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Adamantane

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1. Microwave Optimized Synthesis of N-(adamantan-1-yl)-4-[(adamantan-1-yl)-sulfamoyl]benzamide and Its Derivatives for Anti-Dengue Virus Activity (PubMed)

Microwave Optimized Synthesis of N-(adamantan-1-yl)-4-[(adamantan-1-yl)-sulfamoyl]benzamide and Its Derivatives for Anti-Dengue Virus Activity Dengue fever is a major public health concern in many tropical and sub-tropical regions. The development of agents that are able to inhibit the dengue virus (DENV) is therefore of utmost importance. This study focused on the synthesis of dual acting hybrids comprising structural features of known DENV inhibitors, amantadine (1) and benzsulfonamide (...) derivatives. Hybrid compound 3, N-(adamantan-1-yl)-4-[(adamantan-1-yl)sulfamoyl]benzamide, was synthesized by reacting amantadine (1) with 4-(chlorosulfonyl)benzoic acid (2), after optimization, in a 2:1 ratio under microwave irradiation conditions in a one-pot reaction. Mono-adamantane derivatives 6 and 7 were synthesised via acyl halide formation of benzoic acid (4) and 4-sulfamoyl benzoic acid (5), respectively, followed by conjugation with amantadine (1) through a conventional or microwave irradiation

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2018 Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry

2. Symmetric dimeric adamantanes for exploring the structure of two viroporins: influenza virus M2 and hepatitis C virus p7 (PubMed)

Symmetric dimeric adamantanes for exploring the structure of two viroporins: influenza virus M2 and hepatitis C virus p7 Adamantane-based compounds have been identified to interfere with the ion-channel activity of viroporins and thereby inhibit viral infection. To better understand the difference in the inhibition mechanism of viroporins, we synthesized symmetric dimeric adamantane analogs of various alkyl-spacer lengths.Symmetric dimeric adamantane derivatives were synthesized where two (...) 700-fold and 150-fold more potent than amantadine in genotypes 2a and 3a, respectively. An amino group appears to be important for inhibiting the ion-channel activity of p7 protein in genotype 2a, while its importance was minimal in all other genotypes.Symmetric dimeric adamantanes can be considered a prospective class of p7 inhibitors that are able to address the differences in adamantane sensitivity among the various genotypes of HCV.

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2018 Drug design, development and therapy

3. Adamantane/Cucurbituril: A Potential Pretargeted Imaging Strategy in Immuno-PET (PubMed)

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

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2018 Molecular imaging

4. Synthesis, Characterization, Crystal Structure, and DFT Study of a New Square Planar Cu(II) Complex Containing Bulky Adamantane Ligand (PubMed)

Synthesis, Characterization, Crystal Structure, and DFT Study of a New Square Planar Cu(II) Complex Containing Bulky Adamantane Ligand A copper complex with square planar geometry, [(L)CuBr₂] (1), (L = N'-(furan-2-ylmethylene)adamantne-1-carbohydrazide) has been synthesized and characterized by Fourier transfer infrared (FTIR) spectroscopy, elemental analysis, mass spectrometry, and single crystal X-ray diffraction. The crystal of 1 is solved as monoclinic, space group P2₁/m with unit cell

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2018 Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry

5. Detection of adamantane-sensitive influenza A(H3N2) viruses in Australia, 2017: a cause for hope? (PubMed)

Detection of adamantane-sensitive influenza A(H3N2) viruses in Australia, 2017: a cause for hope? For over a decade virtually all A(H3N2) influenza viruses have been resistant to the adamantane class of antivirals. However, during the 2017 influenza season in Australia, 15/461 (3.3%) adamantane-sensitive A(H3N2) viruses encoding serine at residue 31 of the M2 protein were detected, more than the total number identified globally during the last 6 years. A return to wide circulation of adamantane

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2017 Euro Surveillance

6. Adamantane in Drug Delivery Systems and Surface Recognition (PubMed)

Adamantane in Drug Delivery Systems and Surface Recognition The adamantane moiety is widely applied in design and synthesis of new drug delivery systems and in surface recognition studies. This review focuses on liposomes, cyclodextrins, and dendrimers based on or incorporating adamantane derivatives. Our recent concept of adamantane as an anchor in the lipid bilayer of liposomes has promising applications in the field of targeted drug delivery and surface recognition. The results reported here (...) encourage the development of novel adamantane-based structures and self-assembled supramolecular systems for basic chemical investigations as well as for biomedical application.

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2017 Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry

7. Adamantane-Isothiourea Hybrid Derivatives: Synthesis, Characterization, In Vitro Antimicrobial, and In Vivo Hypoglycemic Activities (PubMed)

Adamantane-Isothiourea Hybrid Derivatives: Synthesis, Characterization, In Vitro Antimicrobial, and In Vivo Hypoglycemic Activities A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl (Z)-N'-(adamantan-1-yl)-morpholine-4-carbothioimidates 7a-e and 4-arylmethyl (Z)-N'-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidates 8a-e were prepared via the reaction of N-(adamantan-1-yl)morpholine-4-carbothioamide 5 and N-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioamide 6

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2017 Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry

8. Encapsulating Active Pharmaceutical Ingredients in Self‐Assembling Adamantanes with Short DNA Zippers (PubMed)

Encapsulating Active Pharmaceutical Ingredients in Self‐Assembling Adamantanes with Short DNA Zippers Formulating pharmaceutically active ingredients for drug delivery is a challenge. There is a need for new drug delivery systems that take up therapeutic molecules and release them into biological systems. We propose a novel mode of encapsulation that involves matrices formed through co-assembly of drugs with adamantane hybrids that feature four CG dimers as sticky ends. Such adamantanes (...) -835 nm average diameter, and ζ potentials were found to be between -29 and +28 mV. Release of doxorubicin into serum at near-constant rates for 10 days was shown, demonstrating the potential for slow release. The encapsulation and release in self-assembling matrices of dinucleotide-bearing adamantanes appears to be broadly applicable and may thus lead to new drug delivery systems for APIs.© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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2017 ChemMedChem

9. Adamantane

Adamantane Adamantane Toggle navigation Brain Head & Neck Chest Endocrine Abdomen Musculoskeletal Skin Infectious Disease Hematology & Oncology Cohorts Diagnostics Emergency Findings Procedures Prevention & Management Pharmacy Resuscitation Trauma Emergency Procedures Ultrasound Cardiovascular Emergencies Lung Emergencies Infectious Disease Pediatrics Neurologic Emergencies Skin Exposure Miscellaneous Abuse Cancer Administration 4 Adamantane Adamantane Aka: Adamantane , Amantadine , Symmetrel (...) on antivirals in (2011) Images: Related links to external sites (from Bing) These images are a random sampling from a Bing search on the term "Adamantane." Click on the image (or right click) to open the source website in a new browser window. Related Studies (from Trip Database) Cost: Medications amantadine (on 5/17/2017 at ) AMANTADINE 100 MG CAPSULE Generic $1.03 each AMANTADINE 100 MG TABLET Generic $1.50 each AMANTADINE 50 MG/5 ML SOLUTION Generic $0.02 per ml FPNotebook does not benefit financially

2018 FP Notebook

10. Crystal structure of 3-(adamantan-1-yl)-4-(4-chloro­phen­yl)-1H-1,2,4-triazole-5(4H)-thione (PubMed)

Crystal structure of 3-(adamantan-1-yl)-4-(4-chloro­phen­yl)-1H-1,2,4-triazole-5(4H)-thione The title compound, C18H20ClN3S, is a functionalized triazoline-3-thione derivative. The benzene ring is almost perpendic-ular to the planar 1,2,4-triazole ring [maximum deviation = 0.007 (1) Å] with a dihedral angle of 89.61 (5)° between them and there is an adamantane substituent at the 3-position of the triazole-thione ring. In the crystal, N-H⋯S hydrogen-bonding inter-actions link the mol-ecules

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2015 Acta Crystallographica Section E: Crystallographic Communications

11. Crystal structure of 2-(adamantan-1-yl)-5-(4-bromo­phen­yl)-1,3,4-oxa­diazole (PubMed)

Crystal structure of 2-(adamantan-1-yl)-5-(4-bromo­phen­yl)-1,3,4-oxa­diazole In the title mol-ecule, C18H19BrN2O, the benzene ring is inclined to the oxa-diazole ring by 10.44 (8)°. In the crystal, C-H⋯π inter-actions link the mol-ecules in a head-to-tail fashion, forming chains extending along the c-axis direction. The chains are further connected by π-π stacking inter-actions, with centroid-centroid distances of 3.6385 (7) Å, forming layers parallel to the bc plane.

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2014 Acta Crystallographica Section E: Structure Reports Online

12. 3-(Adamantan-1-yl)-4-benzyl-1H-1,2,4-triazole-5(4H)-thione (PubMed)

3-(Adamantan-1-yl)-4-benzyl-1H-1,2,4-triazole-5(4H)-thione The title compound, C19H23N3S, is a functionalized triazoline-3-thione derivative. The benzyl ring is almost normal to the planar 1,2,4-triazole ring (r.m.s. deviation = 0.007 Å) with a dihedral angle of 86.90 (7)°. In the crystal, molecules are linked by pairs of N-H⋯S hydrogen bonds, forming inversion dimers that enclose R 2 (2)(8) loops. The crystal packing is further stabilized by weak C-H⋯π inter-actions that link adjacent dimeric

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2014 Acta Crystallographica Section E: Structure Reports Online

13. Soluble epoxide hydrolase inhibitor trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid is neuroprotective in rat model of ischemic stroke (PubMed)

Soluble epoxide hydrolase inhibitor trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid is neuroprotective in rat model of ischemic stroke Soluble epoxide hydrolase (sEH) diminishes vasodilatory and neuroprotective effects of epoxyeicosatrienoic acids by hydrolyzing them to inactive dihydroxy metabolites. The primary goals of this study were to investigate the effects of acute sEH inhibition by trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid (t-AUCB) on infarct

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2013 American Journal of Physiology - Heart and Circulatory Physiology

14. 3-(Adamantan-1-yl)-1-[(4-benzyl­piperazin-1-yl)meth­yl]-4-ethyl-1H-1,2,4-triazole-5(4H)-thione (PubMed)

3-(Adamantan-1-yl)-1-[(4-benzyl­piperazin-1-yl)meth­yl]-4-ethyl-1H-1,2,4-triazole-5(4H)-thione In the title compound, C26H37N5S, the piperazine ring adopts a chair conformation with the exocyclic N-C bonds in pseudo-equatorial orientations. The piperazine ring (all atoms) subtends dihedral angles of 79.47 (9) and 73.07 (9)° with the triazole and benzene rings, respectively, resulting in an approximate U-shape for the mol-ecule. No significant inter-molecular inter-actions are observed

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2013 Acta Crystallographica Section E: Structure Reports Online

15. N-(Adamantan-1-yl)-1,2,3,4-tetra­hydro­iso­quinoline-2-carbo­thio­amide (PubMed)

N-(Adamantan-1-yl)-1,2,3,4-tetra­hydro­iso­quinoline-2-carbo­thio­amide In the title compound, C20H26N2S, the N-containing six-membered ring adopts a boat conformation and the dihedral angle between the thio-carbamide group and the benzene ring is 49.67 (9)°. An intra-molecular C-H⋯S hydrogen bond generates an S(6) ring motif. The N-H group is sterically hindered and there are no significant inter-molecular inter-actions beyond van der Waals contacts.

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2013 Acta Crystallographica Section E: Structure Reports Online

16. 3-(Adamantan-1-yl)-4-ethyl-1-{[4-(2-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-1H-1,2,4-triazole-5(4H)-thione (PubMed)

3-(Adamantan-1-yl)-4-ethyl-1-{[4-(2-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-1H-1,2,4-triazole-5(4H)-thione In the title compound, C26H37N5OS, the piperazine ring adopts a chair conformation. The triazole ring forms dihedral angles of 67.85 (9) and 59.41 (9)° with the piperazine and benzene rings, respectively, resulting in an approximate V-shaped conformation for the mol-ecule. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure features C-H⋯π inter

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2013 Acta Crystallographica Section E: Structure Reports Online

17. N′-(Adamantan-2-yl­idene)benzo­hydrazide (PubMed)

N′-(Adamantan-2-yl­idene)benzo­hydrazide The title mol-ecule, C(17)H(20)N(2)O, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine N atoms. In the crystal, mol-ecules are linked via N-H⋯N hydrogen bonds, forming chains propagating along the a-axis direction. There are also C-H⋯O, C-H⋯N and C-H⋯π inter-actions present within the chains.

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2012 Acta Crystallographica Section E: Structure Reports Online

18. 3-(Adamantan-1-yl)-4-ethyl-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione (PubMed)

3-(Adamantan-1-yl)-4-ethyl-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione The title compound, C(25)H(35)N(5)S, has an approximately C-shaped conformation. The dihedral angle between the triazole and phenyl planes is 79.5 (2)°. The crystal structure consists of infinite chains parallel to the b axis, constructed by C-H⋯S hydrogen bonds between translation-related mol-ecules. Adjacent chains are linked via weak C-H⋯C inter-actions between the adamantyl and phenyl groups.

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2012 Acta Crystallographica Section E: Structure Reports Online

19. 5-(Adamantan-1-yl)-3-(benzyl­sulfan­yl)-4-methyl-4H-1,2,4-triazole (PubMed)

5-(Adamantan-1-yl)-3-(benzyl­sulfan­yl)-4-methyl-4H-1,2,4-triazole In the asymmetric unit of the title adamantyl derivative, C(20)H(25)N(3)S, there are two crystallographic independent mol-ecules with slightly different conformations. In one mol-ecule, the whole benzyl group is disordered over two orientations with the refined site-occupancy ratio of 0.63 (2):0.37 (2). The dihedral angles between the 1,2,4-triazole and phenyl rings are 24.3 (8) (major component) and 25.8 (13)° (minor

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2012 Acta Crystallographica Section E: Structure Reports Online

20. 3-(Adamantan-1-yl)-4-[(E)-(2,6-difluoro­benzyl­idene)amino]-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione (PubMed)

3-(Adamantan-1-yl)-4-[(E)-(2,6-difluoro­benzyl­idene)amino]-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione The imine residue [C=N = 1.268 (3) Å; conformation = E] is twisted [N-N-C-N = 87.8 (2)°] out of the plane (r.m.s. deviation = 0.016 Å) of the central 1,2,4-triazole ring in the title compound, C(30)H(34)F(2)N(6)S. A small twist also occurs between the imine and terminal benzene rings [N-C-C-C = -169.8 (2)°]. The piperazine ring (chair conformation) occupies

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2012 Acta Crystallographica Section E: Structure Reports Online

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