(-)-cis-4,5,7a,8,9,10,11,11a-octahydro-7H-10-methylindolo<1,7-bc><2,6>naphthyridine | 141474-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (-)-cis-4,5,7a,8,9,10,11,11a-octahydro-7H-10-methylindolo<1,7-bc><2,6>naphthyridine
• 英文别名: SDZ SER-082；(2R,7S)-4-methyl-4,9-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),12(16),13-triene
• CAS: 141474-59-1；141474-54-6
• 化学式: C₁₅H₂₀N₂
• 分子量: 228.337
• InChiKey: YASBOGFWAMXINH-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-cis-4,5,7a,8,9,10,11,11a-octahydro-7H-10-methylindolo<1,7-bc><2,6>naphthyridine 生成 (+)-cis-4,5,7a,8,9,10,11,11a-octahydro-7H-10-methylindolo<1,7-bc><2,6>naphthyridine
  参考文献：
  名称：

  (+)-cis-4,5,7a,8,9,10,11,11a-Octahydro-7H-10-methylindolo[1,7-bc][2,6]- naphthyridine: A 5-HT2C/2B Receptor Antagonist with Low 5-HT2A Receptor Affinity

  摘要：

  The indolonaphthyridine 8 is described as a selective 5-HT2C/2B vs 5-HT2A receptor antagonist. The compound was synthesized in seven steps starting from indoline and isonicotinic acid chloride. The key step is a photocyclization of the indolinyl tetrahydropyridinocarbamic acid ethyl ester 4 to the cis-octahydroindolo[1,7-bc][2,6]naphthyrdinecarbamic acid ethyl ester 5. The synthesis was accomplished by reduction with aluminum hydride and racemic resolution. The indolonaphthyridine 8 exerted the binding profile of a selective 5-HT2C receptor ligand (pK(D) 7.8) and behaved as an antagonist on the 5-HT-induced accumulation of inositol phosphates in pig choroid plexus cells (pK(B) 7.13). Compound 8 dose-dependently inhibited the ACTH response to MK-212 in rats and the MK-212-induced hypophagic effect with an ID50 value of 0.3 mg/kg sc. Compound 8 acted as a 5-HT2B receptor antagonist at the rat stomach fundus with a pK(B) value of 7.34.

  DOI：

  10.1021/jm00001a007
• 作为产物：
  描述：

  <4-<(2,3-dihydro-1H-indol-1-yl)carbonyl>-1,2,3,6-tetrahydro-1-pyridino>carbamic acid ethyl ester 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 甲苯 为溶剂， 反应 14.5h， 生成 (-)-cis-4,5,7a,8,9,10,11,11a-octahydro-7H-10-methylindolo<1,7-bc><2,6>naphthyridine
  参考文献：
  名称：

  (+)-cis-4,5,7a,8,9,10,11,11a-Octahydro-7H-10-methylindolo[1,7-bc][2,6]- naphthyridine: A 5-HT2C/2B Receptor Antagonist with Low 5-HT2A Receptor Affinity

  摘要：

  The indolonaphthyridine 8 is described as a selective 5-HT2C/2B vs 5-HT2A receptor antagonist. The compound was synthesized in seven steps starting from indoline and isonicotinic acid chloride. The key step is a photocyclization of the indolinyl tetrahydropyridinocarbamic acid ethyl ester 4 to the cis-octahydroindolo[1,7-bc][2,6]naphthyrdinecarbamic acid ethyl ester 5. The synthesis was accomplished by reduction with aluminum hydride and racemic resolution. The indolonaphthyridine 8 exerted the binding profile of a selective 5-HT2C receptor ligand (pK(D) 7.8) and behaved as an antagonist on the 5-HT-induced accumulation of inositol phosphates in pig choroid plexus cells (pK(B) 7.13). Compound 8 dose-dependently inhibited the ACTH response to MK-212 in rats and the MK-212-induced hypophagic effect with an ID50 value of 0.3 mg/kg sc. Compound 8 acted as a 5-HT2B receptor antagonist at the rat stomach fundus with a pK(B) value of 7.34.

  DOI：

  10.1021/jm00001a007

文献信息

• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• 2-SUBSTITUTED-5-HYDROXY-4H-CHROMEN-4-ONES AS NOVEL LIGANDS FOR THE SEROTONIN RECEPTOR 2B (5-HT2B)
  申请人：VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：US20170029399A1

  公开（公告）日：2017-02-02

  A family of compounds which function as selective ligands for the serotonin receptor 2B (5-HT 2B ) is identified. Some of the compounds are synthetic non-natural ligands which have a relatively strong interaction with 5-HT2B compared to naturally occurring compounds (some of which are identified for the first time herein as ligands for 5-HT 2B ). Because the compounds, both naturally occurring and synthetically produced, function as ligands for 5-HT 2B they will have application in, for example, the treatment and/or prevention of nervous system disorders such as Alzheimer's disease.
• COMBINATION TREATMENT OF SPECIFIC FORMS OF EPILEPSY
  申请人：ZOGENIX INTERNATIONAL LIMITED

  公开号：US20170071949A1

  公开（公告）日：2017-03-16

  Formulations for and methods of treatment of Dravet syndrome that avoid side effects are disclosed. The formulations comprise a 5-HT receptor agonists which does not agonize selected 5-HT receptor subtypes, and in particular does not agonize the receptor subtype 5-HT2B. Also disclosed are combinations of such 5-HT receptor agonists. Also disclosed are combinations of such 5-HT receptor agonists and SSRIs, SNRIs, and triptans for treating co-morbidities associated with Dravet syndrome.
• US8569481B2
  申请人：——

  公开号：US8569481B2

  公开（公告）日：2013-10-29
• US9034798B2
  申请人：——

  公开号：US9034798B2

  公开（公告）日：2015-05-19