Heterocyclic Building Blocks-Isothiazole

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Medicinal chemistry inspired fragment-based drug discovery

Abstract Lead generation can be a very challenging phase of the drug discovery process. The two principal methods for this stage of research are blind screening and rational design. Among the rational or semirational design approaches, fragment-based drug discovery (FBDD) has emerged as a useful tool for the generation of lead structures. It is particularly powerful as a complement to high-throughput screening approaches when the latter failed to yield viable hits for further development. Engagement of medicinal chemists early in the process can accelerate the progression of FBDD efforts by incorporating drug-friendly properties in the earliest stages of the design process. Medium-chain acyl-CoA synthetase 2b and ketohexokinase are chosen as examples to illustrate the importance of close collaboration of medicinal chemists, crystallography, and modeling.

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Improvement of Verdejo white wines by contact with oak chips at different winemaking stages

The effect that the addition of wood at different stages of the winemaking process has on the volatile composition and sensory characteristics of Verdejo wines has been studied. Verdejo control wine was made by the traditional winemaking process without oak chips. Oak chips (7 g/L) were added at different stages of the winemaking process: during alcoholic fermentation (OCAF) and in the young wine (OCW). Higher alcohols, ethyl acetate, hexyl acetate, isoamyl acetates and ethyl esters of straight-chain fatty acids were present at higher concentrations in wines that had contact with oak chips during alcoholic fermentation when compared to control wines. The highest concentrations of benzene compounds, oak lactones and furanic compounds were found in both wines in contact with oak chips, particularly in CW samples. Different sensorial profiles were obtained for the wines depending on the stage of the winemaking process at which the chips were added. All wines investigated in this study can provide a viable alternative to traditional Verdejo wines.

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Design strategies of oxidosqualene cyclase inhibitors: Targeting the sterol biosynthetic pathway

Targeting the sterol biosynthesis pathway has been explored for the development of new bioactive compounds. Among the enzymes of this pathway, oxidosqualene cyclase (OSC) which catalyzes lanosterol cyclization from 2,3-oxidosqualene has emerged as an attractive target. In this work, we reviewed the most promising OSC inhibitors from different organisms and their potential for the development of new antiparasitic, antifungal, hypocholesterolemic and anticancer drugs. Different strategies have been adopted for the discovery of new OSC inhibitors, such as structural modifications of the natural substrate or the reaction intermediates, the use of the enzyme’s structural information to discover compounds with novel chemotypes, modifications of known inhibitors and the use of molecular modeling techniques such as docking and virtual screening to search for new inhibitors. This review brings new perspectives on structural insights of OSC from different organisms and reveals the broad structural diversity of OSC inhibitors which may help evidence lead compounds for further investigations with various therapeutic applications.

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Solvent effect on nitrogen NMR shieldings in thiazole and thiadiazole systems

High precision 14N NMR measurements are reported for all six possible thiazole and thiadiazole molecules in a variety of solvents.Both solvent polarity and hydrogen bonding effects on the nitrogen nuclear shielding of the solutes are significant.Both types of effect produce an increase in the solute nitrogen shielding.Analysis of experimental data, and molecular orbital studies, indicate that an increase in the polarity of the solvent favours the delocalization of the lone pair electrons from the sulfur atoms into the conjugated rings.This leads to an increase in electronic charge at the nitrogen atom(s) concerned.This effect is more pronounced than analogous effects observed for pyridine type nitrogen atoms in the corresponding diazole and triazole systems.The significant shielding effects which result from solvent to solute hydrogen bonding to ring nitrogen atoms are shown to be essentially local in origin.Thus the shielding concerned is that of the nitrogen atom directly involved in the hydrogen bonding.

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One-step synthesis of 2-alkenecarbodithioate esters from substituted propargyl ethers, and their conversion into isothiazole ring through a [4+1] type oxidative ring closure

Treatment of substituted propargyl methyl ethers with a base and elemental sulfur in the presence of a thiolate ion afforded 2-alkenecarbodithioate esters in good yields. The reaction is assumed to proceed through a pathway involving in situ generation of propadienethione intermediates. Further conversion of 2-alkenecarbodithioate esters into 2,3-dihydroisothiazoles were efficiently performed by treating with chloramine-T through a [4+1] type oxidative ring closure via thiocarbonyl S-tosylimides.

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A Synopsis of the Properties and Applications of Heteroaromatic Rings in Medicinal Chemistry

Five- and six-membered heteroaromatic rings and their benzo-fused homologues are well established as important structural elements in drug design and are well represented in approved drugs. The key properties of these heterocycles that are of?interest to medicinal chemists include lipophilicity, pKa, aromaticity, ionization potential, H-bond acceptor, and H-bond donor (N?H, O?H, C?H) capability, electron withdrawing effects, dipole values, and bond angles. The judicious and productive application of azoles and azines in drug design requires an understanding of the intrinsic physical chemical properties of the individual heterocycles and how these interact with substituents. In this article, the key properties of azole and azine heterocycles are summarized followed by a synopsis of applications where some of these factors play a role in drug?target interactions and/or potency.

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Structural and energetic characterization of the emissive RNA alphabet based on the isothiazolo[4,3-: D] pyrimidine heterocycle core

We present theoretical characterization of fluorescent non-natural nucleobases, tzA, tzG, tzC, and tzU, derived from the isothiazolo[4,3-d]pyrimidine heterocycle. Consistent with the experimental evidence, our calculations show that the non-natural bases have minimal impact on the geometry and stability of the classical Watson-Crick base pairs, allowing them to accurately mimic natural bases in a RNA duplex, in terms of H-bonding. In contrast, our calculations indicate that H-bonded base pairs involving the Hoogsteen edge are destabilized relative to their natural counterparts. Analysis of the photophysical properties of the non-natural bases allowed us to correlate their absorption/emission peaks to the strong impact of the modification on the energy of the lowest unoccupied molecular orbital, LUMO, which is stabilized by roughly 1.0-1.2 eV relative to the natural analogues, while the highest occupied molecular orbital, HOMO, is not substantially affected. As a result, the HOMO-LUMO gap is reduced from 5.3-5.5 eV in the natural bases to 4.0-4.4 eV in the modified ones, with a consequent bathochromic shift in the absorption and emission spectra.

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A new supramolecular assembly obtained by reaction between thiosaccharin and hexamethylenediamine

The crystal structure of hexamethylenediammonium bis(thiosaccharinate) dihydrate, [H3N-(CH2)6-NH3](tsac) 2 ¡¤ 2 H2O (tsac = C7H4NO 2S2, the anion of thiosaccharin), was determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group P21/a with Z = 4. The thiosaccharinate moiety is planar and shows small but significant modifications in the bonding of the thioamide functional group as compared with the protonated neutral molecule. The ionic crystal is further stabilized by an extensive H-bonding network, which links the anions and cations into an infinite three-dimensional supramolecular assembly. The FTIR spectrum of the compound is briefly discussed in comparison with those of the neutral constituent molecules.

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.Recommanded Product: Benzo[d]isothiazole-3(2H)-thione 1,1-dioxide, Name is Benzo[d]isothiazole-3(2H)-thione 1,1-dioxide, molecular formula is C7H5NO2S2, Recommanded Product: Benzo[d]isothiazole-3(2H)-thione 1,1-dioxide. In a Article, authors is Tarulli, Susana H.£¬once mentioned of Recommanded Product: Benzo[d]isothiazole-3(2H)-thione 1,1-dioxide

Structural and Spectroscopic Characterization of Two New Thallium(I)/Thiosaccharinate Complexes

The crystal structures of [Tl(tsac)] (1) and [Tl(tsac)-(ophen)] (2) (tsac = anion of thiosaccharin; ophen = 1,10 phenanthroline) have been determined at 116 K by single crystal X-ray diffractometry. Complex 1 crystallizes in the monoclinic space group P21/a with Z = 4 and complex 2 in the monoclinic space group C2/c with Z = 8.In both complexes TI is coordinated to a thiosaccharinate anion through its sulphur and nitrogen atoms. A distorted eight fold coordination sphere around the cation in complex 1 is completed with two other longer Tl-S bonds and four Tl…O contacts with five symmetry related neighbouring thiosaccharinate anions. A phenanthroline molecule acting as a bidentate ligand through its nitrogen atoms completes a four-fold coordination around the metal atom in complex 2. The infrared spectra of both complexes were also recorded and their most important features discussed on the basis of its structural peculiarities.

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ARYLOSULFONAMIDES FOR THE TREATMENT OF CNS DISEASES

Arylsulphonamide derivatives of formula (I) and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of disorders of the central nervous system.

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