(4-indanyl)guanidine | 1191273-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (4-indanyl)guanidine
• 英文别名: 1-(4-Indanyl)guanidine；2-(2,3-dihydro-1H-inden-4-yl)guanidine
• CAS: 1191273-14-9
• 化学式: C₁₀H₁₃N₃
• 分子量: 175.233
• InChiKey: YZWCKPZTGKNZLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-indanyl)guanidine 、 methyl 4-(3-(dimethylamino)-2-methylacryloyl)-1-tosyl-1H-pyrrole-2-carboxylate 以 甲苯 为溶剂， 反应 20.0h， 生成 methyl 4-[2-(2,3-dihydro-1H-inden-4-ylamino)-5-methylpyrimidin-4-yl]-1-(4-methylphenyl)sulfonylpyrrole-2-carboxylate
  参考文献：
  名称：

  使用构象控制的细胞外信号调节激酶（ERK）的有效和选择性嘧啶吡咯抑制剂的结构指导设计。

  摘要：

  Ras / Raf / MEK / ERK信号转导是涉及多种人类癌症的致癌途径，是抗癌药物设计中的关键目标。已经鉴定出一系列新的嘧啶基吡咯ERK抑制剂。发现相对于抗靶标GSK3与ERK2结合的前导化合物2的构象变化，实现了结构引导的选择性优化，从而导致了11e的发现，这是一种有效，选择性和口服生物利用的ERK抑制剂。

  DOI：

  10.1021/jm900630q

文献信息

• EP0516748A4
  申请人：——

  公开号：EP0516748A4

  公开（公告）日：1994-04-13
• N,N'-DISUBSTITUTED GUANIDINES AND THEIR USE AS EXCITATORY AMINO ACID ANTAGONISTS
  申请人：STATE OF OREGON, acting by and through THE OREGON STATE BOARD OF HIGHER EDUCATION, acting for and on behalf of

  公开号：EP0516748A1

  公开（公告）日：1992-12-09
• [EN] N,N'-DISUBSTITUTED GUANIDINES AND THEIR USE AS EXCITATORY AMINO ACID ANTAGONISTS
  申请人：STATE OF OREGON, acting by and through THE OREGON STATE BOARD OF HIGHER EDUCATION, acting for and on behalf of THE OREGON HEALTH SCIENCES UNIVERSITY PORTLAND, OREGON, and THE UNIVERSITY OF OREGON, EUGENE, OREGON

  公开号：WO1991013056A1

  公开（公告）日：1991-09-05

  (EN) Disubstituted guanidines, e.g., bis-1,3-(o-isopropylphenyl) guanidine, bis-1, 3-(m-isopropylphenyl) guanidine, bis-1,3-(1-naphthyl)guanidine, bis-1,3-(m-methoxyphenyl)guanidine, N-(1-naphthyl)-N'-(o-iodophenyl)-guanidine, N-(1-naphthyl)-N'-(m-ethylphenyl)guanidine, and N-(1-naphthyl)-N'-(o-isopropylphenyl)guanidine, exhibit a high binding affinity to phencyclidine (PCP) receptors. These N,N'-disubstituted guanidine derivatives act as non-competitive inhibitors of glutamate-induced responses generated via the NMDA receptor by acting as blockers for the ion channel of the NMDA receptor-ion channel complex. These compounds thus exert a neuroprotective property and are useful in the therapeutic treatment of neuronal loss in hypoxia, hypoglycemia, brain or spinal cord ischemia, brain or spinal cord trauma, as well as being useful for the treatment of epilepsy, Alzheimer's disease, Amyotrophic Lateral Sclerosis, Huntington's disease, Down's Syndrome, Korsakoff's disease and other neurodegenerative disorders.(FR) Des guanidines disubstituées, par exemple bis-1,3-(o-isopropylphényle)guanidine, bis-1,3-(m-isopropylphényle)guanidine, bis-1,3-(1-naphtyle)guanidine, bis-1,3-(m-methoxyphényle)guanidine, N-(1-naphtyle)-N'-(o-iodophényle)-guanidine, N-(1-naphtyle)-N'-(m-éthylphényle)guanidine, et N-(1-naphthyle)-N'-(o-isopropylphényle)guanidine, présentent une grande affinité de liaison au récepteurs de phencyclidine (PCP). Ces dérivés de guanidine N,N'-bisubstituées agissent comme inhibiteurs non compétitifs des réponses induites par le glutamate générées via le récepteur NMDA en agissant comme bloquant du canal d'ions du complexe récepteur NMDA-canal d'ions. Ces composés excercent ainsi une activité neuroprotectrice et sont utiles dans le traitement thérapeutique de perte neuronale en hypoxie, hypoglycémie, ischemie du cerveau ou du cordon médullaire, traumatisme du cerveau ou du cordon médullaire, et sont également utiles pour le traitement de l'épilepsie, de la maladie d'Alzheimer, de la sclérose latérale amiotrophique, de la maladie de Huntington, du syndrome de Down, de la maladie de Korsakoff et d'autres troubles neurodégénératifs.
• Structure-Guided Design of Potent and Selective Pyrimidylpyrrole Inhibitors of Extracellular Signal-Regulated Kinase (ERK) Using Conformational Control
  作者：Alex M. Aronov、Qing Tang、Gabriel Martinez-Botella、Guy W. Bemis、Jingrong Cao、Guanjing Chen、Nigel P. Ewing、Pamella J. Ford、Ursula A. Germann、Jeremy Green、Michael R. Hale、Marc Jacobs、James W. Janetka、Francois Maltais、William Markland、Mark N. Namchuk、Suganthini Nanthakumar、Srinivasu Poondru、Judy Straub、Ernst ter Haar、Xiaoling Xie

  DOI：10.1021/jm900630q

  日期：2009.10.22

  anticancer drug design. A novel series of pyrimidylpyrrole ERK inhibitors has been identified. Discovery of a conformational change for lead compound 2, when bound to ERK2 relative to antitarget GSK3, enabled structure-guided selectivity optimization, which led to the discovery of 11e, a potent, selective, and orally bioavailable inhibitor of ERK.

  Ras / Raf / MEK / ERK信号转导是涉及多种人类癌症的致癌途径，是抗癌药物设计中的关键目标。已经鉴定出一系列新的嘧啶基吡咯ERK抑制剂。发现相对于抗靶标GSK3与ERK2结合的前导化合物2的构象变化，实现了结构引导的选择性优化，从而导致了11e的发现，这是一种有效，选择性和口服生物利用的ERK抑制剂。