9-aminotriamantane | 1001164-43-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 9-aminotriamantane
• 英文别名: Heptacyclo[7.7.1.13,15.01,12.02,7.04,13.06,11]octadecan-9-amine
• CAS: 1001164-43-7
• 化学式: C₁₈H₂₅N
• 分子量: 255.403
• InChiKey: PMPNJFHBBUHLAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 9-aminotriamantane 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Chemical Probes for Blocking of Influenza A M2 Wild-type and S31N Channels

  摘要：

  We report on using the synthetic aminoadamantane-CH2-aryl derivatives 1-6 as sensitive probes for blocking M2 S31N and influenza A virus (IAV) M2 wild-type (WT) channels as well as virus replication in cell culture. The binding kinetics measured using electrophysiology (EP) for M2 S31N channel are very dependent on the length between the adamantane moiety and the first ring of the aryl headgroup realized in 2 and 3 and the girth and length of the adamantane adduct realized in 4 and 5. Study of 1-6 shows that, according to molecular dynamics (MD) simulations and molecular mechanics Poisson-Boltzmann surface area (MM/PBSA) calculations, all bind in the M2 S31N channel with the adamantyl group positioned between V27 and G34 and the aryl group projecting out of the channel with the phenyl (or isoxazole in 6) embedded in the V27 cluster. In this outward binding configuration, an elongation of the ligand by only one methylene in rimantadine 2 or using diamantane or triamantane instead of adamantane in 4 and 5, respectively, causes incomplete entry and facilitates exit, abolishing effective block compared to the amantadine derivatives 1 and 6. In the active M2 S31N blockers 1 and 6, the phenyl and isoxazolyl head groups achieve a deeper binding position and high kon/low koff and high kon/high koff rate constants, compared to inactive 2-5, which have much lower kon and higher koff. Compounds 1-5 block the M2 WT channel by binding in the longer area from V27-H37, in the inward orientation, with high kon and low koff rate constants. Infection of cell cultures by influenza virus containing M2 WT or M2 S31N is inhibited by 1-5 or 1-4 and 6, respectively. While 1 and 6 block infection through the M2 block mechanism in the S31N variant, 2-4 may block M2 S31N virus replication in cell culture through the lysosomotropic effect, just as chloroquine is thought to inhibit SARS-CoV-2 infection.

  DOI：

  10.1021/acschembio.0c00553
• 作为产物：
  描述：

  N-chloroacetyltriamantane-9-amine 在 溶剂黄146 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以96%的产率得到9-aminotriamantane
  参考文献：
  名称：

  氨基三金刚烷的合成途径，神经保护剂Memantine®的拓扑类似物

  摘要：

  金刚烷和金刚烷胺的氨基衍生物是神经保护药Memantine®的紧密拓扑类似物，是通过相应的羧酸或醇的胺化反应制备的。 胺-二醇-药物-碳氢化合物-药物化学

  DOI：

  10.1055/s-0028-1087979

文献信息

• Diamondoid derivatives possessing therapeutic activity in the treatment of neurologic disorders
  申请人：Liu Shenggao

  公开号：US20080009546A1

  公开（公告）日：2008-01-10

  This invention relates to diamondoid derivatives which exhibit therapeutic activity. Specifically, the diamondoid derivatives herein exhibit therapeutic effects in the treatment of neurologic disorders. Also provided are methods of treatment, prevention and inhibition of neurologic disorders in a subject in need.

  本发明涉及表现出治疗活性的金刚烷衍生物。具体而言，本发明中的金刚烷衍生物在治疗神经疾病方面表现出治疗效果。同时提供了治疗、预防和抑制需要治疗神经疾病的受试者的方法。
• Platinum (IV) complex with increased anti-tumor efficacy
  申请人：VUAB PHARMA A.S.

  公开号：US10017532B2

  公开（公告）日：2018-07-10

  The invention relates to a new platinum (IV) complex with substantially increased antitumor efficacy. The invention further discloses a process for preparing of said complex and a pharmaceutical composition for the therapy of tumor diseases containing said complex.

  本发明涉及一种新型铂(IV)复合物，其抗肿瘤功效大大提高。本发明进一步公开了制备上述复合物的工艺和含有上述复合物的治疗肿瘤疾病的药物组合物。
• [EN] PLATINUM (IV) COMPLEX WITH INCREASED ANTITUMOR EFFICACY<br/>[FR] COMPLEXE DE PLATINE (IV) AYANT UNE EFFICACITÉ ANTITUMORALE ACCRUE
  申请人：VUAB PHARMA A S

  公开号：WO2016034214A1

  公开（公告）日：2016-03-10

  The invention relates to a new platinum (IV) complex with substantially increased antitumor efficacy. The invention further discloses a process for preparing of said complex and a pharmaceutical composition for the therapy of tumor diseases containing said complex.
• Chemical Probes for Blocking of Influenza A M2 Wild-type and S31N Channels
  作者：Christina Tzitzoglaki、Kelly McGuire、Panagiotis Lagarias、Athina Konstantinidi、Anja Hoffmann、Natalie A. Fokina、Chulong Ma、Ioannis P. Papanastasiou、Peter R. Schreiner、Santiago Vázquez、Michaela Schmidtke、Jun Wang、David D. Busath、Antonios Kolocouris

  DOI：10.1021/acschembio.0c00553

  日期：2020.9.18

  We report on using the synthetic aminoadamantane-CH2-aryl derivatives 1-6 as sensitive probes for blocking M2 S31N and influenza A virus (IAV) M2 wild-type (WT) channels as well as virus replication in cell culture. The binding kinetics measured using electrophysiology (EP) for M2 S31N channel are very dependent on the length between the adamantane moiety and the first ring of the aryl headgroup realized in 2 and 3 and the girth and length of the adamantane adduct realized in 4 and 5. Study of 1-6 shows that, according to molecular dynamics (MD) simulations and molecular mechanics Poisson-Boltzmann surface area (MM/PBSA) calculations, all bind in the M2 S31N channel with the adamantyl group positioned between V27 and G34 and the aryl group projecting out of the channel with the phenyl (or isoxazole in 6) embedded in the V27 cluster. In this outward binding configuration, an elongation of the ligand by only one methylene in rimantadine 2 or using diamantane or triamantane instead of adamantane in 4 and 5, respectively, causes incomplete entry and facilitates exit, abolishing effective block compared to the amantadine derivatives 1 and 6. In the active M2 S31N blockers 1 and 6, the phenyl and isoxazolyl head groups achieve a deeper binding position and high kon/low koff and high kon/high koff rate constants, compared to inactive 2-5, which have much lower kon and higher koff. Compounds 1-5 block the M2 WT channel by binding in the longer area from V27-H37, in the inward orientation, with high kon and low koff rate constants. Infection of cell cultures by influenza virus containing M2 WT or M2 S31N is inhibited by 1-5 or 1-4 and 6, respectively. While 1 and 6 block infection through the M2 block mechanism in the S31N variant, 2-4 may block M2 S31N virus replication in cell culture through the lysosomotropic effect, just as chloroquine is thought to inhibit SARS-CoV-2 infection.
• Synthetic Routes to Aminotriamantanes, Topological Analogues of the Neuroprotector Memantine^®
  作者：Andrey Fokin、Anika Merz、Natalie Fokina、Hartmut Schwertfeger、Shenggao Liu、Jeremy Dahl、Robert Carlson、Peter Schreiner

  DOI：10.1055/s-0028-1087979

  日期：——

  The amino derivatives of diamantane and triamantane, representing close topological analogues of the neuroprotective drug Memantine®, were prepared via amination of the respective carboxylic acids or alcohols. amines - diols - drugs - hydrocarbons - medicinal chemistry

  金刚烷和金刚烷胺的氨基衍生物是神经保护药Memantine®的紧密拓扑类似物，是通过相应的羧酸或醇的胺化反应制备的。 胺-二醇-药物-碳氢化合物-药物化学