3-(5-bromonicotinoyl)-1-methylpyrrolidin-2-one | 88909-26-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(5-bromonicotinoyl)-1-methylpyrrolidin-2-one
• 英文别名: 3-(5-Bromopyridine-3-carbonyl)-1-methylpyrrolidin-2-one
• CAS: 88909-26-6
• 化学式: C₁₁H₁₁BrN₂O₂
• 分子量: 283.125
• InChiKey: IPEXPXISDSHQHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-bromonicotinoyl)-1-methylpyrrolidin-2-one 生成 1-methyl-3-(5-tritiopyridine-3-carbonyl)pyrrolidin-2-one
  参考文献：
  名称：

  WILEY, JAMES C. , JR.;CHIEN, DAVID H. T.;NUNGESSER, NANCY A.;LIN, DOROTHY+, J. LABELL. COMPOUNDS AND RADIOPHARM., 25,(1988) N 7, 707-716

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴烟酸 在 硫酸 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 25.0h， 生成 3-(5-bromonicotinoyl)-1-methylpyrrolidin-2-one
  参考文献：
  名称：

  Novel nicotine derivatives

  摘要：

  本文描述了一种新型尼古丁衍生物，其通式为（I）和（III），以及它们的盐，以及包含它们作为活性成分的除草剂和药物组合物。该化合物及其盐可以在极小的剂量下控制年生或多年生杂草在各种作物如水稻、小麦、棉花和玉米生长的土地上，时间范围从发芽前到生长期。该化合物及其盐可用作抗菌和抗真菌剂，也可用于治疗血压、骨骼肌、注意力缺陷障碍、精神障碍、精神分裂症、阿尔茨海默病、帕金森病和抑郁症。本文还描述了具有式（I）和（III）的尼古丁衍生物的制备方法。

  公开号：

  US20130123106A1

文献信息

• Nicotine derivatives
  申请人：Gandhi Paresh T.

  公开号：US08835640B1

  公开（公告）日：2014-09-16

  Described are novel nicotine derivatives represented by general formulas (I) and (III), and salts thereof, and herbicide & pharmaceutical compositions containing the same as the active ingredient. The compound and salts thereof can control annual or perennial weed growing on the land where various crops such as rice plant, wheat, cotton and corn grow for a wide period ranging from the pre-emergence to growth in a remarkably small dose. The compounds and salts thereof can be useful as an anti-microbial and anti-fungal agents and also for the treatment of blood pressure, skeletal muscle, attention deficit disorder, mental disorders, schizophrenia, Alzheimer disease, Parkinson's disease and depression. Also described is the preparation of the nicotine derivatives having formula (I) and (III).

  本文介绍了一种新型尼古丁衍生物，其通式为（I）和（III），以及其盐，以及含有其作为活性成分的除草剂和药物组合物。该化合物及其盐可以在极小剂量下控制各种作物如水稻、小麦、棉花和玉米生长的土地上的年生或多年生杂草，从萌芽到生长期都可以。该化合物及其盐可用作抗微生物和抗真菌剂，并可用于治疗血压、骨骼肌肉、注意力缺陷障碍、精神障碍、精神分裂症、阿尔茨海默病、帕金森病和抑郁症。本文还介绍了具有通式（I）和（III）的尼古丁衍生物的制备方法。
• Novel nicotine analogues with potential anti-mycobacterial activity
  作者：Paresh T. Gandhi、Thimmasandra Narayanappa Athmaram、Gundaiah Ramesh Arunkumar

  DOI：10.1016/j.bmc.2016.02.035

  日期：2016.4

  Tuberculosis (TB) is the second leading lethal infectious disease in the world after acquired immuno deficiency (AIDs). We have developed a series of twenty-five novel nicotine analogues with de-addiction property and tested them for their activity against Mycobacterium tuberculosis (MTB). In an effort to increase the specificity of action and directing nicotine analogues to target MTB, four promising compounds were further optimized via molecular docking studies against the Dihydrofolate reductase of MTB. After lead optimization, one nicotine analogue [3-(5-(3fluorophenyl)nicotinoyl)-1-methylpyrrolidin-2-one] exhibited minimum inhibitory concentration of 1 mu g/mL (2.86 nM) against M. tuberculosis (H37Rv strain), a human pathogenic strain of clinically significant importance. Pharmacokinetic analysis of [3-(5-(3fluorophenyl) nicotinoyl)-1methylpyrrolidin-2-one] with lowest MIC value via oral route in Wistar rats revealed that at a dosage of 5 mg/kg body weight gave a maximum serum drug concentration (C-max) of 2.86 mu g/mL, T-max of one hour and a half-life (T-1/2) of more than 24 h and Volume of distribution (V-d) of 27.36 L. Whereas the parenteral (intra venous) route showed a Cmax of 3.37 mu g/mL, Tmax of 0.05 h, T-1/2 of 24 h and Vd equivalent to 23.18 L. The acute oral toxicity and repeated oral toxicity studies in female Wistar rats had an LD50 > 2000 mg/kg body weight. Our data suggests that nicotine derivatives developed in the present study has good metabolic stability with tunable pharmacokinetics (PK) with therapeutic potential to combat MTB. However, further in vivo studies for anti-tuberculosis activity and elucidation of mode of action could result in more promising novel drug for treating MTB. To the best of our knowledge this is the first report revealing the anti-mycobacterial potential of nicotine analogue at potential therapeutic concentrations. (C) 2016 Elsevier Ltd. All rights reserved.
• WILEY, JAMES C. , JR.;CHIEN, DAVID H. T.;NUNGESSER, NANCY A.;LIN, DOROTHY+, J. LABELL. COMPOUNDS AND RADIOPHARM., 25,(1988) N 7, 707-716
  作者：WILEY, JAMES C. , JR.、CHIEN, DAVID H. T.、NUNGESSER, NANCY A.、LIN, DOROTHY+

  DOI：——

  日期：——
• US20140256773A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Kim, Kee D.; Lerner-Marmarosh, Nicole; Wang, David X., Medicinal Chemistry Research, 1996, vol. 6, # 1, p. 40 - 51
  作者：Kim, Kee D.、Lerner-Marmarosh, Nicole、Wang, David X.、Kende, Andrew S.、Abood, Leo G.

  DOI：——

  日期：——