3-(2-((1H-benzo[d]imidazol-2-yl)thio)acetamido)benzoic acid | 302601-85-0

• 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: 3-(2-((1H-benzo[d]imidazol-2-yl)thio)acetamido)benzoic acid
• 英文别名: ZINC02765569；3-[[2-(1H-benzimidazol-1-ium-2-ylsulfanyl)acetyl]amino]benzoate
• CAS: 302601-85-0
• 化学式: C₁₆H₁₃N₃O₃S
• 分子量: 327.364
• InChiKey: XFQXWICQPYLELC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-((1H-benzo[d]imidazol-2-yl)thio)acetamido)benzoic acid 、 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以15 %的产率得到3-(2-((1H-benzo[d]imidazol-2-yl)thio)acetamido)-N-(6-(2-(2-(2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)-2-oxoethoxy)ethoxy)ethoxy)hexyl)benzamide
  参考文献：
  名称：

  10.1021/acs.jmedchem.4c00356

  摘要：

  DOI：

  10.1021/acs.jmedchem.4c00356
• 作为产物：
  描述：

  间氨基苯甲酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.0h， 生成 3-(2-((1H-benzo[d]imidazol-2-yl)thio)acetamido)benzoic acid
  参考文献：
  名称：

  Molecular modeling and synthesis of ZINC02765569 derivatives as protein tyrosine phosphatase 1B inhibitors: lead optimization study

  摘要：

  This article describes design, synthesis, and molecular modeling studies of the ZINC02765569 derivatives as potent protein tyrosine phosphatase 1B (PTP1B) inhibitors, which was previously reported as a vHTS hit (ZINC02765569) by our laboratory. Ten compounds were synthesized and characterized by IR, MASS, and NMR followed by in vitro screening for PTP1B inhibition and glucose uptake in skeletal muscle L6 myotubes. The most potent compound 3j shows 66.4 % in vitro PTP1B inhibition and 39.6 % increase in glucose uptake. Glide was used to study the nature of interactions governing binding of designed molecules with active site of the PTP1B enzyme.

  DOI：

  10.1007/s00044-012-0165-0

文献信息

• TARGETING NAD BIOSYNTHESIS IN BACTERIAL PATHOGENS
  申请人：Mackerell, JR. Alexander

  公开号：US20120190708A1

  公开（公告）日：2012-07-26

  The emergence of multidrug-resistant pathogens necessitates the search for new antibiotics acting on previously unexplored targets. Nicotinate mononucleotide adenylyltransferase of the NadD family, an essential enzyme of NAD biosynthesis in most bacteria, was selected as a target for structure-based inhibitor development. To this end, the inventors have identified small molecule compounds that inhibit bacterial target enzymes by interacting with a novel inhibitory binding site on the enzyme while having no effect on functionally equivalent human enzymes.

  多重耐药病原体的出现需要寻找作用于先前未被开发的靶标的新抗生素。Nicotinate单核苷酸腺苷转移酶（NadD家族），是大多数细菌NAD生物合成的必需酶，被选为基于结构的抑制剂开发的目标。为此，发明人已经鉴定出小分子化合物，通过与酶上的新型抑制性结合位点相互作用来抑制细菌靶标酶，而对功能相当的人类酶没有影响。
• Molecular modeling and synthesis of ZINC02765569 derivatives as protein tyrosine phosphatase 1B inhibitors: lead optimization study
  作者：Prashant Joshi、Girdhar Singh Deora、Vandana Rathore、Arun K. Rawat、A. K. Srivastava、Deepti Jain

  DOI：10.1007/s00044-012-0165-0

  日期：2013.4

  This article describes design, synthesis, and molecular modeling studies of the ZINC02765569 derivatives as potent protein tyrosine phosphatase 1B (PTP1B) inhibitors, which was previously reported as a vHTS hit (ZINC02765569) by our laboratory. Ten compounds were synthesized and characterized by IR, MASS, and NMR followed by in vitro screening for PTP1B inhibition and glucose uptake in skeletal muscle L6 myotubes. The most potent compound 3j shows 66.4 % in vitro PTP1B inhibition and 39.6 % increase in glucose uptake. Glide was used to study the nature of interactions governing binding of designed molecules with active site of the PTP1B enzyme.
• US8785499B2
  申请人：——

  公开号：US8785499B2

  公开（公告）日：2014-07-22
• 10.1021/acs.jmedchem.4c00356
  作者：Yang, Zunhua、Ying, Yuqi、Cheng, Shaobing、Wu, Jiamin、Zhang, Ziwei、Hu, Pei、Xiong, Jian、Li, Huilan、Zeng, Qing、Cai, Zhifang、Feng, Yulin、Fang, Yuanying

  DOI：10.1021/acs.jmedchem.4c00356

  日期：——