-4-氯苯甲酸potassium carbonate 作用下, 以 乙醇 为溶剂, 反应 1.5h, 以87%的产率得到2-((2-carboxy-4-chlorophenyl)amino)-3-methoxybenzoic acid
    参考文献:
    名称:
    Synthesis of New Acridone Derivatives, Inhibitors of NS3 Helicase, Which Efficiently and Specifically Inhibit Subgenomic HCV Replication
    摘要:
    A new goup of acridone derivatives, obtained by reaction of acridone-4-carboxylic acid derivatives with aromatic amines, was tested to determine the inhibitory properties toward the NS3 helicase of hepatitis C virus (HCV). Six compounds inhibited the NS3 helicase at low concentrations (IC(50) from 1.5 to 20 mu M). The acridone derivatives probably act via intercalation into double-stranded nucleic acids with a strong specificity for double-stranded RNA, although an interaction with the enzyme cannot be excluded. Testing in the subgenomic HCV replicon system revealed that compounds 10 and 13 are efficient RNA replication inhibitors, with EC(50) of 3.5 and 1 mu M and therapeutic indexes of > 28 and 20, respectively. Compound 16, with EC(50) < 1 mu M and TI > 1000, is extremely specific and practically noncytotoxic at the concentrations tested, proving that the acridone derivatives may be regarded as potential antiviral agents. Although the mechanism of action of 16 in the replicon system remains unclear, it is the key lead compound for further development of anti-HCV drugs.
    DOI:
    10.1021/jm901741p
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文献信息

  • Radiosynthesis and in vivo evaluation of 1-[18F]fluoroelacridar as a positron emission tomography tracer for P-glycoprotein and breast cancer resistance protein
    作者:Bernd Dörner、Claudia Kuntner、Jens P. Bankstahl、Thomas Wanek、Marion Bankstahl、Johann Stanek、Julia Müllauer、Florian Bauer、Severin Mairinger、Wolfgang Löscher、Donald W. Miller、Peter Chiba、Markus Müller、Thomas Erker、Oliver Langer
    DOI:10.1016/j.bmc.2011.02.039
    日期:2011.4
    Aim of this study was to label the potent dual P-glycoprotein (Pgp) and breast cancer resistance protein (BCRP) inhibitor elacridar (1) with F-18 to provide a positron emission tomography (PET) radiotracer to visualize Pgp and BCRP. A series of new 1- and 2-halogen- and nitro-substituted derivatives of 1 (4a-e) was synthesized as precursor molecules and reference compounds for radiolabelling and shown to display comparable in vitro potency to 1 in increasing rhodamine 123 accumulation in a cell line overexpressing human Pgp (MDCKII-MDR1). 1-[F-18]fluoroelacridar ([F-18]4b) was synthesized in a decay-corrected radiochemical yield of 1.7 +/- 0.9% by a 1-step no-carrier added nucleophilic aromatic F-18-substitution of 1-nitro precursor 4c. Small-animal PET imaging of [F-18]4b was performed in naive rats, before and after administration of unlabelled 1 (5 mg/kg, n = 3), as well as in wild-type and Mdr1a/b((-/-)) Bcrp1((-/-)) mice (n = 3). In PET experiments in rats, administration of unlabelled 1 increased brain activity uptake by a factor of 9.5 (p = 0.0002, 2-tailed Student's t-test), whereas blood activity levels remained unchanged. In Mdr1a/b((-/-)) Bcrp1((-/-)) mice, the mean brain-to-blood ratio of activity at 60 min after tracer injection was 7.6 times higher as compared to wild-type animals (p = 0.0002). HPLC analysis of rat brain tissue extracts collected at 40 min after injection of [F-18]4b revealed that 93 +/- 7% of total radioactivity in brain was in the form of unchanged [F-18] 4b. In conclusion, the in vivo behavior of [F-18]4b was found to be similar to previously described [C-11]1 suggesting transport of [F-18]4b by Pgp and/or BCRP at the rodent BBB. However, low radiochemical yields and a significant degree of in vivo defluorination will limit the utility of [F-18]4b as a PET tracer. (C) 2011 Elsevier Ltd. All rights reserved.
  • Synthesis of New Acridone Derivatives, Inhibitors of NS3 Helicase, Which Efficiently and Specifically Inhibit Subgenomic HCV Replication
    作者:Anna Stankiewicz-Drogoń、Bernd Dörner、Thomas Erker、Anna M. Boguszewska-Chachulska
    DOI:10.1021/jm901741p
    日期:2010.4.22
    A new goup of acridone derivatives, obtained by reaction of acridone-4-carboxylic acid derivatives with aromatic amines, was tested to determine the inhibitory properties toward the NS3 helicase of hepatitis C virus (HCV). Six compounds inhibited the NS3 helicase at low concentrations (IC(50) from 1.5 to 20 mu M). The acridone derivatives probably act via intercalation into double-stranded nucleic acids with a strong specificity for double-stranded RNA, although an interaction with the enzyme cannot be excluded. Testing in the subgenomic HCV replicon system revealed that compounds 10 and 13 are efficient RNA replication inhibitors, with EC(50) of 3.5 and 1 mu M and therapeutic indexes of > 28 and 20, respectively. Compound 16, with EC(50) < 1 mu M and TI > 1000, is extremely specific and practically noncytotoxic at the concentrations tested, proving that the acridone derivatives may be regarded as potential antiviral agents. Although the mechanism of action of 16 in the replicon system remains unclear, it is the key lead compound for further development of anti-HCV drugs.
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