bicucullin | 26687-87-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 邻苯二甲酸异喹啉类
• 英文名称: bicucullin
• 英文别名: bicuculline；(+/-)-Adlumidin；6-(6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)furo[3,4-E][1,3]benzodioxol-8(6H)-one；6-(6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3,4-g][1,3]benzodioxol-8-one
• CAS: 26687-87-6
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: IYGYMKDQCDOMRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  细果角茴香碱 生成 bicucullin
  参考文献：
  名称：

  BLASKO;G.;KARDOS, J.;KEREKES, P.;KOVACS, I.;SIMONYI, M.;ELANGO, V.;FREYER+, BIO-ORG. HETEROCYSLES, 1986: SYNTH., MECH. AND BIOACTIV.: PROC. 4TH FECHE+

  摘要：

  DOI：

文献信息

• Synthesis, anti-GABA activity and preferred conformation of bicuculline and norbicuculline enantiomers
  作者：J Kardos、T Blandl、ND Luyen、G Dörnyei、E Gács-Baitz、M Simonyi、DJ Cash、G Blaskó、Cs Szántay

  DOI：10.1016/0223-5234(96)83969-9

  日期：1996.1

  Synthesis of erythro-(+/-)-[1SR,9RS]-norbicuculline and threo-(+/-)-[1SR,9SR]-noradlumidine from piperonal was performed using Bischler-Napieralski cyclization as a key step. Resolution gave rise to (+)-[1S,9R]-norbicuculline ([1S,9R] norBIC) and (-)-[1R,9S]-norbicuculline ([1R,9S] norBIC) in >99.5% enantiomeric purity. Bicuculline enantiomers were readily obtained by methylation of the latter products

  使用Bischler-Napieralski环化作为关键步骤，从胡椒醛中合成了赤型-（+/-）-[1SR，9RS]-核苷和苏型-（+/-）-[1SR，9SR]-去甲rad啶。拆分产生对映体纯度> 99.5％的（+）-[1S，9R]-冰核碱（[1S，9R] norBIC）和（-）-[1R，9S]-冰核碱（[1R，9S] norBIC）。通过将后面的产物甲基化，可以容易地获得双瓜氨酸对映异构体。作为抑制GABA（A）受体结合的抑制剂，[1S，9R] BIC的效力比[1R，9S] BIC的效力高约70倍，在pH 7.1和5.0时，[1S，9R] BIC的效力比[1S，9R] norBIC约高100到900倍分别。同样，[1S，9R] norBIC作为[1S，9R] BIC作为GABA特异性（36）Cl（-）离子通量的抑制剂的效力要低得多。观察到[1S中，由N2-CH（3）取代引起的体外生物活性增加了大约两个数量级，
• Methods and treatments for the learning and memory deficits associated with Noonan syndrome
  申请人：The Regents of the University of California

  公开号：US10835513B2

  公开（公告）日：2020-11-17

  Disclosed herein are methods and compositions for treating learning and memory deficits associated with Noonan Syndrome.

  本文公开了治疗与努南综合征相关的学习和记忆缺陷的方法和组合物。
• Treating Learning Deficits With Inhibitors of Hmg CoA Reductase
  申请人：Silva J. Alcino

  公开号：US20070299096A1

  公开（公告）日：2007-12-27

  The disclosure provides methods of treating cognitive disorders by administering a HMG CoA reductase inhibitor. Cognitive deficits treatable with the inhibitor compound include those associated with Angelman Syndrome, Neurofibromatosis-1, certain forms of X-linked mental retardation, tuberous sclerosis, Down Syndrome, autism, and attention deficit/hyperactivity disorder.
• Treating Learning Deficits with Inhibitors of HMG CoA Reductase
  申请人：Silva Alcino

  公开号：US20120283323A1

  公开（公告）日：2012-11-08

  The disclosure provides methods of treating cognitive disorders by administering a HMG CoA reductase inhibitor. Cognitive deficits treatable with the inhibitor compound include those associated with Angelman Syndrome, Neurofibromatosis-1, certain forms of X-linked mental retardation, tuberous sclerosis, Down Syndrome, autism, and attention deficit/hyperactivity disorder.
• US8222293B2
  申请人：——

  公开号：US8222293B2

  公开（公告）日：2012-07-17