Synthesis and biological properties of dihydro-oxadiazine-based heterocyclic derivatives.

Dihydro-oxadiazine and its derivatives have been demonstrated to be important heterocyclic scaffold platform with bioactive diversity, which present wide activities such as cardiovascular, antitumor, antibacterial, antimicrobial, acricidal, insecticidal, plant-growth regulating, chitin biosynthesis inhibitors and monoamine oxidase inhibition. Versatile features of dihydro-oxadiazine heterocycles have emerged, so the aim of the present paper was to review the recent advances of dihydro-oxadiazine-based heterocyclic derivatives mainly including synthesis and biological activities.

[1]  B. B. Hassine,et al.  Synthesis, antibacterial and antifungal activities of new chiral 5-alkyl-3-(1′-benzenesulfonylpyrrolidin-2′-yl)-4,5-dihydro-1,2,4-oxadiazin-6-ones , 2010 .

[2]  R. Mohareb,et al.  Hydrazide-Hydrazones in the Synthesis of 1,3,4-Oxadiazine, 1,2,4-Triazine and Pyrazole Derivatives with Antitumor Activities~!2010-02-19~!2010-06-08~!2010-08-27~! , 2010 .

[3]  Kate L. Edler,et al.  Synthesis and X‐ray crystal structures of chiral, nonracemic 5,6‐dihydro‐4H‐1,3,4‐oxadiazines , 2010 .

[4]  S. Mousavi,et al.  Synthesis and Anticancer Evaluation of New Derivatives of 3-Phenyl-1,5-Dimethyl-1H-[1,2,4]Triazolo[4′,3′:1,2]Pyrimido[4,5-e][1,3,4]Oxadiazine , 2010 .

[5]  R. Mohareb,et al.  The Reaction of Cyanoacetylhydrazine with ω-Bromo(4-methyl)acetophenone: Synthesis of Heterocyclic Derivatives with Antitumor Activity , 2010, Molecules.

[6]  J. Rao,et al.  CNS activity of some new 2-{(benzalamino-4-hydroxybenzyl) (1,3,4)-oxadiazino[6,5-b]} indole derivatives , 2010 .

[7]  J. Rao,et al.  Antihelminthic and antiinflammatory activity of a novel series of new (1,3,4) oxadiazino-[6,5-b] Indole derivatives. , 2010 .

[8]  A. Shelar,et al.  Synthesis of New Chiral and Nonchiral Pyrido [3,2-e],[1,3,4] oxadiazine Derivatives , 2010 .

[9]  J. Rao,et al.  CNS Activity of New Indole Derivatives , 2010 .

[10]  K. Jayaveera,et al.  Synthesis and Antimicrobial Activity of New Indole Derivatives , 2010 .

[11]  Chen Liang Synthesis and bioactivity of 4-substituted-2-[2-(3-(trifluoromethyl-phenyl)-vinyl)]-4H-[1,3,4]-oxadiazin-5-one , 2010 .

[12]  Jeevan M. Kondre,et al.  Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazine and 1,3,4-Thiadiazine from Substituted Acetophenones and Acid Hydrazides Using [Hydroxy(tosyloxy)iodo]benzene. , 2009 .

[13]  S. Milioto,et al.  Extended investigation of the aqueous self-assembling behavior of a newly designed fluorinated surfactant. , 2009, Langmuir : the ACS journal of surfaces and colloids.

[14]  R. Beckert,et al.  Novel diazadienes based on 1,3,4-oxadiazines: Ligands in iron carbonyl complexes and substrates in catalytic [2+2+1] cycloaddition reactions , 2009 .

[15]  H. S. Patel,et al.  Synthesis and Biological Activity of 3-[4H-(1,2,4)-Triazolyl]-2,6-diaryl-1,3,5-oxadiazine-4-thione , 2009 .

[16]  F. Eissa Preparation, Antibacterial Activity and Absorption Spectra of Pyrazolo-Oxadiazine Cyanine Dyes , 2009 .

[17]  G. Favi,et al.  Efficient, High-Yield, One-PotProtocol for the Synthesis of 1,2,4-Oxadiazine Derivatives , 2009 .

[18]  Jeevan M. Kondre,et al.  Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazine and 1,3,4-Thiadiazine from Substituted Acetophenones and Acid Hydrazides Using [Hydroxyl(tosyloxy)iodo]benzene , 2009 .

[19]  X. Qian,et al.  Novel 4H-1,3,4-oxadiazin-5(6H)-ones with hydrophobic and long alkyl chains: design, synthesis, and bioactive diversity on inhibition of monoamine oxidase, chitin biosynthesis and tumor cell. , 2009, European journal of medicinal chemistry.

[20]  G. Giorgi,et al.  Synthesis of fluorinated 1,2,4-oxadiazin-6-ones through ANRORC rearrangement of 1,2,4-oxadiazoles , 2009 .

[21]  Pan‐Lin Shao,et al.  [4+2] cycloaddition of ketenes with N-benzoyldiazenes catalyzed by N-heterocyclic carbenes. , 2009, Angewandte Chemie.

[22]  T. Naito Development of new synthetic reactions for nitrogen-containing compounds and their application. , 2008, Chemical & pharmaceutical bulletin.

[23]  Ryan A. Davis,et al.  Synthesis, asymmetric aldol reactions, and x-ray crystallography of some oxadiazinanone derivatives , 2008 .

[24]  B. Dülger,et al.  Synthesis and Antimicrobial Activities of 1,2,4-Oxadiazin-5-one, 6-one and 5-Thiones , 2008 .

[25]  Roland E. Dolle,et al.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2007. , 2008, Journal of combinatorial chemistry.

[26]  N. Takamura,et al.  New entry for synthesis of N-acylhydrazones, pyridazinones, and 1,3,4-oxadiazin-6-ones from alpha-amino acid esters. , 2007, Chemical & pharmaceutical bulletin.

[27]  T. Kurz,et al.  Synthesis of 3‐Alkoxy‐5,6‐dihydro‐4H‐1,2,5‐oxadiazines from Alkyl α‐Aminohydroximates. , 2007 .

[28]  F. Albericio,et al.  Advances in solid-phase cycloadditions for heterocyclic synthesis. , 2007, Journal of combinatorial chemistry.

[29]  R. Mohareb,et al.  THE REACTION OF CYANOACETYLHYDRAZINE WITH w-BROMOACETOPHENONE: NOVEL SYNTHESIS OF 1,3,4-OXADIAZINE, PYRIDAZINE AND COUMARIN DERIVATIVES , 2007 .

[30]  Astrid A. Ortiz,et al.  3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl ]-1,3,4-oxadiazol-2(3H)-one, BMS-191011: opener of large-conductance Ca(2+)-activated potassium (maxi-K) channels, identification, solubility, and SAR. , 2007, Journal of medicinal chemistry.

[31]  C. Altug,et al.  Thiophene-Substituted 1,2,4-Oxadiazoles and Oxadiazines , 2007 .

[32]  J. Ahn,et al.  Scandium(III) triflate–TMSCl promoted cyclization of aziridin-1-yl oximes to 5,6-dihydro-4H-[1,2,4]oxadiazines , 2006 .

[33]  A. Kudelko,et al.  Synthesis of novel 1,3,4-oxadiazin-5(6H)-ones and 2-hydroxymethyl-1,3,4-oxadiazoles , 2006 .

[34]  E. V. Abramova,et al.  Reactions of 1,1,4,4-tetramethylsemicarbazide with prop-2-ynyl bromide, allyl bromide, and 1,3-dibromoprop-1-yne , 2006 .

[35]  K. A. Volkova,et al.  Synthesis of functionally-substituted 2-phenyl(2-furyl)-1,3,4-oxadiazine hydrobromides from benzoyl(2-furoyl)hydrazines and 1,3-dibromopropyne , 2006 .

[36]  Zhiqi Liu,et al.  Molecular basis of differential sensitivity of insect sodium channels to DCJW, a bioactive metabolite of the oxadiazine insecticide indoxacarb. , 2006, Neurotoxicology.

[37]  H. Shindy,et al.  Synthesis, photosensitization and antimicrobial activity of certain oxadiazine cyanine dyes , 2006 .

[38]  J. Fernández-Bolaños,et al.  New trends in pest control: the search for greener insecticides , 2005 .

[39]  Ryan A. Davis,et al.  Synthesis, X-ray crystallography and computational studies concerning an oxadiazinone derived from d-camphor: a structural limitation of oxadiazinones as chiral auxiliaries , 2005 .

[40]  D. Döpp,et al.  New access to pyrazole, oxa(thia)diazole and oxadiazine derivatives , 2005 .

[41]  S. Hitchcock,et al.  Synthesis of 3,4,5,6‐Tetrahydro‐2H‐1,3,4‐oxadiazin‐2‐ones Employing a Metal Hydride and Diethyl Carbonate: An Alternative Cyclization Method over 1,1′‐Carbonyldiimidazole , 2004 .

[42]  Y. Kono,et al.  Modulation of sodium channels by the oxadiazine insecticide indoxacarb and its N-decarbomethoxylated metabolite in rat dorsal root ganglion neurons. , 2003, Pest management science.

[43]  M. Grce,et al.  Novel 1,2,5-oxadiazine derivatives--synthesis and in vitro biological studies. , 2003, Acta pharmaceutica.

[44]  S. Hitchcock,et al.  Synthesis of N4‐substituted[1,3,4]oxadiazinan‐2‐ones derived from norephedrine , 2002 .

[45]  A. Vesselinova,et al.  Protective effect of Oxadin on experimental Yersinia enterocolitica infection in rats. , 2002, Die Pharmazie.

[46]  Atta-ur-rahman,et al.  Synthesis and Biological Screening of 2‐Substituted 5,6‐Dihydro‐5‐oxo‐ 4H‐1,3,4‐oxadiazine‐4‐propanenitriles and of Their Intermediates , 2002 .

[47]  H. Madkour Simple One-Step Syntheses of Heterocyclic Systems from (4Z)-2-Phenyl-4-(thien-2-ylmethylene)-1,3(4H)-oxazol-5-one , 2002 .

[48]  K. D. Wing,et al.  The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides. , 2001, Pest management science.

[49]  V. Andrisano,et al.  Potential of Pyrazolooxadiazinone Derivatives as Serine Protease Inhibitors , 2001, Journal of enzyme inhibition.

[50]  K. D. Wing,et al.  Bioactivation and mode of action of the oxadiazine indoxacarb in insects , 2000 .

[51]  Y. Bessard,et al.  Rate Acceleration of Nucleophilic Substitution of 2-Chloro-4,6-dimethoxypyrimidine by Sulfinate Catalysis , 2000 .

[52]  F. Roussi,et al.  Diastereoselective Cycloadditions of Chiral Non-racemic Azomethine Imines , 2000 .

[53]  F. Roussi,et al.  Asymmetric 1,3-dipolar cycloadditions of a chiral non-racemic azomethine imine , 1999 .

[54]  B. Steffan,et al.  Alboinon, an oxadiazinone alkaloid from the ascidian Dendrodoa grossularia , 1997 .

[55]  R. Baines,et al.  Dihydrooxadiazines : octopaminergic system as a potential site of insecticidal action , 1996 .

[56]  A. Hammam,et al.  Synthesis and properties of some naphtho (Quinolino)-quinone heterocyclic dimethine cyanine dyes , 1996 .

[57]  D. Mitchell,et al.  Improved synthesis and spectral characterization of D5281, an oxadiazine miticide/insecticide , 1994 .

[58]  R. Downer,et al.  Synthesis and miticidal and insecticidal activities of 4-(2-fluoroethyl)-5,6-dihydro-4H-1,3,4-oxadiazines , 1993 .

[59]  W. A. Harrison,et al.  Design and synthesis of 5,6‐dihydro‐4H‐1,3,4‐oxadiazines as potential octopaminergic insecticides , 1993 .

[60]  Richard C. Moore,et al.  Quantitative structure-activity relationships in acaricidal 4H-1,3,4-oxadiazin-5(6H)-ones , 1991 .

[61]  C. Burstein,et al.  Inhibition of monoamine oxidase types A and B by 2-aryl-4H-1,3,4-oxadiazin-5(6H)-one derivatives , 1988 .

[62]  H. Kanno An approach to a novel insect growth regulator buprofezin (Applaud) , 1987 .

[63]  R. K. Robins,et al.  Synthesis and antimicrobial activity of certain 6H-1,2,4-oxadiazin-3(2H)-ones. , 1977, Journal of medicinal chemistry.

[64]  J. Eble,et al.  Substituted 5,6-dihydro-2-(2-, 3-, and 4-pyridyl)-4H-1,3,4-oxadiazines. , 1965, Journal of medicinal chemistry.