4411-26-1

Usage

Uses

1. Used in Chemical Synthesis:
1-Adamantyl isothiocyanate is used as a key intermediate in the synthesis of various organic compounds, including tris(2-mercapto-1-adamantylimidazolyl)hydroborato ligand and 1-adamantyl-3-(2-(7-methoxy-1,2,3,4-tetrahydroacridin-9-ylamino)alkane)thiourea 2,3-dihydroxysuccinates. Its reactivity and structural properties make it a valuable building block for creating complex molecules with potential applications in various fields.
2. Used in Pharmaceutical Industry:
1-Adamantyl isothiocyanate is used as a starting material for the development of new pharmaceutical compounds. Its ability to form thiourea derivatives with various amines opens up possibilities for designing drugs with specific biological activities, such as potential therapeutic agents for various diseases.
3. Used in Material Science:
The unique chemical properties of 1-Adamantyl isothiocyanate make it a candidate for the development of new materials with specific properties. Its reactivity and structural characteristics can be exploited to create novel materials with potential applications in areas such as electronics, coatings, and adhesives.
4. Used in Research and Development:
1-Adamantyl isothiocyanate is used as a research tool in academic and industrial laboratories. Its reactivity and structural properties make it an interesting compound for studying various aspects of organic chemistry, such as reaction mechanisms, stereochemistry, and the development of new synthetic methods.

Purification Methods

Dissolve it in Et2O, wash with H2O, dry (Na2SO4), evaporate and sublime the residue in a vacuum at 140o, then recrystallise it from MeOH. Irritant. [Stetter & Wulff Chem Ber 95 2302 1962.]

InChI:InChI=1/C11H15NS/c13-7-12-11-4-8-1-9(5-11)3-10(2-8)6-11/h8-10H,1-6H2

Upstream product

• 75-15-0 carbon disulfide 
• 768-94-5 1-Adamantanamine 
• 123933-30-2 O-methyl adamantane-1-carbothioate 
• 61704-47-0 1,2-di(but-3-en-1-yl)disulfide 
• 22110-53-8 1-adamantyl isocyanide 
• 711-01-3 methyl adamantane-1-carboxylate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 811-68-7 silver(I) trifluoromethanethiolate 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 32314-61-7 1-nitroxyadamantane 
• 333-20-0 potassium thioacyanate 
• 84298-45-3 (N-adamantyldithiocarbamato)potassium 
• 1147550-11-5 ammonium thiocyanate 
• 2094-72-6 1-Adamantanecarbonyl chloride 

Downstream Products

• 4411-25-0 1-adamantyl isocyanate 
• 880-52-4 N-(1-adamantyl)acetamide 
• 857030-07-0 C₁₈H₂₃N₃OS 
• 934842-40-7 C₁₈H₂₂FN₃OS 
• 934842-41-8 C₁₈H₂₂ClN₃OS 
• 934842-42-9 C₁₈H₂₂BrN₃OS 
• 329903-53-9 C₁₈H₂₂N₄O₃S 
• 318467-53-7 5-[4-adamantan-1-yl-5-(4-methoxy-benzylsulfanyl)-4H-[1,2,4]triazol-3-yl]-4-methyl-[1,2,3]thiadiazole 
• 318467-48-0 4-adamantan-1-yl-3-(2,4-dimethyl-thiazol-5-yl)-5-(4-methoxy-benzylsulfanyl)-4H-[1,2,4]triazole 
• 318467-55-9 5-[4-adamantan-1-yl-5-(4-trifluoromethyl-benzylsulfanyl)-4H-[1,2,4]triazol-3-yl]-4-methyl-[1,2,3]thiadiazole 
• 318467-51-5 4-adamantan-1-yl-3-(2,4-dimethyl-thiazol-5-yl)-5-(4-trifluoromethyl-benzylsulfanyl)-4H-[1,2,4]triazole 

Relevant academic research and scientific papers

Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas

1-(adamantan-1-ylcarbonyl)-3-(2,3-dichlorophenyl)thiourea, 1, and 1-(adamantan-1-ylcarbonyl)-3-(2,5-dichlorophenyl)thiourea, 2, were synthesized in reasonable yields from admanantyl-1-carbonyl chloride and ammonium thiocyanate followed by treatment of the resulting adamantane-1-carbonylisothiocyanate with the 2,3- and 2,5-dichloroanilines. A complete vibrational analysis was performed on the basis of FTIR and Raman spectra. The formation of intramolecular N[sbnd]H?O and intermolecular N[sbnd]H?S hydrogen bonds in the solids affect vibrational modes, with low frequency values observed for the ν(C[dbnd]O) and ν(C[dbnd]S) stretching modes. Structural data obtained by single-crystal X-ray diffraction at low temperature confirm this picture. Compound 1 crystallizes in the triclinic system and compound 2 crystallizes with two unique molecules in the asymmetric unit of the orthorhombic unit cell. The molecular structures reveal that the carbonylthiourea units in 1 and both molecules of 2 are planar due in part to the formation of intramolecular N[sbnd]H?O[dbnd]C hydrogen bonds that generate S (6) rings. Moreover, the crystal structures are stabilized by an extensive series of classical and non-classical hydrogen bonds and, in the case of 1 by an intermolecular Cl?Cl halogen bond.

Design, synthesis, and molecular docking study of new tyrosyl-dna phosphodiesterase 1 (Tdp1) inhibitors combining resin acids and adamantane moieties

In this paper, a series of novel abietyl and dehydroabietyl ureas, thioureas, amides, and thioamides bearing adamantane moieties were designed, synthesized, and evaluated for their in-hibitory activities against tyrosil-DNA-phosphodiesterase 1 (TDP1). The synthesized compounds were able to inhibit TDP1 at micromolar concentrations (0.19–2.3 μM) and demonstrated low cytotox-icity in the T98G glioma cell line. The effect of the terpene fragment, the linker structure, and the adamantane residue on the biological properties of the new compounds was investigated. Based on molecular docking results, we suppose that adamantane derivatives of resin acids bind to the TDP1 covalent intermediate, forming a hydrogen bond with Ser463 and hydrophobic contacts with the Phe259 and Trp590 residues and the oligonucleotide fragment of the substrate.

Synthesis, antimicrobial and hypoglycemic activities of novel N-(1-adamantyl)carbothioamide derivatives

The reaction of 1-adamantyl isothiocyanate 4 with the various cyclic secondary amines yielded the corresponding N-(1-adamantyl)carbothioamides 5a-e, 6, 7, 8a-c and 9. Similarly, the reaction of 4 with piperazine and trans-2,5-dimethylpiperazine in 2:1 molar ratio yielded the corresponding N,N′-bis(1-adamantyl)piperazine-1,4-dicarbothioamides 10a and 10b, respectively. The reaction of N-(1-adamantyl)-4-ethoxycarbonylpiperidine-1-carbothioamide 8c with excess hydrazine hydrate yielded the target carbohydrazide 11, in addition to 4-(1-adamantyl)thiosemicarbazide 12 as a minor product. The reaction of the carbohydrazide 11 with methyl or phenyl isothiocyanate followed by heating in aqueous sodium hydroxide yielded the 1,2,4-triazole analogues 14a and 14b. The reaction of the carbohydrazide 11 with various aromatic aldehydes yielded the corresponding N′-arylideneamino derivatives 15a-g. The compounds 5a-e, 6, 7, 8a-c, 9, 10a, 10b, 14a, 14b and 15a-g were tested for in vitro antimicrobial activity against certain strains of pathogenic Gram-positive and Gram-negative bacteria and the yeast-like fungus Candida albicans. The compounds 5c, 5d, 5e, 6, 7, 10a, 10b, 15a, 15f and 15g showed potent antibacterial activity against one or more of the tested microorganisms. The oral hypoglycemic activity of compounds 5c, 6, 8b, 9, 14a and 15b was determined in streptozotocin (STZ)-induced diabetic rats. Compound 5c produced significant reduction of serum glucose levels, compared to gliclazide.

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)-N1-(adamantan-1-yl)-morpholine-4-carbothioimidates 7a-e and 4-arylmethyl (Z)-N0-(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 with benzyl or substituted benzyl bromides, in acetone, in the presence of anhydrous potassium carbonate. The structures of the synthesized compounds were confirmed by 1H-NMR, 13C-NMR, electrospray ionization mass spectral (ESI-MS) data, and X-ray crystallographic data. The in vitro antimicrobial activity of the new compounds was determined against certain standard strains of pathogenic bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 7b, 7d and 7e displayed potent broad-spectrum antibacterial activity, while compounds 7a, 7c, 8b, 8d and 8e were active against the tested Gram-positive bacteria. The in vivo oral hypoglycemic activity of the new compounds was carried on streptozotocin (STZ)-induced diabetic rats. Compounds 7a, 8ab, and 8b produced potent dose-independent reduction of serum glucose levels, compared to the potent hypoglycemic drug gliclazide.

A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur

Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is

Synthesis of isothiocyanates using DMT/NMM/TsO? as a new desulfurization reagent

Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3 N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO? ) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L-and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e.

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

Mutant p53 rescue by small molecules is a promising therapeutic strategy. In this structure-activity relationship study, we examined a series of adamantyl isothiocyanates (Ad-ITCs) to discover novel agents as therapeutics by targeting mutant p53. We demonstrated that the alkyl chain connecting adamantane and ITC is a crucial determinant for Ad-ITC inhibitory potency. Ad-ITC 6 with the longest chain between ITC and adamantane displayed the maximum growth inhibition in p53R280K, p53R273H, or p53R306Stop mutant cells. Ad-ITC 6 acted in a mutant p53-dependent manner. It rescued p53R280K and p53R273H mutants, thereby resulting in upregulating canonical wild-type (WT) p53 targets and phosphorylating ATM. Ad-ISeC 14 with selenium showed a significantly enhanced inhibitory potency, without affecting its ability to rescue mutant p53. Ad-ITCs selectively depleted mutant p53, but not the WT, and this activity correlates with their inhibitory potencies. These data suggest that Ad-ITCs may serve as novel promising leads for the p53-targeted drug development.

Reactions of Cage Substrates with Sulfur Nucleophiles

Abstract: Reactions of alcohols of the adamantane series and adamantan-1-yl nitrates with sulfur nucleophiles in 94% sulfuric acid afforded a number of new sulfur-containing adamantane derivatives such as carbamo-thioates, isothiocyanates, and carbamodithioates. Di(adamantan-1-yl) disulfide was synthesized by reaction of admantan-1-yl nitrate with sodium sulfide nonahydrate in 94% sulfuric acid.

Synthesis of thiocarbamoyl fluorides and isothiocyanates using amines with CF3SO2Cl

A practical and efficient method to synthesize thiocarbamyl fluorides and isothiocyanates from amines with trifluoromethanesulfonyl chloride was developed. In the presence of the reducing agent triphenylphosphine and sodium iodide, thiocarbamyl fluorides and isothiocyanates were synthesized from secondary/primary amine in moderate to excellent yields, respectively. A broad scope of substrates and good functional group compatibility were observed.

Synthesis of thiocarbamoyl fluorides and isothiocyanates using CF3SiMe3 and elemental sulfur or AgSCF3 and KBr with amines

Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CF3SiMe3, elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF3 reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.