(S)-[2-(3-bromo-phenyl)-ethyl]-{1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethyl}-carbamic acid tert-butyl ester | 851678-89-2

• 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: (S)-[2-(3-bromo-phenyl)-ethyl]-{1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-(3-bromophenyl)ethyl]-N-[(1S)-1-[6-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]ethyl]carbamate
• CAS: 851678-89-2
• 化学式: C₂₇H₄₁BrN₂O₃Si
• 分子量: 549.624
• InChiKey: FKZWIOZVMXZIEZ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.91
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-[2-(3-bromo-phenyl)-ethyl]-{1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethyl}-carbamic acid tert-butyl ester 在 四丁基氟化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-[2-(3-bromo-phenyl)-ethyl]-{1-[6-(3-trifluoromethyl-3H-[1,2,4]triazolo[3,4-a]phthalazin-6-yloxymethyl)-pyndin-2-yl]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Identification and synthesis of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to the α2δ-1 subunit of voltage gated calcium channel

  摘要：

  We have identified and synthesized a series of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to alpha(2)delta-1 subunit of voltage gated calcium channels. Structure-activity relationship studies directed toward improving the potency and physical properties of 2 lead to the discovery of 20 (IC50 = 15 nM) and (S)-22 (IC50 = 30 nM). A potent and selective radioligand, [H-3]-(S)-22 was also synthesized to demonstrate that this ligand binds to the same site as gabapentin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.008
• 作为产物：
  描述：

  2-acetyl-6-(((tert-butyldimethylsilyl)oxy)methyl)pyridine 在 硼烷四氢呋喃络合物 、 (S)-8,8-diphenyl-2-methyl-1,3,2-oxazaborolidine 、 NaBH(AcO)2 、 二苯基膦叠氮化物 、 溶剂黄146 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 (S)-[2-(3-bromo-phenyl)-ethyl]-{1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Identification and synthesis of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to the α2δ-1 subunit of voltage gated calcium channel

  摘要：

  We have identified and synthesized a series of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to alpha(2)delta-1 subunit of voltage gated calcium channels. Structure-activity relationship studies directed toward improving the potency and physical properties of 2 lead to the discovery of 20 (IC50 = 15 nM) and (S)-22 (IC50 = 30 nM). A potent and selective radioligand, [H-3]-(S)-22 was also synthesized to demonstrate that this ligand binds to the same site as gabapentin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.008

文献信息

• [EN] TRIAZOLO-PYRIDAZINE COMPOUNDS AND DERIVATIVES THEREOF USEFUL IN THE TREATMENT OF NEUROPATHIC PAIN<br/>[FR] COMPOSES DE TRIAZOLO-PYRIDAZINE ET LEURS DERIVES, DESTINES AU TRAITEMENT DE LA DOULEUR NEUROPATHIQUE
  申请人：MERCK & CO INC

  公开号：WO2005041971A1

  公开（公告）日：2005-05-12

  The present invention is directed to a method of use of triazolo-pyridazine compounds in the treatment of neuropathic pain. The present invention is also directed to the use of triazolo-pyridazine compounds in the treatment of psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, bipolar disorders, and panic, as well as in the treatment of pain, Parkinson’s disease, cognitive dysfunction, epilepsy, circadian rhythm and sleep disorders - such as shift-work induced sleep disorder and jet-lag, drug addiction, drug abuse, drug withdrawal and other diseases. The present invention is also directed to novel triazolo-pyridazine compounds that selectively bind to α2δ-1 subunit of Ca channels.

  本发明涉及一种在治疗神经病性疼痛中使用三唑吡啶化合物的方法。本发明还涉及在治疗精神和情绪障碍，如精神分裂症、焦虑、抑郁、躁郁症和恐慌，以及在治疗疼痛、帕金森病、认知功能障碍、癫痫、昼夜节律和睡眠障碍（如倒班引起的睡眠障碍和时差反应）、药物成瘾、药物滥用、药物戒断和其他疾病中使用三唑吡啶化合物的方法。本发明还涉及选择性结合到Ca通道α2δ-1亚基的新型三唑吡啶化合物。
• Identification and synthesis of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to the α2δ-1 subunit of voltage gated calcium channel
  作者：Alec D. Lebsack、Janet Gunzner、Bowei Wang、Richard Pracitto、Hervé Schaffhauser、Angelina Santini、Jayashree Aiyar、Robert Bezverkov、Benito Munoz、Wensheng Liu、Shankar Venkatraman

  DOI：10.1016/j.bmcl.2004.03.008

  日期：2004.5

  We have identified and synthesized a series of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to alpha(2)delta-1 subunit of voltage gated calcium channels. Structure-activity relationship studies directed toward improving the potency and physical properties of 2 lead to the discovery of 20 (IC50 = 15 nM) and (S)-22 (IC50 = 30 nM). A potent and selective radioligand, [H-3]-(S)-22 was also synthesized to demonstrate that this ligand binds to the same site as gabapentin. (C) 2004 Elsevier Ltd. All rights reserved.