1-p-methoxyphenyl-2,4-dithiobiuret | 57494-95-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-p-methoxyphenyl-2,4-dithiobiuret
• 英文别名: p-anisylthiobiuret；1-(4-methoxy-phenyl)-dithiobiuret；p-Methoxyphenyldithiobiuret；BIURET, 1-(p-METHOXYPHENYL)-2,4-DITHIO-；1-carbamothioyl-3-(4-methoxyphenyl)thiourea
• CAS: 57494-95-8
• 化学式: C₉H₁₁N₃OS₂
• 分子量: 241.338
• InChiKey: HWODISAUIHCFDB-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  382.4±44.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-p-methoxyphenyl-2,4-dithiobiuret 在 溶剂黄146 、 三乙胺 、 肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成
  参考文献：
  名称：

  Highly Potent Inhibitors of Methionine Aminopeptidase-2 Based on a 1,2,4-Triazole Pharmacophore

  摘要：

  High-throughput screening for inhibitors of the human metalloprotease, methionine aminopeptidase-2 (MetAP2), identified a potent class of 3-anilino-5-benzylthio-1,2,4-triazole compounds. Efficient array and interative synthesis of triazoles led to rapid SAR development around the aniline, benzylthio, and triazole moeities. Evaluation of these analogs in a human MetAP2 enzyme assay led to the identification of several inhibitors with potencies in the 50-100 picomolar range. The deleterious effects on inhibitor potency by methylation of the anilino-triazole nitrogens, as well as the X-ray crystal structure of triazole 102 bound in the active site of MetAP2, confirm the key interactions between the triazole nitrogens, the active site cobalt atoms, and the His-231 side-chain. The structure has also provided a rationale for interpreting SAR within the triazole series. Key aniline (2-isopropylphenyl) and sulfur substituents (furanylmethyl) identified in the SAR studies led to the identification of potent inhibitors (103 and 104) of endothelial cell proliferation. Triazoles 103 and 104 also exhibited dose-dependent activity in an aortic ring tissue model of angiogenesis highlighting the potential utility of MetAP2 inhibitors as anticancer agents.

  DOI：

  10.1021/jm061182w
• 作为产物：
  描述：

  硫脲 、 4-甲氧基苯基 异硫氰酸酯 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 12.33h， 生成 1-p-methoxyphenyl-2,4-dithiobiuret
  参考文献：
  名称：

  Highly Potent Inhibitors of Methionine Aminopeptidase-2 Based on a 1,2,4-Triazole Pharmacophore

  摘要：

  High-throughput screening for inhibitors of the human metalloprotease, methionine aminopeptidase-2 (MetAP2), identified a potent class of 3-anilino-5-benzylthio-1,2,4-triazole compounds. Efficient array and interative synthesis of triazoles led to rapid SAR development around the aniline, benzylthio, and triazole moeities. Evaluation of these analogs in a human MetAP2 enzyme assay led to the identification of several inhibitors with potencies in the 50-100 picomolar range. The deleterious effects on inhibitor potency by methylation of the anilino-triazole nitrogens, as well as the X-ray crystal structure of triazole 102 bound in the active site of MetAP2, confirm the key interactions between the triazole nitrogens, the active site cobalt atoms, and the His-231 side-chain. The structure has also provided a rationale for interpreting SAR within the triazole series. Key aniline (2-isopropylphenyl) and sulfur substituents (furanylmethyl) identified in the SAR studies led to the identification of potent inhibitors (103 and 104) of endothelial cell proliferation. Triazoles 103 and 104 also exhibited dose-dependent activity in an aortic ring tissue model of angiogenesis highlighting the potential utility of MetAP2 inhibitors as anticancer agents.

  DOI：

  10.1021/jm061182w

文献信息

• Chande; Joshi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 5, p. 403 - 409
  作者：Chande、Joshi

  DOI：——

  日期：——
• Chande, Madhukar S.; Bhandari, Jayesh D.; Karyekar, Anita S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 11, p. 985 - 989
  作者：Chande, Madhukar S.、Bhandari, Jayesh D.、Karyekar, Anita S.

  DOI：——

  日期：——
• SYNTHESIS AND CHARACTERIZATION OF MOLYBDENUM AND TUNGSTEN COMPLEXES OF 1-ARYL-2,4-DITHIOBIURETS
  作者：R. B. Rastogi、M. Yadav、Karuna Singh

  DOI：10.1081/sim-100105257

  日期：2001.6.30

  Several molybdenum and tungsten 1-aryl-2,4-dithiobiuret complexes of the type M2O4L2(H2O)(2) [where M = Mo(V) or W(V), LH = 1-phenyl-2,4-dithiobiuret (PDTBH), 1-methylphenyl-2,4-dithiobiuret (MePDTBH), 1-p-methoxyphenyl-2A-dithiobiuret (MeOPDTBH) and 1-p-chlorophenyl-2,4,-dithiobiuret (ClPDTBH) have been synthesized and characterized. Molar conductance measurements in DMF show non-ionic behaviour for all complexes. Magnetic susceptibility measurements indicate diamagnetic behaviour of the complexes. On the basis of electronic spectral studies, an octahedral environment around the M(V) ion has been suggested. IR spectral studies, together with electronic spectra, are indicative of dinuclear-type complexes possessing a M2O42+ moiety. The complexes were found to be ESR-inactive. A monoanionic bidenate mode of bonding has been inferred on the basis of IR spectral studies. X-ray powder diffraction of the complexes shows their amorphous nature. H-1 NMR and C-13 NMR spectra of the metal complexes of 1-phenyl-2,4-dithiobiuret were found to be in agreement with the proposed stoichiometry.
• Chande, Madhukar S.; Bhandari, Jayesh D.; Karyekar, Anita S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 11, p. 990 - 991
  作者：Chande, Madhukar S.、Bhandari, Jayesh D.、Karyekar, Anita S.

  DOI：——

  日期：——
• Swaminathan; Guha, Journal of the Indian Chemical Society, 1946, vol. 23, p. 319,322
  作者：Swaminathan、Guha

  DOI：——

  日期：——