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Adamantane

$52

  • Brand : BIOFRON

  • Catalogue Number : BD-P0684

  • Specification : 98.0%(GC)

  • CAS number : 281-23-2

  • PUBCHEM ID : 9238

  • Volume : 100mg

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Catalogue Number

BD-P0684

Analysis Method

HPLC,NMR,MS

Specification

98.0%(GC)

Storage

2-8°C

Molecular Weight

Appearance

Colorless crystal

Botanical Source

Structure Type

Aliphatic Compounds

Category

Standards;Natural Pytochemical;API

SMILES

C1C2CC3CC1CC(C2)C3

Synonyms

4-05-00-00469/Adamantane/1901173/Tricyclo[3.3.1.1(3,7)]decane/L66 B6/B-H/DI A B- C 1B ITJ/Adamantane (8CI)/Adamantan/Tricyclo(3.3.1.1(3,7))decane/Tricyclo[3.3.1.1]decane/Tricyclo[3.3.1.13,7]decane

IUPAC Name

adamantane

Applications

Density

1.0±0.1 g/cm3

Solubility

Chloroform; Ethyl Acetate

Flash Point

48.9±11.7 °C

Boiling Point

187.1±7.0 °C at 760 mmHg

Melting Point

209-212 °C (subl.)(lit.

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2902190000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:281-23-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

28124614

Abstract

Background: Intrigued by the fact that aminoadamantane derivatives, bearing the active 1,2-ethylenediamine moiety, are promising antitubercular agents, we report herein the synthesis and the antitubercular evaluation of N,N’-substituded-4,4′-[adamantane-2,2-diyl]bis(phe-noxyalkylamines) 1a-g, N,N’-substituded-4,4′-[adamantane-1,3-diyl]bis(phenoxyalkylamines) 2a-f, N,N’- substituded-[4-(1-adamantyl)phenoxy]alkylamines 3a-d and N,N’-substituded-[4-(2-adamantyl)- phenoxy]alkylamines 4a,b.
Method: A substituted diarylmethane moiety was introduced on the adamantane skeleton of the new derivatives. The synthesis of the above compounds involved the nucleophilic attack of the corresponding phenoxide, to the appropriate aminoalkylchloride hydrochloride under heating.
Results: The double substituted adamantane derivatives with an aminoether side chain exhibit significant activity against Mycobacterium tuberculosis.
Conclusion: The length and the nature of the amino end of the side chain influence the antitubercular activity. The double phenolic substitution of the adamantane scaffold and the aminoether side chain with a three-methylene spacer between the phenoxy group and the nitrogen atom present the better results. (analogues 1f,g and 2e,f). These findings merit further investigation aiming at the design of more potent adamantane antituberculars, bearing a number of different substituents on the diarylmethane pharmacophore, which will also be translocated to other posititions on the adamantane ring.

KEYWORDS

(Adamantane-2; (adamantane-1; 2-diyl) substitution; 3-diyl) substitution; Tuberculosis (TB); aminoethers; antitubercular activity; antitubercular chemotherapy.

Title

Synthesis of Adamantane Aminoethers With Antitubercular Potential

Author

Angeliki-Sofia Foscolos 1 , Ioannis Papanastasiou 2 , Andrew Tsotinis 1 , Nicolas Kolocouris 1 , George B Foscolos 1 , Anthony Vocat 3 , Stewart T Cole 3

Publish date

2017

PMID

30354934

Abstract

Positron emission tomography (PET) imaging with biological macromolecules greatly expands the possibilities of molecular imaging. There are, however, practical aspects limiting the potential of the approach, including the dosimetric consequences of the slow kinetics of radiolabeled biomacromolecules. Pretargeting strategies have led to impactful improvements in the field but are themselves limited by shortcomings of available bioconjugation methodology. We report our initial findings concerning the suitability of the adamantane/cucurbit[7]uril system for pretargeted immuno-PET imaging and provide proof-of-concept PET/computed tomography imaging experiments to establish the stability and rapid formation of host-guest complexes in vivo. The adamantane/cucurbit[7]uril system itself without antibody conjugation has shown remarkably fast association kinetics and clearance in vivo. We further demonstrate the modulation of biodistribution achievable by cucurbituril complexation with relevance for pharmaceutical formulation as well as the radiosynthetic access to relevant reporter molecules labeled with 11C or 18F. This work, an early proof-of-concept, supports the notion that the adamantane/cucurbit[7]uril system warrants further exploration in pretargeted PET imaging applications.

KEYWORDS

(Adamantane-2; (adamantane-1; 2-diyl) substitution; 3-diyl) substitution; Tuberculosis (TB); aminoethers; antitubercular activity; antitubercular chemotherapy.

Title

Adamantane/Cucurbituril: A Potential Pretargeted Imaging Strategy in Immuno-PET

Author

Martin G Strebl 1 , Jane Yang 1 , Lyle Isaacs 2 , Jacob M Hooker 1

Publish date

Jan-Dec 2018

PMID

29559277

Abstract

Previously we have shown that pentacycloundecylamine-chloroquinoline (PCU-CQ) conjugates possess significant chemosensitizing abilities and can circumvent the resistance associated with chloroquine (CQ) resistant plasmodia. In order to further explore structurally related polycyclic compounds as reversed CQ agents we synthesized a series of eight aza-adamantanol (1-4) and adamantane-imine (5-8) CQ conjugates. All conjugates showed limited cytotoxicity against CHO cells (IC50 > 37 µM). Compounds 1, 2 and 5 were highly active (K1 IC50 < 100 nM) exhibiting a 3-4-fold increase in antiplasmodial activity against CQ resistant strain K1 compared to CQ. Reduced cross-resistance (resistance index, RI: 2-4.3) relative to CQ (RI = 38) was also observed for these compounds. Compound 1 which showed an 18-fold enhancement at retaining its activity against the K1 strain compared to CQ is a promising candidate to substitute CQ in P. falciparum resistant malaria.

KEYWORDS

Copyright © 2019 The Japanese Society for the Study of Xenobiotics. Published by Elsevier Ltd. All rights reserved.

Title

Adamantane Amine-Linked Chloroquinoline Derivatives as Chloroquine Resistance Modulating Agents in Plasmodium Falciparum

Author

Opute M Yvette 1 , Sarel F Malan 1 , Dale Taylor 2 , Erika Kapp 1 , Jacques Joubert 3

Publish date

2018 May 15;