Tris(4-acetamido­phenoxy­methyl)methanol 0.7-hydrate

The asymmetric unit of the title compound, C28H31N3O7·0.7H2O, contains a mol­ecule of tris­(4-acetamido­phenoxy­meth­yl)methanol and 0.7 of a water mol­ecule. An extensive hydrogen-bonding network includes inter­actions between all components of the crystal structure

Control of Biohazards: A High Performance Energetic Polycyclized Iodine-Containing Biocide

The article of record as published may be found at http://dx.doi.org/10.1021/acs.inorgchem.8b01600Biohazards and chemical hazards as well as radioactive hazards have always been a threat to human health. The search for solutions to these problems is an ongoing worldwide effort. In order to control biohazards by chemical methods, a synthetically useful fused tricyclic iodine-rich compound, 2,6-diiodo-3,5-dinitro-4,9-dihydrodipyrazolo [1,5a:5',1'-d][1,3,5]triazine (5), with good detonation performance was synthesized, characterized, and its properties determined. This compound which acts as an agent defeat weapon has been shown to destroy certain microorganisms effectively by releasing iodine after undergoing decomposition or combustion. The small iodine residues remaining will not be deleterious to human life after 1 month.Financial support of the Office of Naval Research (N00014-16- 1-2089), and the Defense Threat Reduction Agency (HDTRA 1-15-1-0028) is gratefully acknowledged. The M. J. Murdock Charitable Trust (No. 2014120) is thanked for funds supporting the purchase of a 500 MHz NMR.Financial support of the Office of Naval Research (N00014-16- 1-2089), and the Defense Threat Reduction Agency (HDTRA 1-15-1-0028) is gratefully acknowledged. The M. J. Murdock Charitable Trust (No. 2014120) is thanked for funds supporting the purchase of a 500 MHz NMR

Hydrolytic Reactivity Trends among Potential Prodrugs of the O2-Glycosylated Diazeniumdiolate Family. Targeting Nitric Oxide to Macrophages for Antileishmanial Activity

Glycosylated diazeniumdiolates of structure R2NN(O)dNO-R ′ (R ′ ) a saccharide residue) are potential prodrugs of the nitric oxide (NO)-releasing but acid-sensitive R2NN(O)dNO- ion. Moreover, cleaving the acid-stable glycosides under alkaline conditions provides a convenient protecting group strategy for diazeniumdiolate ions. Here, we report comparative hydrolysis rate data for five representative glycosylated diazeniumdiolates at pH 14, 7.4, and 3.8-4.6 as background for further developing both the protecting group application and the ability to target NO pharmacologically to macrophages harboring intracellular pathogens. Confirming the potential in the latter application, adding R2NN(O)dNO-GlcNAc (where R2N) diethylamino or pyrrolidin-l-yl and GlcNAc) N-acetylglucosamin-l-yl) to cultures of infected mouse macrophages that were deficient in inducible NO synthase caused rapid death of the intracellular protozoan parasite Leishmania major with no host cell toxicity

Inhibition of Human Acetyl- and Butyrylcholinesterase by Novel Carbamates of (−)- and (+)-Tetrahydrofurobenzofuran and Methanobenzodioxepine

A new enantiomeric synthesis utilizing classical resolution provided two novel series of optically active inhibitors of cholinesterase: (−)- and (+)- O-carbamoyl phenols of tetrahydrofurobenzofuran and methanobenzodioxepine. An additional two series of (−)- and (+)-O-carbamoyl phenols of pyrroloindole and furoindole were obtained by known procedures, and their anticholinesterase actions were similarly quantified against freshly prepared human acetyl- (AChE) and butyrylcholinesterase (BChE). Both enantiomeric forms of each series demonstrated potent cholinesterase inhibitory activity (with IC50 values as low as 10 nM for AChE and 3 nM for BChE), with the exception of the (+)-O-carbamoyl phenols of pyrroloindole that lacked activity (IC50 values > 1 µM). Based on the biological data of these four series, a SAR analysis was provided by molecular volume calculations. In addition, a probable transition state model was established according to the known X-ray structure of a transition state complex of Torpedo californica AChE-m-(N,N,N,trimethylammonio)-2,2,2-trifluoroacetophenone (TcAChE-TMTFA). This model proved valuable in explaining the enantio-selectivity and enzyme subtype selectivity of each series. These carbamates are more or similarly potent to anticholinesterases in current clinical use; providing not only inhibitors of potential clinical relevance but also pharmacological tools to define drug-enzyme binding interactions within an enzyme crucial in the maintenance of cognition and numerous systemic physiological functions in health, aging and disease

Mono- and diioso-1,2,3-trizoles and their mono nitro derivatives

The article of record as published may be found at http://dx.doi.org/10.1039/c6dt01731b4-Iodo-1H-1,2,3-triazole (2) and 4,5-diiodo-1H-1,2,3-triazole (3) were synthesized using an efficient and viable synthetic route. The N-alkylation of 3 resulted in the formation of two tautomers. The N-alkyldiiodo- triazoles were nitrated with 100% nitric acid to form monoiodo–mononitro-triazoles. The structures of 2-methyl-4,5-diiodo-1,2,3-triazole (5), 1-ethyl-4,5-diiodo-1,2,3-triazole (6), 1-methyl-4-nitro- 5-iodo-1,2,3-triazole (8) and 1-ethyl-4-nitro-5-iodo-1,2,3-triazole (10) were confirmed by X-ray crystal analysis. All of the new triazoles were fully characterized via NMR, and infrared spectra, and elemental analyses as well as by their thermal and sensitivity properties. Decomposition products calculated using Cheetah 7 software show that these iodo–nitro triazoles liberate iodine.Office of Naval ResearchDefense Threat Reduction AgencyN00014-16-1-2089 (ONR)HDTRA 1-15-1-002

2-Nitro-1,3-dinitrooxypropane

The title compound, C3H5N3O8, was synthesized by reacting 2-nitropropane-1,3-diol with acetyl nitrate. The molecule is bisected by a crystallograpic mirror plane. In the crystal, the molecules pack in a ribbon-like fashion along the c axis, with the central nitro groups pointing in the same direction. C—H...O contacts apparently provide some additional packing stabilization

Energetic Multifunctionalized Nitraminopyrazoles and Their Ionic Derivatives: Ternary Hydrogen-Bond Induced High Energy Density Materials

Diverse functionalization was introduced into the pyrazole framework giving rise to a new family of ternary hydrogen-bond induced high energy density materials. By incorporating extended cationic interactions, nitramine-based ionic derivatives exhibit good energetic performance and enhanced molecular stability. Performance parameters including heats of formation and detonation properties were calculated by using <i>Gaussian 03</i> and <i>EXPLO5</i> v6.01 programs, respectively. It is noteworthy to find that 5-nitramino-3,4-dinitropyrazole, <b>4</b>, has a remarkable measured density of 1.97 g cm^–3 at 298 K, which is consistent with its crystal density (2.032 g cm^–3, 150 K), and ranks highest among azole-based CHNO compounds. Energetic evaluation indicates that, in addition to the molecular compound <b>4</b>, some ionic derivatives, <b>9</b>, <b>11</b>, <b>12</b>, <b>17</b>, <b>19</b>, and <b>22</b>, also have high densities (1.83–1.97 g cm^–3), excellent detonation pressures and velocities (<i>P</i>, 35.6–41.6 GPa; <i>v</i>_D, 8880–9430 m s^–1), as well as acceptable impact and friction sensitivities (IS, 4–30 J; FS, 40–240 N). These attractive features highlight the application potential of nitramino hydrogen-bonded interactions in the design of advanced energetic materials