2-<<(1-carboxy-2-phenyl)sulfanyl>methyl>benzoic acid | 74053-48-8

• 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: 2-<<(1-carboxy-2-phenyl)sulfanyl>methyl>benzoic acid
• 英文别名: NRB00557；α-(2-Carboxyphenylthio)-o-toluolsaeure；2-[(2-Carboxyphenyl)sulfanylmethyl]benzoic acid
• CAS: 74053-48-8
• 化学式: C₁₅H₁₂O₄S
• 分子量: 288.324
• InChiKey: ZUUVYLSDELICND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<<(1-carboxy-2-phenyl)sulfanyl>methyl>benzoic acid 在 氯化亚砜 作用下， 反应 4.0h， 生成 2-[(2-Carbonochloridoylphenyl)sulfanylmethyl]benzoyl chloride
  参考文献：
  名称：

  Biophysical Characterization of Zinc Ejection from HIV Nucleocapsid Protein by Anti-HIV 2,2‘-Dithiobis[benzamides] and Benzisothiazolones

  摘要：

  HIV nucleocapsid protein (NCp7) has been suggested as a possible target for 2,2'-dithiobis[benzamide] and benzisothiazolone agents that inhibit viral replication in infected cells (Rice et al. Science 1995, 270, 1194-1197). The solution behavior of these compounds and the mechanistic events leading to removal of Zn from HIV nucleocapsid protein in vitro has been studied by electrospray ionization mass spectrometry, 500 MHz one- and two-dimensional nuclear magnetic resonance spectroscopy, and circular dichroism spectroscopy. We demonstrate that (1) Zn ejection is accompanied by formation of covalent complexes formed between the 2,2'-dithiobis[benzamide] monomers and Cys residues of Zn-depleted NCp7, (2) the rate of Zn ejection is faster for the C-terminal Zn finger and slower for the N-terminal finger, (3) Zn ejection results in a loss of structural integrity of the NCp7 protein, and (4) there is no appreciable interaction between a nonreactive iso stere of the lead 2,2'-dithiobis[benzamide] and NCp7 in buffered aqueous solution. These findings are discussed in terms of the mechanism of action of Zn ejection by aromatic 2,2'-dithiobis[benzamides].

  DOI：

  10.1021/jm960253w
• 作为产物：
  描述：

  苯酞 在 氢氧化钾 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 20.08h， 生成 2-<<(1-carboxy-2-phenyl)sulfanyl>methyl>benzoic acid
  参考文献：
  名称：

  Biophysical Characterization of Zinc Ejection from HIV Nucleocapsid Protein by Anti-HIV 2,2‘-Dithiobis[benzamides] and Benzisothiazolones

  摘要：

  HIV nucleocapsid protein (NCp7) has been suggested as a possible target for 2,2'-dithiobis[benzamide] and benzisothiazolone agents that inhibit viral replication in infected cells (Rice et al. Science 1995, 270, 1194-1197). The solution behavior of these compounds and the mechanistic events leading to removal of Zn from HIV nucleocapsid protein in vitro has been studied by electrospray ionization mass spectrometry, 500 MHz one- and two-dimensional nuclear magnetic resonance spectroscopy, and circular dichroism spectroscopy. We demonstrate that (1) Zn ejection is accompanied by formation of covalent complexes formed between the 2,2'-dithiobis[benzamide] monomers and Cys residues of Zn-depleted NCp7, (2) the rate of Zn ejection is faster for the C-terminal Zn finger and slower for the N-terminal finger, (3) Zn ejection results in a loss of structural integrity of the NCp7 protein, and (4) there is no appreciable interaction between a nonreactive iso stere of the lead 2,2'-dithiobis[benzamide] and NCp7 in buffered aqueous solution. These findings are discussed in terms of the mechanism of action of Zn ejection by aromatic 2,2'-dithiobis[benzamides].

  DOI：

  10.1021/jm960253w

文献信息

• Diaryldiacyloxyspirosulfuranes—II
  作者：I. Kapovits、J. Rábai、F. Ruff、Á. Kucsman、B. Tanács

  DOI：10.1016/0040-4020(79)80013-7

  日期：1979.1

  The preparations of spirocyclic sulfuranes from bis(2-carboxyaryl) sulfoxides with dehydrating agents were investigated. Depending on the manner of dehydration, spirosulfurane formation follows different courses established by using 18O-labelled 2,2'-sulfinyldibenzoic acid. Sulfoxides with 2-carboxybenzyl group failing to form spirosulfuranes undergo the Pummerer reaction yielding lactones. In aqueous

  研究了双（2-羧基芳基）亚砜与脱水剂制备螺环硫烷的过程。取决于脱水的方式，螺硫隆的形成遵循通过使用18 O-标记的2,2'-亚磺酰基二苯甲酸建立的不同过程。具有2-羧基苄基的亚砜不能形成螺硫脲，会发生Pummerer反应，生成内酯。在二恶烷水溶液中，螺硫脲通常会水解成亚砜。在同一芳环上具有两个硝基的螺硫磺烷通过SC ar键断裂而水解。
• SUBSTITUTED POLYCYCLIC CARBAMOYL PYRIDONE DERIVATIVE PRODRUG
  申请人：Shionogi & Co., Ltd.

  公开号：EP2620436A1

  公开（公告）日：2013-07-31

  The present invention provides a compound having antiviral effects, particularly having growth inhibitory activity on influenza viruses, a preferred example of the compound being a substituted 3 - hydroxy-4-pyridone derivative prodrug having cap-dependent endonuclease inhibitory activity.

  本发明提供了一种具有抗病毒作用，特别是对流感病毒具有生长抑制活性的化合物，该化合物的一个优选实例是一种具有帽依赖性内切酶抑制活性的取代 3-羟基-4-吡啶酮衍生物原药。
• Substituted polycyclic carbamoyl pyridone derivative prodrug
  申请人：Shionogi & Co., Ltd.

  公开号：US10202379B2

  公开（公告）日：2019-02-12

  The present invention provides a compound having antiviral effects, particularly having growth inhibitory activity on influenza viruses, a preferred example of the compound being a substituted 3-hydroxy-4-pyridone derivative prodrug having cap-dependent endonuclease inhibitory activity.

  本发明提供了一种具有抗病毒作用，特别是对流感病毒具有生长抑制活性的化合物，该化合物的一个优选实例是具有帽依赖性内切酶抑制活性的取代 3-羟基-4-吡啶酮衍生物原药。
• PRODRUG SUBSTITUTED POLYCYCLIC CARBAMOYL PYRIDONE DERIVATIVE
  申请人：Shionogi & Co., Ltd.

  公开号：US20200339565A1

  公开（公告）日：2020-10-29

  The present invention provides a compound having antiviral effects, particularly having growth inhibitory activity on influenza viruses, a preferred example of the compound being a substituted 3-hydroxy-4-pyridone derivative prodrug having cap-dependent endonuclease inhibitory activity.
• US8987441B2
  申请人：——

  公开号：US8987441B2

  公开（公告）日：2015-03-24