2-(biphenyl-4-sulfanyl)-acetic acid methyl ester | 19813-94-6

• 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: 2-(biphenyl-4-sulfanyl)-acetic acid methyl ester
• 英文别名: 4-Biphenyl-thioglykolsaeure-methylester；Methyl 2-(4-phenylphenyl)sulfanylacetate
• CAS: 19813-94-6
• 化学式: C₁₅H₁₄O₂S
• 分子量: 258.341
• InChiKey: DBCYDSJYDPEUPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(biphenyl-4-sulfanyl)-acetic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 以88%的产率得到2-(biphenyl-4-sulfanyl)acetic acid lithium salt
  参考文献：
  名称：

  Discovery of Small-Molecule Inhibitors of the ATPase Activity of Human Papillomavirus E1 Helicase

  摘要：

  The Boehringer Ingelheim compound collection was screened for inhibitors of the ATPase activity of human papillomavirus El helicase to develop antiviral agents that inhibit human papillomavirus (HPV) DNA replication. This screen led to the discovery of (biphenyl-4-sulfonyl)acetic acid 1, which inhibits the ATPase activity of HPV type 6 E1 helicase with a low micromolar IC50 value. A hit-to-lead exercise rapidly converted 1 into a low nanomolar lead series.

  DOI：

  10.1021/jm034206x
• 作为产物：
  描述：

  4-溴苯硫酚 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(biphenyl-4-sulfanyl)-acetic acid methyl ester
  参考文献：
  名称：

  N-Acylhydrazones as inhibitors of PDE10A

  摘要：

  Cyclic nucleotide phosphodiesterases (PDEs) are represented by a large superfamily of enzymes. A series of hydrazone-based inhibitors was synthesized and shown to be novel, potent, and selective against PDE10A. Optimized compounds of this class were efficacious in animal models of schizophrenia and may be useful for the treatment of this disease. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.100

文献信息

• Discovery of a structurally novel, potent, and once-weekly free fatty acid receptor 1 agonist for the treatment of diabetes
  作者：Bin Wang、Zongyu Cai、Huixin Yao、Shixuan Jiao、Siliang Chen、Zhongcheng Yang、Wanqiu Huang、Qiang Ren、Zhijun Cao、Ya Chen、Luyong Zhang、Zheng Li

  DOI：10.1016/j.ejmech.2022.114883

  日期：2023.1

  Type 2 diabetes mellitus (T2DM) is a lifelong disease that requires long-term medication to control glucose levels, and thereby long-acting drug has been clinically needed for improving medical adherence. The free fatty acid receptor 1 (FFA1) was considered as a promising target for several diseases, such as T2DM, pain and fatty liver. However, no once-weekly FFA1 agonist has been reported until now

  2型糖尿病（T2DM）是一种终生性疾病，需要长期服药来控制血糖水平，因此临床上需要长效药物来提高医疗依从性。游离脂肪酸受体 1 (FFA1) 被认为是治疗多种疾病（如 T2DM、疼痛和脂肪肝）的有希望的靶标。然而，直到现在还没有报道过每周一次的 FFA1 激动剂。在此，我们报告了 ZLY50 的成功发现，这是第一个每周一次的 FFA1 激动剂，具有全新的化学类型、高度激动活性和对 FFA1 的选择性。此外，ZLY50 有足够的脑暴露来激活脑中的 FFA1，它是第一个具有镇痛活性的口服 FFA1 激动剂。值得注意的是，ZLY50（每周一次）的长期抗糖尿病和抗脂肪肝作用优于 HWL-088（每日一次），一种高效的 FFA1 激动剂，具有比 3 期临床候选药物 TAK-875 更强的降糖作用。进一步的机制研究表明，ZLY50通过调节肝脏脂质代谢、线粒体功能和氧化应激相关基因的表达来减轻脂肪肝。
• Discovery of Small-Molecule Inhibitors of the ATPase Activity of Human Papillomavirus E1 Helicase
  作者：Anne-Marie Faucher、Peter W. White、Christian Brochu、Chantal Grand-Maître、Jean Rancourt、Gulrez Fazal

  DOI：10.1021/jm034206x

  日期：2004.1.1

  The Boehringer Ingelheim compound collection was screened for inhibitors of the ATPase activity of human papillomavirus El helicase to develop antiviral agents that inhibit human papillomavirus (HPV) DNA replication. This screen led to the discovery of (biphenyl-4-sulfonyl)acetic acid 1, which inhibits the ATPase activity of HPV type 6 E1 helicase with a low micromolar IC50 value. A hit-to-lead exercise rapidly converted 1 into a low nanomolar lead series.
• N-Acylhydrazones as inhibitors of PDE10A
  作者：Jennifer L. Gage、Rene Onrust、Derek Johnston、Andrew Osnowski、Wendy MacDonald、Lee Mitchell、László Ürögdi、Alex Rohde、Kevin Harbol、Sasha Gragerov、György Dormán、Tom Wheeler、Vince Florio、Neil S. Cutshall

  DOI：10.1016/j.bmcl.2011.05.100

  日期：2011.7

  Cyclic nucleotide phosphodiesterases (PDEs) are represented by a large superfamily of enzymes. A series of hydrazone-based inhibitors was synthesized and shown to be novel, potent, and selective against PDE10A. Optimized compounds of this class were efficacious in animal models of schizophrenia and may be useful for the treatment of this disease. (C) 2011 Elsevier Ltd. All rights reserved.