MRZ 2/23 | 73980-84-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: MRZ 2/23
• 英文别名: MRZ-223；1-amino-3-(adamantan-1-yl)propane；3-(1-adamantyl)propylamine；3-(adamant-1-yl)propan-1-amine；3-(adamant-1-yl)propylamine；1-(1-Adamantyl)-3-aminopropan；3-(Adamantan-1-yl)propan-1-amine；3-(1-adamantyl)propan-1-amine
• CAS: 73980-84-4
• 化学式: C₁₃H₂₃N
• mdl: MFCD02632247
• 分子量: 193.332
• InChiKey: HNXIGOCDOCHMQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  MRZ 2/23 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 1-isothiocyanato-3-(adamantan-1-yl)propane
  参考文献：
  名称：

  Adamantyl Isothiocyanates as Mutant p53 Rescuing Agents and Their Structure–Activity Relationships

  摘要：

  DOI：

  10.1021/acs.jmedchem.0c01971
• 作为产物：
  描述：

  3-(adamantan-1-yl)propanenitrile 在 lithium aluminium tetrahydride 作用下， 生成 MRZ 2/23
  参考文献：
  名称：

  2-巯基乙acet及其衍生物为抗辐射剂。

  摘要：

  DOI：

  10.1021/jm00282a027

文献信息

• [EN] HISTONE DEACETYLASE INHIBITORS FOR THE TREATMENT OF FUNGAL INFECTIONS<br/>[FR] INHIBITEURS D'HISTONE DÉACÉTYLASE POUR LE TRAITEMENT D'INFECTIONS FONGIQUES
  申请人：ORCHID RES LAB LTD

  公开号：WO2011058582A1

  公开（公告）日：2011-05-19

  Described are bridged compounds of the formula (I), their analogs, tautomeric forms, stereoisomers, geometrical isomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites and prodrugs thereof. The invention relates to compositions and methods to treat fungal infection. These compounds are selective HDAC inhibitors that act as inherent antifungal compounds or enhance the activity of other antifungal compounds such as azoles.

  描述了式(I)的桥联化合物，它们的类似物、互变异构体、立体异构体、几何异构体、多晶形态、水合物、溶剂合物、药学上可接受的盐、药物组合物、代谢产物和其前药。该发明涉及用于治疗真菌感染的组合物和方法。这些化合物是选择性HDAC抑制剂，可作为固有的抗真菌化合物或增强其他抗真菌化合物（如唑类药物）的活性。
• 2-Mercaptoacetamidine and derivatives as antiradiation agents
  作者：Roger D. Westland、Mary M. Merz、Susan M. Alexander、Linda S. Newton、Ludwig Bauer、Terry T. Conway、Jerry M. Barton、Krishan K. Khullar、Prabhakar B. Devdhar、Marie M. Grenan

  DOI：10.1021/jm00282a027

  日期：1972.12
• Chemistry of adamantane. VII. Adamantanealkanamines as potential antidepressant and anti-Parkinson agents
  作者：Jiban K. Chakrabarti、Michael J. Foulis、Terrence M. Hotten、Stephen S. Szinai、Alec Todd

  DOI：10.1021/jm00252a007

  日期：1974.6
• US4064258A
  申请人：——

  公开号：US4064258A

  公开（公告）日：1977-12-20
• Evaluation of Antiproliferative Effect of N-(alkyladamantyl)phthalimides In vitro
  作者：Margareta Horvat、Lidija Uzelac、Marko Marjanović、Nikola Cindro、Oliver Franković、Kata Mlinarić-Majerski、Marijeta Kralj、Nikola Basarić

  DOI：10.1111/j.1747-0285.2011.01305.x

  日期：2012.4

  A series of (1‐adamantyl)phthalimides, 1–4, and (2‐adamantyl)phthalimides, 5–8, characterized by different chain length between the adamantyl and the phthalimide moiety were synthesized, as well as 1‐ and 2‐adamantylphthalimides substituted by nitro 9, 10, and amino group 11, 12, and phthalimides bearing homoadamantyl 13 and protoadamantyl substituent 14 and 15. The compounds were tested for antiproliferative activity in vitro on a series of five human cancer lines: MCF‐7 (breast carcinoma), SW 620 (colon carcinoma), HCT 116 (colon carcinoma), MOLT‐4 (acute lymphoblastic leukemia), H 460 (lung carcinoma), and a non‐tumor cell line HaCaT (human keratinocytes). All compounds except nitro derivatives 9 and 10 exhibited antiproliferative activity. The activity was generally better in the 2‐adamantyl series 5–8 and in the compounds having the longest alkyl spacers as in 4 and 8, or with an amino group as in 9 and 10. The most active compounds with the propylene spacer 4 and 8 showed the highest selectivity toward tumor cells. The activity was found to be due to a delay in the progress through the cell cycle at G1/S phase.