N''-(phenylsulfonyl)quinoline-6-carbohydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N''-(phenylsulfonyl)quinoline-6-carbohydrazide
• 英文别名: N'-(benzenesulfonyl)quinoline-6-carbohydrazide
• 化学式: C₁₆H₁₃N₃O₃S
• 分子量: 327.364
• InChiKey: YPRPLJAGGWUKMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  喹啉-6-甲酰肼 、 苯磺酰氯 以 吡啶 为溶剂， 反应 18.0h， 生成 N''-(phenylsulfonyl)quinoline-6-carbohydrazide
  参考文献：
  名称：

  The design and synthesis of human branched-chain amino acid aminotransferase inhibitors for treatment of neurodegenerative diseases

  摘要：

  The inhibition of the cytosolic isoenzyme BCAT that is expressed specifically in neuronal tissue is likely to be useful for the treatment of neurodegenerative and other neurological disorders where glutamatergic mechanisms are implicated. Compound 2 exhibited an IC50 of 0.8 microM in the hBCATc assays; it is an active and selective inhibitor. Inhibitor 2 also blocked calcium influx into neuronal cells following inhibition of glutamate uptake, and demonstrated neuroprotective efficacy in vivo. SAR, pharmacology, and the crystal structure of hBCATc with inhibitor 2 are described.

  DOI：

  10.1016/j.bmcl.2005.07.058

文献信息

• Branched chain amino acid-dependent aminotransferase inhibitors and their use in the treatment of neurodegenerative diseases
  申请人：Bora Martin Keenan

  公开号：US20050004167A1

  公开（公告）日：2005-01-06

  The invention relates to BCAT inhibitor compounds of formula (I) and use thereof for treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the overstimulation of the excitatory amino acids, treating anxiety, psychosis, convulsions, aminoglycoside antibiotics-induced hearing loss, migraine headache, chronic pain, neuropathic pain, Parkinson's disease, diabetic retinopathy, glaucoma, CMV retinitis, urinary incontinence, opioid tolerance or withdrawal, and inducing anesthesia, as well as for enhancing cognition.

  本发明涉及公式（I）的BCAT抑制剂化合物及其用于治疗或预防与中风、缺血、中枢神经系统创伤、低血糖和手术相关的神经元丢失，以及治疗神经退行性疾病，包括阿尔茨海默病、肌萎缩性侧索硬化症、亨廷顿病和唐氏综合症，治疗或预防兴奋性氨基酸过度刺激的不良后果，治疗焦虑、精神病、惊厥、氨基糖苷类抗生素引起的听力损失、偏头痛、慢性疼痛、神经病性疼痛、帕金森病、糖尿病视网膜病变、青光眼、巨细胞病毒性视网膜炎、尿失禁、阿片类耐受或戒断，以及诱导麻醉和增强认知功能。
• BRANCHED CHAIN AMINO ACID-DEPENDENT AMINOTRANSFERASE INHIBITORS AND THEIR USE IN THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：Warner-Lambert Company LLC

  公开号：EP1320523A2

  公开（公告）日：2003-06-25
• [EN] BRANCHED CHAIN AMINO ACID-DEPENDENT AMINOTRANSFERASE INHIBITORS AND THEIR USE IN THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] INHIBITEURS D'AMINOTRANSFERASE DEPENDANT D'AMINOACIDES A CHAINE RAMIFIEE, ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES NEURODEGENERATIVES
  申请人：WARNER LAMBERT CO

  公开号：WO2002024672A2

  公开（公告）日：2002-03-28

  The invention relates to BCAT inhibitor compounds of formula (I) and use thereof for treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the overstimulation of the excitatory amino acids, treating anxiety, psychosis, convulsions, aminoglycoside antibiotics-induced hearing loss, migraine headache, chronic pain, neuropathic pain, Parkinson's disease, diabetic retinopathy, glaucoma, CMV retinitis, urinary incontinence, opioid tolerance or withdrawal, and inducing anesthesia, as well as for enhancing cognition.
• The design and synthesis of human branched-chain amino acid aminotransferase inhibitors for treatment of neurodegenerative diseases
  作者：Lain-Yen Hu、Peter A. Boxer、Suzanne R. Kesten、Huangshu J. Lei、David J. Wustrow、David W. Moreland、Liming Zhang、Kay Ahn、Todd R. Ryder、Xiaohong Liu、John R. Rubin、Kelly Fahnoe、Richard T. Carroll、Satavisha Dutta、Douglass C. Fahnoe、Albert W. Probert、Robin L. Roof、Michael F. Rafferty、Catherine R. Kostlan、Jeffrey D. Scholten、Molly Hood、Xiao-Dan Ren、Gerald P. Schielke、Ti-Zhi Su、Charles P. Taylor、Anil Mistry、Patrick McConnell、Charles Hasemann、Jeffrey Ohren

  DOI：10.1016/j.bmcl.2005.07.058

  日期：2006.5

  The inhibition of the cytosolic isoenzyme BCAT that is expressed specifically in neuronal tissue is likely to be useful for the treatment of neurodegenerative and other neurological disorders where glutamatergic mechanisms are implicated. Compound 2 exhibited an IC50 of 0.8 microM in the hBCATc assays; it is an active and selective inhibitor. Inhibitor 2 also blocked calcium influx into neuronal cells following inhibition of glutamate uptake, and demonstrated neuroprotective efficacy in vivo. SAR, pharmacology, and the crystal structure of hBCATc with inhibitor 2 are described.