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Compound 1 (20 g, 0.235 mol) was added under stirring with nitrogen to dry 100 ml of ether and stirred and dissolvedThe temperature is 0 C or lower, n-butyllithium (0.24 mol) is added dropwise thereto, and the mixture is kept at 0 C or lower during the dropwise addition.Temperature reaction until no compound 1.To the reaction solution was added dropwise bromine (0.5 mol), and the mixture was kept below 0 C during the dropwise addition, and the mixture was gradually raised toAfter stirring for half an hour, the reaction was quenched by adding hydrochloric acid solution (2N, 500 ml) thereto.And the aqueous phase was extracted with ether (200 ml * 3) and discarded. The organic phase was combined and washed with sodium dithionite solution(100 ml * 2), dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give compound 2 as a yellow oil.

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Reference£º
Patent; Tianjin Jinyao Group Co., Ltd.; Li Jing; He Guangjie; Yang Xinyi; Wang Shuli; Chen Liying; Hu Xiaoyun; Sun Liang; (38 pag.)CN106890180; (2017); A;,
Isothiazole – Wikipedia
Isothiazole – ScienceDirect.com

 

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Photooxidation of the Antimicrobial, Nonribosomal Peptide Bacitracin A by Singlet Oxygen under Environmentally Relevant Conditions

Bacitracin is a mixture of nonribosomal peptides (NRPs) that is extensively used as an antibiotic in both human and veterinary medicine. Despite its widespread use over the past six decades, very few studies have addressed the environmental fate of bacitracin and zinc-bacitracin complexes. In this study, the photochemical transformation of bacitracin components (i.e., cyclic dodecapeptides) in the aquatic environment was investigated. A high resolution mass spectrometry (HRMS)-based approach enabled monitoring of the photochemical degradation kinetics of individual bacitracin components, investigation of the relative contribution of reactive oxygen species (e.g., singlet oxygen, 1O2) in dissolved organic matter-sensitized photoreactions, and identification of oxidative modifications in bacitracin photoproducts. The results of this study support the hypothesis that indirect photochemical oxidation of the histidine (His) residue by 1O2 is a major degradation pathway for bacitracin A, the most potent congener of the mixture. Furthermore, the photooxidation rate of bacitracin A with 1O2 decreased upon bacitracin A coordination with Zn2+, demonstrating that the photochemistry of metal-bound His is different from that of metal-free His. Overall, these results provide insight into the fate of bacitracin components in the aquatic environment and highlight the potential of utilizing this HRMS-based methodology to study transformations of other environmentally relevant NRPs.

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Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

 

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The synthesis and solvatochromic properties of some novel heterocyclic disazo dyes derived from barbituric acid

5-Amino-4-arylazo-3-methyl-1H-pyrazoles were diazotised and coupled with barbituric acid to provide 13 novel heterocyclic disazo barbituric acid dyes that were characterized by elemental analysis and spectral methods. The effects of varying the pH and solvent on the absorption of the dyes substituted with electron-withdrawing and electron-donating groups at their o-, m-, p-position were examined in detail.

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Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

 

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Quantification of Aromaticity of Heterocyclic Systems Using Interaction Coordinates

Recently, we proposed an aromaticity index based on interaction coordinates (AIBIC) (J. Phys. Chem. A 2016, 120, 2894a’2901). This index works well for the aromatic hydrocarbons. However, in the case of heterocyclic systems, the AIBIC overestimates the aromaticity indicating many of them to be more aromatic than benzene, which seems unlikely. Because of the differences in the electronegativity of the carbon and the other heteroatoms, the electron density is partially localized near the more electronegative atom(s) of the aromatic fragment. This localized electron density does not contribute to the aromaticity that is due to the delocalized electron density over the central ring. To account for this reduction in the delocalized electron density, a correction is introduced based on Pauling’s electronegativity equation. When the corrected interaction coordinates are used in the computation of AIBIC, we get a new index-aromaticity index based on interaction coordinates corrected. This new index, when computed for a variety of heterocyclic systems, yields results in line with the expectations, and its usefulness in quantifying aromaticity appears to be very promising.

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Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

 

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Heterocyclic Analogues of Chlorcyclizine with Potent Hypolipidemic Activity

A series of piperazines was synthesized and their effect of reducing serum cholesterol and triglyceride levels in the rat was evaluated.A systematic exploration of the structure-activity relationships led to the synthesis of (R,S)-(3,5-dimethylisoxazol-4-yl)<4-(1-methylethyl)phenyl>(4-methylpiperazin-1-yl)methane dihydrochloride (M and B 31426), which had potent activity in lowering serum lipid levels at a daily oral dose of 2 mg/kg and was 100 times more potent than clofibrate.

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Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

 

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Biocidal poly (vinyl alcohol) films incorporated with N-halamine siloxane

An N-halamine siloxane precursor gamma-(beta-hydroxyl-gamma-5,5- dimethylhydantoin)aminopropyltrithoxysilane (abbreviated as GHAPA) was synthesized in this study. GHAPA was mixed with PVA solution to prepare PVA/GHAPA cross linked film with an antimicrobial function. The obtained PVA/GHAPA cross linked film was characterized by TGA, DSC and XRD. Upon dilute household bleach treatment, the chlorinated PVA/GHAPA cross linked film could inactivate Staphylococcus aureus and Escherichia coli O157:H7 completely with concentrations of 4.57 ¡Á 107cfu and 2.70 ¡Á 107cfu within 5 and 10 min, respectively, and 99.9995% of Escherichia coli O157:H7 could be inactivated within 5 min. The antimicrobial results showed that the chlorinated films substantially outperformed the unchlorinated control samples. The biocidal films may serve as potential materials for food packaging and biomedical applications.

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Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

 

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Structural, topological and vibrational properties of an isothiazole derivatives series with antiviral activities

Abstract In this work, the structural, topological and vibrational properties of an isothiazole derivatives series with antiviral activities in gas and aqueous solution phases were studied by using DFT calculations. The self consistent reaction field (SCRF) method was combined with the polarized continuum (PCM) model in order to study the solvent effects and to predict their reactivities and behaviours in both media. Thus, the 3-mercapto-5-phenyl-4-isothiazolecarbonitrile (I), 3-methylthio-5-phenyl-4-isothiazolecarbonitrile (II), 3-Ethylthio-5-phenyl-4-isothiazolecarbonitrile (III), S-[3-(4-cyano-5-phenyl)isothiazolyl] ethyl thiocarbonate (IV), 5-Phenyl-3-(4-cyano-5-phenylisothiazol-3-yl) disulphanyl-4-isothiazolecarbonitrile (V) and 1,2-Bis(4-cyano-5-phenylisothiazol-3-yl) sulphanyl Ethane (VI) derivatives were studied by using the hybrid B3LYP/6-31G?method. All the properties were compared and analyzed in function of the different R groups linked to the thiazole ring. This study clearly shows that the high polarity of (I) probably explains its elevated antiviral activity due to their facility to traverse biological membranes more rapidly than the other ones while in the (IV) and (V) derivatives the previous hydrolysis of both bonds increasing their antiviral properties inside the cell probably are related to their low S-R bond order values. In addition, the complete vibrational assignments and force constants are presented.

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Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

 

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Five-Membered Ring Systems: With N and S Atoms

This review chapter describes the syntheses and reactions of five-membered heterocyclic ring systems containing nitrogen and sulfur published in 2017.

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Recent advances in aminopyrazoles synthesis and functionalization

Aminopyrazoles represent an important class of heterocycles in medicinal chemistry due to their numerous biological activities. This chapter aims to cover the synthesis and reactivity of aminopyrazoles since 2009. Specific regio and chemoselectivity problematics have been emphasized.

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Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

 

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A retrospect on antimicrobial potential of thiazole scaffold

Due to its appreciable diversity in biological actions, thiazole and its substituted components, a significant class of heterocyclic compounds has developed as an influential scaffold in the field of chemical sciences. The variability of thiazole core has been expressed through the effective instigation of its anticancer (Dasatinib, Tiazofurin), antiretroviral (Ritonavir, Brecanavir), antimicrobial (Sulfathiazole, Ravuconazole) and anti-inflammatory (Fenclozic acid, Meloxicam) derivatives. This reasonable diversity in the physiological reaction pattern led many scientists to refine and develop new structural alternatives with much more efficient pharmacological action. This review is crucial for previous studies and projects to survey the antimicrobial activity of thiazole and thiazole related compounds to the mid of 2019.

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Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com