1,2-bis(5-phenyl-4H-1,2,4-triazol-3-yl)disulfane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,2-bis(5-phenyl-4H-1,2,4-triazol-3-yl)disulfane
• 英文别名: 5-phenyl-3-[(5-phenyl-1H-1,2,4-triazol-3-yl)disulfanyl]-1H-1,2,4-triazole
• 化学式: C₁₆H₁₂N₆S₂
• 分子量: 352.443
• InChiKey: GOXBXVJYZLZQBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,10-菲罗啉 、 manganese (II) acetate tetrahydrate 、 1,2-bis(5-phenyl-4H-1,2,4-triazol-3-yl)disulfane 以 甲醇 为溶剂， 以55%的产率得到Mn(o-phen)2(ptds)
  参考文献：
  名称：

  A seven membered chelate ring complex of Mn(II) derived from bis(5-phenyl-2H-1,2,4-triazole)-3-yl-disulfane and cleavage of the S–S bond in a Co(II) complex: Synthesis, spectral and structural characterization

  摘要：

  The reaction of Mn(OAc)(2)center dot 4H(2)O with bis(5-phenyl-2H-1,2,4-triazole)-3-yl-disulfane (H(2)ptds center dot 2H(2)O) (1) yielded new complex [Mn(ptds)(o-phen)(2)] (2). It is observed that under similar conditions the reaction of Co(OAc)(2) with H(2)ptds center dot 2H(2)O (1) leads to thermolysis of the S-S bond of the disulfane to yield [Co(pts)(o-phen)(2)]center dot H(2)O center dot 0.5C(2)H(5)OH, with the newly generated organic ligand 5-phenyl-2H-1,2,4-triazole-3-sulfinate, (pts)(2-). The ligand H(2)ptds center dot 2H(2)O (1), [Mn(ptds)(o-phen)(2)] (2) and [Co(pts)(o-phen)(2)]center dot H(2)O center dot 0.5C(2)H(5)OH (3) crystallized into monoclinic, trigonal and triclinic crystal systems, respectively. The triazole ring nitrogen of the bidentate ligand chelates the Mn(II) center forming a seven membered chelate ring, while N, O donor sites of the resulting triazole sulfinate bond Co(II) to form a five membered chelate. The resulting complexes are paramagnetic and have a distorted octahedral geometry. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.03.050
• 作为产物：
  描述：

  (苯甲酰基氨基)硫脲 在 硫酸 、 sodium hydroxide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 34.0h， 生成 1,2-bis(5-phenyl-4H-1,2,4-triazol-3-yl)disulfane
  参考文献：
  名称：

  苯基三唑硫醇基衍生物作为DCN1-UBC12相互作用的高效抑制剂的开发

  摘要：

  cullin neddylation 1（DCN1）中的缺陷是co-E3连接酶，对cullin neddylation很重要。DCN1的失调与各种癌症的发生高度相关。在此，从最初的高通量筛选中，发现了含有苯基三唑硫醇核（对于DCN1-UBC12相互作用的IC 50值为0.95μM）的新型命中化合物5a。进一步的基于结构的优化导致了SK-464的发展（IC 50值为26 nM）。我们发现SK-464不仅在体外直接与DCN1结合，但也参与细胞DCN1，抑制cullin3的二联化，并阻碍了两个DCN1过表达的鳞状癌细胞系（KYSE70和H2170）的迁移和侵袭。这些发现表明，SK-464可能是靶向DCN1-UBC12相互作用的新型先导化合物。

  DOI：

  10.1016/j.ejmech.2021.113326

文献信息

• JPS59164783A
  申请人：——

  公开号：JPS59164783A

  公开（公告）日：1984-09-17
• Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction
  作者：Wenjuan Zhou、Chenhao Xu、Guanjun Dong、Hui Qiao、Jing Yang、Hongmin Liu、Lina Ding、Kai Sun、Wen Zhao

  DOI：10.1016/j.ejmech.2021.113326

  日期：2021.5

  Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads

  cullin neddylation 1（DCN1）中的缺陷是co-E3连接酶，对cullin neddylation很重要。DCN1的失调与各种癌症的发生高度相关。在此，从最初的高通量筛选中，发现了含有苯基三唑硫醇核（对于DCN1-UBC12相互作用的IC 50值为0.95μM）的新型命中化合物5a。进一步的基于结构的优化导致了SK-464的发展（IC 50值为26 nM）。我们发现SK-464不仅在体外直接与DCN1结合，但也参与细胞DCN1，抑制cullin3的二联化，并阻碍了两个DCN1过表达的鳞状癌细胞系（KYSE70和H2170）的迁移和侵袭。这些发现表明，SK-464可能是靶向DCN1-UBC12相互作用的新型先导化合物。
• A seven membered chelate ring complex of Mn(II) derived from bis(5-phenyl-2H-1,2,4-triazole)-3-yl-disulfane and cleavage of the S–S bond in a Co(II) complex: Synthesis, spectral and structural characterization
  作者：A. Singh、M.K. Bharty、S.K. Kushawaha、R.J. Butcher、N.K. Singh

  DOI：10.1016/j.poly.2011.03.050

  日期：2011.8

  The reaction of Mn(OAc)(2)center dot 4H(2)O with bis(5-phenyl-2H-1,2,4-triazole)-3-yl-disulfane (H(2)ptds center dot 2H(2)O) (1) yielded new complex [Mn(ptds)(o-phen)(2)] (2). It is observed that under similar conditions the reaction of Co(OAc)(2) with H(2)ptds center dot 2H(2)O (1) leads to thermolysis of the S-S bond of the disulfane to yield [Co(pts)(o-phen)(2)]center dot H(2)O center dot 0.5C(2)H(5)OH, with the newly generated organic ligand 5-phenyl-2H-1,2,4-triazole-3-sulfinate, (pts)(2-). The ligand H(2)ptds center dot 2H(2)O (1), [Mn(ptds)(o-phen)(2)] (2) and [Co(pts)(o-phen)(2)]center dot H(2)O center dot 0.5C(2)H(5)OH (3) crystallized into monoclinic, trigonal and triclinic crystal systems, respectively. The triazole ring nitrogen of the bidentate ligand chelates the Mn(II) center forming a seven membered chelate ring, while N, O donor sites of the resulting triazole sulfinate bond Co(II) to form a five membered chelate. The resulting complexes are paramagnetic and have a distorted octahedral geometry. (C) 2011 Elsevier Ltd. All rights reserved.