3-(4-(tert-butyloxycarbonyl)piperazin-1-yl)-4,5-dihydro-2-methyl-2H-benzo[g]indazole | 164154-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-(4-(tert-butyloxycarbonyl)piperazin-1-yl)-4,5-dihydro-2-methyl-2H-benzo[g]indazole
• 英文别名: Tert-butyl 4-(2-methyl-4,5-dihydrobenzo[g]indazol-3-yl)piperazine-1-carboxylate
• CAS: 164154-68-1
• 化学式: C₂₁H₂₈N₄O₂
• 分子量: 368.479
• InChiKey: OMZSHYUMDXOJFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-(tert-butyloxycarbonyl)piperazin-1-yl)-4,5-dihydro-2-methyl-2H-benzo[g]indazole 生成 3-(4-(2-phenylethyl)piperazin-1-yl)-4,5-dihydro-2-methyl-2H-benzo[g]indazole oxalate salt
  参考文献：
  名称：

  Fused tricyclic heteroaromatic derivatives as dopamine receptor subtype

  摘要：

  一类融合的三环杂芳化合物，其化学式为（I），如权利要求书中所定义的，或其盐或前药，含有融合的吡唑、噁唑或嘧啶环，是体内多巴胺受体亚型的配体，因此可用于治疗和/或预防多巴胺系统紊乱，如精神分裂症。

  公开号：

  US06080745A1
• 作为产物：
  描述：

  N-Boc-哌嗪 以 乙醇 、 乙腈 为溶剂， 反应 28.0h， 生成 3-(4-(tert-butyloxycarbonyl)piperazin-1-yl)-4,5-dihydro-2-methyl-2H-benzo[g]indazole
  参考文献：
  名称：

  3-(1-Piperazinyl)-4,5-dihydro-1H-benzo[g]indazoles: high affinity ligands for the human dopamine D4 receptor with improved selectivity over ion channels

  摘要：

  3-(4-Piperidinyl)-5-arylpyrazole such as 1, were selective for the cloned human dopamine Dq receptor (hD(4)), but also showed affinity at voltage sensitive calcium, sodium and potassium ion channels. A combination of substituent changes to reduce the basicity of the piperidine nitrogen and conformational restriction to give 4,5-dihydro-1H-benzo[g]indazoles reduced this ion channel affinity at the expense of selectivity for hD4 over other dopamine receptors. Incorporation of piperazine into the 4,5-dihydro-1H-benzo[g]indazoles in place of piperidine gave a novel series of high affinity, selective, orally bioavailable hD(4) ligands, such as 16, with improved selectivity over ion channels. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00028-5

文献信息

• [EN] FUSED TRICYCLIC HETEROAROMATIC DERIVATIVES AS DOPAMINE RECEPTOR SUBTYPE LIGANDS<br/>[FR] DERIVES HETEROAROMATIQUES TRICYCLIQUES FUSIONNES EN TANT QUE LIGANDS POUR LES SOUS-TYPES DE RECEPTEURS DOPAMINERGIQUES
  申请人：MERCK SHARP & DOHME LIMITED

  公开号：WO1995007893A1

  公开（公告）日：1995-03-23

  (EN) A class of fused tricyclic heteroaromatic compounds of formula (I), or a salt thereof or a prodrug thereof, containing a fused pyrazole, oxazole or pyrimidine ring are ligands for dopamine receptor subtypes within the body and are therefore of use in the treatment and/or prevention of disorders of the dopamine system, such as schizophrenia.(FR) L'invention se rapporte à une classe de composés hétéroaromatiques tricycliques de formule (I) ou à un de leurs sels ou de leurs promédicaments; ces composés comprenant un cycle pyrazole, oxazole ou pyrimidine fusionné sont des ligands pour les sous-types de récepteurs dopaminergiques dans le corps et s'avèrent donc utiles pour le traitement des troubles du système dopaminergique, et en particulier pour le traitement de la schizophrénie.

  研究一种三环芳香族杂环化合物及其衍生物的生物技术与药物应用,这些杂环化合物含有融合的三环结构以及杂环环基,作为多巴胺受体的配体或辅助药物,具有治疗或预防多巴胺系统相关病症的能力,尤其是精神分裂症。
• FUSED TRICYCLIC HETEROAROMATIC DERIVATIVES AS DOPAMINE RECEPTOR SUBTYPE LIGANDS
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0724572B1

  公开（公告）日：1998-12-16
• US6080745A
  申请人：——

  公开号：US6080745A

  公开（公告）日：2000-06-27
• Fused tricyclic heteroaromatic derivatives as dopamine receptor subtype
  申请人：Merck Sharp & Dohme Limited

  公开号：US06080745A1

  公开（公告）日：2000-06-27

  A class of fused tricyclic heteroaromatic compounds of formula (I) as defined in claim 1 or a salt thereof or a prodrug thereof, containing a fused pyrazole, oxazole or pyrimidine ring are ligands for dopamine receptor subtypes within the body and are therefore of use in the treatment and/or prevention of disorders of the dopamine system, such as schizophrenia.

  一类融合的三环杂芳化合物，其化学式为（I），如权利要求书中所定义的，或其盐或前药，含有融合的吡唑、噁唑或嘧啶环，是体内多巴胺受体亚型的配体，因此可用于治疗和/或预防多巴胺系统紊乱，如精神分裂症。
• 3-(1-Piperazinyl)-4,5-dihydro-1H-benzo[g]indazoles: high affinity ligands for the human dopamine D4 receptor with improved selectivity over ion channels
  作者：Ian Collins、Michael Rowley、William B Davey、Frances Emms、Rosemarie Marwood、Shil Patel、Smita Patel、Alan Fletcher、Ian C Ragan、Paul D Leeson、Ann L Scott、Theodore Broten

  DOI：10.1016/s0968-0896(98)00028-5

  日期：1998.6

  3-(4-Piperidinyl)-5-arylpyrazole such as 1, were selective for the cloned human dopamine Dq receptor (hD(4)), but also showed affinity at voltage sensitive calcium, sodium and potassium ion channels. A combination of substituent changes to reduce the basicity of the piperidine nitrogen and conformational restriction to give 4,5-dihydro-1H-benzo[g]indazoles reduced this ion channel affinity at the expense of selectivity for hD4 over other dopamine receptors. Incorporation of piperazine into the 4,5-dihydro-1H-benzo[g]indazoles in place of piperidine gave a novel series of high affinity, selective, orally bioavailable hD(4) ligands, such as 16, with improved selectivity over ion channels. (C) 1998 Elsevier Science Ltd. All rights reserved.