3-nitro-5-phenylsulfamoyl-benzoic acid

• 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-nitro-5-phenylsulfamoyl-benzoic acid
• 英文别名: 3-Nitro-5-phenylsulfamoyl-benzoesaeure；3-Nitro-5-(phenylsulfamoyl)benzoic acid
• 化学式: C₁₃H₁₀N₂O₆S
• 分子量: 322.298
• InChiKey: IHXNSESIGGKWFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-nitro-5-phenylsulfamoyl-benzoic acid 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  N-pyridin-2-yl benzamide analogues as allosteric activators of glucokinase: Design, synthesis, in vitro,in silico and in vivo evaluation

  摘要：

  AbstractGlucokinase (GK) is the key enzyme controlling levels of blood glucose under normal physiological range, and GK activators are emerging class of drug candidates with promising hypoglycaemic activity. The current study was planned to design, synthesize and evaluate novel N‐pyridin‐2‐yl benzamide analogues as allosteric activators of GK. A novel series of N‐pyridin‐2‐yl benzamide analogues were synthesized starting from 3‐nitrobenzoic acid and evaluated in vitro for GK activation followed by in silico studies to predict the binding interactions of the designed molecules with GK protein. The selected synthesized molecules (compounds 5b, 5c, 5e, 5g, 5h and 6d) which displayed excellent GK activity (GK fold activation around 2) in GK assay and appreciable binding interaction with GK in docking studies were further evaluated for their antihyperglycaemic potential using oral glucose tolerance test (OGTT) in rats. Amongst the compounds tested in vivo (OGTT assay) for antihyperglycaemic potential, compounds 5c, 5e and 5g displayed significant reduction in blood glucose levels. Compound 5e displayed most significant antidiabetic activity and comparable to that of standard drug in animal studies. The N‐pyridin‐2‐yl benzamide analogues discovered in the current study can provide some lead molecules for the development of potent oral GK activators with minimum side‐effects for the management of type 2 diabetes.

  DOI：

  10.1111/cbdd.13423
• 作为产物：
  描述：

  间硝基苯甲酸 在 氯磺酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 3-nitro-5-phenylsulfamoyl-benzoic acid
  参考文献：
  名称：

  N-pyridin-2-yl benzamide analogues as allosteric activators of glucokinase: Design, synthesis, in vitro,in silico and in vivo evaluation

  摘要：

  AbstractGlucokinase (GK) is the key enzyme controlling levels of blood glucose under normal physiological range, and GK activators are emerging class of drug candidates with promising hypoglycaemic activity. The current study was planned to design, synthesize and evaluate novel N‐pyridin‐2‐yl benzamide analogues as allosteric activators of GK. A novel series of N‐pyridin‐2‐yl benzamide analogues were synthesized starting from 3‐nitrobenzoic acid and evaluated in vitro for GK activation followed by in silico studies to predict the binding interactions of the designed molecules with GK protein. The selected synthesized molecules (compounds 5b, 5c, 5e, 5g, 5h and 6d) which displayed excellent GK activity (GK fold activation around 2) in GK assay and appreciable binding interaction with GK in docking studies were further evaluated for their antihyperglycaemic potential using oral glucose tolerance test (OGTT) in rats. Amongst the compounds tested in vivo (OGTT assay) for antihyperglycaemic potential, compounds 5c, 5e and 5g displayed significant reduction in blood glucose levels. Compound 5e displayed most significant antidiabetic activity and comparable to that of standard drug in animal studies. The N‐pyridin‐2‐yl benzamide analogues discovered in the current study can provide some lead molecules for the development of potent oral GK activators with minimum side‐effects for the management of type 2 diabetes.

  DOI：

  10.1111/cbdd.13423

文献信息

• Characteristics of patients presenting with central retinal artery occlusion with and without giant cell arteritis
  作者：Brian P. Connolly、Aruna Krishnan、Gaurav K. Shah、James Whelan、Gary C. Brown、Ralph C. Eagle、Eric P. Shaking

  DOI：10.1016/s0008-4182(00)80125-8

  日期：2000.12

  Background: In patients with concurrent central retinal artery occlusion (CRAO) and giant cell arteritis (GCA), prompt recognition and early treatment are crucial to prevent further visual loss in the contralateral eye. The objective of this study was to describe a series of patients with CRAO resulting from GCA and to compare them with patients with isolated CRAO.Methods: The patient database for a retina service in Philadelphia was searched to identify patients admitted between 1983 and 1993 with a diagnosis of biopsy-proven GCA and CRAO. For every patient with CRAO caused by GCA, the next patient admitted for management of acute isolated CRAO was identified; these latter patients constituted the control group, The visual acuity and baseline characteristics of the two groups were compared.Results: Eleven patients with acute CRAO and GCA were admitted during the study period. In both the case and control groups seven patients (64%) were women and nine patients (82%) were white. Six subjects (54%) in the case group and seven (64%) in the control group had a history of hypertension; the values for diabetes mellitus were two (18%) and zero respectively. Four patients (36%) with CRAO and GCA were cigarette smokers, compared with eight patients (73%) with CRAO alone. None of these differences were statistically significant. Patients with CRAO related to GCA were more likely than those with isolated CRAO to have counting fingers or better vision at presentation (odds ratio 2.22 [95% confidence interval 0.37 to 13.2]), but this trend was not statistically significant.Interpretation: Patients who presented with CRAO related to GCA were more than twice as likely as those with CRAO alone to have counting fingers or better visual acuity at the time of presentation, However, owing to the small sample, the power of this study to detect a true difference between the two groups was limited.