6-methoxynaphthalene-2-carbothioamide | 926234-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methoxynaphthalene-2-carbothioamide
• CAS: 926234-18-6
• 化学式: C₁₂H₁₁NOS
• mdl: MFCD09047385
• 分子量: 217.291
• InChiKey: SZNBNJFTZHUGPB-UHFFFAOYSA-N

物化性质

• 沸点：
  396.9±34.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methoxynaphthalene-2-carbothioamide 在 sodium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,2,3,4-tetrahydro-6,7-dimethoxy-2-((2-(2-methoxynaphthalen-6-yl)thiazol-4-yl)methyl)isoquinoline
  参考文献：
  名称：

  Naphthalenyl derivatives for hitting P-gp/MRP1/BCRP transporters

  摘要：

  Substituted naphthalenyl derivatives bearing oxazole, or thiazole or furyl heteronuclei have been carried out as bioisosters of aryl-oxazoles and -thiazoles derivatives previously reported in order to investigate the role of the hindrance on the activity towards P-gp/BCRP/and MRP1 transporters. In addition, the role of naphthalenyl group to modulate P-gp intrinsic activity of these compounds was ascertained.The results demonstrated that all naphthalenyl derivatives displayed comparable P-gp activity with respect to lead compounds previously characterized in our SAR studies but were less active towards BCRP and MRP1 pumps. In terms of intrinsic activity, the replacement of aryl with naphthalenyl moiety led to P-gp inhibitors, unambiguous or ambiguous substrates on the base of the heteronucleus and the substituent on the naphthalenyl fragment. Indeed, oxazole derivatives were: inhibitors (R = H, F, OH), unambiguous substrates (R = OCH3), or ambiguous substrate (R = Br); thiazole derivatives were: unambiguous substrates (R = OCH3, Br), or ambiguous substrates (R = H, F). Finally furyl derivatives were ambiguous substrates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.021
• 作为产物：
  描述：

  6-methoxy-2-naphthamide 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以59%的产率得到6-methoxynaphthalene-2-carbothioamide
  参考文献：
  名称：

  Naphthalenyl derivatives for hitting P-gp/MRP1/BCRP transporters

  摘要：

  Substituted naphthalenyl derivatives bearing oxazole, or thiazole or furyl heteronuclei have been carried out as bioisosters of aryl-oxazoles and -thiazoles derivatives previously reported in order to investigate the role of the hindrance on the activity towards P-gp/BCRP/and MRP1 transporters. In addition, the role of naphthalenyl group to modulate P-gp intrinsic activity of these compounds was ascertained.The results demonstrated that all naphthalenyl derivatives displayed comparable P-gp activity with respect to lead compounds previously characterized in our SAR studies but were less active towards BCRP and MRP1 pumps. In terms of intrinsic activity, the replacement of aryl with naphthalenyl moiety led to P-gp inhibitors, unambiguous or ambiguous substrates on the base of the heteronucleus and the substituent on the naphthalenyl fragment. Indeed, oxazole derivatives were: inhibitors (R = H, F, OH), unambiguous substrates (R = OCH3), or ambiguous substrate (R = Br); thiazole derivatives were: unambiguous substrates (R = OCH3, Br), or ambiguous substrates (R = H, F). Finally furyl derivatives were ambiguous substrates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.021

文献信息

• [EN] NOVEL TETRAHYDROISOQUINOLINE COMPOUNDS FOR USE IN THE DIAGNOSIS AND TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] NOUVEAUX COMPOSÉS DE TÉTRAHYDRO-ISOQUINOLINE POUR DIAGNOSTIC ET TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：UNIV BARI

  公开号：WO2012159666A1

  公开（公告）日：2012-11-29

  The invention relates to a new class of compounds with high affinity and selectivity towards P-glycoprotein. The invention also relates to the utilization of such compounds in the in vivo diagnosis of neurodegenerative diseases and as medicaments for use in the prevention and treatment of neurodegenerative disease involving P-glycoprotein.

  该发明涉及一类新的化合物，具有高亲和力和选择性，可用于P-糖蛋白。该发明还涉及利用这类化合物在体内诊断神经退行性疾病以及作为药物用于预防和治疗涉及P-糖蛋白的神经退行性疾病。
• NOVEL TETRAHYDROISOQUINOLINE COMPOUNDS FOR USE IN THE DIAGNOSIS AND TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：UNIVERSITA' DEGLI STUDI DI BARI "ALDO MORO"

  公开号：US20140112868A1

  公开（公告）日：2014-04-24

  The invention relates to a new class of compounds with high affinity and selectivity towards P-glycoprotein. The invention also relates to the utilization of such compounds in the in vivo diagnosis of neurodegenerative diseases and as medicaments for use in the prevention and treatment of neurodegenerative disease involving P-glycoprotein.

  这项发明涉及一类新的化合物，具有高亲和力和选择性，可作用于P-糖蛋白。该发明还涉及利用这些化合物在体内诊断神经退行性疾病，并作为药物用于预防和治疗涉及P-糖蛋白的神经退行性疾病。
• EP2714682B1
  申请人：——

  公开号：EP2714682B1

  公开（公告）日：2016-03-16
• US9095631B2
  申请人：——

  公开号：US9095631B2

  公开（公告）日：2015-08-04