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Methyl 4-[(pyridine-2-carbonylamino)carbamoyl]benzoate

中文名称
——
中文别名
——
英文名称
Methyl 4-[(pyridine-2-carbonylamino)carbamoyl]benzoate
英文别名
——
Methyl 4-[(pyridine-2-carbonylamino)carbamoyl]benzoate化学式
CAS
——
化学式
C15H13N3O4
mdl
——
分子量
299.286
InChiKey
WJUUNPHLPNRSEC-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):
    0.9
  • 重原子数:
    22
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.07
  • 拓扑面积:
    97.4
  • 氢给体数:
    2
  • 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

  • 作为反应物:
    参考文献:
    名称:
    Sterol 14α-Demethylase Structure-Based Optimization of Drug Candidates for Human Infections with the Protozoan Trypanosomatidae
    摘要:
    Sterol 14 alpha-demethylases (CYP51) are cytochrome P450 enzymes essential for sterol biosynthesis in eukaryotes and therapeutic targets for antifungal azoles. Multiple attempts to repurpose antifungals for treatment of human infections with protozoa (Trypanosomatidae) have been undertaken, yet so far none of them have revealed sufficient efficacy. VNI and its derivative VFV are two potent experimental inhibitors of Trypanosomatidae CYP51, effective in vivo against Chagas disease, visceral leishmaniasis, and sleeping sickness and currently under consideration as antiprotozoal drug candidates. However, VNI is less potent against Leishmania and drug-resistant strains of Trypanosoma cruzi and VFV, while displaying a broader spectrum of antiprotozoal activity, and is metabolically less stable. In this work we have designed, synthesized, and characterized a set of close analogues and identified two new compounds (7 and 9) that exceed VNI/VFV in their spectra of antiprotozoal activity, microsomal stability, and pharmacokinetics (tissue distribution in particular) and, like VNI/VFV, reveal no acute toxicity.
    DOI:
    10.1021/acs.jmedchem.8b01671
  • 作为产物:
    描述:
    对苯二甲酸二甲酯氯化亚砜 、 potassium hydroxide 作用下, 以 甲醇氯仿N,N-二甲基甲酰胺 为溶剂, 反应 32.0h, 生成 Methyl 4-[(pyridine-2-carbonylamino)carbamoyl]benzoate
    参考文献:
    名称:
    含有双齿 1,3,4-噻二唑基配体的新型 Pt(II) 二碘配合物:合成、表征、细胞毒性
    摘要:
    制备了两个二碘化铂 (II) 配合物 [PtI 2 (L1)] ( 1 ) 和 [PtI 2 (L2)] ( 2 ) 与异构双齿 1,3,4-噻二唑基N供体配体 (L1, L2)并通过多核NMR光谱、元素分析、红外光谱和质谱进行表征。配合物1和2在 50% DMF- d 7 /50% D 2 O 和 50% DMF - d 7 /50% PBS 中的 D 2 O (pH 7.4)中是水解稳定的。在五种人类癌细胞系上评估了1和2的细胞毒性,即肺癌 (A549)、肝细胞癌 (HepG2)、黑色素瘤 (A375)、前列腺癌 (DU-145) 和乳腺癌 (MCF-7)。只有 HepG2(IC 50  = 22.0 和 17.8 μM 分别对1和2)和 A549(IC 50  = 18.5 μM 对1)细胞对所研究的复合物敏感,但它们的体外细胞毒性略低于参考确定的药物顺铂(对 HepG2 和 A549
    DOI:
    10.1016/j.ica.2022.120891
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文献信息

  • Sterol 14α-Demethylase Structure-Based Optimization of Drug Candidates for Human Infections with the Protozoan Trypanosomatidae
    作者:Laura Friggeri、Tatiana Y. Hargrove、Girish Rachakonda、Anna L. Blobaum、Paxtyn Fisher、Gabriel Melo de Oliveira、Cristiane França da Silva、Maria de Nazaré C. Soeiro、W. David Nes、Craig W. Lindsley、Fernando Villalta、F. Peter Guengerich、Galina I. Lepesheva
    DOI:10.1021/acs.jmedchem.8b01671
    日期:2018.12.13
    Sterol 14 alpha-demethylases (CYP51) are cytochrome P450 enzymes essential for sterol biosynthesis in eukaryotes and therapeutic targets for antifungal azoles. Multiple attempts to repurpose antifungals for treatment of human infections with protozoa (Trypanosomatidae) have been undertaken, yet so far none of them have revealed sufficient efficacy. VNI and its derivative VFV are two potent experimental inhibitors of Trypanosomatidae CYP51, effective in vivo against Chagas disease, visceral leishmaniasis, and sleeping sickness and currently under consideration as antiprotozoal drug candidates. However, VNI is less potent against Leishmania and drug-resistant strains of Trypanosoma cruzi and VFV, while displaying a broader spectrum of antiprotozoal activity, and is metabolically less stable. In this work we have designed, synthesized, and characterized a set of close analogues and identified two new compounds (7 and 9) that exceed VNI/VFV in their spectra of antiprotozoal activity, microsomal stability, and pharmacokinetics (tissue distribution in particular) and, like VNI/VFV, reveal no acute toxicity.
  • New Pt(II) diiodido complexes containing bidentate 1,3,4-thiadiazole-based ligands: Synthesis, characterization, cytotoxicity
    作者:Lukáš Masaryk、Pavel Zoufalý、Karolina Słoczyńska、Eva Zahradniková、David Milde、Paulina Koczurkiewicz-Adamczyk、Pavel Štarha
    DOI:10.1016/j.ica.2022.120891
    日期:2022.6
    Two diiodidoplatinum(II) complexes [PtI2(L1)] (1) and [PtI2(L2)] (2) with isomeric bidentate 1,3,4-thiadiazole-based N-donor ligands (L1, L2) were prepared and characterized by multinuclear NMR spectroscopy, elemental analysis, infrared spectroscopy and mass spectrometry. Complexes 1 and 2 were hydrolytically stable in 50% DMF-d7/50% D2O and 50% DMF-d7/50% PBS in D2O (pH 7.4). Cytotoxicity of 1 and
    制备了两个二碘化铂 (II) 配合物 [PtI 2 (L1)] ( 1 ) 和 [PtI 2 (L2)] ( 2 ) 与异构双齿 1,3,4-噻二唑基N供体配体 (L1, L2)并通过多核NMR光谱、元素分析、红外光谱和质谱进行表征。配合物1和2在 50% DMF- d 7 /50% D 2 O 和 50% DMF - d 7 /50% PBS 中的 D 2 O (pH 7.4)中是水解稳定的。在五种人类癌细胞系上评估了1和2的细胞毒性,即肺癌 (A549)、肝细胞癌 (HepG2)、黑色素瘤 (A375)、前列腺癌 (DU-145) 和乳腺癌 (MCF-7)。只有 HepG2(IC 50  = 22.0 和 17.8 μM 分别对1和2)和 A549(IC 50  = 18.5 μM 对1)细胞对所研究的复合物敏感,但它们的体外细胞毒性略低于参考确定的药物顺铂(对 HepG2 和 A549
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