纳曲吲哚苯并呋喃 | 111555-58-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 中文名称: 纳曲吲哚苯并呋喃
• 英文名称: naltriben
• 英文别名: 17-(cyclopropylmethyl)-6,7-didehydro-3,14β-dihydroxy-4,5α-epoxy-6,7-2',3'-benzofuranomorphinan；NTB；17-(cyclopropylmethyl)-6,7-didehydro-3,14β-dihydroxy-4,5α-epoxy-6,7-2',3'-benzo[b]furanomorphinan；(1S,2S,13R,21R)-22-(cyclopropylmethyl)-11,14-dioxa-22-azaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15,17,19(25)-heptaene-2,16-diol
• CAS: 111555-58-9
• 化学式: C₂₆H₂₅NO₄
• 分子量: 415.489
• InChiKey: ZHVWWEYETMPAMX-IFKAHUTRSA-N

物化性质

• 沸点：
  605.3±55.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO: 14 mg/mL ， 60 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.1
• 氢给体数：
  2
• 氢受体数：
  5

制备方法与用途

Naltriben 是一种选择性的 δ2-奥秘肽受体拮抗剂和 TRPM7 激活剂，能够增强胶质母细胞瘤细胞的迁移和侵袭能力。Naltriben 在神经系统疾病和癌症研究中具有应用价值。

反应信息

• 作为反应物：
  描述：

  纳曲吲哚苯并呋喃 在 间氯过氧苯甲酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 2.0h， 以52%的产率得到(S)-naltriben N-oxide
  参考文献：
  名称：

  [EN] N-OXIDES OF 4,5-EPOXY-MORPHINANIUM ANALOGS
  [FR] N-OXYDES D'ANALOGUES 4,5-ÉPOXY-MORPHINANIUM

  摘要：

  揭示了4,5-环氧吗啡啉盐类的新型N-氧化物。还揭示了含有4,5-环氧吗啡啉盐类的N-氧化物的药物组合物，以及它们的药用方法。所揭示的化合物可用作阿片受体调节剂等用途。

  公开号：

  WO2009067275A1
• 作为产物：
  描述：

  纳曲酮 生成 纳曲吲哚苯并呋喃
  参考文献：
  名称：

  PORTOGHESE, PHILIP S.

  摘要：

  DOI：

文献信息

• Methods and compositions to prevent addiction
  申请人：FLORIDA STATE UNIVERSITY RESEARCH FOUNDATION, INC.

  公开号：US11045465B2

  公开（公告）日：2021-06-29

  Disclosed herein is a method of reducing or preventing the development of aversion to a CNS stimulant in a subject comprising, administering a therapeutic amount of the neurological stimulant and administering an antagonist of the kappa opioid receptor, to thereby reduce or prevent the development of aversion to the CNS stimulant in the subject. Also disclosed is a method of reducing or preventing the development of addiction to a CNS stimulant in a subject, comprising, administering the CNS stimulant and administering a mu opioid receptor antagonist to thereby reduce or prevent the development of addiction to the CNS stimulant in the subject. Also disclosed are pharmaceutical compositions comprising a central nervous system stimulant and an opioid receptor antagonist. Examples of central nervous system stimulants (such as methylphenidate) and opioid receptor antagonists (such as naltrexone) are provided.

  本文公开了一种减少或防止受试者对中枢神经系统兴奋剂产生厌恶感的方法，包括施用治疗量的神经兴奋剂和施用卡巴阿片受体拮抗剂，从而减少或防止受试者对中枢神经系统兴奋剂产生厌恶感。还公开了一种减少或防止受试者对中枢神经刺激物成瘾的方法，包括施用中枢神经刺激物和施用μ阿片受体拮抗剂，从而减少或防止受试者对中枢神经刺激物成瘾。还公开了包含中枢神经系统兴奋剂和阿片受体拮抗剂的药物组合物。提供了中枢神经系统兴奋剂（如哌醋甲酯）和阿片受体拮抗剂（如纳曲酮）的实例。
• Role of spacer and address components in peptidomimetic .delta.-opioid receptor antagonists related to naltrindole
  作者：P. S. Portoghese、H. Nagase、K. E. MaloneyHuss、C. E. Lin、A. E. Takemori

  DOI：10.1021/jm00109a027

  日期：1991.5

  A series of heterocyclic analogues 2-5 related to naltrindole (1) (NTI) and 6-arylnaltrexone derivatives 6-8 were synthesized in order to determine the role of the spacer and the address moieties in conferring delta opioid receptor antagonist activity. The benzofuran (NTB), quinoxaline, and quinoline analogues (2, 3, and 4, respectively) were delta-selective opioid antagonists in vitro and bound selectively to delta receptors. The tetrahydroindole derivative 5, while delta-selective, was considerably less potent than its indole analogue 13. The data for 2-4 indicate that heterocycles other than pyrrole can serve as a spacer for the delta address moiety. Moreover, the lower delta antagonist potency of 5 illustrates the importance of the aromatic address component. Molecular dynamics simulations of enkephalin using a zipper binding model are consistent with a delta address subsite that may accommodate the benzene moiety of NTI or the Phe4 phenyl group of leucine enkephalin. The considerably lower delta opioid receptor antagonist potencies of the 6-aryl derivatives 6-8 are consistent with the conformational mobility of the aryl group and its location in the molecule.
• Application of the message-address concept in the design of highly potent and selective non-peptide .delta. opioid receptor antagonists
  作者：P. S. Portoghese、M. Sultana、H. Nagase、A. E. Takemori

  DOI：10.1021/jm00397a001

  日期：1988.2
• USE OF OPIOID RECEPTOR ANTAGONISTS
  申请人：DSM IP Assets B.V.

  公开号：EP1926490A2

  公开（公告）日：2008-06-04
• EP2576778B1
  申请人：——

  公开号：EP2576778B1

  公开（公告）日：2017-08-09