2-mercapto-4-nitrobenzoic acid | 150443-58-6

• 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-mercapto-4-nitrobenzoic acid
• 英文别名: 2-mercapto-4-nitro-benzoic acid；2-Mercapto-4-nitro-benzoesaeure；4-Nitro-2-sulfanylbenzoic acid
• CAS: 150443-58-6
• 化学式: C₇H₅NO₄S
• 分子量: 199.187
• InChiKey: HABGGBBWFAJWIB-UHFFFAOYSA-N

物化性质

• 沸点：
  385.4±37.0 °C(Predicted)
• 密度：
  1.575±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-mercapto-4-nitrobenzoic acid 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 6-nitro-2-phenethylbenzo[d]isothiazol-3(2H)-one
  参考文献：
  名称：

  Benzisothiazolinone Derivatives as Potent Allosteric Monoacylglycerol Lipase Inhibitors That Functionally Mimic Sulfenylation of Regulatory Cysteines

  摘要：

  We describe a set of benzisothiazolinone (BTZ) derivatives that are potent inhibitors of monoacylglycerol lipase (MGL), the primary degrading enzyme for the endocannabinoid 2-arachidonoyl-sn-glycerol (2-AG). Structure-activity relationship studies evaluated various substitutions on the nitrogen atom and the benzene ring of the BTZ nucleus. Optimized derivatives with nanomolar potency allowed us to investigate the mechanism of MGL inhibition. Site-directed mutagenesis and mass spectrometry experiments showed that BTZs interact in a covalent reversible manner with regulatory cysteines, Cys201 and Cys208, causing a reversible sulfenylation known to modulate MGL activity. Metadynamics simulations revealed that BTZ adducts favor a closed conformation of MGL that occludes substrate recruitment. The BTZ derivative 13 protected neuronal cells from oxidative stimuli and increased 2-AG levels in the mouse brain. The results identify Cys201 and Cys208 as key regulators of MGL function and point to the BTZ scaffold as a useful starting point for the discovery of allosteric MGL inhibitors.

  DOI：

  10.1021/acs.jmedchem.9b01679
• 作为产物：
  描述：

  methyl 2-((dimethylcarbamothioyl)oxy)-4-nitrobenzoate 在 sodium hydroxide 作用下， 以 甲醇 、 二苯醚 、 水 为溶剂， 反应 16.33h， 生成 2-mercapto-4-nitrobenzoic acid
  参考文献：
  名称：

  Benzisothiazolinone Derivatives as Potent Allosteric Monoacylglycerol Lipase Inhibitors That Functionally Mimic Sulfenylation of Regulatory Cysteines

  摘要：

  We describe a set of benzisothiazolinone (BTZ) derivatives that are potent inhibitors of monoacylglycerol lipase (MGL), the primary degrading enzyme for the endocannabinoid 2-arachidonoyl-sn-glycerol (2-AG). Structure-activity relationship studies evaluated various substitutions on the nitrogen atom and the benzene ring of the BTZ nucleus. Optimized derivatives with nanomolar potency allowed us to investigate the mechanism of MGL inhibition. Site-directed mutagenesis and mass spectrometry experiments showed that BTZs interact in a covalent reversible manner with regulatory cysteines, Cys201 and Cys208, causing a reversible sulfenylation known to modulate MGL activity. Metadynamics simulations revealed that BTZ adducts favor a closed conformation of MGL that occludes substrate recruitment. The BTZ derivative 13 protected neuronal cells from oxidative stimuli and increased 2-AG levels in the mouse brain. The results identify Cys201 and Cys208 as key regulators of MGL function and point to the BTZ scaffold as a useful starting point for the discovery of allosteric MGL inhibitors.

  DOI：

  10.1021/acs.jmedchem.9b01679

文献信息

• Spiro compounds, process for their preparation and pharmaceutical compositions containing them
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0026000A1

  公开（公告）日：1981-04-01

  Newspirocompoundsoftheformula: wherein n is an integer of 1 to 4, and X is halogen, lower alkyl, nitro, amino which may be substituted, hydroxyl which may be substituted, acyl, carboxyl, lower alkoxycarbonyl, carbamoyl which may be substituted, sulfamoyl which may be substituted, lower alkylthio or lower alkylsulfonyl, or two of X at the 5- and 6-positions together form -CH=CH-CH=CH-, exhibit inhibitory activity to thrombocyte aggregation and are useful for the prophylaxis or treatment of cardiovascular disturbance such as thrombosis.

  式中 n 为 1 至 4 的整数，X 为卤素、低级烷基、硝基、可被取代的氨基、可被取代的羟基、酰基、羧基、低级烷氧基羰基、可被取代的氨基甲酰基、可被取代的氨基磺酰基、低级烷硫基或低级烷基磺酰基，或位于 5 位和 6 位的两个 X 共同形成-CH=CH-CH=CH-，具有抑制血小板聚集的活性，可用于预防或治疗血栓等心血管疾病。
• Silberg; Simiti, Academia Republicii Populare Romine, Filiala Cluj, Studii si Cercetari de Chimie, 1954, vol. 5, p. 135,138
  作者：Silberg、Simiti

  DOI：——

  日期：——
• Magnetic polarity ages of the fossil-bearing strata at the Si-hetun section, West Liaoning: A preliminary result
  作者：Yongxin Pan、Rixiang Zhu、Shaw John、Yaoxiu Zhou

  DOI：10.1007/bf03187035

  日期：2001.9

  Rock-magnetic and palaeomagnetic studies have been carried out on the interval of famous fossil-bearing sedimentary rocks and its overlying basalts and underlying basalts at the Sihetun section, West Liaoning Province. Normal polarity was obtained for the sedimentary Interval and the underlying basalts, while reversed polarity was found In the overlying basalts. Taking account of the new Ar-40/Ar-39 ages (Swisher et al., 1999), we classified the fossil-bearing sedimentary Interval into the Barremian M3n zone (Early Cretaceous age). Several abnormal horizons on magnetic properties, probably corresponding to the tuffs, were observed In the fossil-bearing sedimentary interval. This implies that the massive bio-extinction may link to dramatic environmental changes that were caused by volcanic eruptions.
• NITRO-SULFOBENZAMIDES
  申请人：Bayer CropScience AG

  公开号：EP1242386B1

  公开（公告）日：2009-08-26
• US3954994A
  申请人：——

  公开号：US3954994A

  公开（公告）日：1976-05-04